Stem cells treated with drug candidates generate distinct metabolite profiles aiding in predictive assessment of cellular toxicity

Volume 3, Number 7

BioFilesLife Science

Stem Cell Models for Drug Discovery and Metabolomics Research

Stemline® Stem Cell Media

Stem Cell Reagents and Antibodies

Drug Discovery

Metabolite Libraries

Stable Isotope Labeled Metabolites

Metabolite Chromatographic Analysis

2

Life Science

BioFilesVolume 3, Number 7

Table of Contents

Introduction .........................................................3

Stemline® Stem Cell Media .................................5

Stem Cell Reagents and Antibodies ....................6 Reagents ............................................................ 6 Antibodies .......................................................... 8

Drug Discovery ..................................................10 DiscoveryCPR: Discover with Custom

Packaged Pharmacologically Active Compounds and Metabolites ........................... 10

LOPAC™1280: Library of Pharmacologically Active Compounds ........................................... 11

Metabolite Libraries ..........................................12 Amino Acid Metabolite Library ........................ 13 Carbohydrate Metabolite Library ..................... 14 Lipid Metabolite Library ................................... 15 New Metabolites From Sigma-Aldrich.............. 16

Stable Isotope Labeled Metabolites .................17 Labeled Compounds for

Lipid Metabolism Research .............................. 18 Other Stable Isotope Labeled Metabolites ....... 19

Metabolite Chromatographic Analysis ..............20 Ascentis® Express HILIC from Supelco® ............ 20

CHROMASOLV® Solvents .................................. 21 CHROMASOLV LC-MS ................................. 21

CHROMASOLV LC-MS Blends ..................... 21

CHROMASOLV Plus .................................... 21

CHROMASOLV HPLC .................................. 22

CHROMASOLV HPLC Blends ....................... 22

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LOPAC™1280 NavigatorThe Library of Pharmacologically Active Compounds (LOPAC) is a collection of 1,280 pharmacologically active compounds. Explore this flexible assay validation library offered by Sigma-Aldrich® with the LOPAC1280 Navigator.

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Our Innovation, Your Research — Shaping the Future of Life Science 3

Intro

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IntroductionRobert GatesProduct Managerrobert.gates@sial.com

Over the past three decades non-cellular and cellular systems have supplanted whole animal studies for the preliminary screening of drug candidates and well as for initial drug metabolism and toxicology studies. In

1991 inadequate metabolic and pharmacokinetic parameters were a major reason for the failure of new drug candidates submitted for FDA approval. In vitro testing methods allowed xenobiotics to be tested in human cells or with human enzymes with more clearly defined study parameters and end points. Toxic or metabolically inert compounds could be identified earlier in the drug development process, and these methods coupled with animal studies and Phase I clinical trials provided more complete information on drug metabolism, availability, and pharmacokinetics in humans. The failure rate for deficiencies in these metabolic parameters decreased to 10% by 2000. (1)

Orally delivered drugs are primarily metabolized in the liver. Phase I reactions are carried out by a series of cytochrome P450-containing enzymes (CYP) that carry out primarily oxidation, reduction and hydrolysis reactions. The CYP isoforms most involved in drug metabolism are the CYP1A family, CYP2A6, CYP2B6, the CYP2C family, CYP2D6, CYP2E1, and the CYP3A family. CYP3A4 is the most abundant isoform in human liver and is involved in the metabolism of approximately half of all currently marketed drugs. (1,2) Phase II reactions are conjugation reactions with glucuronide, glutathione, and sulfonates. Conjugation tends to make the molecules more water soluble. Phase III is excretion by the kidneys (hydrophilic compounds and conjugates) or via the bile into the intestine (lipophilic molecules). (1,3)

Model System for Drug Metabolism Studies

Several cellular models have been used to study drug metabolism in vitro. Human hepatocyte primary cultures are the closest model to the in vivo situation. The hepatocyte membrane retains transporters for the uptake and excretion of xenobiotics and intact intracellular Phase I and Phase II metabolic pathways. (3,4) This model has been of limited use due to the low availability and high variability of human liver samples; although primarily hepatocytes can be cryopreserved. Cultured hepatocytes are also phenotypically unstable; by 48 hrs enzyme activity has declined by 60–80%, and mRNA declines to 15% of original levels by 4 hrs. (3)

Hepatoma cell lines (HepG2 and Mz-Hep-1) have the advantage of being highly available. They are easy to culture, have an unlimited life span and stable phenotype. Unfortunately these cells express drug metabolizing enzymes only at very low levels or not at all. Hepatomas transfected with a single CYP are used to screen for enzyme compounds that inhibit CYP activity. These cells can also be used to study hepatotoxicity in vitro. (3,4)

Recently methods have been reported for producing hepatocyte-like cells from embryonic stem cells. Embryonic

stem cells are pluripotent cells that can be maintained in a undifferentiated state. In nonadherent culture they aggregate to form embryoid bodies (EBs) that differentiate into primordial ectoderm, mesoderm and endoderm cells that can further differentiate into progenitors of organ-specific cell types. Methods for culturing mouse embryonic stem cells (mESC) are well established, and methods obtaining mouse hepatocyte-like cells have been described. (5-7) In their study, Tsutsui, et al., (7) showed that mESC-derived hepatocyte-like cells expressed several p450 isoforms and that the products of testosterone hydroxylation by these hepatocytes were identical to those produced by cultured fetal hepatocytes. However, several hydroxylation products characteristic of metabolism by adult hepatocytes were not produced by mESC-derived hepatocytes.

Standardized protocols for culturing human embryonic stem cells (hESCs) are not well established (5), but methods for the production of hepatocyte-like cells from hESCs have recently been described. (2,6,8-11) Both hepatoblasts and bile duct (cholangiocyte) progenitors are separated from the EBs derived from hESCs. The cholangiocyte progenitors are distinguished from hepatic progenitors by having high levels of cytokeratins 7 and 17. Unlike adult hepatic stem cells, hepatoblasts from hESC express α-fetoprotein (AFP) and do not express the adult stem cell markers NCAM and claudin 3. (2,6) In addition to AFP, hepatocyte-like cells expressed the markers Foxa2, α-1-antitrypsin, albumin, HNF4a, and GATA4. Hepatocyte functions were also observed, such as albumin secretion, glycogen accumulation, urea production, and the accumulation of dyes and low density

Infinite Expansion, Infinite Potential—the Sigma-Aldrich® Stem Cell Biology Platform.

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Intr

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lipoproteins. (2,6,8,9,11) By 21 days in culture, Phase I enzymes such as Cyp 1A2, Cyp 3A4, and Cyp 7A1 and phase II conjugating enzymes such as glutathione transferase were expressed or could be induced by xenobiotic challenge. (2,6,8,11)

Model Systems for Metabolomics and Drug Toxicity Studies

hESCs and hESC-derived progenitor cells may also be useful in determining the effect of xenobiotics on cellular metabolism. The metabolome comprises all the small molecule substrates, intermediates and products of cellular metabolism. Approximately 7500 compounds currently make up the human metabolome including about 2500 metabolites, 3500 food components, and 1200 drug products. (12) These metabolites can be separated chromatographically from tissue, urine, or serum samples and identified by nuclear magnetic resonance (NMR) or mass spectroscopy (MS). The Consortium on Metabonomic Toxicology has proposed predicting the liver or kidney toxicity of novel compounds by multivariate analysis of the urine metabolome, assuming that compounds with similar adverse effects would produce similar abnormalities in the metabolic profile of urine. (13)

Xenobiotics are sometimes teratogenic and knowing the effects of these compounds on cellular metabolism of ESCs or various organ progenitor cells may indicate the pathways involved in drug action and/or toxicity in utero. (14) Human and mouse ESC-derived neurons or cardiomyocytes have also been used to screen for drug toxicities. (5,15-17)

Changes in the metabolome of hESCs or differentiated cells derived from hESC may provide markers of potential drug toxicity. Recently, Cezar, et al. (14) studied the effect of valproate, an anticonvulsant compound with higher teratogenic risk, on the secreted metabolome of three hESC cell lines. Compounds were separated chromatographically and identified by electrospray ionization time-of-flight MS. At moderate valproate concentrations the tryptophan breakdown product, kynurenine, and several glutamate pathway metabolites were elevated. At higher concentrations, the GABA pathway metabolites were also elevated. This study showed that metabolomics methodology could be applied to ESCs in culture.

In the future hESCs and cells derived from hESCs may provide suitable model systems for studying drug metabolism and toxicity in vitro.

References1. Baranczewski, P., et al. Introduction to in vitro estimation of metabolic stability and

drug interactions of new chemical entities in drug discovery and development. Pharmacol. Rep. 58, 453-472 (2006).

2. Agarwal, S., et al., Efficient differentiation of functional hepatocytes from human embryonic stem cells., Stem Cells, 16, 1117-1127 (2008).

3. Castell, J.V., et al., Hepatocyte cell lines: their use, scope, and limitations in drug metabolism studies. Expert Opin. Drug Metab. Toxicol., 2, 183-212 (2006).

4. Donato, M.T., et al., Cell lines: a tool for in vitro drug metabolism studies. Curr. Drug Metab., 9, 1-11 (2008).

5. Pouton, C.W., and Haynes, J.M., Embryonic stem cells as a source of models for drug discovery. Nat. Rev. Drug Disc. 6, 605-616 (2007).

6. Shiraki, N., et al., Differentiation of mouse and human embryonic stem cells into hepatic lineages. Genes Cells, e-pub, May 20, 2008.

7. Tsutsui, M., et al., Characterization of cytochrome p450 expression in murine embry-onic stem cell-derived hepatic tissue system. Drug Metab. Disp. 34, 696-701 (2006).

8. Baharvand, H., et al., Differentiation of human embryonic stem cells into functional hepatocyte-like cells in a serum-free adherent culture condition. Differentiation, 76, 465-477 (2008).

9. Chiao, E., et al., Isolation and transcriptional profiling of purified hepatic cells derived from human embryonic stem cells. Stem Cells, e-pub, June 5, 2008.

10. Lavon, N., and Benvenisty, N., Directed differentiation of human embryonic stem cells into hepatic cells, in Human Embryonic Stem Cells: the practical handbook. (Sullivan, S., et al., eds.) pp 186-194. Wiley: Chichester, 2007.

11. Soderdahl, E.M, et al., Expression of drug metabolizing enzymes in hepatocyte-like cells derived from human embryonic stem cells. Biochem. Pharmacol., 74, 496-503 (2007).

12. Fiehn, O., Combining genomics, metabolome analysis, and biochemical modeling to understand metabolic networks. Comp. Funct. Genomics, 2, 155-168 (2001).

13. Ebbels, T.M.D., et al., Prediction and classification of drug toxicity using probabilistic modeling of temporal metabolic data: the Consortium on Metabonomic Toxicology screening approach. J. Proteome Res. 6, 4407-4422 (2007).

14. Cezar, G.G., et al., Identification of small molecules from human embryonic stem cells using metabolomics. Stem Cells Dev. 16, 869-882 (2007).

15. Cezar, G.G., Can human embryonic stem cells contribute to the discovery of safer and more effective drugs? Curr. Opin. Chem. Biol. 11, 405-409 (2007).

16. Chaudhary, K.W., et al., Embryonic stem cells in predictive cardiotoxicity: laser capture microscopy enables assay development. Tox. Sci., 90, 149-158 (2006).

17. Davila, J.C., et al., Use and application of stem cells in toxicology. Tox. Sci., 79, 214-223 (2004).

Our Innovation, Your Research — Shaping the Future of Life Science 5

Stemlin

e® Stem

Cell M

edia

The optimized formulations and proven consistent results have made Sigma-Aldrich®’s Stemline Media a must-have for the challenge of stem cell expansion and maturation in blood and bone marrow samples. Our media platform, as well as our broad selection of reagents, supplements, antibodies, and cytokines, assures maximum performance in human hematopoietic and non-hematopoietic stem cell types. No more hit-or-miss, just great expansion of robust cells!

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S1569 Stemline Mesenchymal Stem Cell Expansion Medium—1 Ln Maximum expansion of mesenchymal stem cells of human origin

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S3444 Stemline Dendritic Cell Maturation Medium—1 Ln Serum-free medium

n Supports high density cultures of mature Dendritic Cells (DC)

n Cultures maintain morphologic and phenotypic characteristics

n Promotes maturation of DCs from human CD14+ monocytes

S3194 Stemline Neural Stem Cell Expansion Media—500 mLn Serum-free formulation

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n Cells retain differentiate capacity

n Expansion rates amazingly superior to DMEM/F12

S0196 Stemline Keratinocyte Medium II—500 mLn Serum-free formulation

n Two supplement cocktails available yields

n Rigorous expansion of NHEK cells

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Stem Cell Reagents and AntibodiesReagents

Name Description Cat. No.

Ciliary Neurotrophic Factor Ciliary neurotrophic factor was first identified as a survival factor for neurons from the ciliary ganglion of chicken embryos. Most of its known actions are restricted to cells of the nervous system, including motor neurons, sympathetic ganglion neurons, sensory neurons, hippocampal neurons and medial septal neurons. CNTF also prevents degeneration of motor axons after axotomy and promotes astrocyte differentiation and oligodendrocyte survival and maturation.

C3710-10UG

Ciliary Neurotrophic Factor CNTF prevents degeneration of motor axons after axotomy and promotes astrocyte differentiation and oligodendrocyte survival and maturation; most of its known actions are restricted to cells of the nervous system.

C3835-10UG

Fibroblast Growth Factor-4 FGF-4 (hst-1, hst/KS53) is a mitogen for fibroblasts and endothelial cells and a potent promoter of angiogenesis. FGF-4 is believed to be critical in embryonic limb development. FGF-4 (19 kDa) includes a secretory signal sequence and shares 42% sequence identity with bFGF at the amino acid level. Both FGF-4 and bFGF bind to the same receptors. Mouse and human FGF-4 shares 82% homology with species cross-reactivity.

F8424-25UG

gp130 Soluble Fragment human The signal-transducing subunit of the functional IL-6 receptor complex. G7534-10UG

Interleukin-6 Interleukin-6 is a multifunctional protein originally discovered in the media of cells stimulated with double stranded RNA. IL-6 appears to be directly involved in the responses that occur after infection and injury and may prove to be as important as IL-1 and TNF-α in regulating the acute phase response. IL-6 is reported to be produced by fibroblasts, activated T cells, activated monocytes or macrophages, and endothelial cells. It acts upon a variety of cells, including fibroblasts, myeloid progenitor cells, T cells, B cells and hepatocytes. IL-6 induces multiple effects, as indicated by its numerous synonyms: plasmacytoma growth factor (PCT-GF), interferon-β-2 (IFN-β2), monocyte derived human B cell growth factor, B cell stimulating factor (BSF-2), hepatocyte stimulating factor (HSF), Interleukin Hybridoma/Plasmacytoma-1 (IL-HP1). In addition, IL-6 appears to interact with IL-2 in the proliferation of T lymphocytes. IL-6 also potentiates the proliferative effect of IL-3 on multipotential hematopoietic progenitors.

I1395-10UG

Interleukin-6 Interleukin-6 is a multifunctional protein that is involved in the responses that occur after infec-tion and injury and may prove to be as important as IL-1 and TNF-α in regulating the acute phase response. IL-6 induces multiple effects. It interacts with IL-2 in the proliferation of T lymphocytes, and potentiates the proliferative effect of IL-3 on multipotential hematopoietic progenitors.

I3268-10KU

Interleukin-6 Interleukin-6 is a multifunctional protein originally discovered in the media of cells stimulated with double stranded RNA. IL-6 appears to be directly involved in the responses that occur after infection and injury and may prove to be as important as IL-1 and TNF-α in regulating the acute phase response. IL-6 is reported to be produced by fibroblasts, activated T cells, activated monocytes or macrophages, and endothelial cells. It acts upon a variety of cells, including fibroblasts, myeloid progenitor cells, T cells, B cells and hepatocytes. IL-6 induces multiple effects, as indicated by its numerous synonyms: plasmacytoma growth factor (PCT-GF), interferon-β-2 (IFN-β2), monocyte derived human B cell growth factor, B cell stimulating factor (BSF-2), hepatocyte stimulating factor (HSF), Interleukin Hybridoma/Plasmacytoma-1 (IL-HP1). In addition, IL-6 appears to interact with IL-2 in the proliferation of T lymphocytes. IL-6 also potentiates the proliferative effect of IL-3 on multipotential hematopoietic progenitors.

I9646-5UG

Interleukin-6 Interleukin-6 is a multifunctional protein originally discovered in the media of cells stimulated with double stranded RNA. IL-6 appears to be directly involved in the responses that occur after infection and injury and may prove to be as important as IL-1 and TNF-α in regulating the acute phase response. IL-6 is reported to be produced by fibroblasts, activated T cells, activated monocytes or macrophages, and endothelial cells. It acts upon a variety of cells, including fibroblasts, myeloid progenitor cells, T cells, B cells and hepatocytes. IL-6 induces multiple effects, as indicated by its numerous synonyms: plasmacytoma growth factor (PCT-GF), interferon-β-2 (IFN-β2), monocyte derived human B cell growth factor, B cell stimulating factor (BSF-2), hepatocyte stimulating factor (HSF), Interleukin Hybridoma/Plasmacytoma-1 (IL-HP1). In addition, IL-6 appears to interact with IL-2 in the proliferation of T lymphocytes. IL-6 also potentiates the proliferative effect of IL-3 on multipotential hematopoietic progenitors.

I0406-10UG

Interleukin-6 Receptor Soluble Fragment human The receptor mediated activity of human IL-6 receptor soluble fragment is measured by its ability to increase the IL-6 inhibition of M1 cells.

I5771-25UG

Interleukin-11 Interleukin-11, also called adipogenesis inhibitory factor (AGIF), is a pleotropic cytokine that acts on hematopoietic progenitor cells and stromal cells. Although recombinant human IL-11 has a predicted molecular mass of 19 kDa, it migrates as a 23 kDa band in SDS-PAGE. It is a functional homolog of IL-6, inducing the proliferation of certain plasmacytoma cell lines and acute phase protein secretion in the liver. IL-11 stimulates the production of erythrocytes, megakaryocytes, and T cell development of antibody producing B cells.

I2406-5UG

Interleukin-11 Interleukin-11, also called adipogenesis inhibitory factor (AGIF), is a pleotropic cytokine that acts on hematopoietic progenitor cells and stromal cells. Although recombinant human IL-11 has a predicted molecular mass of 19 kDa, it migrates as a 23 kDa band in SDS-PAGE. It is a functional homolog of IL-6, inducing the proliferation of certain plasmacytoma cell lines and acute phase protein secretion in the liver. IL-11 stimulates the production of erythrocytes, megakaryocytes, and T cell development of antibody producing B cells.

I9279-5UG

Leukemia Inhibitory Factor Leukemia Inhibitory Factor (LIF) is a pleiotropic glycoprotein that inhibits the proliferation of the murine myeloid leukemic cell line M1, while inducing differentiation into macrophages. Human and mouse LIF share 78% sequence homology. Human LIF can activate mouse cells, but mouse LIF cannot activate human cells.

L5283-10UG

Leukemia Inhibitory Factor Leukemia Inhibitory Factor (LIF) is a pleiotropic glycoprotein that inhibits the proliferation of the murine myeloid leukemic cell line M1, while inducing differentiation into macrophages. Human and mouse LIF share 78% sequence homology. Human LIF can activate mouse cells, but mouse LIF cannot activate human cells.

L5158-5UG

Leukemia Inhibitory Factor soluble Receptor α Binds LIF and is antagonistic. L0915-50UG

Our Innovation, Your Research — Shaping the Future of Life Science 7

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sigma-aldrich.com

Name Description Cat. No.

MISSION® shRNA Human Gene Family Set, Bacterial Glycerol Stock

The clones are sequenced-verified shRNA lentiviral plasmids (pLKO.1-puro) provided as frozen bacterial glycerol stocks (Terrific Broth, carbenicillin at 100 µg/ml and 10% glycerol). The set comes in 96-well plates that are barcoded for simple identification. A CD containing RefSeq, gene description, gene symbol, clone ID, hairpin sequence, locus link, and plate map positions are provided with the gene family set.

SH0811

MISSION® shRNA Human Gene Family Set, Lentiviral Particles

Lentiviral particles are provided in 96-well plates that are barcoded for simple identification. Each gene family set is representationally titered (10% of clones). Fully titered sets are available on a custom basis. A CD containing RefSeq, gene description, gene symbol, clone ID, hairpin sequence, locus link, and plate map positions are provided with the gene family set.

SH0831

Oncostatin M Oncostatin M, LIF, G-CSF, IL-6, and ciliary neurotrophic factor (CNTF) are structurally related members of the same cytokine family sharing similarities in their primary amino acid sequences, predicted secondary structure, and receptor components. Oncostatin M is a growth-regulating cytokine, affecting a number of tumor and normal cells. This material was first identified by its ability to inhibit the growth of A375 melanoma cells and other human tumor cells, but not inhibit the growth of normal human fibroblasts. It acts synergistically with TGF β1 to inhibit the proliferation of tumor cells like A375 melanoma cells. It induces an increase in LDL receptor expression and LDL uptake by hepatoma cells. OSM activates synovial fibroblast-like cells to produce urokinase type plasminogen activator. Oncostatin M is secreted by macrophages and activated T lymphocytes.

O9635-10UG

Oncostatin M Oncostatin M, LIF, G-CSF, IL-6, and ciliary neurotrophic factor (CNTF) are structurally related members of the same cytokine family sharing similarities in their primary amino acid sequences, predicted secondary structure, and receptor components. Oncostatin M is a growth-regulating cytokine, affecting a number of tumor and normal cells. This material was first identified by its ability to inhibit the growth of A375 melanoma cells and other human tumor cells, but not inhibit the growth of normal human fibroblasts. It acts synergistically with TGF β1 to inhibit the proliferation of tumor cells like A375 melanoma cells. It induces an increase in LDL receptor expression and LDL uptake by hepatoma cells. OSM activates synovial fibroblast-like cells to produce urokinase type plasminogen activator. Oncostatin M is secreted by macrophages and activated T lymphocytes.

O1637-25UG

Oncostatin M Receptor β/Fc Chimera Exclusive signal transducing receptor protein for mouse OSM. Mouse and human OSM Rβ share 55% sequence identity.

O8762-100UG

Tyrphostin AG 490 Jak-2 protein tyrosine kinase (PTK) inhibitor. Inhibits interleukin 2 (IL-2) driven mitogenesis and triggers apoptosis of tumor cells in Sezary syndrome, a leukemic variant of cutaneous T cell lymphoma.

T3434-5MGT3434-25MG

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Antibodies

Product Name Host Clone No Form Gene Symbol Species Reactivity Application Cat. No.

Anti-Ciliary Neurotrophic Factor antibody produced in

goat

- IgG fraction of antiserum

Cntf, rat rat Neutral C4085

Anti-Ciliary Neurotrophic Factor antibody produced in

goat

- IgG fraction of antiserum

CNTF, human human Neutral C3960-1MG

Anti-phospho-ERK1 (pThr202/pTyr204) and ERK2 (pThr185/pTyr187)

antibody produced in

rabbit

- affinity isolated antibody

MAPK3, humanMapk3, mouse

Mapk3, rat

chickenhumanmouse

rat

ICCWB

E7028-1VL

Monoclonal Anti-Fibroblast Growth Factor-4

antibody produced in

mouse

19805.11 purified immunoglobulin

FGF4, human human ELISA (i)Neutral

WB

F2153-.5MG

Anti-Fibroblast Growth Factor Receptor-2, Extracellular

antibody produced in

rabbit

- affinity isolated antibody

FGFR2, human human IHC (p)IP

WB

F6796-.2ML

Anti-Fibroblast Growth Factor Receptor-2, Cytoplasmic

antibody produced in

rabbit

- affinity isolated antibody

FGFR2, human human IHC (p)IP

WB

F0300-.5ML

Anti-gp130 antibody produced in

rabbit

- IgG fraction of antiserum

IL6ST, humanIl6st, mouse

humanmouse

IPWB

G4165-200UG

Anti-IL11RA antibody produced in

rabbit

- affinity isolated antibody

IL11RA, human human IHC (p)PAWB

HPA004868-100UL

Anti-IL11RA antibody produced in

rabbit

- affinity isolated antibody

IL11RA, human human IHC (p)PAWB

HPA005729-100UL

Anti-IL6ST antibody produced in

rabbit

- affinity isolated antibody

IL6ST, human human IHC (p)PA

HPA010558-100UL

Monoclonal Anti-Integrin β1 antibody produced in

mouse

W1B10 purified immunoglobulin

ITGB1, chicken chicken IF (i)IP

WB

I8638-.2ML

Anti-Interleukin-6 antibody produced in

rabbit

- IgG fraction of antiserum

Il6, mouse mouse DBNeutral

RIA

I3393

Anti-Interleukin-6 antibody produced in

rabbit

- IgG fraction of antiserum

IL6, human human DBNeutral

RIA

I2143-.5ML

Monoclonal Anti-Interleukin-6 antibody produced in

mouse

6708.11 purified immunoglobulin

IL6, human human ELISA (i)Neutral

WB

I7901-.5MG

Anti-Interleukin-11 antibody produced in

goat

- IgG fraction of antiserum

IL11, human human Neutral I5270-1MG

Our Innovation, Your Research — Shaping the Future of Life Science 9

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sigma-aldrich.com

Product Name Host Clone No Form Gene Symbol Species Reactivity Application Cat. No.

Monoclonal Anti-JAK1 antibody produced in

mouse

JAK1-193 purified immunoglobulin

JAK1, humanJak1, mouse

Jak1, rat

humanmouse

rat

ARRELISA (i)

WB

J3774-200UL

Anti-Leukemia Inhibitory Factor antibody produced in

goat

- IgG fraction of antiserum

Lif, mouse mouse ELISA (i)IHC

NeutralWB

L9152-1MG

Anti-Leukemia Inhibitory Factor antibody produced in

goat

- IgG fraction of antiserum

LIF, human human Neutral L9277-1MG

Monoclonal Anti-Nanog antibody produced in

mouse

NNG-811 purified immunoglobulin

NANOG, human human ELISA (i)ICCIP

WB

N3038-25ULN3038-200UL

Monoclonal Anti-Oncostatin M antibody produced in

mouse

17001.31 purified immunoglobulin

OSM, human human ELISA (i)Neutral

WB

O0884-.5MG

Anti-POU5F1 (Oct4) antibody produced in

rabbit

- affinity isolated antibody

POU5F1, humanPou5f1, mouse

Pou5f1, rat

humanrodent

IHCWB

P0873-100UG

Anti-phospho-Tyk2 (pTyr1054/1055)

antibody produced in

rabbit

- affinity isolated antibody

TYK2, human human IPWB CL

T0442-.1ML

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Drug Discovery

DiscoveryCPR

Compounds for High Throughput Screening

Sigma-Aldrich® is pleased to announce the availability of the MyriaScreen Diversity Collection of drug-like screening compounds. The collection, produced in collaboration with TimTec Inc., is the result of careful evaluation, filtering, and refinement of selections from each of our screening compound collections. The MyriaScreen Diversity Collection is comprised of 10,000 high-purity screening compounds handpicked to maximize chemical diversity while maintaining drug-likeness.

Medicinal Chemistry

We produce an extensive list of building blocks and reactive intermediates for medicinal chemistry applications. From complex bifunctional heterocycles to amines, alcohols, carboxylic acids and sulfonyl chlorides, these building blocks are useful in all phases of parallel, organic, and medicinal chemistry applications.

Structure Activity Relationship (SAR) plays an important role in the drug discovery process in optimizing the activity of new drug leads. Effective SAR encompasses a wide variety of substituents ranging from aliphatic, cycloalkyl to aromatic fragments.

To learn more about our Drug Discovery products, visit sigma.com/drugdiscovery

DiscoveryCPR: Discover with Custom Packaged Pharmacologically Active Compounds and Metabolites

To register for an online ordering account or to submit inquiries: discoverycpr.com

Our Innovation, Your Research — Shaping the Future of Life Science 11

Dru

g D

iscoveryRelevant Compounds and

Pharmacological Activities

n Antiproliferatives

n Enzyme inhibitors

n Antibiotics

n Cell cycle regulators

n Apoptosis inducers

n GPCR ligands

LOPAC1280 compounds are also indexed in the NCBI’s PubChem database.

Sigma-Aldrich® invites you to use this interactive tool to easily browse through LOPAC1280, a collection of 1,280 pharmacologically active compounds. The power and convenience of the known actives in Sigma®’s Library of Pharmacologically Active Compounds is assured. This annotated collection of small molecule modulators and approved drugs impacts most cellular processes and covers all major drug target classes.

Consider the bioactives you want in your library and reveal why researchers worldwide trust the ones in ours:

n 1,280 pharmacologically active compounds – All major target classes are represented, including GPCRs and kinases, making LOPAC the most flexible assay validation library available.

n Marketed drugs and pharmaceutically relevant structures – Predictable activities and proven scaffolds directed against a wide range of drug targets.

n Annotated structure/activity database – Convenient management of individual samples, subsets, or the entire collection.

n Guaranteed Sigma quality and easy re-supply – Highly pure compounds, each available as an individual catalog item.

n Pre-solubilized and normalized compounds – Ready-to-use DMSO stocks require less time-consuming sample preparation.

LOPAC™1280: Library of Pharmacologically Active Compounds

New Insights With Predictable Activities and Proven Scaffolds

Reveal!To browse the compounds on the LOPAC1280 Navigator or request a complete list of components, please visit sigma.com/lopac

Rare Chemical LibraryThe Sigma-Aldrich® Rare Chemical Library consists of over 140,000 unique chemical compounds, including:

• Private and academic collections released upon the researcher’s retirement• One-time synthetic series from remote and obscure sources• Products no longer available from the Sigma-Aldrich catalogs• Plus synthetic analogs and precursors• Available in standard sizes between 1 mg and 1 g

Rare Chemical Library items may also be packed to order through DiscoveryCPR.

FREE!Request the Rare Chemical Library compound list on USB flash drive.

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DiscoveryCPR

sigma-aldrich.com

12 Order: sigma.com/order Technical service: sigma.com/techinfosigma.com/lifescience

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sigma-aldrich.com

Metabolite LibrariesChoose your own components, and build a custom library online using the Sigma-Aldrich® Metabolomics Resources.

Many Metabolite Standards are available in specialized 10 mg sizes packaged in autosampler vials.

Libraries Currently Available—Choose from:

Amino Acids and Metabolic Intermediates

Carbohydrates and Metabolic Intermediates

Lipids and Metabolic Intermediates

Currently in development:

Nucleotide Library

Vitamin/Cofactor Library

Hundreds of other metabolites are available in standard packaging and can be found in the Sigma® Life Science Catalog or online (sigma-aldrich.com/metabolites).

Custom Packaging

Our DiscoveryCPR program can custom package metabolites in the sizes and containers you specify. See page 10 for more details.

http://www.sigma-aldrich.com/ProductLookup.html?ProdNo=C7352&Brand=SIGMA

Use the IUBMB–Sigma-Aldrich Interactive Metabolic Pathway Chart to find the Metabolite Standards you need.

The Metabolic Pathways Map contains over

500 hyperlinks to Sigma product listings. Just

click on the metabolite name or the enzyme’s

E.C. number to access product information.

You can access the chart at sigma-aldrich.com/metpath

Online Metabolomics Resource

Our Innovation, Your Research — Shaping the Future of Life Science 13

Metab

olite Lib

raries

Amino Acid Metabolite Library

Metabolite Cat. No. Packaging

Acetyl-l-carnitine hydrochloride A6706 10 mg Autosampler vial

O-Acetyl-l-serine hydrochloride A6262 10 mg Autosampler vial

Adenosine 5’-phosphosulfate sodium salt

A5508 5 mg

S-(5’-Adenosyl)-l-homocysteine A9384 10 mg Autosampler vial

l-Alanine A7469 10 mg Autosampler vial

β-Alanine A9920 10 mg Autosampler vial

γ-Aminobutyric acid A5835 10 mg Autosampler vial

5-Aminolevulinic acid hydrochloride

A7793 10 mg Autosampler vial

Anthranilic acid A89855 10 mg

l-Arginine A8094 10 mg Autosampler vial

Argininosuccinic acid disodium salt A5707 10 mg Autosampler vial

l-Asparagine A0884 10 mg Autosampler vial

l-Aspartic acid A8949 10 mg Autosampler vial

Betaine aldehyde chloride B3650 10 mg Autosampler vial

Betaine hydrochloride B7045 10 mg Autosampler vial

l-Carnitine hydrochloride C0283 10 mg Autosampler vial

l-Carnosine C9625 10 mg Autosampler vial

Choline chloride C7017 10 mg Autosampler vial

Chorismic acid from Enterobacter aerogenes

C1761 10 mg Autosampler vial

l-Citrulline C7629 10 mg Autosampler vial

Creatine C0780 10 mg Autosampler vial

Creatinine C4255 10 mg Autosampler vial

l-Cystathionine C7505 10 mg Autosampler vial

Cysteamine M9768 10 mg Autosampler vial

l-Cysteine C7352 10 mg Autosampler vial

Cystine C7602 10 mg Autosampler vial

N,N-Dimethylglycine D1156 10 mg Autosampler vial

N-Formyl-l-methionine F3377 10 mg Autosampler vial

l-Glutamic acid G8415 10 mg Autosampler vial

l-Glutamine G8540 10 mg Autosampler vial

l-Glutathione, reduced G4251 10 mg Autosampler vial

Glycine G7126 10 mg Autosampler vial

Histamine dihydrochloride H7250 10 mg Autosampler vial

l-Histidine H6034 10 mg Autosampler vial

l-Histidinol dihydrochloride H6647 10 mg Autosampler vial

Metabolite Cat. No. Packaging

dl-Homocysteine H4628 10 mg Autosampler vial

dl-Homocystine H0501 10 mg Autosampler vial

Homogentisic acid H0751 10 mg Autosampler vial

l-Homoserine H6515 10 mg Autosampler vial

cis-4-Hydroxy-d-proline H5877 10 mg Autosampler vial

trans-4-Hydroxy-l-proline H5534 10 mg Autosampler vial

Hypotaurine H1384 10 mg Autosampler vial

l-Isoleucine I7403 10 mg Autosampler vial

α-Keto-γ-(methylthio)butyric acid sodium salt

K6000 10 mg Autosampler vial

l-Leucine L8912 10 mg Autosampler vial

Lithium carbamoylphosphate dibasic

C5625 10 mg Autosampler vial

l-Lysine L5501 10 mg Autosampler vial

l-Methionine M5308 10 mg Autosampler vial

l-Methionine sulfoxide M1126 10 mg Autosampler vial

l-Ornithine monohydrochloride O2375 10 mg Autosampler vial

l-Phenylalanine P5482 10 mg Autosampler vial

Phosphocholine chloride calcium salt tetrahydrate

P0378 10 mg Autosampler vial

Phosphocreatine disodium salt hydrate enzymatic

P7936 10 mg Autosampler vial

O-Phospho-l-serine P0878 10 mg Autosampler vial

Prephenic acid barium salt P2384 10 mg Autosampler vial

l-Proline P0380 10 mg Autosampler vial

Sarcosine S7672 10 mg Autosampler vial

l-Serine S4500 10 mg Autosampler vial

Shikimic acid S5375 10 mg Autosampler vial

Sodium 2-oxobutyrate K0875 10 mg Autosampler vial

Sodium phenylpyruvate P8001 10 mg Autosampler vial

O-Succinyl-l-homoserine S7129 25 mg

Taurine T0625 10 mg Autosampler vial

l-Threonine T8441 10 mg Autosampler vial

N,N,N-Trimethyllysine T1660 25 mg

Tryptamine T2891 10 mg Autosampler vial

l-Tryptophan T8941 10 mg Autosampler vial

Tyramine hydrochloride T2879 10 mg Autosampler vial

l-Tyrosine T8566 10 mg Autosampler vial

l-Valine V0513 10 mg Autosampler vial

14 Order: sigma.com/order Technical service: sigma.com/techinfosigma.com/lifescience

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Carbohydrate Metabolite Library

Metabolite Cat. No. Packaging

N-Acetyl-d-galactosamine A2795 10 mg Autosampler vial

N-Acetyl-d-glucosamine A8625 10 mg Autosampler vial

N-Acetyl-d-lactosamine A7791 10 mg Autosampler vial

N-Acetyl-d-mannosamine A8176 10 mg Autosampler vial

N-Acetylneuraminic acid A2388 10 mg

Adenosine-5’-diphosphoglucose disodium salt

A0627 10 mg Autosampler vial

Adonitol A5502 10 mg Autosampler vial

d-Allose A6390 10 mg Autosampler vial

l-(+)-Arabinose A3256 10 mg Autosampler vial

l-(–)-Arabitol A3506 10 mg Autosampler vial

l-Ascorbic acid A5960 10 mg Autosampler vial

d-(+)-Cellobiose C7252 10 mg Autosampler vial

2-Deoxy-d-glucose D8375 10 mg Autosampler vial

6-Deoxy-d-glucose D9761 10 mg Autosampler vial

2-Deoxy-d-ribose D5899 10 mg Autosampler vial

2-Deoxyribose 5-phosphate sodium salt

D3126 25 mg

Dihydroxyacetone phosphate dilithium salt

D7137 10 mg Autosampler vial

2,3-Diphospho-d-glyceric acid pentasodium salt

D5764 25 mg

Dulcitol D0256 10 mg Autosampler vial

d-Erythrose 4-phosphate sodium salt

E0377 10 mg Autosampler vial

d-(–)-Fructose F0127 10 mg Autosampler vial

d-Fructose 1,6-bisphosphate trisodium salt

F6803 10 mg Autosampler vial

d-Fructose 1-phosphate sodium salt

F1127 10 mg Autosampler vial

d-Fructose 6-phosphate disodium salt dihydrate

F3627 10 mg Autosampler vial

l-(–)-Fucose F2252 10 mg Autosampler vial

α-d-Galactosamine 1-phosphate G5134 25 mg

d-(+)-Galactosamine hydrochloride

G0500 10 mg Autosampler vial

d-(+)-Galactose G0750 10 mg Autosampler vial

α-d-Galactose 1-phosphate dipotassium salt pentahydrate

G0380 10 mg Autosampler vial

d-Gluconic acid sodium salt G9005 10 mg Autosampler vial

d-Glucosamine 6-phosphate G5509 10 mg Autosampler vial

d-(+)-Glucosamine hydrochloride

G4875 10 mg Autosampler vial

d-(+)-Glucose G7528 10 mg Autosampler vial

α-d-Glucose 1-phosphate disodium salt hydrate

G7018 10 mg Autosampler vial

d-Glucose 6-phosphate disodium salt hydrate

G7250 10 mg Autosampler vial

Metabolite Cat. No. Packaging

d-Glucuronic acid G5269 10 mg Autosampler vial

Guanosine 5’-diphosphoglucose sodium salt

G7502 10 mg Autosampler vial

myo-Inositol I5125 10 mg Autosampler vial

Isomaltose I7253 100 mg

d-Lactose monohydrate L8783 10 mg Autosampler vial

d-(–)-Lyxose 220477 1 G

d-(+)-Maltose monohydrate M9171 10 mg Autosampler vial

d-Mannitol M4125 10 mg Autosampler vial

d-Mannosamine hydrochloride M4670 10 mg Autosampler vial

d-(+)-Mannose M4319 5 G

d-Mannose 6-phosphate disodium salt hydrate

M6876 10 mg Autosampler vial

Melibiose M5500 10 mg Autosampler vial

Palatinose P2007 10 mg Autosampler vial

Phospho(enol)pyruvic acid monopotassium salt

P7127 100 mg

6-Phosphogluconic acid trisodium salt

P6888 10 mg Autosampler vial

d-(–)-3-Phosphoglyceric acid disodium salt

P8877 10 mg Autosampler vial

d-Psicose P8043 10 mg Autosampler vial

d-(+)-Raffinose pentahydrate R0514 10 mg Autosampler vial

l-Rhamnose monohydrate R3875 10 mg Autosampler vial

d-(–)-Ribose R7500 10 mg Autosampler vial

d-Ribose 5-phosphate disodium salt hydrate

R7750 10 mg Autosampler vial

d-Ribulose 1,5-bisphosphate sodium salt hydrate

R0878 10 mg Autosampler vial

d-Ribulose 5-phosphate sodium salt

R9875 5 mg

Sodium pyruvate P2256 10 mg Autosampler vial

d-Sorbitol S1876 10 mg Autosampler vial

Stachyose hydrate from Stachys tuberifera

S4001 10 mg Autosampler vial

Sucrose S9378 10 mg Autosampler vial

d-(–)-Tagatose T2751 10 mg Autosampler vial

Trehalose 6-phosphate dipotassium salt

T4272 10 mg

d-(+)-Trehalose dihydrate T9531 10 mg Autosampler vial

Uridine 5’-diphosphogalactose disodium salt

U4500 10 mg

Uridine 5’-diphosphoglucose disodium salt

U4625 10 mg Autosampler vial

Uridine 5’-diphosphoglucuronic acid trisodium salt

U6751 25 mg

Xylitol X3375 10 mg Autosampler vial

d-(+)-Xylose X1500 10 mg Autosampler vial

d-Xylulose X4625 25 mg

Our Innovation, Your Research — Shaping the Future of Life Science 15

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Lipid Metabolite Library

Metabolite Cat. No. Packaging

Acetoacetyl coenzyme A sodium salt hydrate

A1625-10MG 10 mg

Acetone 154598-IL 1 L

O-Acetyl-l-carnitine hydrochloride

A6706-10MG 10 mg Autosampler vial

Acetyl coenzyme A sodium salt A2056-10MG 10 mg

Acetyl coenzyme A trilithium salt A2181-10MG 10 mg

Acetylcholine chloride A6625-10MG 10 mg Autosampler vial

Arachidonic acid from porcine liver A9673-10MG 10 mg

Arachidonoyl coenzyme A lithium salt

A5837-10MG 10 mg

Benzoyl coenzyme A lithium salt B1638-5MG 5 mg

2-Butenoyl Coenzyme A lithium salt

C6146-10MG 10 mg

Butyryl coenzyme A dilithium salt hydrate

B1508-10MG 10 mg

Cardiolipin solution bovine heart C1649-10MG 10 mg

Choline chloride C7017-10MG 10 mg Autosampler vial

Coenzyme A hydrate from yeast C4282-10MG 10 mg

Coenzyme A sodium salt hydrate from yeast

C3144-10MG 10 mg

Coenzyme A trilithium salt from yeast

C3019-10MG 10 mg

Cytidine 5’-diphosphocholine sodium salt dihydrate

C0256-10MG 10 mg

Cytidine 5’-diphosphoethanolamine sodium salt

C0456-10MG 10 mg

Decanoyl coenzyme A monohydrate

D5269-5MG 5 mg

3’-Dephosphocoenzyme A D3385-5MG 5 mg

Desmosterol D6513-10MG 10 mg

dl-erythro-Dihydrosphingosine D6908-10MG 10 mg

γ,γ-Dimethylallyl pyrophosphate ammonium salt

D4287-1VL 1VL (200 μg)

Ethanolamine E9508-10UL 10 μL

Farnesyl pyrophosphate ammonium salt

F6892-1VL 1VL (200 μg)

Geranyl pyrophosphate ammonium salt

G6772-1VL 1VL (200 μg)

Geranylgeranyl pyrophosphate ammonium salt

G6025-1VL 1VL (200 μg)

Glycerol G7757-500ML 500 mL

rac-Glycerol 3-phosphate disodium salt hexahydrate

G2138-10MG 10 mg Autosampler vial

Glycolaldehyde dimer G6805-1G 1 g

Glycolic acid G8284-10MG 10 mg Autosampler vial

Glyoxylic acid solution G1134-20UL 20 μL

n-Heptadecanoyl coenzyme A lithium salt

H1385-5MG 5 mg

Hexanoyl coenzyme A trilithium salt trihydrate

H2012-10MG 10 mg

dl-3-Hydroxy-3-methylglutaryl coenzyme A sodium salt

H6132-10MG 10 mg

γ-Hydroxybutyric acid sodium salt H3635-10MG 10 G

dl-β-Hydroxybutyryl coenzyme A lithium salt

H0261-10MG 10 mg

Metabolite Cat. No. Packaging

Isobutyryl coenzyme A lithium salt I0383-10MG 10 mg

Isopentenyl pyrophosphate ammonium salt solution

I0503-1VL 1VL (200 μg)

Isovaleryl coenzyme A lithium salt I9381-10MG 10 mg

Lanosterol from sheep wool L5768-5MG 5 mg

Lauroyl coenzyme A lithium salt L2659-5MG 5 mg

Leukotriene B4 L0517-50UG 50 μg

Linoleic acid L1376-10MG 10 mg Autosampler vial

γ-Linolenic acid L2378-10MG 10 mg Autosampler vial

Linoleoyl coenzyme A lithium salt L9754-10MG 10 mg

Lithium acetoacetate A8509-10MG 10 mg Autosampler vial

l-α-Lysophosphatidylcholine from bovine brain

L1381-5MG 5 mg

Malonyl coenzyme A lithium salt M4263-10MG 10 mg Autosampler vial

β-Methylcrotonyl coenzyme A lithium salt

M3013-10MG 10 mg

Methylmalonyl coenzyme A tetralithium salt hexahydrate

M1762-5MG 5 mg

(±)-Mevalonolactone M4667-1G 1 G

myo-Inositol I5125-10MG 10 mg Autosampler vial

Myristoyl coenzyme A lithium salt M4414-5MG 5 mg

Octanoyl coenzyme A lithium salt monohydrate

O6877-10MG 10 mg

Oleoyl coenzyme A lithium salt O1012-10MG 10 mg

Oxalic acid dihydrate O0376-10MG 10 mg Autosampler vial

Palmitoleoyl coenzyme A lithium salt

P6775-10MG 10 mg

Palmitoyl coenzyme A lithium salt P9716-10MG 10 mg

3-sn-Phosphatidic acid sodium salt egg yolk lecithin

P9511-10MG 10 mg

l-α-Phosphatidylcholine P3841-10MG 25 mg

l-α-Phosphatidyl-dl-glycerol sodium salt

P8318-10MG 10 mg Autosampler vial

3-sn-Phosphatidylethanolamine from bovine brain

P7693-5MG 5 mg

l-α-Phosphatidylinositol ammonium salt solution

P2517-10MG 10 mg

3-sn-Phosphatidyl-l-serine sodium salt bovine brain

P5660-5MG 5 mg

Phosphocholine chloride calcium salt tetrahydrate

P0378-10MG 10 mg Autosampler vial

O-Phosphorylethanolamine P0503-10MG 10 mg Autosampler vial

5-Pregnen-3β-ol-20-one P9129-10MG 10 mg Autosampler vial

Progesterone P0130-25G 25 G

n-Propionyl coenzyme A lithium salt

P5397-10MG 10 mg

Prostaglandin E2 P5640-10MG 10 mg

Psychosine from bovine brain P9256-10MG 10 mg

Sphingomyelin from bovine brain S7004-10MG 10 mg

Squalene S3626-10ML 10 mg

Stearoyl coenzyme A lithium sal S0802-10MG 10 mg

Succinyl coenzyme A sodium salt S1129-5MG 5 mg

Thromboxane B2 T0516-1MG 1 mg

16 Order: sigma.com/order Technical service: sigma.com/techinfosigma.com/lifescience

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New Metabolites From Sigma-Aldrich®

2-Phosphoglyceric acid is a key metabolite in glycolysis/gluconeogenesis and also substrate for a number of important enzymes like enolase and phosphoglycerate mutase. As the stereochemistry of metabolites is important for structural and functional studies, we have made the two enantiomerically pure forms of d- and l-2-Phosphoglyceric acid available. d-2-Phosphoglycerate has been used in research on the structure and catalytic properties of enolase1-4 and phosphoglyceratemutase.5-6

Mevalonolactone and its open form, Mevalonic acid, have played an important role as a growth factor and as a key precursor in biosynthetic pathways to many natural products.7 The absolute configuration has been established by synthesis from quinic acid8 and the stereochemistry of the enzyme-catalyzed reactions makes use of only one enantiomer.9

Dehydroquinic acid is another important metabolite in the pathway to aromatic amino acids and substrate for dehydroquinase.

References:1. P.A. Sims, A.L. Menefee, T.M. Larsen, S.O. Mansoorabadi, G.H. Reed, Structure and

Catalytic Properties of an Engineered Heterodimer of Enolase Composed of One Active and One Inactive Subunit, J. Mol. Biol., 355, 422-431 (2006).

2. P.A. Sims, T.M. Larsen, R.R. Poyner, W.W. Cleland, G.H. Reed, Reverse Protonation is the Key to General Acid-Base Catalysis in Enolase, Biochemistry, 42, 8298-8306 (2003).

3. H. Liu, Y. Zhang, W. Yang, How is the active site of enolase organized to catalyze two different reaction steps, J. Am. Chem. Soc., 122, 6560-6570 (2000).

4. R.R. Poyner, L.T. Laughlin, G.A. Sowa, G.H. Reed, Toward identification of acid/base catalysts in the active site of enolase: Comparison of the properties of K345A, E168Q and E211Q variants, Biochemistry, 35, 1692-1699 (1996).

5. K. Watabe, E. Freese, Purification and properties of the manganse-dependent phosphoglycerate mutase of Bacillus subtilis, J. Bacteriology, 137, 773-778 (1979).

6. M.J. Jedrzejas, M. Chander, P. Setlow, G. Krishnamurthy, Mechanism of catalysis of the cofactor-independent phosphoglycerate mutase from Bacillus stearothermophilus. Crystal structure of the complex with 2-phosphoglycerate, J. Biol. Chem., 275, 23146-23153 (2000).

7. R.H. Cornforth, J.W. Cornforth, G. Popjak, Preparation of R-and S-Mevalonolactones, Tetrahedron, 18, 1351-1354 (1962).

8. M. Eberle, D. Arigoni, Helv. Chim. Acta, 43, 1508 (1960).9. R.H. Cornforth, K. Fletcher, H. Hellig, G. Popjak, Stereospecificity of Enzymic

Reactions involving Mevalonic Acid, Nature, 185, 923-924 (1960).

L-2-Phos pho gly ceric acid disodium salt hydrate 8

Disodium l-2-phos pho gly cer ate; l-Gly cer ate 2-phos phate disodium salt [23295-92-3] C3H5Na2O7P · xH2O FW 230.02 (Anh) HO ONa

O

OPO

OHONa

HO

H

19710

5-Dehydro quin ic acid potassium salt 8

3-Dehydro quin ic acid potassium salt; (1R,3R,4S)-1,3,4-Tri hydroxy-5-oxo cyclo hexane carboxy lic acid potassium salt [494211-79-9] C7H9KO6 FW 228.24

HO

OH

HO

OO

OK

40216

(R)-(−)-Mevalono lactone 8

(R)-Mevalo lactone; (R)-3-Hydroxy-3-methyl-δ-valero-lactone; d-Mevalonic acid lactone [19115-49-2] MDL MFCD01074894 C6H10O3 FW 130.14 O O

OHH3C

68519

D-Fructose-1,2-cyclic-6-dis phos phate 8

[141875-43-6] C6H12O11P2 FW 322.10

OH

HOO

OPHO

OH

O

OPO OH

O

68872

D(+)2-Phos pho gly ceric acid sodium salt hydrate

d-Gly cer ate 2-phos phate sodium salt; Sodium D-2-phos pho gly cer ate hydrate

[70195-25-4] MDL MFCD00150613

C3H7O7P · H2O FW 252.00 (Anh)

P OO

O

OH

Na+

Na+

OO

• H2O

O

79470-50MG 50 mg

79470-250MG 250 mg

79470-1G 1 g

D-2-Phos pho gly ceric acid barium salt hydrate

2-PG-Ba; d-Gly cer ate 2-phos phate barium salt; Barium d-2-phos pho gly cer ate hydrate

MDL MFCD00150503 C3H5BaO7P · xH2O

FW 321.37 (Anh) P

HO

-O

O

O-

O

OH

O

Ba2+

Substrate for the assay of 3-phosphoglyceric acid mutase1; and enolase2

Lit cited: 1. P. Oesper, Meth. Enzymol. 1, 423 (1955); 2. T. Bücher, Meth. Enzymol. 427

79480

Our Innovation, Your Research — Shaping the Future of Life Science 17

Stable Iso

top

e Labeled

Metab

olites

Stable Isotope Labeled Metabolites• ISOTEC® Stable Isotopes

• Amino acids, glucose and lipids labeled with 13C, 15N, D

• Uniformly labeled and site specific labeling available

• S&P tested material available

Selected Products with 13C, 15N, D

Cat. No. Description Isotopic Purity

608025 l-Alanine-1-13C,15N 99 atom % 13C; 98 atom % 15N

643440 l-Arginine-13C6 HCl 98 atom % 15N; 98 atom % 13C

660795 l-Arginine-15N2 HCl (Guanidineimino-15N2), S&P tested

98 atom % 15N

608033 l-Arginine-13C6,15N4 HCI 98 atom % 13C; 98 atom % 15N

660655 d-Glucose-1-13C, S&P tested 99 atom % 13C

661422 d-Glucose-1,2-13C2, S&P tested 99 atom % 13C

660663 d-Glucose-13C6, S&P tested 99 atom % 13C

661414 d-Glucose-6,6-D2, S&P tested 98 atom % D

660728 Glycine-1-13C, S&P tested 99 atom % 13C

661554 l-Leucine-5,5,5-D3, S&P tested 98 atom % D

661538 l-Leucine-1- 13C, S&P tested 99 atom % 13C

604909 l-Leucine-1,2-13C2, S&P tested 99 atom % 13C

608068 l-Leucine-13C6,15N 98 atom % 13C; 98 atom % 15N

616192 l-Lysine-4,4,5,5-D4 HCl 98 atom % D

643459 l-Lysine -13C6, HCl 98 atom % 13C

608041 l-Lysine -13C6,15N2 HCl 98 atom % 13C; 98 atom % 15N

299154 l-Methionine -13C,D3 (methyl-13C,D3) 99 atom % 13C; 98 atom % D

661600 l-Phenylalanine-1-13C, S&P Tested 99 atom % 13C

660884 l-Phenyl-13C6-Alanine, S&P Tested 99 atom % 13C

660892 l-Phenylalanine-15N, S&P Tested 98 atom % 15N

660752 l-Tyrosine-13C6, (phenyl-13C6) 99 atom % 13C

486027 l-Valine-2,3,4,4,4,5,5,5-D8 98 atom % D

For an extensive listing of isotopically-labeled products including amino acids, fatty acids and carbohydrates labeled with 13C, 15N and/or D visit sigma-aldrich.com/isotec

[13C]-acetyl-CoA

[13C]-citrate

[13C]-isocitrate

[13C]-a-ketoglutarate

[13C]-glutamate

[13C]-succinate[13C]-fumarate

[13C]-malate

[13C]-oxalacetate13C in the

Krebs cycle

Labeled d-Glucose for Metabolic Research Glucose metabolic research continues to grow and Sigma-Aldrich® is committed to meeting the increasing demand. For research programs ranging from brain chemistry to diabetes to childhood obesity, we produce d-Glucose with a variety of isotopic labeling patterns.

18 Order: sigma.com/order Technical service: sigma.com/techinfosigma.com/lifescience

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sigma-aldrich.com

Need more information? Please contact Isotec Customer Service:

Telephone: 937-859-1808

Email: isosales@sial.com

Fatty acids are an important energy source in the heart, muscle and liver. Elucidating the metabolic pathways that release this energy continues to be an intense area of research. Fatty acids labeled with 13C and D are used by scientists to explore the transport and oxidation of fatty acids and determine their metabolic fate. The effects of system stresses that mimic diseased states on fatty acid metabolism are also accessible with labeled substrates.

ISOTEC® provides a wide range of labeled compounds for lipid research• Exclusive producer of Acyl 13C Coenzyme A derivatives

• Fatty acids of various chain lengths (including palmitic and oleic acids)

• Triglycerides

• Glycerol

• Coenzyme A, Li Salts

Still can’t find what you are looking for?Our Expert Custom Synthesis Team will help you design your molecule.

• Isotec has the most experienced group of stable isotope scientists

• Our impressive group of Ph.D.s routinely engage in complex multi-step reactions

Cat. No. Description

658650 Acetyl-1,2-13C2 Coenzyme A, Li salt

655759 Malonyl-13C3 Coenzyme A, Li salt

658200 Palmitoyl-1-13C Coenzyme A, Li salt

655716 Palmitoyl-13C16 Coenzyme A, Li salt

675776 Stearoyl-13C18 Coenzyme A, Li salt

675768 Oleoyl-13C18 Coenzyme A, Li salt

Labeled Compounds for Lipid Metabolism Research

Sigma-Aldrich® New Lab Start-Up Program

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Our Innovation, Your Research — Shaping the Future of Life Science 19

Stable Iso

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Other Stable Isotope Labeled Metabolites

Name Cat. No.

Acetaldehyde-2,2,2-d3 487767-1G

Acetaldehyde-d4 176567-1G176567-5G

Acetaldehyde-1-13C 603805

Acetaldehyde-13C2 531227-1G

Acetyl-1,2-13C2-coenzyme A lithium salt 658650

Citric acid-2,2,4,4-d4 485438-1G

Citric acid-1,5-13C2 488607-100MG

Citric acid-2,4-13C2 492078-100MG

Citric acid-13C6 606081-100MG

Ethanol-1-13C 324523-250MG324523-1G

Ethanol-2-13C 427047-1G

Ethanol-13C2 427039-250MG427039-1G

Fumaric acid-2,3-d2 486671-5G

Fumaric acid-d4 485713

Fumaric acid-2,3-13C2 606073

Fumaric acid-13C4 606014

Fumaric acid-13C4,d4 608475

d-Glucose-d12 616338-250MG

d-Glucose-1-d 310816-250MG310816-1G

d-Glucose-2-d1 310824-1G

d-Glucose-3-d1 615498

d-Glucose-6,6-d2 282650-100MG282650-500MG282650-1G

d-Glucose-1-13C 297046-250MG297046-1G297046-10G

d-Glucose-2-13C 310794-250MG310794-1G

d-Glucose-3-13C 605409

d-Glucose-4-13C 668648

d-Glucose-4,5-13C2 605468

d-Glucose-6-13C 310808-100MG310808-500MG

d-Glucose-1,2-13C2 453188-100MG453188-500MG

Name Cat. No.

d-Glucose-1,6-13C2 453196-100MG453196-250MG

d-Glucose-2,5-13C2 605506

d-Glucose-13C6 389374-100MG389374-250MG389374-1G389374-2G389374-3G389374-10G389374-25G

d-Glucose-13C6,1,2,3,4,5,6,6-d7 552151-500MG552151-1G552151-5G

2-Ketopentanedioic acid-d6 615390

l-Lactic acid-1-13C solution 606057

l-Lactic acid-3,3,3-d3 solution 616567

DL-Malic acid-2,3,3-d3 641049

dl-Malic acid-2-13C 603899

Phospho(enol)pyruvic acid-3-13C potassium salt 571237

Pyruvic-1-13C acid (free acid) 677175

Sodium l-lactate-2-d1 solution 589217

Sodium l-lactate-3,3,3-d3 solution 616702-1G

Sodium l-lactate-1-13C solution 606022-1G

Sodium l-lactate-2-13C solution 589209

Sodium l-lactate-2,3-13C solution 606006

Sodium l-lactate-3-13C solution 490040-250MG

Sodium l-lactate-13C3 solution 660817

Sodium pyruvate-1-13C 490709-250MG

Sodium pyruvate-2-13C 490725-500MG

Sodium pyruvate-3-13C 490733-250MG

Sodium pyruvate-3-13C, 3,3,3-d3 608483

Sodium pyruvate-1,2-13C2 493392-500MG

Sodium pyruvate-2,3-13C2 486191-500MG

Sodium pyruvate-13C3 490717-500MG

Succinic acid-2,2,3,3-d4 293075-1G293075-5G

Succinic acid-d6 488356-5G

Succinic acid-1,2-13C2 491977

Succinic acid-1,4-13C2 485349-500MG

Succinic acid-2,3-13C2 488364-100MG

20 Order: sigma.com/order Technical service: sigma.com/techinfosigma.com/lifescience

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Metabolite Chromatographic AnalysisAscentis® Express HILIC from Supelco®

Ascentis Express columns provide a breakthrough in HPLC column performance.

The complex nature of metabolomic analysis requires superior separation capabilities. The Ascentis Express columns, based on Fused-Core™ technology offer highly efficient separations without the high backpressure associated with sub-2 µm particles. Due to the high efficiencies at low backpressures, Ascentis Express can benefit both conventional HPLC users as well as UPLC® or other ultra pressure system users.

Ascentis Express Extreme Performance benefits include:

� Double the efficiencies of conventional 3 µm particles

� Equal efficiencies of sub-2 µm columns at half of the backpressure

� Rugged design capable of high pressure operation

2520151050

Length 15 cmDiameter 0.46 cmParticle Size 2.7 µmMobile Phase A Water/Acetonitrile (10:90 v/v); 13m M Ammonium Acetate Mobile Phase B Water; 13mM Ammonium AcetateGradient 0-0B (1 min); 0-90B (19 min)Flow Rate 1 mL/minTemperature 35 °CDetector MS TIC (m/z from 50 to 500)

Retention Time (min)

Tryptamine

Tyramine

Tryptophan

Methionine

β-Alanine

Alanine

Ascentis Express HILIC

Analysis of an amino acid mixture on Ascentis Express HILIC Phase with mass spectrometric detection.

Ascentis® Express HILIC HPLC Column 8

Ascentis Express HPLC columns, through the use of Fused-Core particle technology, can provide you with both the high speed and high efficiencies of sub-2 µm particles while maintaining lower backpressures. The combination of high efficiency and low backpressure benefits UPLC (or other ultra high pressure system) users, as well as conventional HPLC users.

Visit the Ascentis Express home page for more information on this new column technology.

particle size 2.7 μm, L 10 cm × I.D. 2.1 mm53939-U 1 pkg

particle size 2.7 μm, L 15 cm × I.D. 4.6 mm53981-U 1 pkg

For more information about Ascentis Express, visit sigma-aldrich.com/express

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Our Innovation, Your Research — Shaping the Future of Life Science

Where Chemistry Meets Biology

Our Innovation, Your Research — Shaping the Future of Life Science 21

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CHROMASOLV® SolventsThe CHROMASOLV family of submicron filtered solvents from Sigma-Aldrich® delivers superior purity, stability and lot-to-lot consistency making them ideal for a variety of analytical and preparative separations utilizing LC-MS, HPLC and Spectrophometric analysis.

CHROMASOLV LC-MSThese LC-MS solvents are designed specifically with low content of alkaline impurities, such as calcium, magnesium, potassium, and sodium, which can interfere in the analysis by forming adducts with the analytes. CHROMASOLV LC-MS solvents are also run through specific UV-spectroscopic quality control tests and LC-MS suitability evaluation to guarantee usability.

CHROMASOLV LC-MS Solvents Cat. No.

2-Propanol, ≥99.9% 34965

Acetonitrile, ≥99.9% 34967

Ethyl acetate, ≥99.7% 34972

Heptane, ≥99% 34999

Hexane, ≥97% 34986

Methanol, ≥99.9% 34966

Water 39253

CHROMASOLV LC-MS BlendsLC-MS allows the detection and quantification of many analytes. The minimization of artifacts requires very well specified solvents spiked with ultra pure salts and acids. These additives are used to improve the chromatographic peak shape and to optimize ionization in the MS interface.

CHROMASOLV LC-MS Solvent Blends Cat. No.

Acetonitrile with 0.1% acetic acid 34678

Acetonitrile with 0.1% ammonium acetate 34669

Acetonitrile with 0.1% formic acid 34668

Acetonitrile with 0.1% formic acid and 0.01% trifluoroacetic acid 34676

Acetonitrile with 0.1% trifluoroacetic acid 34976

Methanol with 0.1% acetic acid 34672

Methanol with 0.1% ammonium acetate 34670

Methanol with 0.1% formic acid 34671

Methanol with 0.1% trifluoroacetic acid 34974

Water with 0.1% acetic acid 34675

Water with 0.1% ammonium acetate 34674

Water with 0.1% formic acid 34673

Water with 0.1% formic acid and 0.01% trifluoroacetic acid 34677

Water with 0.1% trifluoroacetic acid 34978

Rinsing agent for LC-MS 34689

CHROMASOLV PlusManufactured to go beyond our CHROMASOLV for HPLC to be your high-purity, multipurpose solvent. Tested to meet the most demanding HPLC requirements as well as spectrophotometry, residual analysis and LC-MS applications.

CHROMASOLV Plus Solvents Cat. No.

Acetone, ≥99.9% 650501

Acetonitrile, ≥99.9% 34998

Benzene, ≥99.9% 270709

1-Butanol, ≥99.7% 34867

Butyl acetate, 99.7% 270687

tert-Butyl methyl ether, 99.9% 650560

Chloroform, ≥99.9%, contains amylenes as stabilizer 650498

Chloroform, ≥99.9%, contains 0.5-1.0% ethanol as stabilizer 650471

Cyclohexane, ≥99.9% 650455

Dichloromethane, ≥99.9%, contains 50-150 ppm amylene as stabilizer

650463

N,N-Dimethylacetamide, ≥99.9% 270555

N,N-Dimethylformamide, ≥99.9% 270547

Dimethyl sulfoxide, ≥99.7% 34869

1,4-Dioxane, ≥99.5% 34857

Ethyl acetate, 99.9% 650528

Heptane, 99% 650536

Hexane, ≥95% 650552

Hexane, mixture of isomers, ≥98.5% 650544

Methanol, ≥99.9% 646377

1-Methyl-2-pyrrolidinone, ≥99% 270458

2-Propanol, 99.9% 650447

Pyridine, ≥99.9% 270407

Tetrahydrofuran, ≥99.9%, inhibitor-free 34865

Toluene, ≥99.9% 650579

2,2,4-Trimethylpentane, ≥99.5% 650439

Water 34877

o-Xylene, 98% 295884

22 Order: sigma.com/order Technical service: sigma.com/techinfosigma.com/lifescience

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CHROMASOLV HPLCDesigned for use with HPLC instrumentation and organic synthesis applications. CHROMASOLV HPLC solvents are glass distilled; submicron filtered and undergoes rigorous specification testing to provide you with lot-to-lot consistency.

CHROMASOLV HPLC Solvents Cat. No.

Acetone, ≥99.9% 270725

Acetonitrile, gradient, ≥99.9% 34851

Benzonitrile, 99.9% 270318

tert-Butanol, ≥99.5% 308250

2-Butanone, ≥99.7% 34861

tert-Butyl methyl ether, ≥99.8% 34875

Carbon disulfide, ≥99.9% 270660

Carbon tetrachloride, ≥99.9% 270652

Chlorobenzene, 99.9% 270644

1-Chlorobutane, ≥99.8% 34958

Chloroform, ≥99.8%, contains amylenes as stabilizer 34854

Chloroform, ≥99.8%, contains 0.5-1.0% ethanol as stabilizer 366927

Cyclohexane, ≥99.7% 34855

Cyclopentane, ≥75% cyclopentane basis 270601

1,2-Dichlorobenzene, 99% 270598

Dichloromethane, ≥99.8%, contains amylene as stabilizer 34856

Diethylene glycol diethyl ether, ≥99% 308277

Diethyl ether, ≥99.9%, inhibitor-free 309966

1,2-Dimethoxyethane, 99.9% 307432

Ethanol, denatured 270741

Ethyl acetate, ≥99.7% 34858

Heptane, ≥96% 592579

Heptane, ≥99% 34873

Hexane, ≥95% 270504

CHROMASOLV HPLC Solvents Cat. No.

Hexane, ≥97% 34859

Hexane, mixture of isomers, ≥98.5% 293253

Methanol, gradient, ≥99.9% 34885

Methanol, ≥99.9% 34860

2-Methoxyethanol, ≥99.9% 270482

2-Methoxyethyl acetate, ≥99% 308269

2-Methylbutane, ≥99.5% 270342

4-Methyl-2-pentanone, ≥99.5% 293261

2-Methyl-1-propanol, 99.5% 270466

Nitromethane, ≥96% 270423

1-Octanol, ≥99% 293245

Pentane, ≥99% 34956

2-Pentanone, 99.5% 471194

3-Pentanone, 96% 270334

1-Propanol, ≥99.9% 34871

2-Propanol, ≥99.8% 34863

Propylene carbonate, 99.7% 414220

Tetrachloroethylene, ≥99.9% 270393

1,1,2-Trichloro-1,2,2-trifluoroethane, ≥99.7% 34874

2,2,4-Trimethylpentane, ≥99% 34862

Toluene, 99.9% 34866

Water 270733

p-Xylene, ≥99% 317195

CHROMASOLV HPLC BlendsConvenient and accurate pre-blended solvents for HPLC and LC-MS applications. Eliminates time-consuming mobile phase preparation as well as lost sample information and instrument down-time caused by impure mobile phases. For consistent baselines and minimal background noise, these blends are prepared with ultra pure acids.

CHROMASOLV HPLC Solvent Blends Cat. No.

Acetonitrile with 0.1% acetic acid 590754

Acetonitrile with 0.1% ammonium hydroxide 639133

Acetonitrile with 0.1% formic acid 576956

Acetonitrile with 0.035% trifluoroacetic acid 565423

Acetonitrile with 0.05% trifluoroacetic acid 574724

Acetonitrile with 0.1% trifluoroacetic acid 574732

CHROMASOLV HPLC Solvent Blends Cat. No.

Methanol with 0.1% formic acid 632546

Water with 0.1% ammonium hydroxide 639141

Water with 0.1% formic acid 576913

Water with 0.05% trifluoroacetic acid 590142

Water with 0.1% trifluoroacetic acid 576905

Sigma-Aldrich®

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©2008 Sigma-Aldrich Co. All rights reserved. SIGMA, , SAFC, , SIGMA-ALDRICH, ALDRICH, , FLUKA, , and SUPELCO, are trademarks belonging to Sigma-Aldrich Co. and its affiliate Sigma-Aldrich Biotechnology, L.P. Sigma brand products are sold through Sigma-Aldrich, Inc. Sigma-Aldrich, Inc. warrants that its products conform to the information contained in this and other Sigma-Aldrich publications. Purchaser must determine the suitability of the product(s) for their particular use. Additional terms and conditions may apply. Please see reverse side of the invoice or packing slip. Fused-Core is a trademark of Advanced Materials Technology, Inc. TWEEN is a registered trademark of Croda International PLC. Eppendorf is a registered trademark of Eppendorf-Netheler-Hinz GmbH. Sepharose is a registered trademark of GE Healthcare. Coomassie is a registered trademark of Imperial Chemical Industries Ltd. LOPAC, Prestige Antibodies, and ProteoSilver are trademarks of Sigma-Aldrich Biotechnology LP and Sigma-Aldrich Co. Ascentis, CHROMASOLV, ISOTEC, MISSION, Stemline, and TraceSELECT are registered trademarks of Sigma-Aldrich Biotechnology LP and Sigma-Aldrich Co. UPLC is a registered trademark of Waters Corp.

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