Figure 1: Dendrimer and dendron

Figure 2: Crystal structure of a first-generation polyphenylene dendrimerreported by Müllen et al.[5]

DendrimerFrom Wikipedia, the free encyclopedia

Dendrimers [1] are repetitively branched molecules.[2][3] The name comesfrom the Greek word δένδρον (dendron), which translates to "tree".Synonymous terms for dendrimer include arborols and cascade molecules.However, dendrimer is currently the internationally accepted term. Adendrimer is typically symmetric around the core, and often adopts a sphericalthree-dimensional morphology. The word dendron is also encounteredfrequently. A dendron usually contains a single chemically addressable groupcalled the focal point. The difference between dendrons and dendrimers isillustrated in figure one, but the terms are typically encounteredinterchangeably.[4]

The first dendrimers were made by divergent synthesis approaches by FritzVögtle in 1978,[6] R.G. Denkewalter at Allied Corporation in 1981,[7][8] DonaldTomalia at Dow Chemical in 1983[9] and in 1985,[10][11] and by GeorgeNewkome in 1985.[12] In 1990 a convergent synthetic approach was introducedby Jean Fréchet.[13] Dendrimer popularity then greatly increased, resulting inmore than 5,000 scientific papers and patents by the year 2005.

Contents

1 Properties2 Synthesis

2.1 Divergent methods2.2 Convergent methods2.3 Click chemistry

3 Applications3.1 Drug delivery3.2 Gene delivery3.3 Sensors3.4 Blood substitution3.5 Nanoparticles

4 See also5 References

Properties

Dendritic molecules are characterized by structural perfection. Dendrimers and dendrons are monodisperse and usuallyhighly symmetric, spherical compounds. The field of dendritic molecules can be roughly divided into low-molecularweight and high-molecular weight species. The first category includes dendrimers and dendrons, and the latter includes

Figure 3: Synthesis to secondgeneration arborol

dendronized polymers, hyperbranched polymers, and the polymer brush.

The properties of dendrimers are dominated by the functional groups on the molecular surface, however, there areexamples of dendrimers with internal functionality.[14][15][16] Dendritic encapsulation of functional molecules allowsfor the isolation of the active site, a structure that mimics that of active sites in biomaterials.[17][18][19] Also, it ispossible to make dendrimers water soluble, unlike most polymers, by functionalizing their outer shell with chargedspecies or other hydrophilic groups. Other controllable properties of dendrimers include toxicity, crystallinity, tecto-dendrimer formation, and chirality.[4]

Dendrimers are also classified by generation, which refers to the number of repeated branching cycles that areperformed during its synthesis. For example if a dendrimer is made by convergent synthesis (see below), and thebranching reactions are performed onto the core molecule three times, the resulting dendrimer is considered a thirdgeneration dendrimer. Each successive generation results in a dendrimer roughly twice the molecular weight of theprevious generation. Higher generation dendrimers also have more exposed functional groups on the surface, whichcan later be used to customize the dendrimer for a given application.[20]

Synthesis

One of the very first dendrimers, the Newkome dendrimer, was synthesized in1985. This macromolecule is also commonly known by the name arborol.Figure 3 outlines the mechanism of the first two generations of arborol througha divergent route (discussed below). The synthesis is started by nucleophilicsubstitution of 1-bromopentane by triethyl sodiomethanetricarboxylate indimethylformamide and benzene. The ester groups were then reduced bylithium aluminium hydride to a triol in a deprotection step. Activation of thechain ends was achieved by converting the alcohol groups to tosylate groupswith tosyl chloride and pyridine. The tosyl group then served as leaving groupsin another reaction with the tricarboxylate, forming generation two. Furtherrepetition of the two steps leads to higher generations of arborol.[12]

Poly(amidoamine), or PAMAM, is perhaps the most well known dendrimer. The core of PAMAM is a diamine(commonly ethylenediamine), which is reacted with methyl acrylate, and then another ethylenediamine to make thegeneration-0 (G-0) PAMAM. Successive reactions create higher generations, which tend to have different properties.Lower generations can be thought of as flexible molecules with no appreciable inner regions, while medium sized (G-3or G-4) do have internal space that is essentially separated from the outer shell of the dendrimer. Very large (G-7 andgreater) dendrimers can be thought of more like solid particles with very dense surfaces due to the structure of theirouter shell. The functional group on the surface of PAMAM dendrimers is ideal for click chemistry, which gives rise tomany potential applications.[21]

Dendrimers can be considered to have three major portions: a core, an inner shell, and an outer shell. Ideally, adendrimer can be synthesized to have different functionality in each of these portions to control properties such assolubility, thermal stability, and attachment of compounds for particular applications. Synthetic processes can alsoprecisely control the size and number of branches on the dendrimer. There are two defined methods of dendrimersynthesis, divergent synthesis and convergent synthesis. However, because the actual reactions consist of many stepsneeded to protect the active site, it is difficult to synthesize dendrimers using either method. This makes dendrimershard to make and very expensive to purchase. At this time, there are only a few companies that sell dendrimers;Polymer Factory Sweden AB[22] commercializes biocompatible bis-MPA dendrimers and Dendritech[23] is the onlykilogram-scale producers of PAMAM dendrimers. NanoSynthons, LLC[24] from Mount Pleasant, Michigan, USAproduces PAMAM dendrimers and other proprietary dendrimers.Weihai CY Dendrimer Technology Co. Ltd.[25] is the

Figure 4: Schematic of divergentsynthesis of dendrimers

Figure 5: Schematic of convergentsynthesis of dendrimers

Figure 6: Dendrimer DA reactionMullen 1996

1st enterprise in Asia with creative & high technologies to research, develop & produce dendrimers & hyperbranchedpolymers. The Dendrimer material has been well used for scientific research in many colleges and universities such asPeking University, Tsinghua University, Chinese Academy of Sciences, and began to be industrialized in China now.

Divergent methods

The dendrimer is assembled from a multifunctional core, which is extendedoutward by a series of reactions, commonly a Michael reaction. Each step ofthe reaction must be driven to full completion to prevent mistakes in thedendrimer, which can cause trailing generations (some branches are shorterthan the others). Such impurities can impact the functionality and symmetry ofthe dendrimer, but are extremely difficult to purify out because the relative sizedifference between perfect and imperfect dendrimers is very small.[20]

Convergent methods

Dendrimers are built from small molecules that end up at the surface of thesphere, and reactions proceed inward building inward and are eventuallyattached to a core. This method makes it much easier to remove impurities andshorter branches along the way, so that the final dendrimer is moremonodisperse. However dendrimers made this way are not as large as thosemade by divergent methods because crowding due to steric effects along thecore is limiting.[20]

Click chemistry

Dendrimers have been prepared via click chemistry, employing Diels-Alderreactions,[26] thiol-yne reactions [27] and azide-alkyne reactions.[28][29][30] Anexample is the synthesis of certain polyphenylene dendrimers can be seen infigure 6.[31]

There are ample avenues that can be opened by exploring this chemistry indendrimer synthesis.

Applications

Applications of dendrimers typically involve conjugating other chemical species to the dendrimer surface that canfunction as detecting agents (such as a dye molecule), affinity ligands, targeting components, radioligands, imagingagents, or pharmaceutically active compounds. Dendrimers have very strong potential for these applications becausetheir structure can lead to multivalent systems. In other words, one dendrimer molecule has hundreds of possible sitesto couple to an active species. Researchers aimed to utilize the hydrophobic environments of the dendritic media toconduct photochemical reactions that generate the products that are synthetically challenged. Carboxylic acid andphenol terminated water soluble dendrimers were synthesized to establish their utility in drug delivery as well asconducting chemical reactions in their interiors.[32] This might allow researchers to attach both targeting molecules anddrug molecules to the same dendrimer, which could reduce negative side effects of medications on healthy cells.[21]

Dendrimers can also be used as a solubilizing agent. Since their introduction in the mid-1980s, this novel class ofdendrimer architecture has been a prime candidate for host-guest chemistry.[33] Dendrimers with hydrophobic core andhydrophilic periphery have shown to exhibit micelle-like behavior and have container properties in solution.[34] The

Figure 7: Schematic of a G-5 PAMAM dendrimer conjugated to botha dye molecule and a strand of DNA.

use of dendrimers as unimolecular micelles was proposed by Newkome in 1985.[35] This analogy highlighted theutility of dendrimers as solubilizing agents.[36] The majority of drugs available in pharmaceutical industry arehydrophobic in nature and this property in particular creates major formulation problems. This drawback of drugs canbe ameliorated by dendrimeric scaffolding, which can be used to encapsulate as well as to solubilize the drugs becauseof the capability of such scaffolds to participate in extensive hydrogen bonding with water.[37][38][39][40][41][42]

Dendrimer labs throughout the planet are persistently trying to manipulate dendrimer’s solubilizing trait, in their wayto explore dendrimer as drug delivery [43][44] and target specific carrier.[45][46][47]

Drug delivery

Approaches for delivering unaltered naturalproducts using polymeric carriers is of widespreadinterest, dendrimers have been explored for theencapsulation of hydrophobic compounds and forthe delivery of anticancer drugs. The physicalcharacteristics of dendrimers, including theirmonodispersity, water solubility, encapsulationability, and large number of functionalizableperipheral groups, make these macromoleculesappropriate candidates for evaluation as drugdelivery vehicles. There are three methods forusing dendrimers in drug delivery: first, the drug iscovalently attached to the periphery of thedendrimer to form dendrimer prodrugs, second thedrug is coordinated to the outer functional groupsvia ionic interactions, or third the dendrimer acts asa unimolecular micelle by encapsulating apharmaceutical through the formation of adendrimer-drug supramolecular assembly.[48][49]

The use of dendrimers as drug carriers byencapsulating hydrophobic drugs is a potentialmethod for delivering highly active pharmaceuticalcompounds that may not be in clinical use due totheir limited water solubility and resultingsuboptimal pharmacokinetics.[50] Dendrimers havebeen widely explored for controlled delivery of antiretroviral bioactives [51] The inherent antiretroviral activity ofdendrimers enhances their efficacy as carriers for antiretroviral drugs [52][53] The dendrimer enhances both the uptakeand retention of compounds within cancer cells, a finding that was not anticipated at the onset of studies. Theencapsulation increases with dendrimer generation and this method may be useful to entrap drugs with a relatively hightherapeutic dose. Studies based on this dendritic polymer also open up new avenues of research into the furtherdevelopment of drug-dendrimer complexes specific for a cancer and/or targeted organ system. These encouragingresults provide further impetus to design, synthesize, and evaluate dendritic polymers for use in basic drug deliverystudies and eventually in the clinic.[48][54]

Gene delivery

The ability to deliver pieces of DNA to the required parts of a cell includes many challenges. Current research is beingperformed to find ways to use dendrimers to traffic genes into cells without damaging or deactivating the DNA. Tomaintain the activity of DNA during dehydration, the dendrimer/DNA complexes were encapsulated in a water soluble

polymer, and then deposited on or sandwiched in functional polymer films with a fast degradation rate to mediate genetransfection. Based on this method, PAMAM dendrimer/DNA complexes were used to encapsulate functionalbiodegradable polymer films for substratemediated gene delivery. Research has shown that the fast degradingfunctional polymer has great potential for localized transfection.[55][56][57]

Sensors

Scientists have also studied dendrimers for use in sensor technologies. Studied systems include proton or pH sensorsusing poly(propylene imine),[58] cadmium-sulfide/polypropylenimine tetrahexacontaamine dendrimer composites todetect fluorescence signal quenching,[59] and poly(propylenamine) first and second generation dendrimers for metalcation photodetection[60] amongst others. Research in this field is vast and ongoing due to the potential for multipledetection and binding sites in dendritic structures.

Blood substitution

Dendrimers are also being investigated for use as blood substitutes. Their steric bulk surrounding a heme-mimeticcentre significantly slows degradation compared to free heme,[61][62] and prevents the cytotoxicity exhibited by freeheme.

Nanoparticles

Dendrimers also are used in the synthesis of monodisperse metallic nanoparticles. Poly(amidoamide), or PAMAM,dendrimers are utilized for their tertiary amine groups at the branching points within the dendrimer. Metal ions areintroduced to an aqueous dendrimer solution and the metal ions form a complex with the lone pair of electrons presentat the tertiary amines. After complexion, the ions are reduced to their zerovalent states to form a nanoparticle that isencapsulated within the dendrimer. These nanoparticles range in width from 1.5 to 10 nanometers and are aptly calledDendrimer-Encapsulated Nanoparticles.[63]

Microencapsulation:- poly(amido)amine (PAMAM)has been utilized to encapsulate self healing agent for smartcoating by microencapsulation route. The idea has the potential to fabricate microcapsules which could provide betteranticorrosive properties to polymeric coatings. <Pyus D. Tatiya, Rahul K Hedaoo, Pramod P. Mahulikar, and Vikas V.Gite, Novel Polyurea Microcapsules Using Dendritic Functional Monomer: Synthesis, Characterization, and Its Use inSelf-healing and Anticorrosive Polyurethane Coatings, Ind. Eng. Chem. Res. 2013, 52, 1562−1570,dx.doi.org/10.1021/ie301813a>

See also

Dendronized polymerMetallodendrimerFerrocene-containing dendrimers

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