Referências Bibliográficas
221
Referências Bibliográficas
Referências Bibliográficas
222
1. Zutphen S.V., Targeting Platinum Compounds Synthesis and Biological Evaluation, F&N
Boekservice / Eigen Beheer, 2005.
2. Liu S., The role of coordination chemistry in the development of target-specific
radiopharmaceuticals, Chem. Soc. Rev. 33, 445-461, 2004.
3. Abram U., Alberto R., Technetium and Rhenium – Coordination Chemistry and Nuclear
Medical Aplications, J. Braz. Chem. Soc., 8, 1486-1500, 2006.
4. Alberts B., Bray D., Hopkin K., Johnson A., Lewis J., Raff M., Roberts K., Walter P.,
Essential cell biology, Garland Science, 2ª ed., 698 – 736, 2004.
5. Bartsch R., Fromm S., Rudas M., Wenzel C., Harbauer S., Roessler K., Kitz K., Steger G.G.,
Weitmann H.D., Poetter R., Zielinski C.C., Dieckmann K., Intensified local treatment and
systemic therapy significantly increase survival in patients with brain metastases from advanced
breast cancer – a retrospective analysis, Radiot. Oncol., 80, 313-317, 2006.
6. Buchegger F., Perillo-Adamer F., Dupertuis Y.M., Delaloye A.B., Auger Radiation Target
into DNA: a Therapy Perspective, Eur. J. Nucl. Med. Mol. Imag., 33: 1352-1363, 2006.
7. Neal M.J., Medical Pharmacology at a Glance, 3ª ed., Blackwell Science Ltd, 1997.
8. Silverman R.B., The organic chemistry of drug design and drug action, Academic Pres Inc.,
USA, 1992.
9. Dyson P.J., Sava G., Metal-based antitumor drugs in the post genomic era, Dalton Trans.,
1929-1933, 2006.
10. Zubay G., Biochemistry, 3th Ed, Wm. C. Brown Communication, Inc., U.S.A., 1993.
11. Kostakis I. K., Magiatis P., Pouli N., Marakos P., Skaltsounis A.-L., Pratsinis H., Léonce S.,
Pierré A., Design, synthesis, and antiproliferative activity of some new pyrazole-fused amino
derivatives of pyranoxanthenone, pyranothioxanthenone, and pyranoacridone ring systems: a
new class of cytotoxic agents, J. Med. Chem., 45(12), 2599-2609, 2002
Referências Bibliográficas
223
12. Rodger A., Blagbrough I.S., Adlam G., Carpenter M.L., DNA binding of spermine
derivative. Spectroscopic study of anthracene-9-carbonyl-N1-spermine with poly [d(G-C)·d(G-
C)] and poly [d(A-T)·d(A-T)], Biopol., 34(12), 1583-1593,1994.
13. Modukuru N.K., Snow K.J., Scott Perrin Jr. B., Bhambhani A., Duff M., Kumar C.V.,
Tuning the DNA binding modes of an anthracene derivative with salt, J. Photochem. Photobiol.
A: Chem., 177, 43-54, 2006.
14. Langer M., Kratz F., Rothen-Rutishauser B., Wunderli-Allenspach H., Beck-Sickinger A.G.,
Novel peptide conjugate for tumor-specific chemotherapy, J. Med. Chem., 44, 1341-1348, 2001.
15. Berg S.L., Status of new antrapyrazole and pyrazoloacridine derivatives, Crit. Rev.
Oncol./Hematol., 22, 79-87, 1996.
16. Zhang L., Meler. E., Watson E. J., Gibson E. P., Reversal of the regioselectivity of
anthrapyrazole formation. A new synthesis of Losoxantrone (DUP941), Tetrahedron Let.,
35(22), 3675-3678, 1994.
17. Sissi C., Manlio P. Antitumor Potential of Aza-bioisosterism in Anthracenedione-based
Drugs, Cur. Top. Med. Chem., 4 (2), 219-230, 2004.
18. Martins E.T., Baruah H., Kramarczyk J., Saluta G., Day C.S., Kucera G.L., Bierbach U.,
Design, Synthesis, and Biological Activity of a Novel Non-Cisplatin-type Platinum-Acridine
Pharmacophore, J. Med. Chem., 44, 4492-4496, 2001.
19. Luedtke N.W., Hwang J.S., Nava E., Gut Dalia, Kol M., Tor Y., The DNA and RNA
specificity of eilatin Ru(II) complexes as compared to eilatin and ethidium bromide, Nucleic
Acid Res., 31(19), 5732-5740, 2003.
20. Vock C. A., Ang W. H., Scolaro C., Phillips A. D., Lagopoulos L., Juillerat-Jeanneret L.,
Sava G., Scopelliti R., Dyson P. J., Development of ruthenium antitumor drugs that overcome
multidrug resistance mechanisms, J. Med. Chem., 50(9), 2166-75, 2007.
Referências Bibliográficas
224
21. Hambley T.W. Developing new metal-based therapeutics: challenges and opportunities,
Dalton Trans., DOI: 10.1039/b706075k, 2007
22. Kowalsky R.J., Falen S.W, Radiopharmaceuticals in Nuclear Pharmacy and Nuclear
Medicine, 2nd, American Pharmacists Association, 2004.
23. Reichert D. E., Lewis J. S, Anderson C. J, Metal complexes as diagnostic tools, Coordinat.
Chem. Rev., 184, 3-66, 1999.
24. Schibli R., Schubiger P.A., Current use and future potential of organometallic
radiopharmaceuticals, Eur. J. Nucl. Med., 29(11), 1529-1542, 2002.
25. Langer M., Beck-Sickinger A.G., Peptides as carrier for tumor diagnosis and treatment,
Curr. Med. Chem. – Anti-Cancer Agents, 1, 71-93, 2001.
26. Unak P., Targeted Tumor Radiotherapy, Braz. Arch. Biol. Technol., 45, 97-110, 2002.
27. Saha G. B., Fundamentals of Nuclear Pharmacy, 5th Ed, Springer, 2004.
28. http://us.myoview.com/tech/diagtest.html, 10/06/2007
29. Stepanek J., Larsson B., Weinreich R., Auger-electron spectra of radionuclides for therapy
and diagnostics, Acta Oncol., 35(7), 863-868, 1996.
30. Kassis A.I., Adelstein S.J., Radiobiologic principles in radionuclide therapy, J. Nucl. Med.,
46(1), 4S-12S, 2005.
31. Gardin I., Faraggi M., Le Guludec D., Bok B., Cell irradiation caused by diagnostic nuclear
medicine procedures: dose heterogeneity and biological consequences, Eur. J. Nucl. Med., 26,
1617-1626, 1999.
32. Yao Z., Garmestani K., Wong K.J., Park L.S., Dadachova E., Yordanov A., Waldmann
T.A., Eckelman W.C., Paik C.H., Carrasquillo J.A., Comparative cellular catabolism and
Referências Bibliográficas
225
retention of astatine-, bismuth-, and lead-radiolabeled internalizing monoclonal antibody,
J.Nucl.Med., 42(10), 1538-1544, 2001.
33. Howell R.W., Narra V.R., Sastry K.S., Rao D.V., On the equivalent dose for Auger electron
emitters, Radiat Res., 134(1), 71-78, 1993.
34. Boswell C. A., Brechbiel M. W., Invited Perspective: Auger Electrons: Lethal, Low Energy,
and Coming Soon to a Tumor Cell Nucleus Near You, J. Nucl. Med., 46(12), 1946-1947, 2005.
35. http://www.chm.bris.ac.uk/webprojects2002/wrigglesworth/history.htm, 12/04/2007
36. Larson S. M., Krenning E. P., A pragmatic perspective on molecular targeted radionuclide
therapy, J. Nucl. Med., 46(1), 1S-3S, 2005.
37. Brans B., Bodei L., Giammarile F., Linden O., Luster M., Oyen W.J.G., Tennvall J.,
Clinical radionuclide therapy dosimetry: the quest for “Holy Gray”, Eur. J. Med Mol Imag., 34,
772-786, 2007.
38. Boswell C.A., Brechbiel M.W. Development of radioimmunotherapeutic and diagnostic
antibodies: an inside-out view, Nucl. Med. Biol., 34, 757-778, 2007.
39. Essen M.V., Krenning E.P., Jong M.D., Valkema R., Kwekkeboom D.J., Peptide Receptor
Radionuclide Therapy with radiolabelled somatostatin analogues in patients with somatostatin
receptor positive tumours, Acta Oncolog., 46, 723-734, 2007.
40. Panyutin I.G., Neumann R.D., The potential for gene-targeted radiation therapy of cancers,
Trends in Biotec., 23, 492-496, 2005.
41. Ftacnikova S., Bohm R., Monte Carlo calculations of energy deposition in DNA for auger
emitter, Rad. Prot. Dos., 92(4), 269-278, 2000.
42. Faraggi M., Gardin I., Labriolle-Vaylet C, Moretti J. L., Bok B. D., The Influence of Tracer
Localization on the Electron Dose Rate Delivered to the Cell Nucleus, J. Nucl. Med., 35(1),
113-119, 1994.
Referências Bibliográficas
226
43. Kassis A. I., Cancer therapy with auger electrons: are we almost there?, J. Nucl. Med.,
44(9), 1479-1481, 2003.
44. Pouget J.P., Mather S.J., General aspects of cellular response to low- and high-LET
radiation, Eur. J. Nucl. Med., 28, 541-561, 2001.
45. Thierens H.M., Monsieurs M.A., Brans B., Driessche T.V., Christiaens I., Dierckx R.A,
Dosimetry from organ to celular dimensions, Comp. Med. Imag. Graph., 25, 187-193, 2001.
46. Behr T.M., Béhe M., Lohr M., Sgouros G., Angerstein C., Wehrmann E., Nebendahl K.,
Becker W., Therapeutic advantages of Auger electron- over β-emitting radiometals or
radioiodine when conjugated to internalizing antibodies, Eur. J. Nucl. Med., 27, 753-765, 2000.
47. Karamychev V. N., Reed M. W., Neumann R. D., Panyutin I. G., Distribution of DNA
strand breaks produced by iodine-123 and indium-111 in synthetic oligodeoxynucleotides, Acta
Oncolog., 39, 687-692, 2000.
48. Meyers M.O., Anthony L.B., McCarthy K.E., Drouant G., Maloney T.J., Espanan G.D.,
High-dose indium 111In pentetreotide radiotherapy for metastatic atypical carcinoid tumor,
South. Med. J., 93(8), 809-811, 2000.
49. Kwekkeboom D., Krenning E.P., Jong M., Peptide receptor imaging and therapy, J. Nucl.
Med., 41(10), 1704-1713, 2000.
50. Mariani G., Bodei L., Adelstein S.J., Kassis A., Invited commentary: Emerging roles for
radiometabolic therapy of tumors based on auger electron emission, J. Nucl. Med., 41, 1519-
1521, 2000.
51. Escriou V., Carrière M., Scherman D., Wils P., NLS bioconjugates for targeting therapeutic
genes to the nucleus, Adv. Drug Deliv. Rev. 55, 295-306, 2003.
Referências Bibliográficas
227
52. Ginj M., Maecke H.R., Synthesis of trifunctional somatostatin based derivatives for
improved cellular and subcellular uptake, Tetrahedron Let., 46, 2821-2824, 2005.
53. Ginj M., Hinni K., Tschum S., Schulz S., Maecke H.R., Trifunctional somatostatin-based
derivatives designed for targeted radiotherapy using auger electron emitters, J Nucl Med, 46,
2097-2103, 2005.
54. Pouton C.W., Wagstaff K.M., Roth D.M., Moseley G.W., Jans D.A., Targeted delivery to
the nucleus, Adv. Drug Deliv., 59, 698-717, 2007
55. Constantini D.L., Chan C., Cai Z., Vallis K.A., Reilly R.M., 111In-labeled Trastuzumab
(Herceptin) modified with nuclear localization sequences (NLS): an auger electron-emitting
radiotherapeutic agent for HER2/neu-amplified breast cancer, J. Nucl. Med., 48, 8, 1357-1368,
2007.
56. Haefliger P., Agorastos N., Renard A., Giambonini-Brugnoli G., Marty C., Alberto R., Cell
uptake and radiotoxicity studies of an nuclear localization-signal peptide-intercalator conjugate
labeled with [99mTc(CO)3]+, Bioconjugate Chem., 16(3), 582-587, 2005.
57. Chen P., Cameron R., Wang J., Vallis K. A., Reilly Raymond M., Antitumor Effects and
Normal Tissue Toxicity of 111In-Labeled Epidermal Growth Factor Administered to Athymic
Mice Bearing Epidermal Growth Factor Receptor-Positive Human Breast Cancer Xenografs, J.
Nucl. Med., 44(9), 1469-1478, 2003.
58. Reilly R.M., Scollard D.A., Wang J., Mondal H., Chen P., Henderson L.A., Bowen B.M.,
Vallis K.A., A Kit formulated under good manufacturing practices for labeling human
epidermal growth factor with 111In for radiotherapeutic applications, J. Nucl. Med., 45(4), 701-
708, 2004.
59. Reilly R.M., Chen P., Wang J., Scollard D., Cameron R., Vallis K.A., Preclinical
pharmacokinetic, biodistribution, toxicology, and dosimetry studies of 111In-DTPA-human
epidermal growth factor: an auger electron-emitting radiotherapeutic agent for epidermal growth
factor receptor-positive breast cancer, J. Nucl. Med., 47(6), 1023-1031, 2006.
Referências Bibliográficas
228
60. Haefliger P., Agorastos N., Spingler B., Georgiev O., Viola G., Alberto R., Induction of
DNA-double-strand breaks by auger electrons from 99mTc complexes with DNA-binding
ligands, ChemBioChem., 6, 412-421, 2005
61. Dilworth J.R., Parrott S.J., The biomedical chemistry of technetium and rhenium, Chem.
Soc. Rev., 27, 43-55, 1998.
62. Alberto R., Schibli R., Egli A., Schubiger P.A., Abram U, Kaden T.A., A novel
organometallic aqua-complex of technetium for the labeling of biomolecules: synthesis of
[99mTc(OH2)(CO)3]+ from [99mTcO4]- in aqueous solution and its reaction with bifunctional
ligands, J. Am. Chem. Soc., 120, 7987-7988, 1998.
63. Alberto R., Ortner K., Wheatley N., Schibli R., Schubiger P.A., Synthesis and properties of
boranecarbonate: a conveniente in sito CO source for the aqueous preparation of
[99mTc(CO)3(H2O)]+, J. Am. Chem. Soc., 123, 3135-3136, 2001.
64. Banerjee S. R., Levadala M. K., Lazarova N., Wei L., Valliant J.F., Stephenson K.A.,
Babich J. W., Maresca K. P., Zubieta J., Bifunctional Single Amino Acid Chelates for Labeling
of Biomolecules with the {Tc(CO)3}+ and {Re(CO)3}+ Cores. Crystal and Molecular Structures
of [ReBr(CO)3(H2NCH2C5H4N)],
[Re(CO)3{(C5H4NCH2)2NH}]Br,[Re(CO)3{(C5H4NCH2)2NCH2CO2H}]Br,
[Re(CO)3{X(Y)NCH2CO2CH2CH3}]Br (X = Y = 2-pyridylmethyl, X = 2pyridymethyl, Y = 2-
(1-methylimidazolyl)methyl; X = Y = 2-(1-methylimidazolyl)methyl),
[ReBr(CO)3{(C5H4NCH2)NH(CH2C4H3S)}, and
[Re(CO)3{(C5H4NCH2)N(CH2C4H3S)(CH2CO2)}], Inorg. Chem., 41 (24), 6417-6425, 2002.
65. Bayly S.R., Fisher C.L., Storr T., Adam M.J., Orvig C., Carbohydrate Conjugates for
Molecular Imaging and Radiotherapy: 99mTc(I) and 186Re(I) Tricarbonyl Complexes of N-(2 -́
Hydroxybenzyl)-2-amino-2deoxy-D-glucose, Bioconjugate Chem., 15, 923-926, 2004.
66. Benerjee S.R., Maresca K.P., Francesconi L., Valliant J., Babich J.W., New directions in the
coordination chemistry of 99mTc: a reflection on technetium core structures and a strategy for
new chelate design, Nucl. Med. Biol., 32, 1-20, 2005.
Referências Bibliográficas
229
67. Kramer J. D., Davison A., Davis M. W., Jones A. G., N-(2-Mercaptoethyl)picolylamine as a
Diaminomonothiolate Ligand for the “fac-[Re(CO)3]+” Core, Inorg. Chem., 41 (24), 6181-6183,
2002.
68. Maria L., Paulo A., Santos I.C., Kurz P., Spingler B., Alberto R., Santos I., Very small and
soft scorpionates: water stable technetium tricarbonyl complexes combining a bis-agostic (k3-H,
H, S) binding motif with pendant and integrated bioactive molecules, J. Am. Chem. Soc., 128,
14590-14598, 2006.
69. Mundwiler S., Kündig M., Kirstin O., Alberto R., A new [2 + 1] mixed ligand concept based
on [99(m)Tc(OH2)3(CO)3]+: a basic study, Dalton Trans., 1320-1328, 2004.
70. Petrig J., Schibli R., Dumas C., Alberto R., Schubiger P. A., Derivatization of Glucose and
2-Deoxyglucose for Transition Metal Complexation: Substitution Reactions with
Organometallic 99mTc and Re Precursors and Fundamental NMR Investigations, Chem. Eur. J.,
7 (9), 1868-1873, 2001.
71. Santos I., Paulo A., Correia J.D.G., Rhenium and technetium complexes anchored by
phosphines and scorpionates for radiopharmaceutical applications, Top. Curr. Chem., 252, 45-
84, 2005.
72. Schibli R., Bella R.L., Alberto R., Garcia-Garayoa E., Ortner K., Abram U., Schubiger P.A.,
Influence of the denticity of ligand systems on the in vitro and in vivo behavior of 99mTc(I)-
tricarbonyl complexes: a hint for the future functionalization of biomolecules, Bioconjugate
Chem., 11, 345-351, 2000.
73. Garcia R., Paulo A., Domingos A., Santos I., Rhenium(I) organometallic complexes with
novel bis(mercaptoimidazolyl)borates and with hydrotris(mercaptoimidazolyl)borate: chemical
and structural studies, J. Organometallic Chem., 632, 41-48, 2001.
74. Garcia R., Domingos A., Paulo A., Santos I., Alberto R., Reactivity of [Re{k3-H)B(timMe =
2-Mercapto-1-methylimidazolyl) toward Neutral Substrates, Inorg. Chem., 41, 2422-2428,
2002.
Referências Bibliográficas
230
75. Alves S., Paulo A., Correia J. D. G., Domingos A., Santos I., Coordination capabilities of
pyrazolyl containing ligands towards the fac-[Re(CO)3]+ moiety; J. Chem. Soc., Dalt. Trans.,
24, 4714-4719, 2002.
76. Alves S., Paulo A., Correia J.D.G., Gano L., Santos I., in Nicolini M., Mazzi U. (Eds.),
Technetium, Rhenium and Other Metals in Chemistry and Nuclear Medicine, vol 6, SGE
Editor-iali, Padova, Italy, 139-141, 2002a.
77. Alves S., Paulo A., Correia J. D. G., Gano L., Smith C. J., Hoffman T. J., Santos I.,
Pyrazolyl derivatives as bifunctional chelators for labelling biomolecules with the fac-
[M(CO)3]+ moiety (M=99mTc, Re): synthesis, characterization and biological behaviour,
Bioconjugate Chem., 16, 438-449, 2005.
78. Bandoli G., Tisato F., Dolmella A., Agostini S., Structural overview of technetium
compounds (200-2004), Coord. Chem. Rev., 250, 561-573, 2006.
79. Oliveira R., Santos D., Ferreira D., Coelho P., Veiga F., Preparações radiofarmacêuticas e
suas aplicações, Rev. Bras. Cienc. Farm.,42 (2), 2006.
80. Silva C.R., Valsa J.O., Canine M.S., Caldeira-de-Araujo A., Bernardo-Filho M., Evaluation
of 99mtechnetium decay on Escherichia coliminactivation: effects of physical or chemical
agents, Yale J. Biol. Med., 71(1), 7-14, 1998.
81. Pedraza-Lopez M, Ferro-Flores G., Mendiola-Cruz T., Morales-Ramirez P., Assessment of
radiation-induced DNA damage caused by the incorporation of 99mTc-radiopharmaceuticals in
murine lymphocytes using single cell gel electrophoresis, Mutat. Res.-Gen. Tox. Env. Mutag.,
465(1-2), 139-144, 2000
82. Griffiths G.L., Govindan S.V., Sgouros G., Ong G.L., Goldenberg D. M., Mattes M.J.,
Cytotoxicity with auger electron-emitting radionuclides delivered by antibodies, Int. J. Cancer,
81, 985-992, 1999.
83. Schipper M.L., Riese C.G.U., Seitz S., Weber A., Béhé M., Schurrat T., Schramm N., Keil
B., Alfke H., Behr T.M., Efficacy of 99mTc pertechnetate and 131I radioisotope therapy in
Referências Bibliográficas
231
sodium/iodide symporter (NIS)-expressing neuroendocrine tumors in vivo, Eur. J. Nucl. Med.
Mol. Imaging, 34, 638-650, 2007.
84. Agorastos N., Borsig L., Renard A., Antoni P., Viola G., Spingler B., Kurz P., Alberto R.,
Cell-specific and nuclear targeting with [M(CO)3]+ (M=99mTc, Re)-Based Complexes
Conjugated to Acridine Orange and Bombesin, Chem. Eur. J., 13, 3842-3852, 2007.
85. Stephenson K.A., Banerjee S.R., Besanger T., Sogbein O.O., levadala M.K., McFariane N.,
Lemon J.A., Boreham D.R., Maresca K.P., Brennan J.D., Babich J.W., Zubieta J., Valliant J.F.,
Bridging the gap between in vitro and in vivo imaging: isostructural Re and 99mTc complexes for
correlating fluorescence and radioimaging studies, J. Am. Chem. Soc., 126, 8598-8599, 2004.
86. Bullok K.E., Dyszlewski M., Prior J.L., Pica C.M., Sharma V., Piwnica-Worms D.,
Characterization of Novel Histidine-Tagged tat-Peptide Complexes Dual-Labeled with 99mTc-
Tricarbonyl and Fluorescein for Scintigraphy and Fluorescence Microscopy, Bioconjugate
Chem., 13, 1226-1237, 2002.
87. Polyakov V., Sharma V., Dahlheimer J.L., Pica C. M., Luker G. D., Piwnica-Worms D.,
Novel Tat-Peptide Chelates for Direct Transduction of Technetium-99m and Rhenium into
Human Cells for Imaging and Radiotherapy, Bioconjugate Chem., 11, 762-771, 2000.
88. Alves S., Correia J.D.G., Santos I., Veerendra B., Sieckman G.L., Hoffman T.J., Rold T.L.,
Figueroa S.D., Retzloff L., McCrate J., Prasanphanich A., Smith C.J., Pyrazolyl conjugates of
bombesin: a new tridentate ligand framework for the stabilization of fac-[M(CO)3]+ moiety,
Nucl. Med.. Biol., 33 (5), 625-634, 2006
89. Alves S., Correia J.D.G., Gano L., Rold T.L., Prasanphanich A., Haubner R., Rupprich M.,
Alberto R., Decristoforo C., Santos I., Smith C.J., In vitro and in vivo evaluation of a novel 99mTc(CO)3-pyrazolyl conjugate of cyclo-(Arg-Gly-Asp-D-Tyr-Lys), Bioconjugate Chem., 18,
530-537, 2007.
90. Paulo A., Correia J.D.G., Campello M.P.C., Santos I., A short ride on scorpionates: from d-
to f-elements, Polyhedron, 23, 331-360, 2004.
Referências Bibliográficas
232
91. Seymore S.B., Brown S.N., Charge effects on oxygen atom transfer, Inorg. Chem., 39, 325-
332, 2000.
92. Porchia M., Papini G., Santini C., Lobbia G.G., Pellei M., Tisato F., Bandoli G., Dolmella
A., Novel rhenium(V) oxo complexes containing bis(pyrazol-1-yl)acetate and bis(pyrazol-1-yl)
sulfonate as tripodal N,N,O-heteroscorpionate ligands, Inorg. Chem., 44, 4045-4054, 2005.
93. Alegria E.C.B., Martins L.M.D.R.S., Haukka M., Pombeiro A.J.L., Rhenium complexes of
tris(pyrazolyl)methanes and sulfonate derivative, Dalton Trans., 4954-4961, 2006.
94. Cowley A.R., Dilworth J.R., Salichou M., Syntheses and structures of pyrazolylmethane
complexes of rhenium(III), (IV) and (V), Dalton Trans., 1621-1629, 2007.
95. Gabriel M., Decristofore C., Maina T., Nock B., vonGuggenberg E., Cordopatis P.,
Moncayo R., 99mTc-N4-[Tyr3]octreotate versus 99mTc-EDDA/HYNIC-[Tyr3]octreotide: an
intrapatient comparison of two novel technetium-99m labelled tracers for somatostatin receptor
scintigraphy, Cancer Biotherapy & Radiopharmaceuticals, 19(1), 73-79, 2004.
96. Maina T., Nock B.A., Cordopatis P., Bernard B.F., Breeman W.A.P., Gameren A.V., Berg
R.V.D., Reubi J.C., Krenning E.P., Jong M.D., [99mTc]Demotate 2 in the detection of sst2-
positive tumours: a preclinical comparison with [111In]DOTA-tate, Eur. J. Nucl. Med. Mol.
Imag., 33(7), 831-840, 2006.
97. Nock B.A., Nikolopoulou A., Reubi J.C., Maes V., Conrath P., Tourwé D., Maina T.,
Toward stable N4-modified neurotensins for NTS1-receptor-targeted tumor imaging with 99mTc,
J. Med. Chem., 49, 4767-4776, 2006.
98. Pietzsch H.J., Gupta A., Reisgys M., Drews A., Seifert S., Syhre R., Spies H., Alberto R.,
Abram U., Schubiger P.A., Johannsen B., Chemical and biological characterization of
technetium(I) and rhenium(I) tricarbonyl complexes with dithioether ligands serving as linkers
for coupling the Tc(CO)3 and Re(CO)3 moieties to biologically active molecules, Bioconjugate
Chem., 11, 414-424, 2000.
Referências Bibliográficas
233
99. Karagiorgou O., Patsis G., Pelecanou M., Raptopoulou C.P., Terzis A., Siatra-Papastaikoudi
T., Alberto R., Pirmettis I., Papadopoulos M., (S)-(2-(2 -́pyridyl)ethyl)cysteamine and (S)-(2-
(2 -́pyridyl)ethyl)-D,L-homocysteine as ligands for the “fac-[M(CO)3]+” (M = Re, 99mTc) core,
Inorg. Chem., 44, 4118-4120, 2005.
100. Staveren D.R.V., Benny P.D., Wailbel R., Kurz P., Pak J.K., Alberto R., S-Functionalized
cysteine: powerful ligands for the labelling of bioactive molecules with
triaquatricarbonyltechnetium-99m(1+)([99mTc(OH2)3(CO)3]+), Helvetica Chim. Acta, 88, 447-
459, 2005.
101. He H., Lipowska M., Xu X., Taylor A.T., Carlone M., Marzilli L.G., Re(CO)3 complexes
synthesized via an improved preparation of aqueous fac-[Re(CO)3(H2O)3]+ as an aid in assessing 99mTc imaging agents. Structural characterization and solution behaviour of complexes with
thioether-bearing amino acids as tridentate ligands, Inorg. Chem., 44, 5437-5446, 2005.
102. He H., Lipowska M., Xu X., Taylor A.T., Marzilli L.G., Rhenium analogues of promising
renal imaging agents with a {99mTc(CO)3}+ core bound to cysteine-derived dipeptides, including
lanthionine, Inorg. Chem., 46, 3385-3394, 2007.
103. He H., Lipowska M., Christoforou A.M., Marzilli L.G., Taylor A.T., Initial evaluation of
new 99mTc(CO)3 renal imaging agents having carboxyl-rich thioether ligands and chemical
characterization of Re(CO)3 analogues, Nucl. Med. Biol., 34, 709-716, 2007.
104. Pietzsch H.J., Spies H., Leibnitz P., Reck G., Technetium and rhenium complexes with
thioether ligands-IV. Synthesis and structural characterization of binuclear oxorhenium(V)
complexes with bidentate thioether coordination, Polyhedrom, 14(13-14), 1849-1853, 1995.
105. Reisgys M., Spies H., Johannsen B., Leibnitz P., Pietzsch H.J., Technetium and rhenium
complexes with thioether ligands. 6. Synthesis and structural characterization of mixed-ligand
oxorhenium(V) complexes containing bidentate dithioethers and monothiolato ligands, Chem.
Berichte-Recueil, 130(9), 1343-1347, 1997.
106. Pietzsch H.J., Reisgys M., Spies H., Leibnitz P., Johannsen B., Technetium and rhenium
complexes with thioether ligands. 5. Synthesis and structural characterization of neutral
Referências Bibliográficas
234
oxorhenium(V) complexes with tridentate dithioethers, Chem. Berichte-Recueil, 130(3), 357-
364, 1997.
107. Holzer W., Seiringer G., N-1 Substituted ethyl 4-pyrazolecarboxylates: synthesis and
spectroscopic investigations, J. Heterocyclic Chem., 30, 865-872, 1993.
108. Haanstra W.G., Driessen W.L. and Reedijk J., Unusual chelating properties of the ligand
1,8-bis(3,5-dimethyl-1-pyrazolyl)-3,6-dithiaoctane (bddo). Crystal Structures of
Ni(bddo)(NCS)2,Zn(bddo)(NCS)2 and Cd2(bddo)(NCS)4, J. Chem. Soc Dalton Trans., 2309-
2314, 1989.
109. Salvatore R.N., Yoon C.H., Jung K.W., Synthesis of secondary amines, Tetrahedron, 57,
7785-7811, 2001.
110. Rosini M., Bixel M.G., Marucci G., Budriesi R., Krauss M., Bolognesi M.L., Minarini A.,
Tumiatti V., Hucho F., Melchiorre C., Structure-activity relationships of methoctramine-related
polyamines as muscular nicotinic receptor noncompetitive antagonists. 2.1 Role of
polymethylene chain lengths separating amine functions and of substituents on the terminal
nitrogen atoms, J. Med. Chem., 45, 1860-1878, 2002.
111. Holmes R.J., McKeage M.J., Murray V., Denny W. A., McFadyen W.D., cis-
Dichloroplatinum(II) complexes tethered to 9-aminoacridine-4-carboxamides: synthesis and
action in resistant cell lines in vitro, J. Inorg. Bioch., 85, 209-217, 2001.
112. Garcia-Antón J., Pons J., Solans X., Mercè Font-Bardia and Josep Ros, Synthesis,
Characterisation, and X-ray Crystal Structure of New Ni(II), Pd(II), and Pt(II) Complexes of
Tridentate Pyrazole-Based Ligands with an NOS-Donor Set. Eur. J. Inorg. Chem., 2992-3000,
2003.
113. a) Parshall G.W., Shive L.W., Cotton F.A., Phosphine complexes of rhenium, Inorg.
Synth., XVII, 110-111, 1977; b) Ram M.S., Hupp J.T, Generalized synthesis of cis- and trans-
dioxorhenium(V) (bi)pyridyl complexes, Inorg.Chem., 30, 130-133, 1991.
Referências Bibliográficas
235
114. Francesconi L.C., Graczyk G., Wehrli S., Shaikh S.N., McClinton D., Liu S., Zubieta J.,
Kung H.F., Synthesis and characterization of neutral MVO (M = Tc, Re) amine-thiol complexes
containing a pendant phenylpiperidine group, Inorg. Chem., 32, 3114-3124.
115. Hilger C.S., Noll B., Blume F., Leibnitz P., Johannsen B., Tc(V) and Re(V) Complxes of
N-(MAG1)-Histamine, Technetium, Rhenium and Other Metals in Chemistry and Nuclear
Medicine, 221-224, 1999.
116. Parker D., Roy P.S., Synthesis and characterization of stable rhenium(V) dioxo complexes
with acyclic tetraamine ligands, [LReO2]+, Inorg. Chem., 27, 4127-4130, 1988.
117. Luna S.A., Bolzati C., Duatti A., Zucchni G.L., Bandoli G., Refosco F., Formation of the
trans-[ReO2]+ group from the reactions of ReNCl2(PPh3)2, ReCl4(PPh3)2, and
ReCl3(CH3CN)(PPh3)2 with chelating amines and tetraazamacrocycles. Crystal structure of
trans-[ReO2(cyclam)](PF6) (cyclam = 1,4,8,11-tetraazacyclotetradecane), Inorg. Chem., 31,
2595-2598.
118. Nugent W.A., Mayer J.M., Metal-Ligand Multiple Bonds, J. Wiley & Sons, 1988.
119. Hansen L., Lampeka Y.D., Gavrish S.P., Xu X., Taylor A.T., Marzilli L.G., Re(V)
complexes with an open-chain quadridentate ligand containing two amine and two amido
donors. Synthesis, characterization, and solution equilibria of Re2O3(dioxo-tetH4)2 and
[ReO(H2O)(dioxo-tetH4)]Cl (dioxo-tetH6 = 1,4,8,11-tetraazaundecane-5,7-dione), Inorg. Chem.,
39, 5859-5866, 2000.
120. Bélanger S., Beauchamp A., Preparation and protonation studies of trans-dioxorhenium(V)
complexes with imidazoles, Inorg. Chem., 35, 7836-7844, 1996.
121. Xu L., Pierreroy J., Patrick B.O., Orvig C., Chemistry of Re with N,N’-bis(2-
pyridylmethyl)ethylenediamine (H2pmen): hydrolysis, dehydrogenation, and ternary complexes,
Inorg. Chem., 40, 2005-2010, 2001.
122. Paulo A., Domingos A, Santos I, Coordination of Tetrakis(pyrazolyl)borate in Rhenium
Complexes Containing the [ReV=O]3+ Core, Inorg. Chem., 1996, 35, 1798-1807.
Referências Bibliográficas
236
123. Paulo A., Correia J. D. G., Santos I., Rhenium complexes with poly(pyrazolyl)borates,
Trends in Inorg. Chem., 5, 57-86, 1998.
124. Xavier C., Paulo A., Domingos A., Santos I., Synthesis and structural studies of
rhenium(V) complexes stabilized by a monoanionic cyclen ligand, Eur. J. Inorg. Chem., 243-
249, 2004.
125. Lock C.J.L. and Turner G.; Studies of rhenium-oxigen bond. II. The crystal and molecular
structure of µ-oxobis(cis-dihloro-cis-di(pyridine)-trans-oxorhenium(V)),
ORe(C5H5N)2Cl2ORe(C5H5N)2Cl2O, Can. J. Chem. 56, 179-188, 1978.
126. Alberto R., Egli A., Abram U., Hegetschweiler K., Gramlich V., Schubiger P.A., Synthesis
and reactivity of [Net4]2[ReBr3(CO)3]. Formation and structural characterization of the clusters
[Net4][Re(�3-OH)(�-OH)3(CO)9] and [Net4][Re2(�-OH)3(CO)6] by alkaline titration, J. Chem.
Soc. Dalton Trans., 2815-2820, 1994.
127. Garcia R., Complexos Tricarboonilo de Re(I) e 99mTc com Escorpionatos Doadores de
Enxofre, Aplicações no Desenvolvimento de Radiofármacos para Imagiologia Molecular de
Receptores do Sistema Nervoso Central, Tese de Doutoramento em Química (especialidade
Química Inorgânica) apresentada à Faculdade de Ciências – Universidade de Lisboa, 2005
128. Tan W.B., Bhambhani A., Duff M.R., Rodger A., Kumar C.V., Spectroscopic
Identification of Binding Modes of Anthracene Probes and DNA Sequence Recognition,
Photochemistry and Photobiology, 82, 20-30, 2006.
129. Kumar C.V., Asuncion E.H., DNA binding studies and site selective fluorescence
sensitization of an anthryl probe, J. Am. Chem. Soc., 115, 8547-8553, 1993.
130. Duff M.R., Tan W.B., Bhambhani A., Perrin Jr B.S., Thota J., Rodger A., Kumar C.V.,
Contributions of hidroxyethyl group to the DNA binding affinities of anthracene probes, J.
Phys. Chem. B, 110, 20693-20701, 2006.
Referências Bibliográficas
237
131. Sissi C., Leo E., Moro S., Capranico G., Mancia A., Menta E., Krapcho A.P., Palumbo M.,
Antitumor aza-antrapyrazoles: biophysical and biochemical studies on 8- and 9-aza
regioisomers, Biochemical Pharmacology 67, 631-642, 2004.
132. Wang C., Delcros J-G., Biggerstaff J., Phanstiel IV O., Synthesis and Biological
Evaluation of N1-(anthracen-9-ylmethyl)triamines as Molecular Recognition Elements for the
Polyamine Transporter, J. Med. Chem., 46, 2663-2671, 2003.
133. Breitbeil III F., Kaur N., Delcros J.G., Martin B., Abboud K.A., Phanstiel IV O., Modeling
the Preferred Shapes of Polyamine Transporter Ligands and Dihydromotuporamine-C Mimics:
Shovel versus Hoe, J. Med. Chem., 49, 2407-2416, 2006.
134. Bullpitt M., Kitching W., Doddrell D., Adcock W., The substituent effect of the
bromomethyl group. A carbon-13 magnetic resonance study, J. Org. Chem., 5(41), 760-766,
1976.
135. Nicolaou K.C., Rutjes F.P.J.T., Theodorakis E.A., Tiebes J., Sato M., Untersteller E., Total
Synthesis of Brevetoxin B. 3. Final Strategy and Completion, J. Amer. Chem. Soc., 117 (41),
10252-10263, 1995.
136. Mason T.J., The oxidation of secondary alcohols with Cr (VI), J. Chem. Educ., 59, 11,
980-981, 1982.
137. Nagawa Y., Suga J., Hiratani K., Koyama E., Kanesato M., [3]Rotaxane synthesized via
covalent bond formation can recognize cations forming a sandwich structure, Chem. Commun.,
749-751, 2005.
138. Zhang L., Meler W.E., Watson E.J., Gibson E.P., Reversal of the regioselectivity of
antrapyrazole formation. A new synthesis of Losoxantrone (DUP941), Tetrahedron L., 35(22),
3675-3678, 1994.
Referências Bibliográficas
238
139. Hasinoff B.B., Tan K.T., The displacement of iron(III) from its complexes with the
anticancer drugs piroxantrone and losoxantrone by the hydrolyzed form of the cardioprotective
agent dexrazoxane, J. Inorg. Biochem., 77, 257-259, 1999.
140. Joachim J.E., Apostolidis C., Kanellakopulos B., Maier R., Marques N., Meyer D., Muller
J., Matos A.P., Nuber B., Rebizant J., Ziegler M.L., Metallorganische chemie des technetiums
VIII*. Technetium(I)-carbonyl-komplexe mit polypyrazol-1-yl-borato-liganden im vergleich
mit seinen Mn- und Re-homologen, J. Organom. Chem., 448, 119-129, 1993.
141. Schibli R., Katti K.V., Volkert W.A., Barnes C.L., Novel coordination behavior of fac-
[ReBr3(CO)3]2- with 1,3,5-triaza-7-phosphaadamentane (PTA). Systematic investigation on
stepwise replacement of the halides by PTA ligand. Phase transfer studies and x-ray crystal
structure of [Net4]ReBr2(PTA)(CO)3], [ReBr(PTA)2(CO)3], and [Re(PTA)3(CO)3]PF6, Inorg.
Chem., 37, 5306-5312, 1998.
142. Silverstein R.M., Bassler G.C., Morrill T.C., Spectrometric identification of organic
compounds, John Wiley & Sons, 5th ed., 1991.
143. Becker H.C., Nordén B., DNA binding mode and sequence specificity of
piperazinylcarbonyloxyethyl derivatives of anthracene and pyrene, J. Am. Soc., 121, 11947-
11952, 1999.
144. McGhee J.D., Hippel P.H., Theoretical Aspects of DNA-Protein Interactions: Co-operative
and Non-co-operative binding of large ligands to a one-dimensional homogeneous lattice, J.
Mol. Biol., 86, 469-489, 1974.
145. Lo K.K., Tsang K.H., Bifunctional Luminescent Rhenium(I) Complexes Containing an
Extended Planar Diiminne Ligand and a Biotin Moiety, Organometallics, 2004.
146. Ellis L.T., Perkins D.F., Turner P., Hambley T.W., The preparation and characterisation of
cyclam/anthraquinone macrocyle/intercalator complexes and their interations with DNA, Dalton
Trans., 2728-2736, 2003.
Referências Bibliográficas
239
147. Kumar C.V., Punzalan E.H.A., Tan W.B., Adenine-thymine base pair recognition by an
antryl probe from the DNA minor grove, Tetrahedron, 56, 7027-7040, 2000.
148. Madureira J.P.L., Complexos de ruténio com ligandos politioéteres e/ou polipiridílicos:
síntese, caracterização estrutural e interacção com o DNA, Tese de Doutoramento, Aveiro,
Portugal, 2005.
149. Rodger A., Taylor S., Adlam G., Blagbrough I.S., Haworth I.S., Multiple DNA binding
modes of anthracene-9-carbonyl-N1-spermine, Bioorg. Med. Chem., 3(6), 861-872, 1995.
150. Balasundaram G., Takahashi T., Ueno A., Mihara H., Construction of peptide conjugates
with peptide nucleic acids containing an anthracene probe and their interactions with DNA,
Bioorg. Med. Chem., 9, 1115-1121, 2001
151. Mosmann T., Rapid Colorimetric Assay for Cellular Growth and Survival: Application to
Proliferation and Cytotoxicity Assays, J. Immunol. Methods, 65, 55-63, 1983.
152. Wang W., Yan Y.K., Hor T.S.A., Vittal J.J., Wheaton J.R., Hall I.H., Synthesis, X-ray
structures, and cytotoxicity of rhenium(I) carbonyl 2-(dimethylamino)ethoxide complexes,
Polyhedron 21, 1991-1999, 2002.
153. Zobi F., Spingler B., Alberto R., Guanine and plasmid DNA binding of mono- and
trinuclear fac-[Re(CO)3]+ complexes with amino acids ligands, ChemBioChem, 6, 1397-1405,
6, 2005.
154. Zobi F., Blacque O., Schmalle H., Alberto R., Head-to-Head (HH) and Head-to-Tail (HT)
Conformers of cis-bis Purine Ligands Bound to the [Re(CO)3]+ Core, Inorg. Chem.,
43(6), 2087-2096, 2004.
155. Zobi F., Spingler B., Fox Th., Alberto R., Towards Novel DNA Binding Metal Complexes:
Structure and Basic Kinetic Data of [M(9MeG)2(CH3OH)(CO)3]+ (M = 99Tc, Re),
Inorg. Chem., 42(9), 2818-2820, 2003.
Referências Bibliográficas
240
156. Smith, P. J., Blunt, N., Wiltshire, M., Hoy, T., Teesdale-Spittle, P., Craven, M. R., Watson,
J. V., Amos, B. A., Errington, R. J., and Patterson, L. H., Characteristics of a novel deep
red/infrared fluorescent cell-permeant DNA probe, DRAQ5, in intact human cells analyzed by
flow cytometry, confocal and multiphoton microscopy, Cytometry, 40, 280-291, 2000.
157. Lansiaux A., Tanious F., Mishal Z., Dassonneville L., Kumar A., Stephens C.E., Hu Q.,
Wilson W.D., Boykin D.W., Bailly C., Distribution of furamide analogues in tumor cells:
targeting of the nucleus or mitochondria depending on the amide substitution, Cancer Research,
62, 7219-7229, 2002.
158. James S., Maresca K.P., Babich J.W., Valliant J. F., Doering L., Zubieta J., Isostructural
Re and 99mTc Complexes of Biotin Derivatives for Fluorescence and Radioimaging Studies,
Bioconjugate Chem., 17, 590-596, 2006
159. Maublant J.C., Zhang Z., Rapp M., Ollier M., Michelot J., Veyre A., In vitro uptake of
Technetium-99m-Teboroxime in Carcinoma Cell Lines and Normal Cells: Comparison with
Technetium-99m-Sestamibi and Thallium-201, J. Nucl. Med., 34(11), 1949-1952, 1993.
160. Barbarics E., Kronauge J.F., Davison A., Jones A.G., Uptake of Cationic Technetium
Complexes in Cultured Human Carcinoma Cells and Human Xenografts, Nucl. Med. Biol., 25,
667-673, 1998.
161. Madar I., Weiss L., Izbicki G., Preferential Accumulation of 3H-Tetraphenyphosphonium
in Non-Small Cell Lung Carcinoma in Mice: Comparison with 99mTc-MIBI, J. Nucl. Med.,
43(2), 234-238, 2002
162. Chiu M. L., Kronauge J. F., Piwnica-Worms D., Effect of Mitochondrial and Plasma
Membrane Potentials on Accumulation of Hexakis (2-Methoxyisobutylisonitrile) Technetium(I)
in Cultured Mouse Fibroblasts, J. Nucl. Med., 31(10), 1646-1653, 1990.
163. Perrin D.D., Armarego W.L.F., Purification of laboratory chemicals; 3ª Ed. Pergamon
Press, Oxford, 1988.
Referências Bibliográficas
241
164. Ishikawa J., Sakamoto H., Nakao S, Wada H., Silver ion selective fluoroionophores based
on anthracene-linked polythiazaalkane or polythiaalkane derivatives, J. Org. Chem., 64(6),
1913-1921, 1999.
165. Schmidt S.P., Trogler W.C., Basolo F., Reagents for transution metal complex and
organometallic syntheses; Inorg. Synth., Ed R. J. Angelici, Wiley, 28, 162, 1990.
166. Ihmels H., Faulhaber K., Sturm C., Bringmann G., Messer K., Gabellini N., Vedaldi D.,
Viola G., Acridizinium Salts as a Novel Class of DNA-Binding and Site-Selective DNA-
Photodamaging Chromophores, Photochem. Photobiol., 74, 505-511, 2001.
167. Viola G., Dall’Acqua F., Gabellini N., Moro S., Vedaldi D., Ihmels H., Indolo[2,3-b]-
Quinolizinium Bromide: An Efficient Intercalator with DNA-Photodamaging Properties, Chem-
BioChem., 3, 550-558, 2002.
168. Wada A., Kozawa S., Instrument for the studies of differential flow dichroism of polymer
solutions, J. Polym. Sci. Part A, 2, 853-864, 1964
169. Sambrook J., Russell D.W., Molecular Cloning, Chapter 17.26, Cold spring Harbor
Laboratory Press, Cold Spring Harbor, NY, 2001.
170. Fair C.K., Molen, Enraf-Nonius, Delft, The Netherlands, 1990.
171. Sheldrick G.M., SHELXS-97, University of Göttingen, Germany, 1997.
172. Farrugia L.J., ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User
Interface (GUI), J. Appl. Cryst. 30, 565, 1997.
Referências Bibliográficas
242
Publicações Resultantes do Trabalho Descrito
Artigos em Revistas de Circulação Internacional
• 2004 - Vitor R. F., Alves S., Correia J. D. G., Paulo A., Santos I. Rhenium(I)- and
technetium(I) tricarbonyl complexes anchored by bifunctional pyrazole-diamine and
pyrazole-dithioether chelators. Journal of Organometallic Chemistry 689: 4764-4774.
• 2005 - Marques F., Paulo A., Campello M. P., Lacerda S., Vítor R., Gano L., Delgado
R., Santos I., Radiopharmaceuticals for targeted radiotherapy. Radiation Protection
Dosimetry 116: 601-604.
• 2006 - Moura C., Vítor R. F., Maria L., Paulo A., Santos I. C., Santos I., Rhenium (V)
oxocomplexes with novel pyrazolyl-based N4- and N3S- donor chelators. Dalton
Transactions, 5630-5640.
• 2007 – Vitor R. F., Correia I., Videira M., Marques F., Paulo A., Pessoa J. C., Viola
G., Martins G. G., Santos I., Pyrazolyl-diamine ligands that bear anthracenyl moieties
and their rhenium(I) tricarbonyl complexes: synthesis, characterization and DNA-
binding properties, ChemBioChem (in press).
• 2007 – Technetium-99m organometallics complexes containing DNA binding groups
for nuclear targeting: synthesis, characterisation and biological evaluation (manuscrito
em preparação)
Patentes
• 2004 - Bifunctional Tridentate Pyrazolyl Containing Ligands for Re and Tc
Tricarbonyl Complexes (WO2004091669) Inventor: Santos, Isabel; Galamba, João
D.C.; Paulo, António; Alves, Susana; Vítor, Rute. Applicant: Mallinckrodt Inc.
Referências Bibliográficas
243
Publicações em Proceedings
• 2006 - Alves S., Vitor R., Raposinho P.D., Marques F., Correia J.D.G., Paulo A.,
Santos I., Metal-based drugs for diagnosis and therapy. Metal Ions in Biology and
Medicine (9) Lisboa. Portugal.