Synthesis of 131I-labeled glucose-conjugated inhibitors of 06-methylguanine-DNA methyltransferase (MGMT) and comparison with nonconjugated inhibitors as potential tools for in vivo MGMT imaging

Journal of Medicinal Chemistry

Volumn 49, Issue 1, 2006, Pages 263-272

  Mühlhausen, Ute ^a   Schirrmacher, Ralf ^a   Piel, Markus ^a   Lecher, Bernd ^a   Briegert, Manuela ^a   Piee Staffa, Andrea ^a   Kaina, Bernd ^a   Rösch, Frank ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 6 (3 IODOBENZYLOXY) 9H PURINE 6 O (5 IODOBENZYL)GUANINE I 131; 2 AMINO 6 (5 IODOTHENYL) 9H PURINE 6 O (5 IODOTHENYL)GUANINE I 131; ENZYME INHIBITOR; GUANINE DERIVATIVE; IODINE 131; METHYLATED DNA PROTEIN CYSTEINE METHYLTRANSFERASE; METHYLATED DNA PROTEIN CYSTEINE METHYLTRANSFERASE INHIBITOR; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; DRUG DERIVATIVE; GLUCOSE; GUANINE; IODINE; O(6) (5 IODOBENZYL)GUANINE; O(6) (5 IODOTHENYL)GUANINE; O(6)-(5-IODOBENZYL)GUANINE; O(6)-(5-IODOTHENYL)GUANINE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG CONJUGATION; DRUG DISTRIBUTION; DRUG PURIFICATION; DRUG SYNTHESIS; DRUG TARGETING; DRUG UPTAKE; ENZYME ANALYSIS; ENZYME INHIBITION; HELA CELL; HUMAN; HUMAN CELL; IMAGING SYSTEM; IN VIVO STUDY; INCUBATION TIME; ISOTOPE LABELING; MALE; MOUSE; NONHUMAN; RADIOIODINATION; TUMOR BLOOD FLOW; TUMOR CELL; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; DRUG ANTAGONISM; DRUG SCREENING; IN VITRO STUDY; NUDE MOUSE; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TIME; XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; ENZYME INHIBITORS; GLUCOSE; GUANINE; HELA CELLS; HUMANS; IODINE ISOTOPES; MICE; MICE, NUDE; MOLECULAR STRUCTURE; O(6)-METHYLGUANINE-DNA METHYLTRANSFERASE; STRUCTURE-ACTIVITY RELATIONSHIP; TIME FACTORS; TRANSPLANTATION, HETEROLOGOUS; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 30444459779     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050588q     Document Type: Article

References (33)

1. Tew, K.; Colvin, M.; Chabner, B. A. Alkylating agents. In Cancer chemotherapy: principles and practise, 2nd ed.; Chabner, B. A., Longo, D. L., Eds.; Lippincott, J. B.: Philadelphia, 1995.
2. 6-benzylguanine analogues on sensitivity of human tumor cells to the cytotoxic effects of alkylating agents. Cancer Res. 1991, 51, 3367-3373.
3. 6-alkylation of deoxyguanosine to the mutagenicity and carcinogenicity of nitrosamines and nitrosamides. Nature 1969, 223, 206-207.
4. (c) Singer, B. N-nitroso alkylating agents: Formation and persistence of alkyl derivatives in mammalian nucleic acids as contributing factors in carcinogenesis. J. Nat. Cancer Inst. 1979, 62, 1329-1339.
5. (d) Saffhill, R.; Margison, G. P.; O'Connor, P. J. Mechanisms of carcinogenesis induced by alkylating agents. Biochim. Biophys. Acta 1985, 823, 111-145.
6. 6- alkylguanine. FASEB J. 1992, 6, 2302-2310.
7. 6-Alkylguanine-DNA alkyltransferase inactivation in cancer chemotherapy. Mini Rev. Med. Chem. 2003, 3, 471-485.
8. Christmann, M.; Tomicic, M. T.; Roos, W.; Kaina, B. Mechanisms of human DNA repair: An update. Toxicology 2003, 193, 3-34.
9. Erickson, L. C. The role of O-6 methylguanine DNA methyltransferase (MGMT) in drug resistance and strategies for its inhibition. Seminars Cancer Biol. 1991, 2, 257-265.
10. D'Incalci, M.; Citti, L.; Taverna, P.; Cata Pano, C. V. Importance of the DNA repair enzyme O6-alkylguanine alkyltransferase (AT) in cancer chemotherapy. Cancer Treat. Rev. 1988, 15, 279-292.
11. 6-substituted guanine derivatives and their application in medicine. Curr. Org. Synth. 2005, 2, 547-562.
12. Moschel, R. C.; McDougall, M. G.; Dolan, M. E.; Stine, L.; Pegg, A. E. Structural features of substituted purine derivatives compatible with depletion of human O6-alkylguanine DNA alkyltransferase. J. Med. Chem. 1992, 35, 4486-4491.
13. 6- benzylguanine provides a means to evaluate the role of this protein in protection against carcinogenic and therapeutic alkylating agents. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 5368-5372.
14. 6-(hetarylmethyl)guanines having basic rings in the side chain. J. Med. Chem. 1998, 41, 5265-5271.
15. 6-benzylguanine for patients with nitrosourea-resistant recurrent or progressive malignant glioma. J. Clin. Oncol. 2002, 20, 2277-2283.
16. 6-methylguanine-DNA methyltransferase (MGMT): Synthesis, molecular modeling, and structure-activity relationship. J. Med. Chem. 2001, 44, 4050-4061.
17. 18F]fluoroethyl)7H-purin-2-yl-amine. Appl. Radiat. Isot. 2002, 56, 511-517.
18. 6-benzylguanine derivatives as new potential PET tumor imaging agents for the DNA repair protein O6-alkylguanine-DNA alkyltransferase. J. Lab. Compds. Radiopharm. 2002, 45, 1239-1252.
19. 11C]-[(methoxymethyl)]-benzylguanines, new potential PET breast cancer imaging agents for the DNA repair protein AGT. Bioorg. Med. Chem. Lett. 2003, 13, 641-644.
20. 6-benzylguanine derivatives by phase transfer catalysis. Synth. Commun. 2003, 33, 941-952.
21. 6-alkyl-guanine-DNA alkyltransferase in breast cancer. Nucl. Med. Biol. 2003, 30, 405-415.
22. 131I]iodo-benzyloxy)-9H-purin-2-ylamine. Bioconjugate Chem. 2000, 6, 868-875.
23. 131I]-Iodobenzylguanine: Improved synthesis and further evaluation of a potential agent for imaging of alkylguanine-DNA alkyltransferase. Bioconjugate Chem. 2004, 15, 402-408.
24. 6-methylguanine-DNA methyltransferase (MGMT) status of tumour tissue. Tetrahedron Lett. 2002, 43, 6301-6304.
25. 6-methylguanine-DNA methyltransferase (MGMT) by glucose conjugated inhibitors: Comparison with non-conjugated inhibitors and effect on fotemustin-induced cell death. J. Pharmacol. Exp. Ther. 2004, 311, 585-593.
26. D'Auria, M.; De Mico, A.; D'Onofrio, F.; Piancatelli, G. Synthesis of naturally occurring bithiophenes: A photochemical approach. J. Org. Chem. 1987, 52, 5243-5247.
27. Kilburis, J.; Lister, J. H. Nucleophilic Displacement of the trimethyl-ammonia-group: A new route to fluoropyridines. J. Chem. Soc. (C) 1971, 3942-3947.
28. 6-substituted guanine derivatives from alcohols with poor nucleophilicity. Synthesis 2002, 4, 538-542.
29. Chumpradit, S.; Kung, M. P.; Billings, J.; Mach, R.; Kung, H. F. Fluorinated and iodinated dopamine agents: D2 imaging agents for PET and SPECT. J. Med. Chem. 1993, 36, 221-228.
30. Moerlein, S. M. Regiospecific aromatic radioiodination via no-carrier-added copper(I) chloride-assisted iododebromination. Radiochim Acta 1990, 50, 55-61.
31. 6- benzylguanine. Int. J. Pharm. 1993, 90, 239-246.
32. Amersham Biosciences. Radiochemical Decomposition-A Guide to the Properties and Storage of Radiolabeled Compound, p 11.
33. Lindhorst, T. K. Essentials of Carbohydrate Chemistry and Biochemistry; Wiley-VCH: Weinheim, 2000; p 89.