Bioactivation of 2-(alkylthio)-1,3,4-thiadiazoles and 2-(alkylthio)-1,3- benzothiazoles

Chemical Research in Toxicology

Volumn 25, Issue 12, 2012, Pages 2770-2779

  Yang, Yanou ^a   Qiu, Feng ^a   Josephs, Jonathan L ^a   Humphreys, W Griffith ^a   Shu, Yue Zhong ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIAZOLE DERIVATIVE; GLUTATHIONE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SULFONE; SULFOXIDE; THIADIAZOLE DERIVATIVE; UNSPECIFIC MONOOXYGENASE;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DNA ADDUCT; DRUG DESIGN; HUMAN; HUMAN CELL; LIVER MICROSOME; MASS SPECTROMETRY; MOLECULAR MECHANICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; SUBSTITUTION REACTION; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY;

BENZOTHIAZOLES; BIOTRANSFORMATION; GLUTATHIONE; HUMANS; MICROSOMES, LIVER; NADP; THIADIAZOLES;

EID: 84871202984     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx3003998     Document Type: Article

References (24)

1. Baillie, T. A. (2008) Metabolism and toxicity of drugs. Two decades of progress in industrial drug metabolism Chem. Res. Toxicol. 21, 129-137 (Pubitemid 351219714)
2. Liebler, D. C. (2008) Protein damage by reactive electrophiles: Targets and consequences Chem. Res. Toxicol. 21, 117-128 (Pubitemid 351219713)
3. Evans, D. C., Watt, A. P., Nicoll-Griffith, D. A., and Baillie, T. A. (2004) Drug-Protein Adducts: An Industry Perspective on Minimizing the Potential for Drug Bioactivation in Drug Discovery and Development Chem. Res. Toxicol. 17, 3-16 (Pubitemid 38134055)
4. Park, B. K., Boobis, A., Clarke, S., Goldring, C. E. P., Jones, D., Kenna, J. G., Lambert, C., Laverty, H. G., Naisbitt, D. J., Nelson, S., Nicoll-Griffith, D. A., Obach, R. S., Routledge, P., Smith, D. A., Tweedie, D. J., Vermeulen, N., Williams, D. P., Wilson, I. D., and Baillie, T. A. (2011) Managing the challenge of chemically reactive metabolites in drug development Nat. Rev. Drug Discovery 10, 292-306
5. Shu, Y. Z., Johnson, B. M., and Yang, T. J. (2008) Role of biotransformation studies in minimizing metabolism-related liabilities in drug discovery AAPS J. 10, 178-192
6. Kalgutkar, A. S., Gardner, I., Obach, R. S., Shaffer, C. L., Callegari, E., Henne, K. R., Mutlib, A. E., Dalvie, D. K., Lee, J. S., Nakai, Y., O'Donnell, J. P., Boer, J., and Harriman, S. P. (2005) A comprehensive listing of bioactivation pathways of organic functional groups Curr. Drug Metab. 6, 161-225 (Pubitemid 40753853)
7. Teffera, Y., Colletti, A. E., Harmange, J. C., Hollis, L. S., Albrecht, B. K., Boezio, A. A., Liu, J., and Zhao, Z. (2008) Chemical reactivity of methoxy 4-O-aryl quinolines: Identification of glutathione displacement products in vitro and in vivo Chem. Res. Toxicol. 21, 2216-2222
8. Pfefferkorn, J. A., Lou, J., Minich, M. L., Filipski, K. J., He, M., Zhou, R., Ahmed, S., Benbow, J., Perez, A. G., Tu, M., Litchfield, J., Sharma, R., Metzler, K., Bourbonais, F., Huang, C., Beebe, D. A., and Oates, P. J. (2009) Pyridones as glucokinase activators: Identification of a unique metabolic liability of the 4-sulfonyl-2-pyridone heterocycle Bioorg. Med. Chem. Lett. 19, 3247-3252
9. Litchfield, J., Sharma, R., Atkinson, K., Filipski, K. J., Wright, S. W., Pfefferkorn, J. A., Tan, B., Kosa, R. E., Stevens, B., Tu, M., and Kalgutkar, A. S. (2010) Intrinsic electrophilicity of the 4-methylsulfonyl-2-pyridone scaffold in glucokinase activators: Role of glutathione-S-transferases and in vivo quantitation of a glutathione conjugate in rats Bioorg. Med. Chem. Lett. 20, 6262-6267
10. Kalgutkar, A. S., Mascitti, V., Sharma, R., Walker, G. W., Ryder, T., McDonald, T. S., Chen, Y., Preville, C., Basak, A., McClure, K. F., Kohrt, J. T., Robinson, R. P., Munchhof, M. J., and Cornelius, P. (2011) Intrinsic electrophilicity of a 4-substituted-5-cyano-6-(2-methylpyridin-3- yloxy)pyrimidine derivative: Structural characterization of glutathione conjugates in vitro Chem. Res. Toxicol. 24, 269-278
11. Dalvie, D. K., Kalgutkar, A. S., Khojasteh-Bakht, S. C., Obach, R. S., and O'Donnell, J. P. (2002) Biotransformation reactions of five-membered aromatic heterocyclic rings Chem. Res. Toxicol. 15, 269-299 (Pubitemid 34241365)
12. Gupta, J. K., Yadav, R. K., Dudhe, R., and Sharma, P. K. (2010) Recent advancements in the synthesis and pharmacological evaluation of substituted 1, 3, 4-thiadiazole derivatives Int. J. PharmTech Res. 2, 1493-1507
13. Piccionello, A. P. and Guarcello, A. (2010) Bioactive compounds containing benzoxadiazole, benzothiadiazole, benzotriazole Curr. Bioact. Compd. 6, 266-283
14. Pierro, P. and Bellone, G. (2010) Bioactive compounds containing thiadiazole Curr. Bioact. Compd. 6, 243-265
15. Mishra, G., Singh, A. K., and Jyoti, K. (2011) Review article on 1, 3, 4-thiadiazole derivaties and it's pharmacological activities Int. J. ChemTech Res. 3, 1380-1393
16. Kempegowda, Senthil Kumar, G. P., Prakash, D., and Tamiz Mani, T. (2011) Thiadiazoles: Progress report on biological activities Der. Pharma. Chem. 3, 330-341
17. Facchinetti, V., da Reis, R. R., Gomes, C. R. B., and Vasconcelos, T. R. A. (2012) Chemistry and biological activities of 1,3-benzothiazoles Mini-Rev. Org. Chem. 9, 44-53
18. Cooper, J. R. (1958) Studies on 6-uracil methyl sulfone. I. Non-enzymatic metabolism Cancer Res. 18, 1084-1088
19. Koeplinger, K. A., Zhao, Z., Peterson, T., Leone, J. W., Schwende, F. S., Heinrikson, R. L., and Tomasselli, A. G. (1999) Activated sulfonamides are cleaved by glutathione-S-transferases Drug Metab. Dispos. 27, 986-991 (Pubitemid 29409632)
20. Zhao, Z., Koeplinger, K. A., Peterson, T., Conradi, R. A., Burton, P. S., Suarato, A., Heinrikson, R. L., and Tomasselli, A. G. (1999) Mechanism, structure-activity studies, and potential applications of glutathione S-transferase-catalyzed cleavage of sulfonamides Drug Metab. Dispos. 27, 992-998 (Pubitemid 29409633)
21. Conroy, C. W., Schwam, H., and Maren, T. H. (1984) The nonenzymatic displacement of the sulfamoyl group from different classes of aromatic compounds by glutathione and cysteine Drug Metab. Dispos. 12, 614-618 (Pubitemid 14020834)
22. Huwe, J. K., Feil, V. J., Bakke, J. E., and Mulford, D. J. (1991) Studies on the displacement of methylthio groups by glutathione Xenobiotica 21, 179-191
23. Dulik, D. M., Huwe, J. K., Bakke, J. E., Connors, M. S., and Fenselau, C. (1992) Conjugation of polychlorinated agrochemical sulphoxides and sulphones by glutathione Xenobiotica 22, 325-334
24. Laine, R. (2008) Metabolic stability: Main enzymes involved and best tools to assess it Curr. Drug Metab. 9, 921-927