Metabolic profiling of TRPV1 antagonists of the benzothiazole amide series: implications for in vitro genotoxicity assessment

References

• Ashby J, Tennant RW. (1991). Definitive relationships among chemical structure, carcinogenicity and mutagenicity for 301 chemicals tested by the U.S. NTP. Mutat Res 257:229–306.
   PubMed Web of Science ®Google Scholar
• Aubrecht J, Osowski JJ, Persaud P, Cheung JR, Ackerman J, Lopes SH, Ku WW. (2007). Bioluminescent Salmonella reverse mutation assay: a screen for detecting mutagenicity with high throughput attributes. Mutagenesis 22:335–342.
   PubMed Web of Science ®Google Scholar
• Axelsson H, Granhall C, Floby E, Jaksch Y, Svedling M, Sohlenius-Sternbeck AK. (2003). Rates of metabolism of chlorzoxazone, dextromethorphan, 7-ethoxycoumarin, imipramine, quinidine, testosterone and verapamil by fresh and cryopreserved rat liver slices, and some comparisons with microsomes. Toxicol In Vitro 17:481–488.
   PubMed Web of Science ®Google Scholar
• Banoglu E. (2000). Current status of the cytosolic sulfotransferases in the metabolic activation of promutagens and procarcinogens. Curr Drug Metab 1:1–30.
   PubMed Web of Science ®Google Scholar
• Besidski Y, Brown W, Johnstone S, Labrecque D, Munro A, Rotticci D, Walpole C, Zembribo R. (2004). New heterocyclic amides exhibiting an inhibitory activity at the vanilloid receptor 1 (VR1). WO2004096784.
   Google Scholar
• Besidski Y, Brown W, Bylund J, Dabrowski M, Dautrey S, Harter M, Horoszok L, Hu, Y, Johnson D, Johnstone S, Jones P, Leclerc S, Kolmodin K, Kers I, Labarre M, Labrecque D, Laird J, Lundström T, Martino J, Maudet M, Munro A, Nylöf M, Penwell A, Rotticci D, Slaitas A, Sundgren-Andersson A, Svensson M, Terp G, Villanueva H, Walpole C, Zemribo R, Griffin, AM. Potent and Orally Efficacious Benzothiazole Amides as TRPV1 Antagonists. Submitted.
   Google Scholar
• Brandon EF, Raap CD, Meijerman I, Beijnen JH, Schellens JH. (2003). An update on in vitro test methods in human hepatic drug biotransformation research: pros and cons. Toxicol Appl Pharmacol 189:233–246.
   PubMed Web of Science ®Google Scholar
• Cole J, Arlett CF, Green MH, Lowe J, Muriel W. (1983). A comparison of the agar cloning and microtitration techniques for assaying cell survival and mutation frequency in L5178Y mouse lymphoma cells. Mutat Res 111:371–386.
   PubMedGoogle Scholar
• Dobo KL, Obach RS, Luffer-Atlas D, Bercu JP. (2009). A strategy for the risk assessment of human genotoxic metabolites. Chem Res Toxicol 22:348–356.
   PubMed Web of Science ®Google Scholar
• Floby E, Johansson J, Hoogstraate J, Hewitt NJ, Hill J, Sohlenius-Sternbeck AK. (2009). Comparison of intrinsic metabolic clearance in fresh and cryopreserved human hepatocytes. Xenobiotica 39:656–662.
   PubMed Web of Science ®Google Scholar
• Glatt H. (1997). Bioactivation of mutagens via sulfation. FASEB J, 11, 314–321.
   PubMed Web of Science ®Google Scholar
• Glatt H. (2000). Sulfotransferases in the bioactivation of xenobiotics. Chem Biol Interact 129:141–170.
   PubMed Web of Science ®Google Scholar
• ICH Harmonised Tripartite Guideline S2B. Genotoxicity: A Standard Battery for Genotoxicity Testing of Pharmaceuticals, S2B, Step 4, 16 July 1997.
   Google Scholar
• ICH Harmonised Tripartite Guideline M3. Guidance on Nonclinical Safety Studies for the Conduct of Human Clinical Trials and Marketing Authorization for Pharmaceuticals M3 (R2), Step 4, 11 June 2009.
   Google Scholar
• Ku WW, Bigger A, Brambilla G, Glatt H, Gocke E, Guzzie PJ, Hakura A, Honma M, Martus HJ, Obach RS, Roberts S; Strategy Expert Group, IWGT. (2007). Strategy for genotoxicity testing–metabolic considerations. Mutat Res 627:59–77.
   PubMed Web of Science ®Google Scholar
• Li Y, Lindsay J, Wang L-L, Zhou S-F. (2008). Structure, function and polymorphism of human cytosolic sulfotransferases. Curr Drug Metab, 9, 99–105.
   Google Scholar
• Maron DM, Ames BN. (1983). Revised methods for the Salmonella mutagenicity test. Mutat Res 113:173–215.
   PubMed Web of Science ®Google Scholar
• Shimada T, Oda Y, Yamazaki H, Mimura M, Guengerich, FP. (1994). SOS function tests for studies of chemical carcinogenesis in Salmonella typhimurium TA 1535/pSK1002, NM2009, and NM3009 In Adolph, KW, ed. Methods in Molecular Genetics Vol. 5, Gene and Chromosome Analysis. Academic Press, Orlando, 342–55.
   Google Scholar
• Singh NP, McCoy MT, Tice RR, Schneider EL. (1988). A simple technique for quantitation of low levels of DNA damage in individual cells. Exp Cell Res 175:184–191.
   PubMed Web of Science ®Google Scholar
• Soars MG, McGinnity DF, Grime K, Riley RJ. (2007). The pivotal role of hepatocytes in drug discovery. Chem Biol Interact 168:2–15.
   PubMed Web of Science ®Google Scholar
• Sohlenius-Sternbeck AK, Afzelius L, Prusis P, Neelissen J, Hoogstraate J, Johansson J, Floby E, Bengtsson A, Gissberg O, Sternbeck J, Petersson C. (2010). Evaluation of the human prediction of clearance from hepatocyte and microsome intrinsic clearance for 52 drug compounds. Xenobiotica 40:637–649.
   PubMed Web of Science ®Google Scholar
• Szallasi A, Cortright DN, Blum CA, Eid SR. (2007). The vanilloid receptor TRPV1: 10 years from channel cloning to antagonist proof-of-concept. Nat Rev Drug Discov 6:357–372.
   PubMed Web of Science ®Google Scholar
• Testa B, Krämer SD. (2007). The biochemistry of drug metabolism–an introduction: part 3. Reactions of hydrolysis and their enzymes. Chem Biodivers 4:2031–2122.
   PubMed Web of Science ®Google Scholar
• Tice RR, Agurell E, Anderson D, Burlinson B, Hartmann A, Kobayashi H, Miyamae Y, Rojas E, Ryu JC, Sasaki YF. (2000). Single cell gel/comet assay: guidelines for in vitro and in vivo genetic toxicology testing. Environ Mol Mutagen 35:206–221.
   PubMed Web of Science ®Google Scholar
• Venitt S, Parry JM. (1984). Mutagenicity testing: a practical approach. IRL Press Oxford, England, ISBN No.0-904147-72-X, 45–98.
   Google Scholar
• Walker K, Ginsberg G, Hattis D, Johns DO, Guyton KZ, Sonawane B. (2009). Genetic polymorphism in N-Acetyltransferase (NAT): Population distribution of NAT1 and NAT2 activity. J Toxicol Environ Health B Crit Rev 12:440–472.
   PubMed Web of Science ®Google Scholar
• Wiklund SJ, Agurell E. (2003). Aspects of design and statistical analysis in the Comet assay. Mutagenesis 18:167–175.
   PubMedGoogle Scholar
• Zhang Z, Zhu M, Tang W. (2009). Metabolite identification and profiling in drug design: current practice and future directions. Curr Pharm Des 15:2220–2235.
   PubMed Web of Science ®Google Scholar