5,6-Dihydrocyclopenta[c][1,2]-dithiole-3(4H)-thione is a promising cancer chemopreventive agent in the urinary bladder

Komiya, 2005, Human glutathione S-transferase A1 polymorphism and susceptibility to urothelial cancer in the Japanese population, Cancer Lett., 221, 55, 10.1016/j.canlet.2004.10.042 Schulz, 1997, Increased frequency of a null-allele for NAD(P)H:quinone oxidoreductase in patients with urological malignancies, Pharmacogenetics, 7, 235, 10.1097/00008571-199706000-00008 Salagovic, 1999, The role of human glutathione S-transferase M1 and T1 in individual susceptibility to bladder cancer, Physiol. Res., 48, 465 Park, 2003, An association between NQO1 genetic polymorphism and risk of bladder cancer, Mutat. Res., 536, 131, 10.1016/S1383-5718(03)00041-X Marcus, 2000, NAT2 slow acetylation and bladder cancer risk: a meta-analysis of 22 case–control studies conducted in the general population, Pharmacogenetics, 10, 115, 10.1097/00008571-200003000-00003 Long, 2000, NAD(P)H:quinone oxidoreductase 1 deficiency increases susceptibility to benzo(a)pyrene-induced mouse skin carcinogenesis, Cancer Res., 60, 5913 Henderson, 1998, Increased skin tumorigenesis in mice lacking pi class glutathione S-transferases, Proc. Natl. Acad. Sci. U.S.A., 95, 5275, 10.1073/pnas.95.9.5275 Fields, 1994, Protection by transfected glutathione S-transferase isozymes against carcinogen-induced alkylation of cellular macromolecules in human MCF-7 cells, Carcinogenesis, 15, 1155, 10.1093/carcin/15.6.1155 Joseph, 1994, NAD(P)H:quinone oxidoreductase1 (DT diaphorase) specifically prevents the formation of benzo(a)pyrene quinone-DNA adducts generated by cytochrome P4501A1 and P450 reductase, Proc. Natl. Acad. Sci. U.S.A., 91, 8413, 10.1073/pnas.91.18.8413 Talalay, 2000, Chemoprotection against cancer by induction of phase 2 enzymes, Biofactors, 12, 5, 10.1002/biof.5520120102 Zhang, 2004, A strategy for cancer prevention: stimulation of the Nrf2–ARE signaling pathway, Mol. Cancer Ther., 3, 885, 10.1158/1535-7163.885.3.7 Dinkova-Kostova, 2005, The role of Keap1 in cellular protective responses, Chem. Res. Toxicol., 18, 1779, 10.1021/tx050217c Ramos-Gomez, 2001, Sensitivity to carcinogenesis is increased and chemoprotective efficacy of enzyme inducers is lost in nrf2 transcription factor-deficient mice, Proc. Natl. Acad. Sci. U.S.A., 98, 3410, 10.1073/pnas.051618798 Fahey, 2002, Sulforaphane inhibits extracellular, intracellular, and antibiotic-resistant strains of Helicobacter pylori and prevents benzo[a]pyrene-induced stomach tumors, Proc. Natl. Acad. Sci. U.S.A., 99, 7610, 10.1073/pnas.112203099 Iida, 2004, Nrf2 is essential for the chemopreventive efficacy of oltipraz against urinary bladder carcinogenesis, Cancer Res., 64, 6424, 10.1158/0008-5472.CAN-04-1906 Kensler, 1999, Development of cancer chemopreventive agents: oltipraz as a paradigm, Chem. Res. Toxicol., 12, 113, 10.1021/tx980185b Ruggeri, 2002, The chemopreventive agent oltipraz possesses potent antiangiogenic activity in vitro, ex vivo, and in vivo and inhibits tumor xenograft growth, Clin. Cancer Res., 8, 267 Ramos-Gomez, 2003, Interactive effects of nrf2 genotype and oltipraz on benzo[a]pyrene-DNA adducts and tumor yield in mice, Carcinogenesis, 24, 461, 10.1093/carcin/24.3.461 Jacobson, 1997, Oltipraz chemoprevention trial in Qidong, People's Republic of China: study design and clinical outcomes, Cancer Epidemiol. Biomark. Prev., 6, 257 Kelley, 2005, Safety and efficacy of weekly oral oltipraz in chronic smokers, Cancer Epidemiol. Biomark. Prev., 14, 892, 10.1158/1055-9965.EPI-04-0585 Egner, 1994, Regulation of phase 2 enzyme induction by oltipraz and other dithiolethiones, Carcinogenesis, 15, 177, 10.1093/carcin/15.2.177 Munday, 2006, Structure–activity relationships in the induction of Phase II enzymes by derivatives of 3H-1,2-dithiole-3-thione in rats, Chem. Biol. Interact., 160, 115, 10.1016/j.cbi.2005.12.011 Legrand, 1953, Sulfuration des composés organiques (IV). Dithiole-1,2-thiones-3 comportant des substituants hydrocarbonés ou des noyaux condensés, Bull. Soc. Chim. Fr., 327 Wakabayashi, 2004, Protection against electrophile and oxidant stress by induction of the phase 2 response: fate of cysteines of the Keap1 sensor modified by inducers, Proc. Natl. Acad. Sci. U.S.A., 101, 2040, 10.1073/pnas.0307301101 Ye, 2001, Total intracellular accumulation levels of dietary isothiocyanates determine their activity in elevation of cellular glutathione and induction of Phase 2 detoxification enzymes, Carcinogenesis, 22, 1987, 10.1093/carcin/22.12.1987 Richie, 1996, Blood glutathione concentrations in a large-scale human study, Clin. Chem., 42, 64, 10.1093/clinchem/42.1.64 Habig, 1974, Glutathione S-transferase. The first enzymatic step in mercapturic acid formation, J. Biol. Chem., 249, 7130, 10.1016/S0021-9258(19)42083-8 Ernster, 1962, DT diaphorase. I. Purification from the soluble fraction of rat-liver cytoplasm, and properties, Biochim. Biophys. Acta, 58, 171, 10.1016/0006-3002(62)90997-6 Dignam, 1983, Accurate transcription initiation by RNA polymerase II in a soluble extract from isolated mammalian nuclei, Nucleic Acids Res., 11, 1475, 10.1093/nar/11.5.1475 Munday, 2008, Inhibition of urinary bladder carcinogenesis by broccoli sprouts, Cancer Res., 68, 1593, 10.1158/0008-5472.CAN-07-5009 Tang, 2004, Isothiocyanates in the chemoprevention of bladder cancer, Curr. Drug Metab., 5, 193, 10.2174/1389200043489027 Zhang, 2006, Induction of GST and NQO1 in cultured bladder cells and in the urinary bladders of rats by an extract of broccoli (Brassica oleracea italica) sprouts, J. Agric. Food Chem., 54, 9370, 10.1021/jf062109h Kausch, 2001, Bladder cancer. II. Molecular aspects and diagnosis, Eur. Urol., 39, 498, 10.1159/000052495