Thiazolidin-2-cyanamides derivatives as novel potent Escherichia coli β-glucuronidase inhibitors and their structure–inhibitory activity relationships

References

• Guillemette C. Pharmacogenomics of human UDP-glucuronosyltransferase enzymes. Pharmacogenomics J 2003;3:136–58.
   PubMed Web of Science ®Google Scholar
• de Graaf M, Boven E, Scheeren HW, et al. Beta-glucuronidase-mediated drug release. Curr Pharm Des 2002;8:1391–403.
   PubMed Web of Science ®Google Scholar
• Garcia C, Barriga A, Diaz JC, et al. Route of metabolization and detoxication of paralytic shellfish toxins in humans. Toxicon 2010;55:135–44.
   PubMed Web of Science ®Google Scholar
• Cheng KW, Tseng CH, Tzeng CC, et al. Pharmacological inhibition of bacterial β-glucuronidase prevents irinotecan-induced diarrhea without impairing its antitumor efficacy in vivo. Pharmacol Res 2019;139:41–9.
   PubMed Web of Science ®Google Scholar
• Alexander JL, Wilson ID, Teare J, et al. Gut microbiota modulation of chemotherapy efficacy and toxicity. Nat Rev Gastroenterol Hepatol 2017;14:356–65.
   PubMed Web of Science ®Google Scholar
• LoGuidice A, Wallace BD, Bendel L, et al. Pharmacologic targeting of bacterial β-glucuronidase alleviates nonsteroidal anti-inflammatory drug-induced enteropathy in mice. J Pharmacol Exp Ther 2012;341:447–54.
   PubMed Web of Science ®Google Scholar
• Tobin P, Clarke S, Seale JP, et al. The in vitro metabolism of irinotecan (CPT-11) by carboxylesterase and β-glucuronidase in human colorectal tumours. Br J Clin Pharmacol 2006;62:122–9.
   PubMed Web of Science ®Google Scholar
• Wallace BD, Roberts AB, Pollet RM, et al. Structure and inhibition of microbiome β-Glucuronidases essential to the alleviation of cancer drug toxicity. Chem Biol 2015;22:1238–49.
   PubMedGoogle Scholar
• Saitta KS, Zhang C, Lee K, et al. Bacterial β-glucuronidase inhibition protects mice against enteropathy induced by indomethacin, ketoprofen or diclofenac: mode of action and pharmacokinetics. Xenobiotica 2014;44:28–35.
   PubMed Web of Science ®Google Scholar
• Paul A, Nosipho C, Nagaraju K, et al. Therapeutic signifificance of β-glucuronidase activity and its inhibitors: a review. Eur J Med Chem 2020;187:111921.
   PubMed Web of Science ®Google Scholar
• Kong R, Liu T, Zhu X, et al. Old drug new use-amoxapine and its metabolites as potent bacterial β-glucuronidase inhibitors for alleviating cancer drug toxicity. Clin Cancer Res 2014;20:3521–30.
   PubMed Web of Science ®Google Scholar
• Salar U, Khan KM, Syed S, et al. Synthesis, in vitro β-glucuronidase inhibitory activity and in silico studies of novel (E)-4-Aryl-2-(2-(pyren-1-ylmethylene)hydrazinyl)thiazoles. Bioorg Chem 2017;70:199–209.
   PubMed Web of Science ®Google Scholar
• Taha M, Imran S, Alomari M, et al. Synthesis of oxadiazole-coupled-thiadiazole derivatives as a potent β-glucuronidase inhibitors and their molecular docking study. Bioorg Med Chem 2019;27:3145–55.
   PubMed Web of Science ®Google Scholar
• Taha M, Ismail NH, Imran S, et al. Synthesis of novel benzohydrazone-oxadiazole hybrids as β-glucuronidase inhibitors and molecular modeling studies. Bioorg Med Chem Lett 2015;23:7394–404.
   Web of Science ®Google Scholar
• Taha M, Baharudin MS, Ismail NH, et al. Synthesis and in silico studies of novel sulfonamides having oxadiazole ring: as β-glucuronidase inhibitors. Bioorg Chem 2017;71:86–96.
   PubMed Web of Science ®Google Scholar
• Zawawi NK, Taha M, Ahmat N, et al. Novel 2,5-disubtituted-1,3,4-oxadiazoles with benzimidazole backbone: a new class of β-glucuronidase inhibitors and in silico studies. Bioorg Med Chem 2015;23:3119–25.
   PubMed Web of Science ®Google Scholar
• Rani M, Yusuf M, Khan SA, et al. Synthesis, studies and in-vitro antibacterial activity of N-substituted 5-(furan-2-yl)-phenyl pyrazolines. Arab J Chem 2015;8:174–80.
   Web of Science ®Google Scholar
• Huo JQ, Ma LY, Zhang Z, et al. Synthesis and biological activity of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl) amides derivatives. Chin Chem Lett 2016;27:1547–50.
   Web of Science ®Google Scholar
• Tao H, Tian H, Jiang S, et al. Synthesis and biological evaluation of 1,3,4-thiadiazole derivatives as type III secretion system inhibitors against Xanthomonas oryzae. Pestic Biochem Physiol 2019;160:87–94.
   PubMed Web of Science ®Google Scholar
• Cui ZN, Li XH, Nishida Y. Synthesis and bioactivity of novel carvacrol and thymol derivatives containing 5-phenyl-2-furan. Lett Drug Des Discov 2014;11:877–85.
   Web of Science ®Google Scholar
• Xiang XW, Tao H, Jiang S, et al. Synthesis and bioactivity of thiazolidin-2-cyanamide derivatives against type III secretion system of Xanthomonas oryzae on rice. Pestic Biochem Physiol 2018;149:89–97.
   PubMed Web of Science ®Google Scholar
• Cui ZN, Li Y, Ling Y, et al. New class of potent antitumor acylhydrazone derivatives containing furan. Eur J Med Chem 2010;45:5576–84.
   PubMed Web of Science ®Google Scholar
• Jiang S, He M, Xiang XW, et al. Novel S-thiazol-2-yl-furan-2-carbothioate derivatives as potential T3SS inhibitors against Xanthomonas oryzae on rice. J Agric Food Chem 2019;67:11867–76.
   PubMed Web of Science ®Google Scholar
• Wei B, Wang PP, Yan ZX, et al. Characteristics and molecular determinants of a highly selective and efficient glycyrrhizin-hydrolyzing β-glucuronidase from Staphylococcus pasteuri 3I10. Appl Microbiol Biotechnol 2018;102:9193–205.
   PubMed Web of Science ®Google Scholar
• Wei B, Yang W, Yan ZX, et al. Prenylflavonoids sanggenon C and kuwanon G from mulberry (Morus alba L.) as potent broad-spectrum bacterial β-glucuronidase inhibitors: biological evaluation and molecular docking studies. J Funct Foods 2018;48:210–9.
   Web of Science ®Google Scholar
• Xin H, Qi XY, Wu JJ, et al. Assessment of the inhibition potential of Licochalcone A against human UDP-glucuronosyltransferases. Food Chem Toxicol 2016;90:112–22.
   PubMed Web of Science ®Google Scholar
• Lv X, Wang XX, Hou J, et al. Comparison of the inhibitory effects of tolcapone and entacapone against human UDP-glucuronosyltransferases. Toxicol Appl Pharmacol 2016;301:42–9.
   PubMed Web of Science ®Google Scholar
• Weng ZM, Wang P, Ge GB, et al. Structure-activity relationships of flavonoids as natural inhibitors against E. coli β-glucuronidase. Food Chem Toxicol 2017;109:975–83.
   PubMed Web of Science ®Google Scholar
• Salar U, Taha M, Ismail NH, et al. Thiadiazole derivatives as new class of β-glucuronidase inhibitors. Bioorg Med Chem 2016;24:1909–18.
   PubMed Web of Science ®Google Scholar
• Taha M, Almandil NB, Rashid U, et al. 2,5-Disubstituted thiadiazoles as potent β-glucuronidase inhibitors; synthesis, in vitro and in silico studies. Bioorg Chem 2019;91:103126.
   PubMed Web of Science ®Google Scholar
• Khan KM, Karim A, Saied S, et al. Evaluation of the thiazole Schiff bases as β-glucuronidase inhibitors and their in silico studies. Mol Divers 2014;18:295–306.
   PubMed Web of Science ®Google Scholar
• Wallace BD, Wang H, Lane KT, et al. Alleviating cancer drug toxicity by inhibiting a bacterial enzyme. Science 2010;330:831–5.
   PubMed Web of Science ®Google Scholar
• Li XN, Hua LX, Zhou TS, et al. Cinnamic acid derivatives: inhibitory activity against Escherichia coli β-glucuronidase and structure-activity relationships. J Enzym Inhib Med Chem 2020;35:1372–8.
   PubMed Web of Science ®Google Scholar