Amalgamation of in-silico, in-vitro and in-vivo approach to establish glabridin as a potential CYP2E1 inhibitor

References

• Akachi, T., et al., 2010. Hepatoprotective effects of flavonoids from shekwasha (Citrus depressa) against D-galactosamine-induced liver injury in rats. Journal of Nutritional Science and Vitaminology, 56 (1), 60–67.
   PubMed Web of Science ®Google Scholar
• Akbulak, O., et al., 2018. Evaluation of oxidative stress via protein expression of glutathione S-transferase and cytochrome p450 (CYP450) ısoenzymes in psoriasis vulgaris patients treated with methotrexate. Cutaneous and Ocular Toxicology, 37 (2), 180–185.
   PubMed Web of Science ®Google Scholar
• Aoki, F., et al., 2007. Clinical safety of licorice flavonoid oil (LFO) and pharmacokinetics of glabridin in healthy humans. Journal of the American College of Nutrition, 26 (3), 209–218.
   PubMed Web of Science ®Google Scholar
• Arora, S., et al., 2015. In vivo prediction of CYP-mediated metabolic interaction potential of formononetin and biochanin A using in vitro human and rat CYP450 inhibition data. Toxicology Letters, 239 (1), 1–8.
   PubMed Web of Science ®Google Scholar
• Barone, G.W., et al., 2000. Drug interaction between St. John's wort and cyclosporine. The Annals of Pharmacotherapy, 34 (9), 1013–1016.
   PubMed Web of Science ®Google Scholar
• Bu, H.Z., et al., 2000. High-throughput cytochrome P450 inhibition screening via cassette probe-dosing strategy. IV. Validation of a direct injection on-line guard cartridge extraction/tandem mass spectrometry method for simultaneous CYP3A4, 2D6 and 2E1 inhibition assessment. Rapid Communications in Mass Spectrometry, 14 (20), 1943–1948.
   PubMed Web of Science ®Google Scholar
• Cederbaum, A.I., Lu, Y., and Wu, D., 2009. Role of oxidative stress in alcohol-induced liver injury. Archives of Toxicology, 83 (6), 519–548.
   PubMed Web of Science ®Google Scholar
• Chen, L.G., et al., 2017. Hepatoprotective effects of litchi (Litchi chinensis) procyanidin A2 on carbon tetrachloride-induced liver injury in ICR mice. Experimental and Therapeutic Medicine, 13 (6), 2839–2847.
   PubMed Web of Science ®Google Scholar
• Choi, J.S., Piao, Y.J., and Kang, K.W., 2011. Effects of quercetin on the bioavailability of doxorubicin in rats: role of CYP3A4 and P-gp inhibition by quercetin. Archives of Pharmacal Research, 34 (4), 607–613.
   PubMed Web of Science ®Google Scholar
• Discovery Studio Predictive Science Application | Dassault Systèmes BIOVIA. 2019. [Accessed 19 December 2019]. https://www.3dsbiovia.com/products/collaborative-science/biovia-discovery-studio/
   Google Scholar
• Dogra, A., et al., 2018. Intervention of curcumin on oral pharmacokinetics of daclatasvir in rat: A possible risk for long-term use. Phytotherapy Research: PTR, 32 (10), 1967–1974.
   PubMed Web of Science ®Google Scholar
• Dong, G., Zhou, Y., and Song, X., 2018. In vitro inhibitory effects of bergenin on human liver cytochrome P450 enzymes. Pharmaceutical Biology, 56 (1), 620–625.
   PubMed Web of Science ®Google Scholar
• Fuhrman, B., et al., 1997. Licorice extract and its major polyphenol glabridin protect low-density lipoprotein against lipid peroxidation: in vitro and ex vivo studies in humans and in atherosclerotic apolipoprotein E-deficient mice. The American Journal of Clinical Nutrition, 66 (2), 267–275.
   PubMed Web of Science ®Google Scholar
• Ingelman-Sundberg, M., et al., 1993. Ethanol-inducible cytochrome P450 2E1: genetic polymorphism, regulation and possible role in the etiology of alcohol-induced liver disease. Alcohol (Fayetteville, N.Y.), 10 (6), 447–452.
   PubMed Web of Science ®Google Scholar
• Kang, J.S., et al., 2005. Glabridin, an isoflavan from licorice root, inhibits inducible nitric-oxide synthase expression and improves survival of mice in experimental model of septic shock. The Journal of Pharmacology and Experimental Therapeutics, 312 (3), 1187–1194.
   PubMed Web of Science ®Google Scholar
• Kim, M.J., et al., 2005. High-throughput screening of inhibitory potential of nine cytochrome P450 enzymes in vitro using liquid chromatography/tandem mass spectrometry. Rapid Communications in Mass Spectrometry : RCM, 19 (18), 2651–2658.
   PubMed Web of Science ®Google Scholar
• Kumar, V., et al., 2020b. A Multi-layered Variable Selection Strategy for QSAR Modeling of Butyrylcholinesterase Inhibitors. Current Topics in Medicinal Chemistry, 20 (18), 1601–1627.
   PubMed Web of Science ®Google Scholar
• Kumar, V., et al., 2020a. Exploring 2D-QSAR for prediction of beta-secretase 1 (BACE1) inhibitory activity against Alzheimer's disease. SAR and QSAR in Environmental Research, 31 (2), 87–133.
   PubMed Web of Science ®Google Scholar
• Kwon, H.S., Oh, S.M., and Kim, J.K., 2008. Glabridin, a functional compound of liquorice, attenuates colonic inflammation in mice with dextran sulphate sodium-induced colitis. Clinical and Experimental Immunology, 151 (1), 165–173.
   PubMed Web of Science ®Google Scholar
• Laethem, R.M., et al., 1993. Formation of 19 (S)-, 19 (R)-, and 18 (R)-hydroxy eicosatetraenoic acids by alcohol-inducible cytochrome P450 2E1. Journal of Biological Chemistry., 268 (17), 12912–12918.
   PubMed Web of Science ®Google Scholar
• Lieber, C.S., 1997. Cytochrome P-4502E1: its physiological and pathological role. Physiological Reviews, 77 (2), 517–544.
   PubMed Web of Science ®Google Scholar
• Liu, H., and Baliga, R., 2003. Cytochrome P450 2E1 null mice provide novel protection against cisplatin-induced nephrotoxicity and apoptosis. Kidney International, 63 (5), 1687–1696.
   PubMed Web of Science ®Google Scholar
• Lu, Y., et al., 2008. Cytochrome P450 2E1 contributes to ethanol-induced fatty liver in mice. Hepatology (Baltimore, Md.), 47 (5), 1483–1494.
   PubMed Web of Science ®Google Scholar
• Lucas, D., et al., 1993. High-performance liquid chromatographic determination of chlorzoxazone and 6-hydroxychlorzoxazone in serum: a tool for indirect evaluation of cytochrome P4502E1 activity in humans. Journal of Chromatography B: Biomedical Sciences and Applications, 622 (1), 79–86.
   Web of Science ®Google Scholar
• Mai, I., et al., 2000. Hazardous pharmacokinetic interaction of Saint John's wort (Hypericum perforatum) with the immunosuppressant cyclosporin. International Journal of Clinical Pharmacology and Therapeutics, 38 (10), 500–502.
   PubMed Web of Science ®Google Scholar
• Manyike, P.T., et al., 2000. Contribution of CYP2E1 andCYP3A to acetaminophen reactive metabolite formation. Clinical Pharmacology & Therapeutics., 67 (3), 275–282.
   PubMed Web of Science ®Google Scholar
• Martignoni, M., Groothuis, G.M., and de Kanter, R., 2006. Species differences between mouse, rat, dog, monkey and human CYP-mediated drug metabolism, inhibition and induction. Expert Opinion on Drug Metabolism & Toxicology, 2 (6), 875–894.
   PubMed Web of Science ®Google Scholar
• Meng, X.Y., et al., 2011. Molecular docking: a powerful approach for structure-based drug discovery. Current Computer-Aided Drug Design, 7 (2), 146–157.
   PubMed Web of Science ®Google Scholar
• Mishin, V.M., et al., 1998. Chlorzoxazone pharmacokinetics as a marker of hepatic cytochrome P4502E1 in humans. The American Journal of Gastroenterology, 93 (11), 2154–2161.
   PubMed Web of Science ®Google Scholar
• Mohos, V., et al., 2020. Effects of chrysin and its major conjugated metabolites chrysin-7-sulfate and chrysin-7-glucuronide on cytochrome p450 enzymes and on OATP, P-gp, BCRP, and MRP2 transporters. Drug Metabolism and Disposition: The Biological Fate of Chemicals, 48 (10), 1064–1073.
   PubMed Web of Science ®Google Scholar
• Momany, F.A., and Rone, R., 1992. Validation of the general purpose QUANTA® 3.2/CHARMm® force field. Journal of Computational Chemistry, 13 (7), 888–900.
   Web of Science ®Google Scholar
• Moon, Y.J., et al., 2008. Quercetin pharmacokinetics in humans. Biopharmaceutics & Drug Disposition, 29 (4), 205–217.
   PubMed Web of Science ®Google Scholar
• Murzin, A.G., et al., 1995. SCOP: a structural classification of proteins database for the investigation of sequences and structures. Journal of Molecular Biology, 247 (4), 536–540.
   PubMed Web of Science ®Google Scholar
• Neuman, M.G., et al., 2001. CYP2E1-mediated modulation of valproic acid-induced hepatocytotoxicity. Clinical Biochemistry, 34 (3), 211–218.
   PubMed Web of Science ®Google Scholar
• Pandit, A., Sachdeva, T., and Bafna, P., 2012. Drug-induced hepatotoxicity: a review. J Appl Pharm Sci, 2, 233–243.
   Google Scholar
• Patel, M., Tang, B.K., and Kalow, W., 1992. Variability of acetaminophen metabolism in Caucasians and Orientals. Pharmacogenetics, 2, 38–45.
   PubMedGoogle Scholar
• Peter, R., et al., 1990. Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450IIE1. Chemical Research in Toxicology, 3 (6), 566–573.
   PubMed Web of Science ®Google Scholar
• Pingili, R.B., Pawar, A.K., and Challa, S.R., 2019. Effect of chrysin on the formation of N-acetyl-p-benzoquinoneimine, a toxic metabolite of paracetamol in rats and isolated rat hepatocytes. Chemico-Biological Interactions., 302, 123–134.
   PubMed Web of Science ®Google Scholar
• Piscitelli, S.C., et al., 2002. The effect of garlic supplements on the pharmacokinetics of saquinavir. Clinical Infectious Diseases: An Official Publication of the Infectious Diseases Society of America, 34 (2), 234–238.
   PubMed Web of Science ®Google Scholar
• Puratchikody, A., et al., 2016. 3-D structural interactions and quantitative structural toxicity studies of tyrosine derivatives intended for safe potent inflammation treatment. Chemistry Central Journal., 10, 1–19.
   PubMedGoogle Scholar
• Rastogi, H., and Jana, S., 2014. Evaluation of inhibitory effects of caffeic acid and quercetin on human liver cytochrome p450 activities. Phytotherapy Research : PTR, 28 (12), 1873–1878.
   PubMed Web of Science ®Google Scholar
• Schmider, J., et al., 1996. Characterization of six in vitro reactions mediated by human cytochrome P450: application to the testing of cytochrome P450-directed antibodies. Pharmacology, 52 (2), 125–134.
   PubMed Web of Science ®Google Scholar
• Siegers, C.P., et al., 1982. Effects of dithiocarb and (+)-catechin against carbon tetrachloride-alcohol-induced liver fibrosis. Agents and Actions, 12 (5-6), 743–748.
   PubMedGoogle Scholar
• Singh, V., Pal, A., and Darokar, M.P., 2015. A polyphenolic flavonoid glabridin: oxidative stress response in multidrug-resistant Staphylococcus aureus. Free Radical Biology & Medicine, 87, 48–57.
   PubMed Web of Science ®Google Scholar
• USFDA. In vitro metabolism- and transporter-mediated drug-drug interaction studies, 2017. Silver Spring, MD: U.S. Food and Drug Administration.
   Google Scholar
• USFDA. SCOGS (Select Committee on GRAS Substances), 2019. Silver Spring, MD: U.S. Food and Drug Administration.
   Google Scholar
• Vissiennon, C., et al., 2012. Route of administration determines the anxiolytic activity of the flavonols kaempferol, quercetin and myricetin-are they prodrugs? The Journal of Nutritional Biochemistry, 23 (7), 733–740.
   PubMed Web of Science ®Google Scholar
• Wu, G., et al., 2003. Detailed analysis of grid-based molecular docking: A case study of CDOCKER-A CHARMm-based MD docking algorithm. Journal of Computational Chemistry, 24 (13), 1549–1562.
   PubMed Web of Science ®Google Scholar
• Xie, W., et al., 2016. Hepatoprotective effect of isoquercitrin against acetaminophen-induced liver injury. Life Sciences, 152, 180–189.
   PubMed Web of Science ®Google Scholar
• Yan, T., et al., 2016. Glycyrrhizin protects against acetaminophen-induced acute liver injury via alleviating tumor necrosis factor α-Mediated Apoptosis. Drug Metabolism and Disposition: The Biological Fate of Chemicals, 44 (5), 720–731.
   PubMed Web of Science ®Google Scholar
• Zhao, L., and Pickering, G., 2011. Paracetamol metabolism and related genetic differences. Drug Metabolism Reviews, 43 (1), 41–52.
   PubMed Web of Science ®Google Scholar
• Zhao, L., et al., 2019. Protective effect of 7, 3′, 4′-flavon-3-ol (fisetin) on acetaminophen-induced hepatotoxicity in vitro and in vivo. Phytomedicine, 58, 152865.
   PubMed Web of Science ®Google Scholar