Inhibitory effects of Thai herbal extracts on the cytochrome P450 3A-mediated the metabolism of gefitinib, lapatinib and sorafenib

Toxicology Reports - Tập 9 - Trang 1846-1852 - 2022
Chumaphorn Rodseeda1,2,3, Paveena Yamanont4, Darawan Pinthong4, Porntipa Korprasertthaworn1,3,4
1Graduate Program in Toxicology, Faculty of Science, Mahidol University, Bangkok, Thailand
2Department of Occupational Health and Safety, School of Public Health, University of Phayao, Phayao, Thailand
3Center of Excellence on Environmental Health and Toxicology (EHT), OPS, MHESI, Thailand
4Department of Pharmacology, Faculty of Science, Mahidol University, Bangkok, Thailand

Tài liệu tham khảo

Arora, 2005, Role of tyrosine kinase inhibitors in cancer therapy, J. Pharmacol. Exp. Ther., 315, 971, 10.1124/jpet.105.084145 FDA, 2003. Drug approval package: Iressa (gefitinib) NDA #021399. 〈https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/021399_iressa.cfm/〉 (Accessed 26 April 2020). Li, 2007, Differential metabolism of gefitinib and erlotinib by human cytochrome P450 enzymes, Clin. Cancer Res., 13, 3731, 10.1158/1078-0432.CCR-07-0088 McKillop, 2004, In vitro metabolism of gefitinib in human liver microsomes, Xenobiotica, 34, 983, 10.1080/02772240400015222 FDA, 2007a. Drug approval package: Tykerb (lapatinib) NDA #022059. 〈https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022059s000TOC.cfm/〉 (Accessed 31 May 2021). FDA, 2007b. Nexavar (sorafenib) tablets prescribing information. 〈https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021923s004s005s006s007lbl.pdf/〉 (Accessed 26 April 2020). Xia, 2002, Anti-tumor activity of GW572016: a dual tyrosine kinase inhibitor blocks EGF activation of EGFR/erbB2 and downstream Erk1/2 and AKT pathways, Oncogene, 21, 6255, 10.1038/sj.onc.1205794 European Medicines Agency, 2008. Assessment report for Tyverb, international nonproprietary name: lapatinib. 〈https://www.ema.europa.eu/en/documents/assessment-report/tyverb-epar-public-assessment-report_en.pdf/〉 (Accessed 28 May 2021). Teng, 2010, Mechanism-based inactivation of cytochrome P450 3A4 by lapatinib, Mol. Pharm., 78, 693, 10.1124/mol.110.065839 Levy, 2006, Analysis of transcription and protein expression changes in the 786-O human renal cell carcinoma tumor xenograft model in response to treatment with the multi-kinase inhibitor sorafenib (BAY 43-9006), Cancer Res., 66, 213 Wilhelm, 2004, BAY 43-9006 exhibits broad spectrum oral antitumor activity and targets the RAF/MEK/ERK pathway and receptor tyrosine kinases involved in tumor progression and angiogenesis, Cancer Res, 64, 7099, 10.1158/0008-5472.CAN-04-1443 European Medicines Agency, 2014. Sorafenib (Nexavar): summary for the public. 〈https://www.ema.europa.eu/en/medicines/human/EPAR/nexavar/〉 (Accessed 28 May 2021). Ghassabian, 2012, Role of human CYP3A4 in the biotransformation of sorafenib to its major oxidized metabolites, Biochem. Pharm., 84, 215, 10.1016/j.bcp.2012.04.001 Lathia, 2006, Lack of effect of ketoconazole-mediated CYP3A inhibition on sorafenib clinical pharmacokinetics, Cancer Chemother. Pharm., 57, 685, 10.1007/s00280-005-0068-6 Burns, 2015, The nonspecific binding of tyrosine kinase inhibitors to human liver microsomes, Drug Metab. Dispos., 43, 1934, 10.1124/dmd.115.065292 Polasek, 2004, Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro, J. Pharmacol. Exp. Ther., 311, 996, 10.1124/jpet.104.071803 Molee, 2018, Naphthalene derivatives and quinones from Ventilago denticulata and their nitric oxide radical scavenging, antioxidant, cytotoxic, antibacterial, and phosphodiesterase inhibitory activities, Chem. Biodivers., 15, 10.1002/cbdv.201700537 Hakkola, 2020, Inhibition and induction of CYP enzymes in humans: an update, Arch. Toxicol., 94, 3671, 10.1007/s00204-020-02936-7 FDA-center for drug evaluation and research, 2013a. Advises against using oral ketoconazole in drug interaction studies due to serious potential side effects. 〈http://www.fda.gov/Drugs/DrugSafety/ucm371017.htm/〉 (accessed 5 May 2021). Tseng, 2014, Relative contributions of cytochrome CYP3A4 versus CYP3A5 for CYP3A-cleared drugs assessed in vitro using a CYP3A4-selective inactivator (CYP3cide), Drug Metab. Dispos., 42, 1163, 10.1124/dmd.114.057000 Patki, 2003, In vitro metabolism of midazolam, triazolam, nifedipine, and testosterone by human liver microsomes and recombinant cytochromes P450: role of CYP3A4 and CYP3A5, Drug Metab. Dispos., 31, 938, 10.1124/dmd.31.7.938 Dong, 2011, Substrate-dependent modulation of the catalytic activity of CYP3A by erlotinib, Acta Pharmacol. Sin., 32, 399, 10.1038/aps.2010.218 Hao, 2008, Structure-activity relationship and substrate-dependent phenomena in effects of ginsenosides on activities of drug-metabolizing P450 enzymes, PLoS One, 3, 10.1371/journal.pone.0002697 Wang, 2000, Human cytochrome P-450 3A4: in vitro drug-drug interaction patterns are substrate-dependent, Drug Metab. Dispos., 28, 360 Hosea, 2000, Elucidation of distinct ligand binding sites for cytochrome P450 3A4, Biochemistry, 39, 5929, 10.1021/bi992765t Burapan, 2020, Thai curcuma species: antioxidant and bioactive compounds, Foods, 9, 1219, 10.3390/foods9091219 Jayaprakasha, 2005, Chemistry and biological activities of C. longa, Trends Food Sci. Technol., 16, 533, 10.1016/j.tifs.2005.08.006 Paramapojn, 2007, Variation of curcuminoids in ethanolic extract of Curcuma zedoaria rhizomes in Thailand by HPLC, Planta Med., 73, P227, 10.1055/s-2007-987008 Hou, 2007, Possible inhibitory mechanism of Curcuma drugs on CYP3A4 in 1α,25 dihydroxyvitamin D3 treated Caco-2 cells, Int. J. Pharm., 337, 169, 10.1016/j.ijpharm.2006.12.035 Appiah-Opong, 2007, Inhibition of human recombinant cytochrome P450s by curcumin and curcumin decomposition products, Toxicology, 235, 83, 10.1016/j.tox.2007.03.007 Volak, 2008, Curcuminoids inhibit multiple human cytochromes P450, UDP-glucuronosyltransferase, and sulfotransferase enzymes, whereas piperine is a relatively selective CYP3A4 inhibitor, Drug Metab. Dispos., 36, 1594, 10.1124/dmd.108.020552 Jiratchariyakul, 1988, Cytotoxic glycosphingolipid from Murdannia loriformis (Hassk.) Rolla Rao et Kammathy, Thai J. Phytopharm., 5, 10 Pongjanta, 2016, Antioxidant activity and cytotoxic effect of Ventilago denticulata Willd, Leaves Extr. J. Med. Assoc. Thai, 99, S51 Jiratchariyakul, 1996, A steroidal glucoside from Murdannia loriformis (Hassk.) Rolla Rao et Kammathy, Thai J. Phytopharm., 3, 31 Lomchoey, 2017, Antiacetylcholinesterase activity of Ventilago denticulata extracts and its chemical constituents, KKU Sci. J., 45, 701 Liu, 2021, Anthraquinones inhibit cytochromes P450 enzyme activity in silico and in vitro, J. Appl. Toxicol., 41, 1438, 10.1002/jat.4134 Kishore, 2003, Flavonoids from Andrographis lineata, Phytochemistry, 63, 457, 10.1016/S0031-9422(02)00702-1 Pholphana, 2004, Determination and variation of three active diterpenoids in Andrographis paniculata (Burm.f.) Nees, Phytochem. Anal., 15, 365, 10.1002/pca.789 Pan, 2011, In vitro determination of the effect of Andrographis paniculata extracts and andrographolide on human hepatic cytochrome P450 activities,, J. Nat. Med., 65, 440, 10.1007/s11418-011-0516-z Pekthong, 2009, Effects of Andrographis paniculata extract and andrographolide on hepatic cytochrome P450 mRNA expression and monooxygenase activities after in vivo administration to rats and in vitro in rat and human hepatocyte cultures,, Chem. Biol. Inter., 179, 247, 10.1016/j.cbi.2008.10.054 Pekthong, 2008, Differential inhibition of rat and human hepatic cytochrome P450 by Andrographis paniculata extract and andrographolide, J. Ethnopharmacol., 115, 432, 10.1016/j.jep.2007.10.013 Wachtel-Galor, 2011, Ganoderma lucidum (Lingzhi or Reishi) a medicinal mushroom Hsu, 2014, Ganoderic acid and lucidenic acid (triterpenoid),, Enzymes, 36, 33, 10.1016/B978-0-12-802215-3.00003-3 Yang, 2018, Metabolism of ganoderic acids by a Ganoderma lucidum cytochrome P450 and the 3-keto sterol reductase ERG27 from yeast, Phytochemistry, 155, 83, 10.1016/j.phytochem.2018.07.009 Xu, 2020, In vitro inhibitory effects of ganoderic acid A on human liver cytochrome P450 enzymes, Pharm. Biol., 58, 308, 10.1080/13880209.2020.1747500 Wang, 2007, Effects of Ganoderma lucidum polysaccharide on CYP2E1, CYP1A2 and CYP3A activities in BCG-immune hepatic injury in rats, Biol. Pharm. Bull., 30, 1702, 10.1248/bpb.30.1702 Teekachunhatean, 2012, Pharmacokinetics of ganoderic acids A and F after oral administration of Ling Zhi preparation in healthy male volunteers, Evid. Based Complement. Altern. Med., 2012, 10.1155/2012/780892 Fança-Berthon, 2021, Pharmacokinetics of a single dose of turmeric curcuminoids depends on formulation: results of a human crossover study, J. Nutr., 151, 1802, 10.1093/jn/nxab087 Panossian, 2000, Pharmacokinetic and oral bioavailability of andrographolide from Andrographis paniculata fixed combination Kan Jang in rats and human, Phytomedicine, 7, 351, 10.1016/S0944-7113(00)80054-9