Evaluation of the inhibition potential of plumbagin against cytochrome P450 using LC-MS/MS and cocktail approach

Scientific Reports

Volumn 6, Issue , 2016, Pages

  Chen, Ang ^a   Zhou, Xiaojing ^a   Tang, Shuowen ^a   Liu, Mingyao ^a,b   Wang, Xin ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b TEXAS A AND M HEALTH SCIENCE CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; CYTOCHROME P450 INHIBITOR; HERBACEOUS AGENT; NAPHTHOQUINONE; PLUMBAGIN;

ANIMAL; DRUG EFFECTS; ENZYMOLOGY; HUMAN; IN VITRO STUDY; KINETICS; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MALE; METABOLISM; RAT; SPRAGUE DAWLEY RAT; TANDEM MASS SPECTROMETRY;

ANIMALS; CHROMATOGRAPHY, LIQUID; CYTOCHROME P-450 ENZYME INHIBITORS; CYTOCHROME P-450 ENZYME SYSTEM; DRUGS, CHINESE HERBAL; HUMANS; IN VITRO TECHNIQUES; KINETICS; MALE; MICROSOMES, LIVER; NAPHTHOQUINONES; RATS; RATS, SPRAGUE-DAWLEY; TANDEM MASS SPECTROMETRY;

EID: 84975782033     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep28482     Document Type: Article

References (44)

1. Sunil, C., Duraipandiyan, V., Agastian, P. & Ignacimuthu, S. Antidiabetic effect of plumbagin isolated from Plumbago zeylanica L. root and its effect on GLUT4 translocation in streptozotocin-induced diabetic rats. Food and chemical toxicology: an international journal published for the British Industrial Biological Research Association 50, 4356-4363 (2012).
2. Olagunju, J. A., Jobi, A. A. & Oyedapo, O. O. An Investigation into the Biochemical Basis of the Observed Hyperglycaemia in Rats Treated with Ethanol Root Extract of Plumbago zeylanica. Phytotherapy research 13, 346-348 (1999).
3. Hsieh, Y. J., Lin, L. C. & Tsai, T. H. Measurement and pharmacokinetic study of plumbagin in a conscious freely moving rat using liquid chromatography/tandem mass spectrometry. J Chromatogr B-Analyt Technol Biomed Life Sci 844, 1-5 (2006).
4. Nayak, P., Sharma, M., Behera, S. N., Thirunavoukkarasu, M. & Chand, P. K. High-performance liquid chromatographic quantification of plumbagin from transformed rhizoclones of Plumbago zeylanica L.: inter-clonal variation in biomass growth and plumbagin production. Applied biochemistry and biotechnology 175, 1745-1770 (2015).
5. Saritha, K., Rajesh, A., Manjulatha, K., Setty, O. H. & Yenugu, S. Mechanism of antibacterial action of the alcoholic extracts of Hemidesmus indicus (L.) R. Br. ex Schult, Leucas aspera (Wild.), Plumbago zeylanica L., and Tridax procumbens (L.) R. Br. ex Schult. Frontiers in microbiology 6, 577 (2015).
6. Sand, J. M. et al. Plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone), isolated from Plumbago zeylanica, inhibits ultraviolet radiation-induced development of squamous cell carcinomas. Carcinogenesis 33, 184-190 (2012).
7. Zhou, Z. W. et al. Induction of apoptosis and autophagy via sirtuin1- and PI3K/Akt/mTOR-mediated pathways by plumbagin in human prostate cancer cells. Drug design, development and therapy 9, 1511-1554 (2015).
8. Joo, M. K. et al. Antitumorigenic effect of plumbagin by induction of SH2-containing protein tyrosine phosphatase 1 in human gastric cancer cells. International journal of oncology 46, 2380-2388 (2015).
9. Rendic, S. Summary of information on human CYP enzymes: human P450 metabolism data. Drug metabolism reviews 34, 83-448 (2002).
10. Dahlinger, D. et al. Development and validation of an in vitro, seven-in-one human cytochrome P450 assay for evaluation of both direct and time-dependent inhibition. Journal of pharmacological and toxicological methods 77, 66-75 (2015).
11. Arora, S. et al. 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, 1-8 (2015).
12. Daly, A. K. Pharmacogenetics of the cytochromes P450. Current topics in medicinal chemistry 4, 1733-1744 (2004).
13. Ingelman-Sundberg, M. Pharmacogenetics of cytochrome P450 and its applications in drug therapy: the past, present and future. Trends in pharmacological sciences 25, 193-200 (2004).
14. Zheng, L. et al. Evaluation of the impact of Polygonum capitatum, a traditional Chinese herbal medicine, on rat hepatic cytochrome P450 enzymes by using a cocktail of probe drugs. Journal of ethnopharmacology 158, 276-282 (2014).
15. Posadzki, P., Watson, L. & Ernst, E. Herb-drug interactions: an overview of systematic reviews. British journal of clinical pharmacology 75, 603-618 (2013).
16. U.S. Department of Health and Human Services Food and Drug Administration Center for Drug Evaluation and Research. Drug Interaction Studies - Study Design, Data Analysis, Implications for Dosing, and Labeling Recommendations. Draft guidance (2012). Available at: http://www.fda.gov/downloads/Drugs/GuidanceComplianceRegulatoryInformation/Guidances/UCM292362.pdf (Accessed: 24th March 2016).
17. Sumsakul, W., Chaijaroenkul, W. & Na-Bangchang, K. In vitro inhibitory effects of plumbagin, the promising antimalarial candidate, on human cytochrome P450 enzymes. Asian Pacific journal of tropical medicine 8, 914-918 (2015).
18. Spaggiari, D., Geiser, L., Daali, Y. & Rudaz, S. A cocktail approach for assessing the in vitro activity of human cytochrome P450s: an overview of current methodologies. Journal of pharmaceutical and biomedical analysis 101, 221-237 (2014).
19. Frye, R. F. Probing the world of cytochrome P450 enzymes. Molecular interventions 4, 157-162 (2004).
20. Wang, X., Cheung, C. M., Lee, W. Y., Or, P. M. & Yeung, J. H. Major tanshinones of Danshen (Salvia miltiorrhiza) exhibit different modes of inhibition on human CYP1A2, CYP2C9, CYP2E1 and CYP3A4 activities in vitro. Phytomedicine: international journal of phytotherapy and phytopharmacology 17, 868-875 (2010).
21. Lin, J. H. & Lu, A. Y. H. Inhibition and induction of cytochrome P450 and the clinical implications. Clin Pharmacokinet 35, 361-390 (1998).
22. Sun, M., Tang, Y., Ding, T., Liu, M. & Wang, X. Inhibitory effects of celastrol on rat liver cytochrome P450 1A2, 2C11, 2D6, 2E1 and 3A2 activity. Fitoterapia 92, 1-8 (2014).
23. Justenhoven, C. et al. CYP2B6∗ 6 is associated with increased breast cancer risk. International journal of cancer. Journal international du cancer 134, 426-430 (2014).
24. Ragia, G. et al. Frequency of CYP450 enzyme gene polymorphisms in the Greek population: review of the literature, original findings and clinical significance. Drug metabolism and drug interactions 29, 235-248 (2014).
25. Wang, X., Lee, W. Y., Or, P. M. & Yeung, J. H. Effects of major tanshinones isolated from Danshen (Salvia miltiorrhiza) on rat CYP1A2 expression and metabolism of model CYP1A2 probe substrates. Phytomedicine: international journal of phytotherapy and phytopharmacology 16, 712-725 (2009).
26. Wang, X. & Yeung, J. H. Investigation of cytochrome P450 1A2 and 3A inhibitory properties of Danshen tincture. Phytomedicine: international journal of phytotherapy and phytopharmacology 19, 348-354 (2012).
27. Zheng, L. et al. Imperatorin is a mechanism-based inactivator of CYP2B6. Drug metabolism and disposition: the biological fate of chemicals 43, 82-88 (2015).
28. Yuce-Artun, N., Kose, G. & Suzen, H. S. Allele and genotype frequencies of CYP2B6 in a Turkish population. Molecular biology reports 41, 3891-3896 (2014).
29. Koh, K. H. et al. Kruppel-like factor 9 promotes hepatic cytochrome P450 2D6 expression during pregnancy in CYP2D6-humanized mice. Molecular pharmacology 86, 727-735 (2014).
30. Ye, X. H. et al. Association between the CYP2E1 polymorphisms and lung cancer risk: a meta-analysis. Molecular genetics and genomics: MGG 290, 545-558 (2015).
31. Loue, C. & Tod, M. Reliability and extension of quantitative prediction of CYP3A4-mediated drug interactions based on clinical data. The AAPS journal 16, 1309-1320 (2014).
32. Wang, X. & Yeung, J. H. Effects of Salvia miltiorrhiza extract on the liver CYP3A activity in humans and rats. Phytotherapy research: PTR 25, 1653-1659 (2011).
33. Dinger, J., Meyer, M. R. & Maurer, H. H. Development and validation of a liquid-chromatography high-resolution tandem mass spectrometry approach for quantification of nine cytochrome P450 (CYP) model substrate metabolites in an in vitro CYP inhibition cocktail. Analytical and bioanalytical chemistry 406, 4453-4464 (2014).
34. Liu, L. Y. et al. A sensitive and high-throughput LC-MS/MS method for inhibition assay of seven major cytochrome P450s in human liver microsomes using an in vitro cocktail of probe substrates. Biomedical chromatography: BMC 29, 437-444 (2015).
35. Otten, J. N., Hingorani, G. P., Hartley, D. P., Kragerud, S. D. & Franklin, R. B. An in vitro, High Throughput, Seven CYP Cocktail Inhibition Assay for the Evaluation of New Chemical Entities Using LC-MS/MS. Drug Metabolism Letters 5, 17-24 (2011).
36. Venkatakrishnan, K., Obach, R. S. & Rostami-Hodjegan, A. Mechanism-based inactivation of human cytochrome P450 enzymes: strategies for diagnosis and drug-drug interaction risk assessment. Xenobiotica; the fate of foreign compounds in biological systems 37, 1225-1256 (2007).
37. Obach, R. S., Walsky, R. L. & Venkatakrishnan, K. Mechanism-based inactivation of human cytochrome p450 enzymes and the prediction of drug-drug interactions. Drug metabolism and disposition: the biological fate of chemicals 35, 246-255 (2007).
38. Stresser, D. M., Mao, J., Kenny, J. R., Jones, B. C. & Grime, K. Exploring concepts of in vitro time-dependent CYP inhibition assays. Expert opinion on drug metabolism & toxicology 10, 157-174 (2014).
39. Lewis, D. F. V., Loannides, C. & Parke, D. V. Cytochromes P450 and Species Differences in Xenobiotic Metabolism and Activation of Carcinogen. Environmental Health Perspectives 106, 633-641 (1998).
40. Wang, X. & Yeung, J. H. Inhibitory effect of tanshinones on rat CYP3A2 and CYP2C11 activity and its structure-activity relationship. Fitoterapia 82, 539-545 (2011).
41. Kolrep, F. et al. Differences in metabolism of the marine biotoxin okadaic acid by human and rat cytochrome P450 monooxygenases. Archives of toxicology (2015).
42. He, F. et al. Mechanism of Action of Panaxytriol on Midazolam 1′ -Hydroxylation and 4-Hydroxylation Mediated by CYP3A in Liver Microsomes and Rat Primary Hepatocytes. Biol. Pharm. Bull. 38, 1470-1477 (2015).
43. Hutzler, J. M. & Tracy, T. S. Atypical kinetic profiles in drug metabolism reactions. Drug metabolism & disposition 30, 355-362 (2002).
44. Peng, Y. et al. A comprehensive assay for nine major cytochrome P450 enzymes activities with 16 probe reactions on human liver microsomes by a single LC/MS/MS run to support reliable in vitro inhibitory drug-drug interaction evaluation. Xenobiotica; the fate of foreign compounds in biological systems 1-17 (2015).