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GABAA receptor activity modulating piperine analogs: In vitro metabolic stability, metabolite identification, CYP450 reaction phenotyping, and protein binding

Zabela, Volha, Hettich, Timm, Schlotterbeck, Götz, Wimmer, Laurin, Mihovilovic, Marko D., Guillet, Fabrice, Bouaita, Belkacem, Shevchenko, Bénédicte, Hamburger, Matthias, Oufir, Mouhssin·2018·Journal of Chromatography B

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Research works printed but not linked: 16

  1. Zaugg, 2010, HPLC-based activity profiling: discovery of piperine as a positive GABAA receptor modulator targeting a benzodiazepine-independent binding site, J. Nat. Prod., 73, 185, 10.1021/np900656g · DOI
  2. McNamara, 2005, Effects of piperine the pungent component of black pepper, at the human vanilloid receptor (TRPV1), Br. J. Pharmacol., 144, 781, 10.1038/sj.bjp.0706040 · DOI · Paper page
  3. Khom, 2013, GABAA receptor modulation by piperine and a non-TRPV1 activating derivative, Biochem. Pharmacol., 85, 1827, 10.1016/j.bcp.2013.04.017 · DOI
  4. Schöffmann, 2014, Efficient modulation of γ-aminobutyric acid type A receptors by piperine derivatives, J. Med. Chem., 57, 5602, 10.1021/jm5002277 · DOI
  5. Attia, 2010, Deleterious effects of reactive metabolites, Oxid. Med. Cell Longev., 3, 238, 10.4161/oxim.3.4.13246 · DOI
  6. Wimmer, 2015, Developing piperine towards TRPV1 and GABAA receptor ligands–synthesis of piperine analogs via Heck-coupling of conjugated dienes, Org. Biomol. Chem., 13, 990, 10.1039/C4OB02242D · DOI
  7. Giuliano, 2005, Direct determination of unbound intrinsic drug clearance in the microsomal stability assay, Drug Metab. Dispos., 33, 1319, 10.1124/dmd.105.005033 · DOI
  8. Obach, 1999, Prediction of human clearance of twenty-nine drugs from hepatic microsomal intrinsic clearance data: an examination of in vitro half-life approach and nonspecific binding to microsomes, Drug Metab. Dispos., 27, 1350, 10.1016/S0090-9556(24)14938-0 · DOI · Paper page
  9. Gillette, 1971, Factors affecting drug metabolism, Ann. N.Y. Acad. Sci., 179, 43, 10.1111/j.1749-6632.1971.tb46890.x · DOI
  10. Rowland, 1973, Clearance concepts in pharmacokinetics, J. Pharmacokinet. Biopharm., 1, 123, 10.1007/BF01059626 · DOI · Paper page
  11. Wilkinson, 1975, A physiological approach to hepatic drug clearance, Clin. Pharmacol. Ther., 18, 377, 10.1002/cpt1975184377 · DOI · Paper page
  12. Lau, 2002, The use of in vitro metabolic stability for rapid selection of compounds in early discovery based on their expected hepatic extraction ratios, Pharm. Res., 19, 1606, 10.1023/A:1020765025857 · DOI
  13. Parmentier, 2017, Direct and quantitative evaluation of the human CYP3A4 contribution (fm) to drug clearance using the in vitro SILENSOMES model, Xenobiotica, 47, 562, 10.1080/00498254.2016.1208854 · DOI
  14. Eigenmann, 2016, In vitro blood-brain barrier permeability predictions for GABAA receptor modulating piperine analogs, Eur. J. Pharm. Biopharm., 103, 118, 10.1016/j.ejpb.2016.03.029 · DOI
  15. Zhou, 2009, Polymorphism of human cytochrome P450 enzymes and its clinical impact, Drug Metab. Rev., 41, 89, 10.1080/03602530902843483 · DOI
  16. Tomalik-Scharte, 2008, The clinical role of genetic polymorphisms in drug-metabolizing enzymes, Pharmacogenomics J., 8, 4, 10.1038/sj.tpj.6500462 · DOI

Cited by

Metadata

Authors
Zabela, V., Hettich, T., Schlotterbeck, G., Wimmer, L., Mihovilovic, M. D., Guillet, F., Bouaita, B., Shevchenko, B., Hamburger, M., & Oufir, M.
Venue
Journal of Chromatography B
Publisher
Elsevier BV
Published
2018-01
Volume
1072
Pages
379-389
ISSN
1570-0232
Cited by
10
References
2
Language
en
Funders
Swiss National Science Foundation (205320_126888)

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Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.