Quantitative structure-activity relationship (QSAR) analysis of the inhibitory effects of furanocoumarin derivatives on cytochrome P450 3A activities

Pharmazie

Volumn 65, Issue 1, 2010, Pages 41-46

  Uesawa, Y ^a   Mohri, K ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450 3A; CYTOCHROME P450 3A4; FUROCOUMARIN DERIVATIVE;

ARTICLE; BIOLOGICAL ACTIVITY; ELECTRIC POTENTIAL; ENZYME ACTIVITY; ENZYME INHIBITION; HYDROXYLATION; IC 50; LIPOPHILICITY; LIVER MICROSOME; MOLECULAR INTERACTION; MOLECULAR WEIGHT; PHYSICAL CHEMISTRY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM CHEMISTRY;

CYTOCHROME P-450 CYP3A; ELECTROCHEMISTRY; ENZYME INHIBITORS; FORECASTING; HUMANS; LINEAR MODELS; LIPIDS; MODELS, STATISTICAL; MOLECULAR WEIGHT; PSORALENS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUANTUM THEORY;

EID: 76149102911     PISSN: 00317144     EISSN: None     Source Type: Journal    
DOI: 10.1691/ph.2010.9651     Document Type: Article

References (25)

1. Bäärnhielm C, Westerlund C (1986) Quantitative relationships between structure and microsomal oxidation rate of 1,4-dihydropyridines. Chem Biol Interact 58: 277-288.
2. Cruciani G, Baroni M, Clementi S, Costantino G, Riganelli D, Skagerberg B (1992) Predictive ability of regression models. I: Standard deviation of prediction errors (SDEP). J Chemometr 6: 335-346.
3. Devinsky F, Gorrod JW (1987) Microsomal N-oxidation of long chain N,N-dimethylalkylamines: quantitative structure-activity relationships. Eur J Drug Metab Pharmacokinet 12: 267-273.
4. Efron B (1987) Better bootstrap confidence intervals. J Am Statist Assoc 82: 171-200.
5. Fujioka T, Furumi K, Fujii H, Okabe H, Mihashi K, Nakano Y, Matsunaga H, Katano M, Mori M (1999) Antiproliferative constituents from umbelliferae plants. V. A new furanocoumarin and falcarindiol furanocoumarin ethers from the root of Angelica japonica. Chem Pharm Bull (Tokyo) 47: 96-100.
6. Fukuda K, Guo L, Ohashi N, Yoshikawa M, Yamazoe Y (2000) Amounts and variation in grapefruit juice of the main components causing grapefruit-drug interaction. J Chromatogr B, Biomed Sci Appl 741: 195-203.
7. Ghose AK, Crippen GM (1986) Atomic physicochemical parameters for three-dimensional structure-directed quantitative structure-activity relationships I. Partition coefficients as a measure of hydrophobicity. J Comput Chem 7: 565-577.
8. Goosen TC, Cillié D, Bailey DG, Yu C, He K, Hollenberg PF, Woster PM, Cohen L, Williams JA, Rheeders M, Dijkstra HP (2004) Bergamottin contribution to the grapefruit juice-felodipine interaction and disposition in humans. Clin Pharmacol Ther 76: 607-617.
9. Grenier J, Fradette C, Morelli G, Merritt GJ, Vranderick M, Ducharme MP (2006) Pomelo juice, but not cranberry juice, affects the pharmacokinetics of cyclosporine in humans. Clin Pharmacol Ther 79: 255-262.
10. Guo LQ, Fukuda K, Ohta T, Yamazoe Y (2000a) Role of furanocoumarin derivatives on grapefruit juice-mediated inhibition of human CYP3A activity. Drug Metab Dispos 28: 766-771.
11. Guo LQ, Taniguchi M, Xiao YQ, Baba K, Ohta T, Yamazoe Y (2000b) Inhibitory effect of natural furanocoumarins on human microsomal cytochrome P450 3A activity. Japan J Pharmacol 82: 122-129.
12. Hansch C, Fujita T (1964) Rho-sigma-pi Analysis; method for the correlation of biological activity and chemical structure. J Am Chem Soc 86: 1616-1626.
13. Laznicek M, Waisser K, Kvetina J, Beno P (1985) QSAR methods in pharmacokinetic analysis. Pharmacochem Libr 8: 249-256.
14. Leardi R, Boggia R, Terrile M (1992) Genetic algorithms as a strategy for feature selection. J Chemometr 6: 267-281.
15. Lien E (1970) Physicochemical properties and gastrointestinal absorption of drugs. Drug Intell 4: 7-9.
16. Lown KS, Bailey DG, Fontana RJ, Janardan SK, Adair CH, Fortlage LA, Brown MB, Guo W, Watkins PB (1997) Grapefruit juice increases felodipine oral availability in humans by decreasing intestinal CYP3A protein expression. J Clin Invest 99: 2545-2553.
17. Mohri K, Uesawa Y (2001) Effects of furanocoumarin derivatives in grapefruit juice on nifedipine pharmacokinetics in rats. Pharm Res 18: 177-182.
18. Saita T, Fujito H, Mori M (2004) Screening of furanocoumarin derivatives in citrus fruits by enzyme-linked immunosorbent assay. Biol Pharm Bull 27: 974-977.
19. Schmiedlin-Ren P, Edwards DJ, Fitzsimmons ME, He K, Lown KS, Woster PM, Rahman A, Thummel KE, Fisher JM, Hollenberg PF, Watkins PB (1997) Mechanisms of enhanced oral availability of CYP3A4 substrates by grapefruit constituents. Decreased enterocyte CYP3A4 concentration and mechanism-based inactivation by furanocoumarins. Drug Metab Dispos 25: 1228-1233.
20. Schrag ML, Wienkers LC (2001) Covalent alteration of the CYP3A4 active site: evidence for multiple substrate binding domains. Arch Biochem Biophys 391: 49-55.
21. Uesawa Y, Mohri K (2005) [Comprehensive determination of furanocoumarin derivatives in citrus juice by high performance liquid chromatography]. Yakugaku Zasshi 125: 875-879.
22. Uesawa Y, Mohri K (2008a) Food-drug interaction: the case of grapefruit juice. CAB reviews 8: 1-6.
23. Uesawa Y, Mohri K (2008b) Relationship between lipophilicities of 1,4-dihydropyridine derivatives and pharmacokinetic interaction strengths with grapefruit juice. Yakugaku Zasshi 128: 117-122.
24. Viswanadhan VM, Reddy MR, Bacquet RJ, Erion MD (1993) Assessment of methods used for predicting lipophilicity: application to nucleosides and nucleoside bases. J Comput Chem 14: 1019-1026.
25. Wangensteen H, Molden E, Christensen H, Malterud KE (2003) Identification of epoxybergamottin as a CYP3A4 inhibitor in grapefruit peel. Eur J Clin Pharmacol 58: 663-668.