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Design, synthesis and evaluation of furanocoumarin monomers as inhibitors of CYP3A4

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Design, synthesis and evaluation of furanocoumarin monomers as inhibitors of CYP3A4

Content Provider	Royal Society of Chemistry (RSC)
Author	Stachulski, A. V. Row, E. C. Brown, S. A. Lennard, M. S.
Copyright Year	2006
Abstract	A number of furanocoumarins isolated from grapefruit juice have been found to inhibit CYP3A4 activity in vitro. In this study, we have designed and synthesised a range of analogues based on bergamottin to investigate the relationship between chemical structure and inhibition of CYP3A4 activity. Studies were performed using human liver microsomes and human intestinal S9 fraction, with testosterone as the marker substrate. With the exception of the coumarin and phenolic furanocoumarin derivatives, which were inactive, the alkyloxy-furanocoumarin analogues were found to inhibit CYP3A4 activity in a dose dependent manner, with observed IC50 values ranging from 0.13 ± 0.03 to 49.3 ± 1.9 µM. The unsaturated furan derivatives were found to exhibit time-dependent inhibition, showing a 2-, 4- and 14-fold increase in potency for 6′,7′-epoxybergamottin, 6′,7′-dihydroxybergamottin and bergamottin, respectively after a preincubation period of ten minutes. Reduction of the furan moiety resulted in an 11-fold decrease in inhibitory potency, suggesting that this functional group is key to the interaction between these compounds and CYP3A4.
Starting Page	1604
Ending Page	1610
Page Count	7
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	4
Issue Number	8
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b601096b
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Bergamottin Testosterone Furan Grapefruit juice Liver S9 fraction IC50 Furanocoumarin CYP3A4 Coumarin Functional group
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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