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Effect of Cholesterol on the Interaction of Cytochrome P450 Substrate Drug Chlorzoxazone with the Phosphatidylcholine Bilayer.

Abstract：

:Many drugs are oxidized by membrane protein cytochrome P450 (CYP) enzymes during their metabolism process. CYPs are located mainly in endoplasmic reticulum (ER) membranes. Recent studies have suggested that CYP substrate drugs first bind the lipid bilayers of ER membranes and then the drugs reach the active site of CYP by way of an access channel. The entrance of the channel is located in the hydrophobic regions of the lipid bilayers. One of the features of the ER membrane is a cholesterol content that is lower than those of other biomembranes. In this study, the cholesterol concentration dependence of the interaction of a CYP substrate drug, chlorzoxazone (CZX), with model membranes composed of phosphatidylcholine (PC) and cholesterol was examined via differential scanning calorimetry (DSC), UV-visible spectroscopy, and X-ray diffraction. Experimental results indicated that CZX can bind to pure PC bilayers in the absence of cholesterol and that, by contrast, a high cholesterol concentration (30-50 mol %) tends to prevent CZX from binding to PC bilayers. Interestingly, the effect of cholesterol on the binding and insertion of CZX was biphasic. In the case of palmitoyloleoylphosphatidylcholine (POPC) bilayers containing 5-10 mol % cholesterol, the CZX's binding and penetration into the bilayer were found to be greater than those with pure POPC bilayers. The concentration of 5-10 mol % nearly corresponds to the cholesterol concentration of ER membranes. The low cholesterol contents (12-20 mol %) of ER membranes might be the most suitable for the CYP drug metabolism process in ER membranes.

journal_name

Biochemistry

journal_title

Biochemistry

authors

Yamada A,Shimizu N,Hikima T,Takata M,Kobayashi T,Takahashi H

doi

10.1021/acs.biochem.6b00286

subject

Has Abstract

pub_date

2016-07-19 00:00:00

pages

3888-98

issue

28

eissn

0006-2960

issn

1520-4995

journal_volume

55

pub_type

杂志文章

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