Analysis of the inhibition of mammalian carboxylesterases by novel fluorobenzoins and fluorobenzils

被引：43

作者：

Hicks, Latorya D.

Hyatt, Janice L.

Moak, Teri

Edwards, Carol C.

Tsurkan, Lyudmila

Wierdl, Monika

Ferreira, Antonio M.

Wadkins, Randy M.

Potter, Philip M.

机构：

[1] St Jude Childrens Res Hosp, Dept Mol Pharmacol, Memphis, TN 38105 USA

[2] Univ Mississippi, Dept Chem & Biochem, University, MS 38677 USA

[3] St Jude Childrens Res Hosp, Hartwell Ctr Bioinformat & Biotechnol, Memphis, TN 38105 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2007年 / 15卷 / 11期

关键词：

fluorobenzil; fluorobenzoin; carboxylesterase; inhibitor;

D O I：

10.1016/j.bmc.2007.03.012

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

We have synthesized and assessed the ability of symmetrical fluorobenzoins and fluorobenzils to inhibit mammalian carboxylesterases (CE). The majority of the latter were excellent inhibitors of CEs however unexpectedly, the fluorobenzoins were very good enzyme inhibitors. Positive correlations were seen with the charge on the hydroxyl carbon atom, the carbonyl oxygen, and the Hammett constants for the derived K-i values with the fluorobenzoins. (c) 2007 Elsevier Ltd. All rights reserved.

引用

收藏

页码：3801 / 3817

页数：17

相关论文

共 34 条

[11] A NEW AND RAPID COLORIMETRIC DETERMINATION OF ACETYLCHOLINESTERASE ACTIVITY [J].

ELLMAN, GL ;

COURTNEY, KD ;

ANDRES, V ;

FEATHERSTONE, RM .

BIOCHEMICAL PHARMACOLOGY, 1961, 7 (02) :88-&

[12] Inhibition of carboxylesterases by benzil (diphenylethane-1,2-dione) and heterocyclic analogues is dependent upon the aromaticity of the ring and the flexibility of the dione moiety [J].

Hyatt, JL ;

Stacy, V ;

Wadkins, RM ;

Yoon, KJP ;

Wierdl, M ;

Edwards, CC ;

Zeller, M ;

Hunter, AD ;

Danks, MK ;

Crundwell, G ;

Potter, PM .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (17) :5543-5550

[13] Fast, efficient generation of high-quality atomic charges. AM1-BCC model: II. Parameterization and validation [J].

Jakalian, A ;

Jack, DB ;

Bayly, CI .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 2002, 23 (16) :1623-1641

[14] PREDICTING LIGAND-BINDING TO PROTEINS BY AFFINITY FINGERPRINTING [J].

KAUVAR, LM ;

HIGGINS, DL ;

VILLAR, HO ;

SPORTSMAN, JR ;

ENGQVISTGOLDSTEIN, A ;

BUKAR, R ;

BAUER, KE ;

DILLEY, H ;

ROCKE, DM .

CHEMISTRY & BIOLOGY, 1995, 2 (02) :107-118

[15]

Khanna R, 2000, CANCER RES, V60, P4725

[16] MOLSCRIPT - A PROGRAM TO PRODUCE BOTH DETAILED AND SCHEMATIC PLOTS OF PROTEIN STRUCTURES [J].

KRAULIS, PJ .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1991, 24 :946-950

[17] Experimental design and optimization [J].

Lundstedt, T ;

Seifert, E ;

Abramo, L ;

Thelin, B ;

Nystrom, A ;

Pettersen, J ;

Bergman, R .

CHEMOMETRICS AND INTELLIGENT LABORATORY SYSTEMS, 1998, 42 (1-2) :3-40

[18]

MOHRIG JR, 2003, MODERN PROJECTS EXPT, P367

[19]

MOLINOFF PB, 1996, GOODMAN GILMANS PHAR, P1905

[20] Comparison of Escherichia coli, Saccharomyces cerevisiae, Pichia pastoris, Spodoptera frugiperda, and COS7 cells for recombinant gene expression -: Application to a rabbit liver carboxylesterase [J].

Morton, CL ;

Potter, PM .

MOLECULAR BIOTECHNOLOGY, 2000, 16 (03) :193-202

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