Literature DB >> 17399985

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

Latorya D Hicks1, Janice L Hyatt, Teri Moak, Carol C Edwards, Lyudmila Tsurkan, Monika Wierdl, Antonio M Ferreira, Randy M Wadkins, Philip M Potter.   

Abstract

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.

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Year:  2007        PMID： 17399985      PMCID： PMC1995442          DOI： 10.1016/j.bmc.2007.03.012

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  20 in total

1.  Fast, efficient generation of high-quality atomic charges. AM1-BCC model: II. Parameterization and validation.

Authors:  Araz Jakalian; David B Jack; Christopher I Bayly
Journal:  J Comput Chem       Date:  2002-12       Impact factor: 3.376

2.  Bioactive diversity and screening library selection via affinity fingerprinting.

Authors:  S L Dixon; H O Villar
Journal:  J Chem Inf Comput Sci       Date:  1998 Nov-Dec

3.  Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases.

Authors:  Randy M Wadkins; Janice L Hyatt; Xin Wei; Kyoung Jin P Yoon; Monika Wierdl; Carol C Edwards; Christopher L Morton; John C Obenauer; Komath Damodaran; Paul Beroza; Mary K Danks; Philip M Potter
Journal:  J Med Chem       Date:  2005-04-21       Impact factor: 7.446

4.  5D-QSAR: the key for simulating induced fit?

Authors:  Angelo Vedani; Max Dobler
Journal:  J Med Chem       Date:  2002-05-23       Impact factor: 7.446

Review 5.  Mammalian carboxylesterases: from drug targets to protein therapeutics.

Authors:  Matthew R Redinbo; Philip M Potter
Journal:  Drug Discov Today       Date:  2005-03-01       Impact factor: 7.851

6.  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.

Authors:  Janice L Hyatt; Vanessa Stacy; Randy M Wadkins; Kyoung Jin P Yoon; Monika Wierdl; Carol C Edwards; Matthias Zeller; Allen D Hunter; Mary K Danks; Guy Crundwell; Philip M Potter
Journal:  J Med Chem       Date:  2005-08-25       Impact factor: 7.446

7.  Human carboxylesterase 1: from drug metabolism to drug discovery.

Authors:  M R Redinbo; S Bencharit; P M Potter
Journal:  Biochem Soc Trans       Date:  2003-06       Impact factor: 5.407

8.  Discovery of novel selective inhibitors of human intestinal carboxylesterase for the amelioration of irinotecan-induced diarrhea: synthesis, quantitative structure-activity relationship analysis, and biological activity.

Authors:  Randy M Wadkins; Janice L Hyatt; Kyoung Jin P Yoon; Christopher L Morton; Richard E Lee; Komath Damodaran; Paul Beroza; Mary K Danks; Philip M Potter
Journal:  Mol Pharmacol       Date:  2004-06       Impact factor: 4.436

9.  Isolation and partial characterization of a cDNA encoding a rabbit liver carboxylesterase that activates the prodrug irinotecan (CPT-11).

Authors:  P M Potter; C A Pawlik; C L Morton; C W Naeve; M K Danks
Journal:  Cancer Res       Date:  1998-06-15       Impact factor: 12.701

Review 10.  Pharmacokinetics and molecular detoxication.

Authors:  J R Cashman; B Y Perotti; C E Berkman; J Lin
Journal:  Environ Health Perspect       Date:  1996-03       Impact factor: 9.031
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  8 in total

Review 1.  Carboxylesterase inhibitors.

Authors:  M Jason Hatfield; Philip M Potter
Journal:  Expert Opin Ther Pat       Date:  2011-05-24       Impact factor: 6.674

Review 2.  Challenges and Opportunities with Non-CYP Enzymes Aldehyde Oxidase, Carboxylesterase, and UDP-Glucuronosyltransferase: Focus on Reaction Phenotyping and Prediction of Human Clearance.

Authors:  Upendra A Argikar; Philip M Potter; J Matthew Hutzler; Punit H Marathe
Journal:  AAPS J       Date:  2016-08-05       Impact factor: 4.009

3.  Global and local molecular dynamics of a bacterial carboxylesterase provide insight into its catalytic mechanism.

Authors:  Xiaozhen Yu; Sara C Sigler; Delwar Hossain; Monika Wierdl; Steven R Gwaltney; Philip M Potter; Randy M Wadkins
Journal:  J Mol Model       Date:  2011-11-30       Impact factor: 1.810

4.  In Silico Design and Evaluation of Carboxylesterase Inhibitors.

Authors:  Shana V Stoddard; Xiaozhen Yu; Philip M Potter; Randy M Wadkins
Journal:  J Pest Sci (2004)       Date:  2010       Impact factor: 5.918

5.  Modulation of esterified drug metabolism by tanshinones from Salvia miltiorrhiza ("Danshen").

Authors:  M Jason Hatfield; Lyudmila G Tsurkan; Janice L Hyatt; Carol C Edwards; Andrew Lemoff; Cynthia Jeffries; Bing Yan; Philip M Potter
Journal:  J Nat Prod       Date:  2013-01-03       Impact factor: 4.050

6.  Improved, selective, human intestinal carboxylesterase inhibitors designed to modulate 7-ethyl-10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin (Irinotecan; CPT-11) toxicity.

Authors:  Latorya D Hicks; Janice L Hyatt; Shana Stoddard; Lyudmila Tsurkan; Carol C Edwards; Randy M Wadkins; Philip M Potter
Journal:  J Med Chem       Date:  2009-06-25       Impact factor: 7.446

7.  Comparison of benzil and trifluoromethyl ketone (TFK)-mediated carboxylesterase inhibition using classical and 3D-quantitative structure-activity relationship analysis.

Authors:  Toshiyuki Harada; Yoshiaki Nakagawa; Randy M Wadkins; Philip M Potter; Craig E Wheelock
Journal:  Bioorg Med Chem       Date:  2008-11-09       Impact factor: 3.641

8.  Selective Inhibitors of Human Liver Carboxylesterase Based on a β-Lapachone Scaffold: Novel Reagents for Reaction Profiling.

Authors:  M Jason Hatfield; Jingwen Chen; Ellie M Fratt; Liying Chi; John C Bollinger; Randall J Binder; John Bowling; Janice L Hyatt; Jerrod Scarborough; Cynthia Jeffries; Philip M Potter
Journal:  J Med Chem       Date:  2017-02-07       Impact factor: 8.039
  8 in total

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