Document Detail


Inhibitory activity and mechanism of inhibition of the N-[[(4-benzoylamino)phenyl]sulfonyl]amino acid aldose reductase inhibitors.
MedLine Citation:
PMID:  2123105     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A series of substituted N-[[(4-benzoylamino)phenyl]sulfonyl]amino acids (BAPS-amino acids) were synthesized by established methods, and the stereochemistry of the products was confirmed by HPLC analysis after chiral derivatization. When tested against aldose reductase (alditol:NADP+ oxidoreductase; EC 1.1.1.21; ALR2) isolated from rat lens, all of the BAPS-amino acids were determined to be significantly more inhibitory than the corresponding N-(phenylsulfonyl)amino acids. Structure-inhibition and enzyme kinetic analyses suggest that the BAPS-amino acids inhibit ALR2 by a mechanism similar to the N-(phenylsulfonyl)amino acids. However, multiple inhibition analyses indicate that the increased inhibitory activity of the BAPS-amino acids is a result of interaction with multiple sites present on ALR2. Enzyme specificity studies with several of the BAPS-amino acids demonstrated that these compounds do not produce significant inhibition of other nucleotide-requiring enzymes including aldehyde reductase (alcohol: NADP+ oxidoreductase; EC 1.1.1.2; ALR1).
Authors:
J DeRuiter; C A Mayfield
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Publication Detail:
Type:  Comparative Study; Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Biochemical pharmacology     Volume:  40     ISSN:  0006-2952     ISO Abbreviation:  Biochem. Pharmacol.     Publication Date:  1990 Nov 
Date Detail:
Created Date:  1990-12-28     Completed Date:  1990-12-28     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0101032     Medline TA:  Biochem Pharmacol     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  2219-26     Citation Subset:  IM    
Affiliation:
Department of Pharmacal Sciences, School of Pharmacy, Auburn University, AL 36849-5503.
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MeSH Terms
Descriptor/Qualifier:
Alcohol Oxidoreductases / metabolism
Aldehyde Reductase / antagonists & inhibitors*,  isolation & purification
Amino Acids / chemical synthesis,  pharmacology*
Animals
Binding Sites
Chromatography, High Pressure Liquid
Glycine / analogs & derivatives*,  chemical synthesis,  pharmacology
Kinetics
Lens, Crystalline / enzymology
Rats
Stereoisomerism
Sulfones / chemical synthesis,  pharmacology*
Chemical
Reg. No./Substance:
0/Amino Acids; 0/Sulfones; 109065-69-2/N-(((4-benzoylamino)phenyl)sulfonyl)glycine; 56-40-6/Glycine; EC 1.1.-/Alcohol Oxidoreductases; EC 1.1.1.21/Aldehyde Reductase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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