Literature DB >> 8234324

Refined 1.8 A structure of human aldose reductase complexed with the potent inhibitor zopolrestat.

D K Wilson1, I Tarle, J M Petrash, F A Quiocho.   

Abstract

As the action of aldose reductase (EC 1.1.1.21) is believed to be linked to the pathogenesis of diabetic complications affecting the nervous, renal, and visual systems, the development of therapeutic agents has attracted intense effort. We report the refined 1.8 A x-ray structure of the human holoenzyme complexed with zopolrestat, one of the most potent noncompetitive inhibitors. The zopolrestat fits snugly in the hydrophobic active site pocket and induces a hinge-flap motion of two peptide segments that closes the pocket. Excellent complementarity and affinity are achieved on inhibitor binding by the formation of 110 contacts (< or = 4 A) with 15 residues (10 hydrophobic), 13 with the NADPH coenzyme and 9 with four water molecules. The structure is key to understanding the mode of action of this class of inhibitors and for rational design of better therapeutics.

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Year:  1993        PMID: 8234324      PMCID: PMC47669          DOI: 10.1073/pnas.90.21.9847

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN: 0027-8424            Impact factor:   11.205


  11 in total

Review 1.  The role of aldose reductase in the development of diabetic complications.

Authors:  P F Kador
Journal:  Med Res Rev       Date:  1988 Jul-Sep       Impact factor: 12.944

Review 2.  Aldose reductase inhibitors: recent developments.

Authors:  R Sarges; P J Oates
Journal:  Prog Drug Res       Date:  1993

3.  Pharmacophor requirements of the aldose reductase inhibitor site.

Authors:  P F Kador; N E Sharpless
Journal:  Mol Pharmacol       Date:  1983-11       Impact factor: 4.436

4.  An unlikely sugar substrate site in the 1.65 A structure of the human aldose reductase holoenzyme implicated in diabetic complications.

Authors:  D K Wilson; K M Bohren; K H Gabbay; F A Quiocho
Journal:  Science       Date:  1992-07-03       Impact factor: 47.728

5.  Involvement of cysteine residues in catalysis and inhibition of human aldose reductase. Site-directed mutagenesis of Cys-80, -298, and -303.

Authors:  J M Petrash; T M Harter; C S Devine; P O Olins; A Bhatnagar; S Liu; S K Srivastava
Journal:  J Biol Chem       Date:  1992-12-05       Impact factor: 5.157

6.  Molecular cloning of testicular 20 alpha-hydroxysteroid dehydrogenase: identity with aldose reductase.

Authors:  J C Warren; G L Murdock; Y Ma; S R Goodman; W E Zimmer
Journal:  Biochemistry       Date:  1993-02-16       Impact factor: 3.162

7.  Novel, potent aldose reductase inhibitors: 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl] methyl]-1-phthalazineacetic acid (zopolrestat) and congeners.

Authors:  B L Mylari; E R Larson; T A Beyer; W J Zembrowski; C E Aldinger; M F Dee; T W Siegel; D H Singleton
Journal:  J Med Chem       Date:  1991-01       Impact factor: 7.446

8.  Novel NADPH-binding domain revealed by the crystal structure of aldose reductase.

Authors:  J M Rondeau; F Tête-Favier; A Podjarny; J M Reymann; P Barth; J F Biellmann; D Moras
Journal:  Nature       Date:  1992-01-30       Impact factor: 49.962

9.  Aldose reductase from human psoas muscle. Purification, substrate specificity, immunological characterization, and effect of drugs and inhibitors.

Authors:  N A Morjana; T G Flynn
Journal:  J Biol Chem       Date:  1989-02-15       Impact factor: 5.157

10.  The crystal structure of the aldose reductase.NADPH binary complex.

Authors:  D W Borhani; T M Harter; J M Petrash
Journal:  J Biol Chem       Date:  1992-12-05       Impact factor: 5.157

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  16 in total

1.  Structural basis for 18-β-glycyrrhetinic acid as a novel non-GSH analog glyoxalase I inhibitor.

Authors:  Hong Zhang; Qiang Huang; Jing Zhai; Yi-ning Zhao; Li-ping Zhang; Yun-yun Chen; Ren-wei Zhang; Qing Li; Xiao-peng Hu
Journal:  Acta Pharmacol Sin       Date:  2015-08-17       Impact factor: 6.150

2.  Structural and thermodynamic studies of simple aldose reductase-inhibitor complexes.

Authors:  June M Brownlee; Erik Carlson; Amy C Milne; Erika Pape; David H T Harrison
Journal:  Bioorg Chem       Date:  2006-11-02       Impact factor: 5.275

Review 3.  The aldo-keto reductase superfamily and its role in drug metabolism and detoxification.

Authors:  Oleg A Barski; Srinivas M Tipparaju; Aruni Bhatnagar
Journal:  Drug Metab Rev       Date:  2008       Impact factor: 4.518

Review 4.  Comparative anatomy of the aldo-keto reductase superfamily.

Authors:  J M Jez; M J Bennett; B P Schlegel; M Lewis; T M Penning
Journal:  Biochem J       Date:  1997-09-15       Impact factor: 3.857

5.  NAD(P)H-dependent aldose reductase from the xylose-assimilating yeast Candida tenuis. Isolation, characterization and biochemical properties of the enzyme.

Authors:  W Neuhauser; D Haltrich; K D Kulbe; B Nidetzky
Journal:  Biochem J       Date:  1997-09-15       Impact factor: 3.857

6.  Kinetic alteration of a human dihydrodiol/3alpha-hydroxysteroid dehydrogenase isoenzyme, AKR1C4, by replacement of histidine-216 with tyrosine or phenylalanine.

Authors:  T Ohta; S Ishikura; S Shintani; N Usami; A Hara
Journal:  Biochem J       Date:  2000-12-15       Impact factor: 3.857

7.  Identification of amino acid residues responsible for differences in substrate specificity and inhibitor sensitivity between two human liver dihydrodiol dehydrogenase isoenzymes by site-directed mutagenesis.

Authors:  K Matsuura; Y Deyashiki; K Sato; N Ishida; G Miwa; A Hara
Journal:  Biochem J       Date:  1997-04-01       Impact factor: 3.857

8.  Aldose Reductase Acts as a Selective Derepressor of PPARγ and the Retinoic Acid Receptor.

Authors:  Devi Thiagarajan; Radha Ananthakrishnan; Jinghua Zhang; Karen M O'Shea; Nosirudeen Quadri; Qing Li; Kelli Sas; Xiao Jing; Rosa Rosario; Subramaniam Pennathur; Ann Marie Schmidt; Ravichandran Ramasamy
Journal:  Cell Rep       Date:  2016-03-24       Impact factor: 9.423

9.  Roles of the C-terminal domains of human dihydrodiol dehydrogenase isoforms in the binding of substrates and modulators: probing with chimaeric enzymes.

Authors:  K Matsuura; A Hara; Y Deyashiki; H Iwasa; T Kume; S Ishikura; H Shiraishi; Y Katagiri
Journal:  Biochem J       Date:  1998-12-01       Impact factor: 3.857

10.  Path-integral method for predicting relative binding affinities of protein-ligand complexes.

Authors:  Chandrika Mulakala; Yiannis N Kaznessis
Journal:  J Am Chem Soc       Date:  2009-04-01       Impact factor: 15.419

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