AustralieFrV1, Main, Exploration, bibRecord, 00AC48

High-resolution structures of human aldose reductase holoenzyme in complex with stereoisomers of the potent inhibitor fidarestat: Stereospecific interaction between the enzyme and a cyclic imide type inhibitor

Identifieur interne : 00AC48 ( Main/Exploration ); précédent : 00AC47; suivant : 00AC49

High-resolution structures of human aldose reductase holoenzyme in complex with stereoisomers of the potent inhibitor fidarestat: Stereospecific interaction between the enzyme and a cyclic imide type inhibitor

Auteurs : Ossama El-Kabbani [Australie, Japon, Suisse, France] ; Connie Darmanin ; Mitsuru Oka ; Clemens Schulze-Briese ; Takashi Tomizaki ; Isabelle Hazemann ; Andre Mitschler ; Alberto Podjarny

Source :

Journal of medicinal chemistry : (Print) [ 0022-2623 ] ; 2004.

RBID : Pascal:05-0124639

Descripteurs français

Pascal (Inist)
- Analyse structurale, Inhibiteur enzyme, Aldehyde reductase, Homme, Modélisation, Modèle moléculaire, Fidarestat, Stéréoisomère, Imide, Spirane, Hétérocycle oxygène azote, Spiro[1-benzopyrane-4:4p-imidazolidine-2-carboxamide] dérivé.
Wicri :
- topic : Homme.

English descriptors

KwdEn :
- Aldehyde reductase, Enzyme inhibitor, Fidarestat, Human, Imide, Modeling, Molecular model, Oxygen nitrogen heterocycle, Spiran, Stereoisomer, Structural analysis.

Abstract

Structure determinations of human aldose reductase holoenzyme in complex with the 2S4R-, 2R4S- and 2R4R-isomers of the potent inhibitor Fidarestat ((2S,4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazoline]-2-carboxamide) were carried out in order to elucidate the binding modes responsible for the differences in their inhibitory potencies. In the complex structure with the 2R4S-isomer the cyclic imide moiety formed hydrogen bonds with the side-chains of Trplll, Tyr48 and His110. In the attempt to determine the complex structure with the least potent 2R4R-isomer this ligand was not observed, and instead, the active site was simultaneously occupied by two citrate molecules (occupancies of 60% and 40%). In the case of 2S4R, the active site was occupied by a citrate molecule which anchors the 2S4R-isomer from its carbamoyl group. The structures of the complexes suggest that the differences in the interactions between the cyclic imide rings and carbamoyl groups of the compounds with residues His110, Trplll, Trp219 and Cys298 account for differences in their inhibitory potencies.

Affiliations:

Australie, France, Japon, Suisse

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Le document en format XML

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<term>Modeling</term>
<term>Molecular model</term>
<term>Oxygen nitrogen heterocycle</term>
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<front><div type="abstract" xml:lang="en">Structure determinations of human aldose reductase holoenzyme in complex with the 2S4R-, 2R4S- and 2R4R-isomers of the potent inhibitor Fidarestat ((2S,4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazoline]-2-carboxamide) were carried out in order to elucidate the binding modes responsible for the differences in their inhibitory potencies. In the complex structure with the 2R4S-isomer the cyclic imide moiety formed hydrogen bonds with the side-chains of Trplll, Tyr48 and His110. In the attempt to determine the complex structure with the least potent 2R4R-isomer this ligand was not observed, and instead, the active site was simultaneously occupied by two citrate molecules (occupancies of 60% and 40%). In the case of 2S4R, the active site was occupied by a citrate molecule which anchors the 2S4R-isomer from its carbamoyl group. The structures of the complexes suggest that the differences in the interactions between the cyclic imide rings and carbamoyl groups of the compounds with residues His110, Trplll, Trp219 and Cys298 account for differences in their inhibitory potencies.</div>
</front>
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High-resolution structures of human aldose reductase holoenzyme in complex with stereoisomers of the potent inhibitor fidarestat: Stereospecific interaction between the enzyme and a cyclic imide type inhibitor

High-resolution structures of human aldose reductase holoenzyme in complex with stereoisomers of the potent inhibitor fidarestat: Stereospecific interaction between the enzyme and a cyclic imide type inhibitor

Source :

Descripteurs français

English descriptors

Abstract

Links toward previous steps (curation, corpus...)

Le document en format XML

Pour manipuler ce document sous Unix (Dilib)

Pour mettre un lien sur cette page dans le réseau Wicri