A combinatorial approach for the discovery of drug-like inhibitors of 15-lipoxygenase-1.


Journal

European journal of medicinal chemistry
ISSN: 1768-3254
Titre abrégé: Eur J Med Chem
Pays: France
ID NLM: 0420510

Informations de publication

Date de publication:
15 Jul 2019
Historique:
received: 19 12 2018
revised: 02 04 2019
accepted: 09 04 2019
pubmed: 27 4 2019
medline: 18 6 2019
entrez: 27 4 2019
Statut: ppublish

Résumé

Human 15-lipoxygenase-1 (15-LOX-1) is a mammalian lipoxygenase which plays an important regulatory role in several CNS and inflammatory lung diseases. To further explore the role of this enzyme in drug discovery, novel potent inhibitors with favorable physicochemical properties are required. In order to identify such new inhibitors, we established a combinatorial screening method based on acylhydrazone chemistry. This represents a novel application of combinatorial chemistry focusing on the improvement of physicochemical properties, rather than on potency. This strategy allowed us to efficiently screen 44 reaction mixtures of different hydrazides and our previously reported indole aldehyde core structure, without the need for individual synthesis of all possible combinations of building blocks. Our approach afforded three new inhibitors with IC

Identifiants

pubmed: 31026746
pii: S0223-5234(19)30327-7
doi: 10.1016/j.ejmech.2019.04.021
pii:
doi:

Substances chimiques

Hydrazones 0
Indoles 0
Ligands 0
Lipoxygenase Inhibitors 0
ALOX15 protein, human EC 1.13.11.33
Arachidonate 15-Lipoxygenase EC 1.13.11.33

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

45-55

Informations de copyright

Copyright © 2019 Elsevier Masson SAS. All rights reserved.

Auteurs

Ramon van der Vlag (R)

Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, the Netherlands.

Hao Guo (H)

Chemical and Pharmaceutical Biology, Groningen Research Institute of Pharmacy (GRIP), University of Groningen, Antonius Deusinglaan 1, 9713 AV, Groningen, the Netherlands.

Uladzislau Hapko (U)

Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, the Netherlands; Helmholtz Institute for Pharmaceutical Research Saarland (HIPS) - Helmholtz Centre for Infection Research (HZI), Department of Drug Design and Optimization, Campus Building E8.1, 66123, Saarbrücken, Germany; Department of Pharmacy, Saarland University, 66123, Saarbrücken, Germany.

Nikolaos Eleftheriadis (N)

Chemical and Pharmaceutical Biology, Groningen Research Institute of Pharmacy (GRIP), University of Groningen, Antonius Deusinglaan 1, 9713 AV, Groningen, the Netherlands.

Leticia Monjas (L)

Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, the Netherlands.

Frank J Dekker (FJ)

Chemical and Pharmaceutical Biology, Groningen Research Institute of Pharmacy (GRIP), University of Groningen, Antonius Deusinglaan 1, 9713 AV, Groningen, the Netherlands.

Anna K H Hirsch (AKH)

Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, the Netherlands; Helmholtz Institute for Pharmaceutical Research Saarland (HIPS) - Helmholtz Centre for Infection Research (HZI), Department of Drug Design and Optimization, Campus Building E8.1, 66123, Saarbrücken, Germany; Department of Pharmacy, Saarland University, 66123, Saarbrücken, Germany. Electronic address: Anna.Hirsch@helmholtz-hips.de.

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Classifications MeSH