Hydroxyl substituted benzoic acid/cinnamic acid derivatives: Tyrosinase inhibitory kinetics, anti-melanogenic activity and molecular docking studies.

Benzoic Acid / pharmacology Cinnamates / pharmacology Humans Melanoma / drug therapy Molecular Docking Simulation / methods Structure-Activity Relationship
Kinetic mechanism Melanin quantification Methoxy phenol Molecular docking studies Tyrosinase inhibitors

Journal

Bioorganic & medicinal chemistry letters
ISSN: 1464-3405
Titre abrégé: Bioorg Med Chem Lett
Pays: England
ID NLM: 9107377

Informations de publication

Date de publication:
01 01 2020
Historique:
received: 17 06 2019
revised: 26 09 2019
accepted: 27 09 2019
pubmed: 17 11 2019
medline: 9 2 2021
entrez: 17 11 2019
Statut: ppublish

Résumé

The inhibition of tyrosinase is an established strategy for treating hyperpigmentation. Our previous findings demonstrated that cinnamic acid and benzoic acid scaffolds can be effective tyrosinase inhibitors with low toxicity. The hydroxyl substituted benzoic and cinnamic acid moieties of these precursors were incorporated into new chemotypes that displayed in vitro inhibitory effect against mushroom tyrosinase. The most active compound, (2-(3-methoxyphenoxy)-2-oxoethyl (E)-3-(4-hydroxyphenyl) acrylate) 6c, inhibited tyrosinase with an IC

Identifiants

DOI: 10.1016/j.bmcl.2019.126722 PMID: 31732410
pubmed: 31732410
pii: S0960-894X(19)30680-8
doi: 10.1016/j.bmcl.2019.126722
pii:
doi:

Substances chimiques

Cinnamates 0
cinnamic acid 140-10-3
Benzoic Acid 8SKN0B0MIM

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

126722

Subventions

Organisme : Wellcome Trust
ID : WT1104797/Z/14/Z
Pays : United Kingdom

Informations de copyright

Copyright © 2019 Elsevier Ltd. All rights reserved.

Auteurs

Yasir Nazir (Y)

Institute for Molecular Biosciences (IMB), The University of Queensland (UQ), St Lucia 4072, Qld, Australia; Department of Chemistry, Allama Iqbal Open University, Islamabad 44000, Pakistan.

Aamer Saeed (A)

Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan.

Muhammad Rafiq (M)

Department of Physiology and Biochemistry, Cholistan University of Veterinary and Animal Sciences, Bahawalpur, Pakistan.

Samina Afzal (S)

Faculty of Pharmacy, Bahauddin Zakria University, Multan 60800, Pakistan.

Anser Ali (A)

Department of Zoology, Mirpur University of Science and Technology (MUST), 10250 Mirpur, AJK, Pakistan.

Muhammad Latif (M)

College of Medicine, Centre for Genetics and Inherited Diseases (CGID), Taibah University, Al-Madinah Al-Munawwarah, Saudi Arabia.

Johannes Zuegg (J)

Institute for Molecular Biosciences (IMB), The University of Queensland (UQ), St Lucia 4072, Qld, Australia.

Waleed M Hussein (WM)

School of Chemistry and Molecular Biosciences (SCMB) and ARC Training Centre for Biopharmaceutical Innovation, The University of Queensland (UQ), St Lucia 4072, Qld, Australia; Helwan University, Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, EinHelwan, Helwan, Egypt.

Christian Fercher (C)

Australian Institute for Bioengineering and Nanotechnology (AIBN), The University of Queensland (UQ), St Lucia 4072, Qld, Australia.

Ross T Barnard (RT)

School of Chemistry and Molecular Biosciences (SCMB) and ARC Training Centre for Biopharmaceutical Innovation, The University of Queensland (UQ), St Lucia 4072, Qld, Australia.

Matthew A Cooper (MA)

Institute for Molecular Biosciences (IMB), The University of Queensland (UQ), St Lucia 4072, Qld, Australia.

Mark A T Blaskovich (MAT)

Institute for Molecular Biosciences (IMB), The University of Queensland (UQ), St Lucia 4072, Qld, Australia.

Zaman Ashraf (Z)

Department of Chemistry, Allama Iqbal Open University, Islamabad 44000, Pakistan. Electronic address: zaman.ashraf@aiou.edu.pk.

Zyta M Ziora (ZM)

Institute for Molecular Biosciences (IMB), The University of Queensland (UQ), St Lucia 4072, Qld, Australia. Electronic address: z.ziora@imb.uq.edu.au.

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Classifications MeSH

questionsmedicales.fr › Composés chimiques organiques › Hydrocarbures › Hydrocarbures cycliques › Hydrocarbures aromatiques › Dérivés du benzène › Benzoates › Acide benzoïque › Hydroxyl substituted benzoic acid/cinnamic...
questionsmedicales.fr › Composés chimiques organiques › Acides carboxyliques › Acides carbocycliques › Cinnamates › Hydroxyl substituted benzoic acid/cinnamic...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Primates › Haplorhini › Catarrhini › Hominidae › Humains › Hydroxyl substituted benzoic acid/cinnamic...
questionsmedicales.fr › Tumeurs › Tumeurs par type histologique › Naevus et mélanomes › Mélanome › Hydroxyl substituted benzoic acid/cinnamic...
questionsmedicales.fr › Sciences de l'information › Méthodologies informatiques › Simulation numérique › Simulation de docking moléculaire › Hydroxyl substituted benzoic acid/cinnamic...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes pharmacologiques › Relation structure-activité › Hydroxyl substituted benzoic acid/cinnamic...