Abstract
Tyrosinase is a multifunctional, glycosylated and copper-containing oxidase enzyme that can be found in animals, plants, and fungi. It is involved in several biological processes such as melanin biosynthesis. In this work, a series of isobenzofuran-1(3H)-ones was evaluated as tyrosinase inhibitors. It was found that compounds phthalaldehydic acid (1), 3-(2,6-dihydroxy-4-isopropylphenyl)isobenzofuran-1(3H)-one (7), and 2-(3-oxo-1,3-dihydroisobenzofuran-1-yl)-1,3-phenylene diacetate (9) were the most potent compounds inhibiting tyrosinase activity in a concentration dependent manner. Ligand-enzyme NMR studies and docking investigations allowed to map the atoms of the ligands involved in the interaction with the copper atoms present in the active site of the tyrosinase. This behaviour is similar to kojic acid, a well know tyrosinase inhibitor and used as positive control in the biological assays. The findings herein described pave the way for future rational design of new tyrosinase inhibitors.
PMID: 33278593 [PubMed - as supplied by publisher]
[NMR paper] Effect of Temperature on 1H NMR Spectra, Antitrypanosomal Activity, Conformational Analysis, and Molecular Docking of Curine Derivatives from Berberis brevissima.
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J Nat Prod. 2020 May 04;:
Authors: Ali S, Alamzeb M, Rashid MU, Setzer WN
Abstract
The ethanolic root extract of Berberis brevissima afforded a new bisbenzylisoquinoline alkaloid,...
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[NMR paper] Analyzing organophosphate pesticide-serum albumin binding interaction: A combined STD NMR and molecular docking study.
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In Vitro analysis of the interaction of organophosphate pesticides (OP) with bovine serum albumin (BSA) is crucial to understand their potential effects at the molecular level. In this...
[NMR paper] Design, synthesis, biological evaluation, NMR and DFT studies of structurally-simplified trimethoxy benzamides as P-glycoprotein selective inhibitors: the role of molecular flatness.
Design, synthesis, biological evaluation, NMR and DFT studies of structurally-simplified trimethoxy benzamides as P-glycoprotein selective inhibitors: the role of molecular flatness.
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Chem Biol Drug Des. 2016 Jun 22;
Authors: Stefanachi A, Mangiatordi GF, Tardia P, Alberga D, Leonetti F, Niso M, Colabufo NA, Adamo C, Nicolotti O, Cellamare S
Abstract
...
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[NMR paper] Synthesis, spectroscopic investigations (X-ray, NMR and TD-DFT), antimicrobial activity and molecular docking of 2,6-bis(hydroxy(phenyl)methyl)cyclohexanone.
Synthesis, spectroscopic investigations (X-ray, NMR and TD-DFT), antimicrobial activity and molecular docking of 2,6-bis(hydroxy(phenyl)methyl)cyclohexanone.
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Molecules. 2015;20(7):13240-63
Authors: Barakat A, Ghabbour HA, Al-Majid AM, Soliman SM, Ali M, Mabkhot YN, Shaik MR, Fun HK
Abstract
The synthesis of 2,6-bis(hydroxy(phenyl)methyl)cyclohexanone 1...
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[NMR paper] Structure optimization of 2-benzamidobenzoic acids as PqsD inhibitors for Pseudomonas aeruginosa infections and elucidation of binding mode by SPR, STD NMR, and molecular docking.
Structure optimization of 2-benzamidobenzoic acids as PqsD inhibitors for Pseudomonas aeruginosa infections and elucidation of binding mode by SPR, STD NMR, and molecular docking.
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J Med Chem. 2013 Aug 8;56(15):6146-55
Authors: Weidel E, de Jong JC, Brengel...
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[NMR paper] Molecular docking and NMR binding studies to identify novel inhibitors of human phosphomevalonate kinase.
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Biochem Biophys Res Commun. 2013 Jan 4;430(1):313-9
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[NMR paper] Interaction between the type-3 copper protein tyrosinase and the substrate analogue p
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J Am Chem Soc. 2005 Jan 19;127(2):567-75
Authors: Tepper AW, Bubacco L, Canters GW
The interaction of the monooxygenating type-3 copper enzyme Tyrosinase (Ty) from Streptomyces antibioticus with its inhibitor p-nitrophenol (pnp) was studied by paramagnetic NMR methods. The pnp binds to oxidized Ty...
Isobenzofuran-1(3H)-ones as new tyrosinase inhibitors: Biological activity and interaction studies by molecular docking and NMR.
Linear Mode
