title: Hydroxylated biphenyls as tyrosinase inhibitor: A spectrophotometric and electrochemical study.
abstract: A small collection of C2-symmetry hydroxylated biphenyls was prepared by straightforward methods and the capability to act as inhibitors of tyrosinase has been evaluated by both spectrophotometric and electrochemical assays. Our attention was focused on the diphenolase activity of this enzyme characterized by the absence of the characteristic lag time of enzymatic reaction of its monophenolase activity. To this purpose, we evaluated the capability of tyrosinase to oxidize a natural o-diphenol substrate to o-quinone analyzing the changes in the UV-Vis spectrum of a solution of caffeic acid and the reduction of the cathodic current in a tyrosinase-biosensor, respectively. Results of both the methods were comparable. Most of the compounds possessed higher inhibitory activity compared to compound 1, a known hydroxylated biphenyl inhibitor of tyrosinase.
authors.affiliation: Istituto di Chimica Biomolecolare, Consiglio Nazionale Ricerche, Via Marzolo 1, I-35131 Padova, Italy.
authors.forename: Paolo
authors.initials: P
authors.lastname: Ruzza
authors.affiliation: Dipartimento di Medicina Clinica e Sperimentale, Università degli Studi, Viale S. Pietro 43/b, I-07100 Sassari, Italy.
authors.forename: Pier Andrea
authors.initials: PA
authors.lastname: Serra
authors.affiliation: Istituto di Chimica Biomolecolare, Consiglio Nazionale Ricerche, Traversa La Crucca 3, I-07100 Sassari, Italy.
authors.forename: Davide
authors.initials: D
authors.lastname: Fabbri
authors.affiliation: Istituto di Chimica Biomolecolare, Consiglio Nazionale Ricerche, Traversa La Crucca 3, I-07100 Sassari, Italy.
authors.forename: Maria Antonietta
authors.initials: MA
authors.lastname: Dettori
authors.affiliation: Dipartimento di Medicina Clinica e Sperimentale, Università degli Studi, Viale S. Pietro 43/b, I-07100 Sassari, Italy.
authors.forename: Gaia
authors.initials: G
authors.lastname: Rocchitta
authors.affiliation: Istituto di Chimica Biomolecolare, Consiglio Nazionale Ricerche, Traversa La Crucca 3, I-07100 Sassari, Italy. Electronic address: giovanna.delogu@icb.cnr.it.
authors.forename: Giovanna
authors.initials: G
authors.lastname: Delogu
mesh_terms: D000363:Agaricales / Q000201:enzymology; D055162:Biocatalysis; D001713:Biphenyl Compounds / Q000737:chemistry* / Q000494:pharmacology*; D004563:Electrochemistry; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D006900:Hydroxylation; D007700:Kinetics; D008958:Models, Molecular; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism; D010084:Oxidation-Reduction; D011487:Protein Conformation; D013056:Spectrophotometry, Ultraviolet
chemical_list: D001713:Biphenyl Compounds; D004791:Enzyme Inhibitors; D014442:Monophenol Monooxygenase; C010574:biphenyl
keywords: Biosensor; Hydroxylated biphenyls; Spectrophotometric assay; Synthesis; Tyrosinase