title: Design, synthesis and biological evaluation of novel hydroxy-phenyl-1H-benzimidazoles as radical scavengers and UV-protective agents.
abstract: An ever-increasing incidence of skin neoplastic diseases is registered. Therefore, it is important to protect the skin from the UV radiation that reaches the epidermis and dermis but also to block ROS generated by them. Our attention was attracted in developing new compounds provided with both UV filtering and antioxidant capacities. To this end, 2-phenyl-1H-benzimidazole-5-sulfonic acid (PBSA), a known UV filter, was selected as lead compound for its lack of antioxidant activity, high water solubility and good safety profile. PBSA was sequentially modified introducing hydroxyls on the phenyl ring and also substituting the functional group in position 5 of the benzimidazole ring. At the end of the synthetic study, a new, very potent class of antioxidants has been obtained. Surprisingly some of the developed molecules, while devoid of significant UV-filtering activity was endowed with potent UV-filtering booster capability if associated with known commercial UVB and UVA filters.
authors.affiliation: a Department of Life Sciences and Biotechnology, School of Pharmacy and Health Products , University of Ferrara, Master Course in Cosmetic Sciences and Technology, Laboratory of Health Products , Ferrara , Italy.
authors.forename: Alessia
authors.initials: A
authors.lastname: Bino
authors.affiliation: a Department of Life Sciences and Biotechnology, School of Pharmacy and Health Products , University of Ferrara, Master Course in Cosmetic Sciences and Technology, Laboratory of Health Products , Ferrara , Italy.
authors.forename: Anna
authors.initials: A
authors.lastname: Baldisserotto
authors.affiliation: a Department of Life Sciences and Biotechnology, School of Pharmacy and Health Products , University of Ferrara, Master Course in Cosmetic Sciences and Technology, Laboratory of Health Products , Ferrara , Italy.
authors.forename: Emanuela
authors.initials: E
authors.lastname: Scalambra
authors.affiliation: a Department of Life Sciences and Biotechnology, School of Pharmacy and Health Products , University of Ferrara, Master Course in Cosmetic Sciences and Technology, Laboratory of Health Products , Ferrara , Italy.
authors.forename: Valeria
authors.initials: V
authors.lastname: Dissette
authors.affiliation: b Department of Pharmaceutical and Pharmacological Sciences , University of Padua , Padua , Italy.
authors.forename: Daniela Ester
authors.initials: DE
authors.lastname: Vedaldi
authors.affiliation: b Department of Pharmaceutical and Pharmacological Sciences , University of Padua , Padua , Italy.
authors.forename: Alessia
authors.initials: A
authors.lastname: Salvador
authors.affiliation: a Department of Life Sciences and Biotechnology, School of Pharmacy and Health Products , University of Ferrara, Master Course in Cosmetic Sciences and Technology, Laboratory of Health Products , Ferrara , Italy.
authors.forename: Elisa
authors.initials: E
authors.lastname: Durini
authors.affiliation: a Department of Life Sciences and Biotechnology, School of Pharmacy and Health Products , University of Ferrara, Master Course in Cosmetic Sciences and Technology, Laboratory of Health Products , Ferrara , Italy.
authors.forename: Stefano
authors.initials: S
authors.lastname: Manfredini
authors.affiliation: a Department of Life Sciences and Biotechnology, School of Pharmacy and Health Products , University of Ferrara, Master Course in Cosmetic Sciences and Technology, Laboratory of Health Products , Ferrara , Italy.
authors.forename: Silvia
authors.initials: S
authors.lastname: Vertuani
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001562:Benzimidazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013473:Sunscreening Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D014466:Ultraviolet Rays / Q000009:adverse effects*
chemical_list: D000975:Antioxidants; D001562:Benzimidazoles; D016166:Free Radical Scavengers; D013473:Sunscreening Agents; C000614354:hydroxy-phenyl-1H-benzimidazole
keywords: Benzimidazole; UV booster; antioxidant; reactive oxygen species; sunscreens