Phenolic Thiazoles with Antioxidant and Antiradical Activity. Synthesis, In Vitro Evaluation, Toxicity, Electrochemical Behavior, Quantum Studies and Antimicrobial Screening
Gabriel Marc,
Anca Stana,
Ana Horiana Franchini,
Dan Cristian Vodnar,
Gabriel Barta,
Mihaela Tertiş,
Iulia Şanta,
Cecilia Cristea,
Adrian Pîrnău,
Alexandra Ciorîţă,
Bogdan Dume,
Vlad-Alexandru Toma,
Laurian Vlase,
Ilioara Oniga,
Ovidiu Oniga
Affiliations
Gabriel Marc
Department of Pharmaceutical Chemistry, “Iuliu Hațieganu” University of Medicine and Pharmacy, 41 Victor Babeș Street, RO-400012 Cluj-Napoca, Romania
Anca Stana
Department of Pharmaceutical Chemistry, “Iuliu Hațieganu” University of Medicine and Pharmacy, 41 Victor Babeș Street, RO-400012 Cluj-Napoca, Romania
Ana Horiana Franchini
Department of Pharmaceutical Chemistry, “Iuliu Hațieganu” University of Medicine and Pharmacy, 41 Victor Babeș Street, RO-400012 Cluj-Napoca, Romania
Dan Cristian Vodnar
Department of Food Science and Technology, University of Agricultural Sciences and Veterinary Medicine, 3-5 Manăştur Street, RO-400372 Cluj-Napoca, Romania
Gabriel Barta
Department of Food Science and Technology, University of Agricultural Sciences and Veterinary Medicine, 3-5 Manăştur Street, RO-400372 Cluj-Napoca, Romania
Mihaela Tertiş
Department of Analytical Chemistry, Faculty of Pharmacy, “Iuliu Haţieganu” University of Medicine and Pharmacy, 4 Louis Pasteur Street, RO-400349 Cluj-Napoca, Romania
Iulia Şanta
Department of Analytical Chemistry, Faculty of Pharmacy, “Iuliu Haţieganu” University of Medicine and Pharmacy, 4 Louis Pasteur Street, RO-400349 Cluj-Napoca, Romania
Cecilia Cristea
Department of Analytical Chemistry, Faculty of Pharmacy, “Iuliu Haţieganu” University of Medicine and Pharmacy, 4 Louis Pasteur Street, RO-400349 Cluj-Napoca, Romania
Adrian Pîrnău
National Institute for Research and Development of Isotopic and Molecular Technologies, 67-103 Donath Street, RO-400293 Cluj-Napoca, Romania
Alexandra Ciorîţă
National Institute for Research and Development of Isotopic and Molecular Technologies, 67-103 Donath Street, RO-400293 Cluj-Napoca, Romania
Bogdan Dume
Department of Molecular Biology and Biotechnologies, Babeș-Bolyai University, 4-6 Clinicilor Street, RO-400006 Cluj-Napoca, Romania
Vlad-Alexandru Toma
National Institute for Research and Development of Isotopic and Molecular Technologies, 67-103 Donath Street, RO-400293 Cluj-Napoca, Romania
Laurian Vlase
Department of Pharmaceutical Technology and Biopharmaceutics, “Iuliu Hațieganu” University of Medicine and Pharmacy, 41 Victor Babeș Street, RO-400012 Cluj-Napoca, Romania
Ilioara Oniga
Department of Pharmacognosy, “Iuliu Haţieganu” University of Medicine and Pharmacy, 12 Ion Creangă Street, RO-400010 Cluj-Napoca, Romania
Ovidiu Oniga
Department of Pharmaceutical Chemistry, “Iuliu Hațieganu” University of Medicine and Pharmacy, 41 Victor Babeș Street, RO-400012 Cluj-Napoca, Romania
Oxidative stress represents the underlying cause of many chronic diseases in human; therefore, the development of potent antioxidant compounds for preventing or treating such conditions is useful. Starting from the good antioxidant and antiradical properties identified for the previously reported Dihydroxy-Phenyl-Thiazol-Hydrazinium chloride (DPTH), we synthesized a congeneric series of phenolic thiazoles. The radical scavenging activity, and the antioxidant and chelation potential were assessed in vitro, a series of quantum descriptors were calculated, and the electrochemical behavior of the synthesized compounds was studied to evaluate the impact on the antioxidant and antiradical activities. In addition, their antibacterial and antifungal properties were evaluated against seven aerobic bacterial strains and a strain of C. albicans, and their cytotoxicity was assessed in vitro. Compounds 5a-b, 7a-b and 8a-b presented remarkable antioxidant and antiradical properties, and compounds 5a-b, 7a and 8a displayed good Cu+2 chelating activity. Compounds 7a and 8a were very active against P. aeruginosa ATCC 27853 compared to norfloxacin, and proved less cytotoxic than ascorbic acid against the human keratinocyte cell line (HaCaT cells, CLS-300493). Several phenolic compounds from the synthesized series presented excellent antioxidant activity and notable anti-Pseudomonas potential.
