Phenolic Thiazoles with Antioxidant and Antiradical Activity. Synthesis, In Vitro Evaluation, Toxicity, Electrochemical Behavior, Quantum Studies and Antimicrobial Screening

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 Di...

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Autores principales:	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
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	polyphenols thiazole antioxidant activity antiradical activity synthesis cytotoxicity Therapeutics. Pharmacology RM1-950
Acceso en línea:	https://doaj.org/article/1ae4f973a78a4891b144ff0bc09c77f2
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spelling	oai:doaj.org-article:1ae4f973a78a4891b144ff0bc09c77f22021-11-25T16:26:45ZPhenolic Thiazoles with Antioxidant and Antiradical Activity. Synthesis, In Vitro Evaluation, Toxicity, Electrochemical Behavior, Quantum Studies and Antimicrobial Screening10.3390/antiox101117072076-3921https://doaj.org/article/1ae4f973a78a4891b144ff0bc09c77f22021-10-01T00:00:00Zhttps://www.mdpi.com/2076-3921/10/11/1707https://doaj.org/toc/2076-3921Oxidative 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 <i>C. albicans</i>, and their cytotoxicity was assessed in vitro. Compounds <b>5a-b</b>, <b>7a-b</b> and <b>8a-b</b> presented remarkable antioxidant and antiradical properties, and compounds <b>5a-b</b>, <b>7a</b> and <b>8a</b> displayed good Cu<sup>+2</sup> chelating activity. Compounds <b>7a</b> and <b>8a</b> were very active against <i>P. aeruginosa</i> 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-<i>Pseudomonas</i> potential.Gabriel MarcAnca StanaAna Horiana FranchiniDan Cristian VodnarGabriel BartaMihaela TertişIulia ŞantaCecilia CristeaAdrian PîrnăuAlexandra CiorîţăBogdan DumeVlad-Alexandru TomaLaurian VlaseIlioara OnigaOvidiu OnigaMDPI AGarticlepolyphenolsthiazoleantioxidant activityantiradical activitysynthesiscytotoxicityTherapeutics. PharmacologyRM1-950ENAntioxidants, Vol 10, Iss 1707, p 1707 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	polyphenols thiazole antioxidant activity antiradical activity synthesis cytotoxicity Therapeutics. Pharmacology RM1-950
spellingShingle	polyphenols thiazole antioxidant activity antiradical activity synthesis cytotoxicity Therapeutics. Pharmacology RM1-950 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 Phenolic Thiazoles with Antioxidant and Antiradical Activity. Synthesis, In Vitro Evaluation, Toxicity, Electrochemical Behavior, Quantum Studies and Antimicrobial Screening
description	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 <i>C. albicans</i>, and their cytotoxicity was assessed in vitro. Compounds <b>5a-b</b>, <b>7a-b</b> and <b>8a-b</b> presented remarkable antioxidant and antiradical properties, and compounds <b>5a-b</b>, <b>7a</b> and <b>8a</b> displayed good Cu<sup>+2</sup> chelating activity. Compounds <b>7a</b> and <b>8a</b> were very active against <i>P. aeruginosa</i> 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-<i>Pseudomonas</i> potential.
format	article
author	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
author_facet	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
author_sort	Gabriel Marc
title	Phenolic Thiazoles with Antioxidant and Antiradical Activity. Synthesis, In Vitro Evaluation, Toxicity, Electrochemical Behavior, Quantum Studies and Antimicrobial Screening
title_short	Phenolic Thiazoles with Antioxidant and Antiradical Activity. Synthesis, In Vitro Evaluation, Toxicity, Electrochemical Behavior, Quantum Studies and Antimicrobial Screening
title_full	Phenolic Thiazoles with Antioxidant and Antiradical Activity. Synthesis, In Vitro Evaluation, Toxicity, Electrochemical Behavior, Quantum Studies and Antimicrobial Screening
title_fullStr	Phenolic Thiazoles with Antioxidant and Antiradical Activity. Synthesis, In Vitro Evaluation, Toxicity, Electrochemical Behavior, Quantum Studies and Antimicrobial Screening
title_full_unstemmed	Phenolic Thiazoles with Antioxidant and Antiradical Activity. Synthesis, In Vitro Evaluation, Toxicity, Electrochemical Behavior, Quantum Studies and Antimicrobial Screening
title_sort	phenolic thiazoles with antioxidant and antiradical activity. synthesis, in vitro evaluation, toxicity, electrochemical behavior, quantum studies and antimicrobial screening
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/1ae4f973a78a4891b144ff0bc09c77f2
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Phenolic Thiazoles with Antioxidant and Antiradical Activity. Synthesis, In Vitro Evaluation, Toxicity, Electrochemical Behavior, Quantum Studies and Antimicrobial Screening

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