Design, Synthesis and Evaluation of New Multifunctional Benzothiazoles as Photoprotective, Antioxidant and Antiproliferative Agents

A current trend of research in the health field is toward the discovery of multifunctional compounds, capable of interacting with multiple biological targets, thus simplifying multidrug therapies and improving patient compliance. The aim of this work was to synthesize new multifunctional chemical en...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2022-12, Vol.28 (1), p.287
Main Authors: Barbari, Riccardo, Tupini, Chiara, Durini, Elisa, Gallerani, Eleonora, Nicoli, Francesco, Lampronti, Ilaria, Baldisserotto, Anna, Manfredini, Stefano
Format: Article
Language:English
Subjects:
Acids
Analysis
Annexin V
antioxidant
Antioxidants
Antiproliferatives
antitumor
Antitumor activity
Apoptosis
Benzothiazole
benzothiazole derivatives
Cytotoxicity
Design
Diagnosis
Drug interactions
Drug therapy
Filtration
Free radicals
Irradiation
Keratinocytes
Melanoma
Multifactorial diseases
multifunctional
organic sunscreen UV-filter
Oxidative stress
Patient outcomes
Pharmacokinetics
Polyphenols
Post-irradiation
Selectivity
Skin cancer
Sunscreen
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Summary:A current trend of research in the health field is toward the discovery of multifunctional compounds, capable of interacting with multiple biological targets, thus simplifying multidrug therapies and improving patient compliance. The aim of this work was to synthesize new multifunctional chemical entities bearing a benzothiazole nucleus, a structure that has attracted increasing interest for the great variety of biological actions that it can perform, and already used as a scaffold in several multifunctional drugs. Compounds are reported, divided into two distinct series, synthetized and tested in vitro for the antioxidant, and include UV-filtering and antitumor activities. DPPH and FRAP tests were chosen to outline an antioxidant activity profile against different radical species. The UV-filtering activity was investigated, pre- and post-irradiation, through evaluation of a O/W sunscreen standard formulation containing 3% of the synthetic compounds. The antitumor activity was investigated both on human melanoma cells (Colo-38) and on immortalized human keratinocytes as a control (HaCat). A good antiproliferative profile in terms of IC was chosen as a mandatory condition to further investigate apoptosis induction as a possible cytotoxicity mechanism through the Annexin V test. Compound was endowed with excellent activity and a selectivity profile towards Colo-38, supported by a good antioxidant capacity and an excellent broad-spectrum photoprotective profile.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28010287