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Experimental and Computational Study of the Antioxidative Potential of Novel Nitro and Amino Substituted Benzimidazole/Benzothiazole-2- Carboxamides with Antiproliferative Activity

Cindrić, Maja; Sović, Irena; Mioč, Marija; Hok, Lucija; Boček, Ida; Roškarić, Petra; Butković, Kristina; Martin-Kleiner, Irena; Starčević, Kristina; Vianello, Robert; Kralj, Marijeta; Hranjec, Marijana (2019) Experimental and Computational Study of the Antioxidative Potential of Novel Nitro and Amino Substituted Benzimidazole/Benzothiazole-2- Carboxamides with Antiproliferative Activity. Antioxidants, 8 (10). ISSN 2076-3921

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Abstract

We present the synthesis of a range of benzimidazole/benzothiazole-2-carboxamides with a variable number of methoxy and hydroxy groups, substituted with nitro, amino, or amino protonated moieties, which were evaluated for their antiproliferative activity in vitro and the antioxidant capacity. Antiproliferative features were tested on three human cancer cells, while the antioxidative activity was measured using 1, 1- diphenyl-picrylhydrazyl (DPPH) free radical scavenging and ferric reducing/antioxidant power (FRAP) assays . Trimethoxy substituted benzimidazole-2-carboxamide 8 showed the most promising antiproliferative activity (IC50 = 0.6– 2.0 µM), while trihydroxy substituted benzothiazole-2-carboxamide 29 was identified as the most promising antioxidant, being significantly more potent than the reference butylated hydroxytoluene BHT in both assays. Moreover, the latter also displays antioxidative activity in tumor cells. The measured antioxidative capacities were rationalized through density functional theory (DFT) calculations, showing that 29 owes its activity to the formation of two [O•∙∙∙H–O] hydrogen bonds in the formed radical. Systems 8 and 29 were both chosen as lead compounds for further optimization of the benzazole-2-carboxamide scaffold in order to develop more efficient antioxidants and/or systems with the antiproliferative activity

Item Type: Article
Uncontrolled Keywords: benzimidazoles ; benzothiazoles ; carboxamides ; antiproliferative activity ; antioxidative activity ; ROS ; DFT calculations
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Molecular Medicine
Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Dizajn i sinteza novih dušikovih heterocikličkih fluorofora i fluorescentnih nanomaterijala kao kemijskih senzora za pH i metalne ione-iNFiNiTE–SENSRobert VianelloIP-2014-09-3386HRZZ
Istraživanje antioksidativnog djelovanja benzazolskog skeleta u dizajnu novih antitumorskih agensa-AntioxPotMarijana HranjecIP-2018-01-4379HRZZ
Depositing User: Sofija Konjević
Date Deposited: 04 Dec 2019 12:25
Last Modified: 04 Dec 2019 12:25
URI: http://fulir.irb.hr/id/eprint/5217
DOI: 10.3390/antiox8100477

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