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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 et al.
Experimental and Computational Study of the Antioxidative Potential of Novel Nitro and Amino Substituted Benzimidazole/Benzothiazole-2- Carboxamides with Antiproliferative Activity // Antioxidants, 8 (2019), 10; 477, 22 doi:10.3390/antiox8100477 (međunarodna recenzija, članak, znanstveni)


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

Autori
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

Izvornik
Antioxidants (2076-3921) 8 (2019), 10; 477, 22

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Benzimidazoles ; benzothiazoles ; carboxamides ; antiproliferative activity ; antioxidative activity ; ROS ; DFT calculations

Sažetak
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

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
HRZZ-IP-2014-09-3386 - Dizajn i sinteza novih dušikovih heterocikličkih fluorofora i fluorescentnih nanomaterijala kao kemijskih senzora za pH i metalne ione (Robert Vianello, )
HRZZ-IP-2018-01-4379 - Istraživanje antioksidativnog djelovanja benzazolskog skeleta u dizajnu novih antitumorskih agensa (Marijana Hranjec, )

Ustanove
Veterinarski fakultet, Zagreb,
Institut "Ruđer Bošković", Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

Časopis indeksira:


  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
    • Emerging Sources Citation Index (ESCI)
  • Scopus


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