The Antioxidant and Antiproliferative Activities of 1,2,3-Triazolyl-L-Ascorbic Acid Derivatives.

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ID: 58118
2019
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Abstract
The novel 4-substituted 1,2,3-triazole L-ascorbic acid (L-ASA) conjugates with hydroxyethylene spacer as well as their conformationally restricted 4,5-unsaturated analogues were synthesized as potential antioxidant and antiproliferative agents. An evaluation of the antioxidant activity of novel compounds showed that the majority of the 4,5-unsaturated L-ASA derivatives showed a better antioxidant activity compared to their saturated counterparts. -Hydroxyphenyl (), -pentylphenyl () and 2-hydroxyethyl () substituted 4,5-unsaturated 1,2,3-triazole L-ASA derivatives exhibited very efficient and rapid (within 5 min) 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity (, : IC = 0.06 mM; : IC = 0.07 mM). In vitro scavenging activity data were supported by in silico quantum-chemical modelling. Thermodynamic parameters for hydrogen-atom transfer and electron-transfer radical scavenging pathways of anions deprotonated at C2-OH or C3-OH groups of L-ASA fragments were calculated. The structure activity analysis (SAR) through principal component analysis indicated radical scavenging activity by the participation of OH group with favorable reaction parameters: the C3-OH group of saturated C4-C5(OH) derivatives and the C2-OH group of their unsaturated C4=C5 analogues. The antiproliferative evaluation showed that bromophenyl (: IC = 6.72 μM) and pentylphenyl-substituted 1,2,3-triazole L-ASA conjugate (: IC = 26.91 μM) had a selective cytotoxic effect on breast adenocarcinoma MCF-7 cells. Moreover, compound did not inhibit the growth of foreskin fibroblasts (IC > 100 μM). In MCF-7 cells treated with , a significant increase of hydroxylated hypoxia-inducible transcription factor 1 alpha (HIF-1α) expression and decreased expression of nitric oxide synthase 2 (NOS2) were observed, suggesting the involvement of in the HIF-1α signaling pathway for its strong growth-inhibition effect on MCF-7 cells.
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harej2019theinternational Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Anja Harej, Andrijana Meščić Macan, Višnja Stepanić, Marko Klobučar, Krešimir Pavelić, Sandra Kraljević Pavelić, Silvana Raić-Malić
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Journal International journal of molecular sciences
Year 2019
DOI
E4735
URL
Keywords
antioxidant 1,2,3-Triazole antitumor vitamin c hif-1 quantum-chemical modelling Antimicrobial activity antioxidant activity phenolic compounds oregano (origanum vulgare), extraction

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