Novel methyl anthranilate-based organoselenocyanate hybrids were developed, and their structures were confirmed by the state-of-the-art spectroscopic techniques. Their antimicrobial potency was estimated against various microbial strains (e.g., Candida albicans, Escherichia coli, and Staphylococcus aureus). The S. aureus and C. albicans strains were more sensitive than E. coli toward the organoselenocyanates. Interestingly, the azoic derivatives 4 and 9, methyl ester 6, and phenoxy acetamide 15 showed promising antimicrobial activity. Moreover, the antitumor potential was estimated against liver and breast carcinomas, as well as primary fibroblasts. Interestingly, the anticancer properties were more pronounced in the HepG2 cells. The organoselenocyanates 4, 6, 9, 10, and 15 showed interesting anti-HepG2 cytotoxic patterns. Additionally, organoselenocyanates 3, 4, and 10 exhibited promising antioxidant activities in the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid and 2,2-diphenyl-1-picrylhydrazyl in vitro assays compared to ascorbic acid. These data point to promising antimicrobial, anticancer, and antioxidant activities of organoselenocyanates 6, 9, and 15 warrant further studies.
Novel methyl anthranilate-based organodiselenide hybrids were synthesized, and their chemical structures were confirmed by state-of-the-art spectroscopic techniques. Their antimicrobial properties were assessed against Staphylococcus aureus, Escherichia coli, and Candida albicans microbial strains. Moreover, the antitumor potential was estimated against liver and breast carcinomas, as well as primary fibroblast cell lines. The Staphylococcus aureus and Candida albicans strains were more sensitive than Escherichia coli toward the OSe compounds. Interestingly, methyl 2-amino-5-(methylselanyl) benzoate (14) showed similar antifungal activity to the standard drug clotrimazole (IA% = 100%) and manifested promising antibacterial activity against E. coli (IA% = 91.3%) and S. aureus (IA% = 90.5%). Furthermore, the minimum inhibitory concentration experiments confirmed the antimicrobial activity of the OSe 14, which in turn was comparable to clotrimazole and ampicillin drugs. Interestingly, the anticancer properties were more pronounced in the HepG2 cells. The OSe 14 was the most cytotoxic (IC50 = 3.57 ± 0.1 µM), even more than the Adriamycin drug (IC50 = 4.50 ± 0.2 µM), and with therapeutic index (TI) 17 proposing its potential selectivity and safety. Additionally, OSe compounds 14 and dimethyl 5,5′-diselanediylbis(2-aminobenzoate) (5) exhibited promising antioxidants in the 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) in vitro assays with 96%, 92%, 91%, and 86% radical scavenging activities compared to 95% by vitamin C in the DPPH and ABTS assays, respectively. These results point to promising antimicrobial, anticancer, and antioxidant activities of OSe 14 and 5 and warrant further studies.
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