Abstract
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 (IC
50
= 3.57 ± 0.1 µM), even more than the Adriamycin drug (IC
50
= 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.