Design, Synthesis, and Biological Evaluation of Novel Hydroxamic Acid-Based Organoselenium Hybrids

Abstract

We report the design and synthesis of novel hydroxamic acid-tethered organoselenium (OSe) hybrids. Their antimicrobial and anticancer activities were assessed against different microbes (e.g., Candida albicans (C. albicans), Escherichia coli (E. coli), and Staphylococcus aureus (S. aureus)), as well as liver and breast carcinomas. OSe hybrid 8 showed promising anticancer activity, with IC50 = 7.57 ± 0.5 µM against HepG2 and IC50 = 9.86 ± 0.7 µM against MCF-7 cells. Additionally, OSe compounds 8 and 15 exhibited promising antimicrobial activities, particularly against C. albicans (IA% = 91.7 and 83.3) and S. aureus (IA% = 90.5 and 71.4). The minimum inhibitory concentration (MIC) assay confirmed the potential antimicrobial activity of OSe compound 8. OSe compounds 8 and 16 displayed good antioxidant activities compared to vitamin C in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and the 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid (ABTS) assays. These results indicate that hydroxamic acid-based organoselenium hybrids have promising biological activities such as anticancer, antimicrobial, and antioxidant properties, especially compounds 8, 13, 15, and 16, which warrant further studies.

New Chalcogen-Functionalized Naphthoquinones: Design, Synthesis, and Evaluation, In Vitro and In Silico, against Squamous Cell Carcinoma

“… 16 , 17 Sulfur, selenium, and tellurium-containing compounds have been important subjects of investigation due to their expressive number of pharmacological properties. 18 , 19 Among them, antimicrobial, 20 anticancer cell proliferation, 21 , 22 anti-HIV, 23 anti-Alzheimer’s, 24 and potential infection control by SARS-CoV-2 can be highlighted. 25 In this context, we would like to highlight the research developed by Gritzenco et al 26 where the authors obtained encouraging results regarding the alkynyl selenide compounds as a potential anticancer agent ( Figure 1 b) and the recent successful examples of selenium molecules against breast cancer ( Figure 1 c).…”

Repurposed organoselenium tethered amidic acids as apoptosis inducers in melanoma cancer via P53, BAX, caspases-3, 6, 8, 9, BCL-2, MMP2, and MMP9 modulations

“…[27][28][29] Hence, OSe hybrids are considered privileged scaffolds in drug discovery for cancer treatment. 18,[30][31][32][33][34] Recently, we reported the OSe-containing isomaleimide V with good antioxidant, cytoprotective, and antiapoptotic activity against oligodendrocytes. 17,19,35 Additionally, the OSe-bearing Nsuccinimide VI, synthesized in our laboratory, exhibited good anticancer activity against HEPG2 cells.…”

Synthesis of New Organoselenium-Based Succinanilic and Maleanilic Derivatives and In Silico Studies as Possible SARS-CoV-2 Main Protease Inhibitors

“…A recent high-throughput screening study by Jin et al [18,21] identified ebselen as a promising antiviral agent among more than 10,000 candidates as a lead inhibitor of M pro [18,22]. Within this context, the antiviral activity of ebselen suggested the promise of OSe agents as possible M pro inhibitors by interaction with the virus infection cycle [23,24]. Ebselen can efficiently bind to the cysteine located in the M pro active site, thus forming selenosulfide, which causes the inactivation of the virus with an IC 50 = 0.67 µM [22,23,25].…”

“…Within this context, the antiviral activity of ebselen suggested the promise of OSe agents as possible M pro inhibitors by interaction with the virus infection cycle [23,24]. Ebselen can efficiently bind to the cysteine located in the M pro active site, thus forming selenosulfide, which causes the inactivation of the virus with an IC 50 = 0.67 µM [22,23,25].…”