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Organoselenocyanates and symmetrical diselenides redox modulators: Design, synthesis and biological evaluation
Saad Shaaban1, Amr Negm2, Mohamed A Sobh3
1Organic Chemistry Division, Department of Chemistry, Faculty of Science, Mansoura University, El-Gomhorya Street, 35516 Mansoura, Egypt; Leibniz Institute of Plant Biochemistry, Department of Bioorganic Chemistry, Weinberg 3, D-06120 Halle (Saale), Germany.
Abstract:
Oxidative stress (OS) and disturbed intracellular redox balance have been predominantly observed in different types of cancer, including hepatocellular carcinoma (HCC). Agents which can stop OS multi-stressor events and modulate the intracellular redox state are becoming a major focus in HCC prevention. Among them, compounds with glutathione peroxidase (GPx)-like activity are of particularly concern. We herein report the synthesis of novel series of organoselenocyanates and symmetrical diselenide antioxidants, inspired by the natural redox enzyme, GPx and the synthetic organoselenium ebselen antioxidants. Their cytotoxic activity was evaluated against Hep G2 cells and their antimicrobial activities were evaluated against Candida albicans (C. albicans) fungus as well as against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus), gram-negative and gram-positive bacteria, respectively. These compounds were also tested for their antioxidant activities using 2,2-diphenyl-1-picrylhydrazyl (DPPH), GPx-like activity and bleomycin dependent DNA damage assays and a basic structure-activity relationship was subsequently established. The physicochemical parameters and drug-likeness were computed employing the Molinspiration online property calculation toolkit and MolSoft software. Interestingly, some compounds proved to be more cytotoxic than ebselen and the known anticancer drug 5-Fu and in the same time they showed similar, sometime even more, antifungal activity than the reference antifungal drugs. Among these compounds, compound 16 was considered to be the most interesting with free radical-scavenging activity comparable to ascorbic acid and a GPx-like activity similar to ebselen. As most of these compounds comply with Lipinski's Rule of Five, they promise good bioavailability, which needs to be studied as part of future investigations.
Insights
Novel organoselenium compounds show potent antioxidant and anticancer properties, acting as glutathione peroxidase mimics. These compounds exhibit significant cytotoxic and antifungal activity, offering promise for hepatocellular carcinoma prevention.
Area of Science:
- Medicinal Chemistry
- Organic Chemistry
- Biochemistry
Background:
- Oxidative stress (OS) and altered redox balance are hallmarks of hepatocellular carcinoma (HCC).
- Targeting OS and redox modulation is crucial for HCC prevention strategies.
- Glutathione peroxidase (GPx)-like compounds are of significant interest for their therapeutic potential.
Purpose of the Study:
- To synthesize novel organoselenocyanates and diselenide antioxidants inspired by GPx and ebselen.
- To evaluate the cytotoxic, antimicrobial, and antioxidant activities of these novel compounds.
- To establish a structure-activity relationship and assess drug-likeness for potential HCC therapeutics.
Main Methods:
- Synthesis of novel organoselenium compounds.
- Cytotoxicity assays against Hep G2 cells.
- Antimicrobial activity testing against Candida albicans, Escherichia coli, and Staphylococcus aureus.
- Antioxidant assays including DPPH, GPx-like activity, and DNA damage assays.
- Physicochemical parameter and drug-likeness computation (Molinspiration, MolSoft).
Main Results:
- Several synthesized compounds demonstrated superior cytotoxicity compared to ebselen and 5-Fu.
- Compounds exhibited strong antifungal activity, comparable or exceeding reference drugs.
- Compound 16 displayed significant free radical-scavenging and GPx-like activity.
- Most compounds adhered to Lipinski's Rule of Five, suggesting good bioavailability.
Conclusions:
- Novel organoselenium compounds possess promising cytotoxic, antimicrobial, and antioxidant properties.
- Compound 16 is a particularly promising candidate for further investigation in HCC prevention.
- The favorable physicochemical properties indicate potential for good oral bioavailability.
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