Organoselenocyanates, a class of small-molecule organoselenium compounds, have gained significant attention due to their synthetic utilities and therapeutic potentials. They play a crucial role in maintaining cellular redox homeostasis during oxidative stress and cancer. This article discusses recent developments in the design, synthesis, and pharmaceutical applications of organoselenocyanates, including their anticancer, chemopreventive, and antioxidant activities.
Facts
- 🔬 Organoselenium compounds are used for cellular redox homeostasis and in the treatment of oxidative stress and cancer.
- 🧪 Small-molecule organoselenocyanates have synthetic utilities and therapeutic potentials.
- ⚕️ Organoselenocyanates show remarkable anticancer and cancer chemopreventive activities.
- 🌱 Recently developed synthetic methods include nucleophilic substitution reactions and visible-light-induced selenocyanation.
- 🧪 Organoselenocyanates have been conjugated with existing drugs and natural products to enhance drug potencies and reduce side-effects.
- 💊 Synthetic methodologies have been developed for different classes of organoselenocyanates, including α-carbonyl selenocyanates and benzimidazole-based compounds.
- 🏭 Metal-free and green methods have been developed for the synthesis of organoselenocyanates.
Organoselenocyanates are a class of small-molecule organoselenium compounds that have attracted significant research attention due to their synthetic utilities and therapeutic potentials. They play a crucial role in maintaining cellular redox homeostasis during oxidative stress and cancer. Oxidative stress can disrupt cellular development and function, and the notable antioxidant activities of organoselenium compounds help counteract this stress.
Among organoselenium compounds, small-molecule organoselenocyanates have gained particular interest. They have synthetic utilities and exhibit remarkable anticancer and cancer chemopreventive activities. Researchers have explored convenient synthetic methodologies to different classes of organoselenocyanates from various precursors. Nucleophilic substitution reactions involving organic halides and highly nucleophilic sodium or potassium selenocyanate are commonly used.
In recent years, visible-light-induced selenocyanation methods have been developed, which offer a greener approach to synthesizing organoselenocyanates. These methods utilize transition metal catalysts and provide a convenient route to various cyano- and selenocyanato-containing compounds.
Moreover, considering the redox and antioxidant properties of organoselenocyanates, researchers have conjugated them with existing drugs and natural products. This strategy aims to enhance drug potencies and ameliorate drug-induced side effects.
In summary, recent developments in the synthesis and pharmaceutical applications of organoselenocyanates have opened up new avenues for the development of therapeutic agents with anticancer, chemopreventive, and antioxidant activities. The synthetic methodologies and conjugation strategies discussed in this report contribute to the advancement of organoselenocyanate research and hold promise for future drug development.
Small-molecule organoselenocyanates: Recent developments toward synthesis, anticancer, and antioxidant activities
Badirujjaman; Pal; Bhabak
Full text link: https://doi.org/10.1016/j.cbpa.2023.102337
What this paper is about
- The 3selenocyanoalkoxyestradiol derivatives were synthesized upon the bromoalkylation of the phenolic 3hydroxyl group of estradiol with dibromoalkanes followed by the selenocyanation with KSeCN.
- With the reported anticancer and chemopreventive activities of various organoselenocyanates, the innovative ionic and nonionic compounds were evaluated for their antiproliferative activities in highly aggressive triple-negative breast cancer cells.
- Anticancer and antioxidant activities of organoselenocyanates.
What you can learn
- While several selenocyanates exhibited significant cytotoxicity in the organ-specific cancer cell lines, 2-selenocyano-3methoxyestradiol-17-benzoate exhibited significantly higher cytotoxicity in HeLa cells as compared to other organ-specific cancer cells and induced dose-dependent programmed apoptosis.
- While the in vitro antioxidant activities of various synthetic organoselenium compounds with underlying mechanistic insights have been well-studied over last 2e3 decades, the potentials of the lead compounds toward chemoprevention with their inherent toxicity profiles are not well-explored and worth further research attention with detailed in vivo investigations.
- In line of this, the recent developments of heterocyclic ionic cyclic and acyclic organoselenium compounds with selenocyanate counteranions are attractive examples for further studies in future.
