Alkyl chain modulated cytotoxicity and antioxidant activity of bioinspired amphiphilic selenolanes

摘要: A series of amphiphilic conjugates dihydroxy selenolane (DHS) and monoamine (MAS), which we had previously reported to inhibit lipid peroxidation assist the oxidative protein folding reaction respectively in cell free systems, were evaluated for cytotoxicity, associated mechanisms antioxidant effects cells. Our results indicated that a fatty acid/alkyl group variable chain lengths (C6–14) as lipophilic moiety DHS/MAS not only improved their ability incorporate within plasma membrane cells but also modulated cytotoxicity. In concentration range 1–50 μM, C6 non-toxic whereas long (≥C8) showed significant The induction toxicity investigated by changes leakage, fluidity, mitochondrial potential annexin-V–propidium iodide (PI) staining using flow cytometry revealed disintegration subsequent necrosis major mechanism. Further, DHS MAS differential well nonlinear tendency cytotoxicity with respect this effect was attributed self-aggregation properties. Compared parent compounds, exhibited better activity terms selenoproteins such glutathione peroxidase 1 (GPx1), GPx4 thioredoxin reductase (TrxR1) protected from AAPH induced stress. conclusion, present study suggests importance hydrophilic–lipophilic balance (HLB) fine tuning bioinspired antioxidants.