Synthesis, structural characterization and cytotoxic effect of 6-amino-6-deoxy-L-ascorbic acid derivatives (CROSBI ID 77433)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Kralj, Marijeta ; Kojić-Prodić, Biserka ; Banić, Zrinka ; Grdiša, Mira ; Vela, Vanja ; Šušković, Božidar ; Pavelić, Krešimir
engleski
Synthesis, structural characterization and cytotoxic effect of 6-amino-6-deoxy-L-ascorbic acid derivatives
The synthesis, extended molecular modelling and cytotoxic effects of 6-amino-6-deoxy-l-ascorbic acid derivatives are described. For structure—function considerations, comparative conformational analysis was performed and X-ray structure analysis, molecular mechanics and molecular dynamics simulations were used in the search for the bioactive conformation(s). The cytotoxic effect of N, N-dimethyl-6-amino-6-deoxy-l-ascorbic acid on human tumour cell lines (Hep2, MiaPaCa2, HeLa) and on diploid human fibroblast (WI 38) was examined. The dimethylamino derivative of ascorbic acid expressed a stronger cytotoxic effect than ascorbic acid itself. This effect was cell-specific and dose dependent. The treatment of the cells with N, N-dimethyl-6-amino-6-deoxy-l-ascorbic acid probably resulted in apoptosis, evidenced by characteristic morphological changes and ladder DNA fragmentation. Apoptosis was not mediated by c-Myc or p53 proteins.
ascorbic acid derivatives ; synthesis ; modelling ; X-ray structure analysis ; cytotoxic effect
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Podaci o izdanju
31 (1)
1996.
23-35
objavljeno
0223-5234
1768-3254
10.1016/S0223-5234(96)80003-1