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Synthesis, structural characterization and cytotoxic effect of 6-amino-6-deoxy-L-ascorbic acid derivatives


Kralj, Marijeta; Kojić-Prodić, Biserka; Banić, Zrinka; Grdiša, Mira; Vela, Vanja; Šušković, Božidar; Pavelić, Krešimir
Synthesis, structural characterization and cytotoxic effect of 6-amino-6-deoxy-L-ascorbic acid derivatives // European journal of medicinal chemistry, 31 (1996), 1; 23-35 doi:10.1016/S0223-5234(96)80003-1 (međunarodna recenzija, članak, znanstveni)


Naslov
Synthesis, structural characterization and cytotoxic effect of 6-amino-6-deoxy-L-ascorbic acid derivatives

Autori
Kralj, Marijeta ; Kojić-Prodić, Biserka ; Banić, Zrinka ; Grdiša, Mira ; Vela, Vanja ; Šušković, Božidar ; Pavelić, Krešimir

Izvornik
European journal of medicinal chemistry (0223-5234) 31 (1996), 1; 23-35

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Ascorbic acid derivatives ; synthesis ; modelling ; X-ray structure analysis ; cytotoxic effect

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



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  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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