članak: 1 od 1  
Hemijska industrija
2009, vol. 63, br. 4, str. 313-318
jezik rada: engleski
naučni članak
doi:10.2298/HEMIND0904313K
Sinteza i citotoksična aktivnost serije novih derivata žučnih kiselina
Kuhajda Ksenija N.a, Cvjetićanin Stanko M.a, Đurendić Evgenija A.a, Sakač Marija N.a, Penov-Gaši Katarina M.a, Kojić Vesna V.b, Bogdanović Gordana M.b
aUniverzitet u Novom Sadu, Prirodno-matematički fakultet, Departman za hemiju
bUniverzitet u Novom Sadu, Medicinski fakultet, Institut za onkologiju

e-adresa: tozchemy@eunet.rs

Projekat Ministarstva nauke Republike Srbije, br. 142052

Sažetak

U ovom radu su sintetizovani novi konjugati 7, 8, 11 i 13 odabranih žučnih kiselina (hioholne (2), deoksiholne (3), hiodeoksiholne (4) i 12-ketoholne (5) kiseline) sa etil 11-amino-undekanoatom. Reakcija konjugacije je izvedena u etil-acetatu u prisustvu N-etoksikarbonil-2-etoksi-1,2-dihidrohinolina (EEDQ) i trietilamina. Pri pomenutim reakcionim uslovima žučnih kiselina sa etil 6-aminoheksanoatom formirao se konjugat 9 samo sa deoksiholnom kiselinom (3), ali je i neočekivano nastao i etil-estar deoksiholne kiseline 10. Kod ostalih žučnih kiselina (holne (1), hiodeoksiholne (4) i 12-ketoholne (5) kiseline) nastali su samo neočekivani estri 6, 12 i 14. Sintetizovanim jedinjenjima je određena citotoksična aktivnost prema četiri linije humanih tumora (adenokarcinom dojke ER-, MDA-MB-231; adenokarcinom dojke ER+, MCF-7; karcinom grlića materice, HeLa S-3 i adenokarcinom prostate, PC-3). Konjugat 8 je pokazao snažnu aktivnost prema HeLa S-3, a konjugat 11 prema PC-3 ćelijama. Etil estar 12-ketoholne kiseline 14 pokazao je veoma snažnu citotoksičnu aktivnost prema MCF-7 i HeLa S-3 ćelijama.

Ključne reči

žučne kiseline; citotoksičnost; Etil 6-aminoheksanoat konjugati; etil 11-aminoundekanoat konjugati

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