Design, synthesis, and preliminary biological evaluation of a novel triazole analogue of ceramide.
The amide bond of ceramide was replaced by the non-hydrolyzable 1,2,3-triazole functionality. Click chemistry was employed for synthesis of the designed analogues. Our preliminary biological evaluation indicated that the amide moiety of ceramide is amenable to bioisosteric substitution with the triazole moiety. Some of the analogues were more potent than C2-ceramide as cytotoxic agents, and the observed cytotoxicity was possibly mediated through the induction of apoptosis.
Kim
Sanghee
S
College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Republic of Korea. pennkim@snu.ac.kr
Cho
Minjae
M
Lee
Taeho
T
Lee
Sukjin
S
Min
Hye-Young
HY
Lee
Sang Kook
SK
D017209:Apoptosis; D002460:Cell Line; D002518:Ceramides / Q000737:chemistry* / Q000494:pharmacology*; D015195:Drug Design; D006801:Humans; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology*
D002518:Ceramides; D014230:Triazoles