Design and synthesis of anti-cancer cyclopeptides containing triazole skeleton

被引:29
|
作者
Tahoori, Fatemeh [1 ]
Balalaie, Saeed [1 ]
Sheikhnejad, Reza [2 ]
Sadjadi, Mahnaz [2 ]
Boloori, Parvin [2 ]
机构
[1] KN Toosi Univ Technol, Peptide Chem Res Ctr, Tehran, Iran
[2] Tofigh Daru Res & Eng Co, Tehran 37515375, Iran
关键词
Ugi ligation; Ligation of peptides; Anti-cancer activity; Cyclopeptides; Click reaction; Huisgen 1,3-Dipolar reaction; CLICK CHEMISTRY; MULTICOMPONENT REACTIONS; STEREOSELECTIVE-SYNTHESIS; AMINO-ACIDS; SOLID-PHASE; CYCLOADDITION; AZIDE; COORDINATION; EFFICIENT; ANALOGS;
D O I
10.1007/s00726-013-1663-1
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
We describe the design and synthesis of some hypothetical heptapeptides specifically to overcome the neoplastic activity of ras oncogene and their anti-cancer activities were studied. To improve the anti-cancer activity of the synthesized peptides, their structure modifications were done based on a sequential Ugi/Huisgen 1,3-Dipolar cyclization reaction. The cyclopeptides which contained triazole skeleton showed significant anti-cancer activity against cancer cells with mutated ras oncogene such as A549, PC3 and C26 cells. This study clearly shows the importance of triazole skeleton in biological activity of the peptides. It might be possible to overcome the difficulties involved in making complex peptides by employing this elegant chemistry.
引用
收藏
页码:1033 / 1046
页数:14
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