Peptides have unparalleled potential applications as nano-materials, surfactants, and drug delivery systems. Here, a new class of amphiphilic triazolyl peptides were designed and synthesized with functionalized peptide-based building blocks containing alkyne and azide functional groups namely linear (W(pG))3, cyclic [W(pG)]3, and Ac-K(N3)R-NH2 where W, R, K, (pG) represent tryptophan, arginine, lysine, and propargyl glycine residues, respectively. The linear (W(pG))3 and cyclic [W(pG)]3 peptides were conjugated with Ac-K(N3)R-NH2 through click chemistry in the presence of CuSO4.5H2O, Cu (powder), sodium ascorbate, and DIPEA in methanol:water to afford amphiphilic triazolyl peptides including linear (WG(triazole-KR-NH2))3 and cyclic [WG(triazole-KR-NH2)]3. CD spectroscopy exhibited that although the secondary structures of both peptides are moderately a-helix, the pattern of the cyclic peptideis slightly different from the linear one. TEM imaging showed that l(WG(triazole-KR-NH2))3 and c[WG(triazole-KR-NH2)]3 form nano-sized structures in the size range of 50-100 nm and 50-80 nm, respectively. Both peptides showed higher toxicity in cancer cells compared to normal cells at a concentration of 100 �M.

Synthesis of amphiphilic triazolyl peptides and evaluation of their cytotoxicity

248th National Meeting (2014)

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