Amphiphilic Triazolyl Peptides: Synthesis and Evaluation as Nanostructures

Author(s): Naser Sayeh, Amir N. Shirazi, Donghoon Oh, Jiadong Sun, David Rowley, Antara Banerjee, Arpita Yadav, Rakesh K. Tiwari, Keykavous Parang.

Journal Name: Current Organic Chemistry

Volume 18 , Issue 20 , 2014

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Abstract:

A new class of amphiphilic triazolyl peptides was designed and synthesized from 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, and pG represent tryptophan, arginine, lysine, and propargylglycine residues, respectively. The linear (W(pG))3 and cyclic [W(pG)]3 peptides containing alkyne residues were conjugated with Ac-K(N3)R-NH2 functionalized with azide group through click chemistry in the presence of CuSO4.5H2O, Cu (powder), sodium ascorbate, and N,N-disopropylethylamine in methanol:water to afford amphiphilic triazolyl linear-linear (WG(triazole-KR-NH2))3 and cyclic-linear [WG(triazole-KR-NH2)]3 peptides, respectively. The secondary structures of both peptides were similar to a distorted α-helix as shown by CD spectroscopy. TEM imaging showed that linear-linear (WG(triazole-KR-NH2))3 and cyclic-linear [WG(triazole-KR-NH2)]3 peptides formed nano-sized structures in the size range of 50-100 nm and 50-80 nm, respectively.

Keywords: Amphiphiles, click chemistry, cyclic peptides, nanoparticles, peptides, triazole.

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Article Details

VOLUME: 18
ISSUE: 20
Year: 2014
Page: [2665 - 2671]
Pages: 7
DOI: 10.2174/138527281820141028110625
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