Cell-Penetrating Helical Peptides Having l-Arginines and Five-Membered Ring 伪,伪-Disubstituted 伪-Amino Acids

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• 作者：Takuma Kato ; Makoto Oba ; Koyo Nishida ; Masakazu Tanaka
• 刊名：Bioconjugate Chemistry
• 出版年：2014
• 出版时间：October 15, 2014
• 年：2014
• 卷：25
• 期：10
• 页码：1761-1768
• 全文大小：432K
• ISSN：1520-4812

文摘

Cell-penetrating peptides are powerful tools in the delivery of drugs, proteins, and nucleic acids into cells; therefore, focus has recently been placed on their development. In this study, we synthesized seven types of peptides possessing three l-arginines (l-Arg) and six l-leucines (l-Leu) and/or 1-aminocyclopentane-1-carboxylic acids (Ac₅c), and investigated their secondary structures and cell-penetrating abilities. The peptide composed of an equal number of l-Arg, l-Leu, and Ac₅c formed 3₁₀/伪-helical structures in TFE solution and exhibited the highest cell-penetrating ability of all the peptides examined. Additional cellular uptake studies revealed that the incorporation of Ac₅c into peptides led to improved tolerability against serum. The results of the present study will help in the design of novel cell-penetrating peptides.