Comparison of Cell Permeability of Cyclic Peptoids and Linear Peptoids

ACS Combinatorial Science
Min-Kyung ShinHyun-Suk Lim

Abstract

Cyclic peptoids are emerging as an attractive class of peptidomimetics. Compared to their linear counterparts, cyclic peptoids should have increased conformational rigidity and preorganized structures, enabling them to bind more tightly to target proteins without major entropy penalty. Because cyclic peptoids lack the amide protons in their backbones like linear peptoids, it is perceived that cyclic peptoids are seemingly cell permeable as much as linear peptoids. However, no systematic investigation for cell permeability of cyclic peptoids has been reported yet. Here, we, for the first time, demonstrate that cyclic peptoids are far more cell permeable than linear counterparts irrespective of their size and side chains. This study highlights that cyclic peptoids, along with combinatorial library and high-throughput screening technologies, will serve as a rich source of protein binding molecules, particularly targeting intracellular proteins, given their excellent cell permeability in addition to their conformational rigidity and proteolytic stability.

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Citations

May 10, 2018·Angewandte Chemie·Leila Peraro, Joshua A Kritzer
Jan 10, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ganesh A SableHyun-Suk Lim
Jun 1, 2019·Biopolymers·Kang Ju LeeHyun-Suk Lim
Sep 2, 2020·Chemical Communications : Chem Comm·Kevin L Bicker, Steven L Cobb
Oct 26, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yen Jea LeeJiwon Seo
Sep 3, 2020·Chemistry : a European Journal·Laura K BucktonShelli R McAlpine
Feb 21, 2021·Journal of Inorganic Biochemistry·Joanna WątłyMagdalena Rowińska-Żyrek
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Naima AgouramAbdeslem Bentama
Jul 13, 2021·Frontiers in Chemistry·Claudine Nicole HerlanStefan Bräse
Jul 9, 2021·Chemical Communications : Chem Comm·Hyun-Soo KimHyun-Suk Lim
Jul 6, 2021·ACS Chemical Biology·Kaley M MientkiewiczJoshua A Kritzer
Oct 31, 2019·Bioconjugate Chemistry·Min Hyeon ShinHyun-Suk Lim
Aug 18, 2018·Journal of the American Chemical Society·Leila PeraroJoshua A Kritzer
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Oct 7, 2021·Chemical Communications : Chem Comm·Claudine Nicole HerlanStefan Bräse

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