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제123회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Assessment of Cell Permeability of Bicyclic Peptoids

2019년 2월 14일 14시 33분 07초
LIFE.P-386 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
4월 19일 (금요일) 11:00~12:30
Life Chemistry
저자 및
Wang Heemyeong, Hyun-Suk Lim*
Department of Chemistry, Pohang University of Science and Technology, Korea
Peptoids, oligomers of N-substituted glycines, are an attractive class of peptidomimetics with several desirable features such as ease of synthesis and proteolytic stability. Notably, it is well known that peptoids have better membrane permeability than native peptides. However, peptoids generally have relatively flexible structures, making it challenging for targeting intracellular proteins with high affinity and specificity. Macrocyclization has emerged as one strategy to solve these kinds of limitations. Macrocyclic peptoids are expected to have relatively rigid and preorganized structures compared to their linear counterparts, allowing them to bind more tightly to target proteins without major entropy penalty. Indeed, we recently demonstrated that monocyclic peptoids have better cell permeability compared to linear peptoids.1 In addition, we preiviously developed highly efficiet cyclization method for bicyclic peptoids which are expected to have improved conformational rigidity.2 However, while the cell permeability of monocyclic peptoids was studied, that of bicyclic peptoids has not been explored yet. Herein, we evaluated the cell permeability of bicyclic peptoids through a systematic investigation method for cell penetration. Halotag-labeled linear and bicyclic peptoids were synthesized priorly, and their penetration was monitered by Confocal microscopy. As expected, bicyclic peptoids showed improved membrane permeability than their linear counterparts indicating that they will serve as potential protein capture agents given their excellent cell permeability in addition to their conformational rigidity and proteolytic stability. References 1. Shin, M. K.; Hyun, Y. J.; Lim, H. S. ACS Comb. Sci., 2018, 20, 237-242. 2. Lee, J. H.; Kim, H. S.; Lim, H. S. Org. Lett. 2011, 13, 5012-5015.