Methyl to trifluoromethyl substitution as a strategy to increase the membrane permeability of short peptides

Takahiro Ono; Kohsuke Aikawa; Takashi Okazoe; Jumpei Morimoto; Shinsuke Sando

doi:10.1039/d1ob01565f

Methyl to trifluoromethyl substitution as a strategy to increase the membrane permeability of short peptides

Org Biomol Chem. 2021 Nov 10;19(43):9386-9389. doi: 10.1039/d1ob01565f.

Authors

Takahiro Ono¹, Kohsuke Aikawa¹, Takashi Okazoe^{1

2}, Jumpei Morimoto¹, Shinsuke Sando^{1

3}

Affiliations

¹ Department of Chemistry & Biotechnology, Graduate School of Engineering, The University of Tokyo, Bunkyo-ku, Tokyo 113-8656, Japan. jmorimoto@chembio.t.u-tokyo.ac.jp.
² Material Integration Laboratories, Yokohama Technical Center, AGC Inc., Yokohama 230-0045, Japan.
³ Department of Bioengineering, Graduate School of Engineering, The University of Tokyo, Bunkyo-ku, Tokyo 113-8656, Japan.

PMID: 34676842
DOI: 10.1039/d1ob01565f

Abstract

Here, we investigated the effect of CH₃ to CF₃ substitution on the membrane permeability of peptides. We synthesized a series of peptides with CF₃ groups and corresponding nonfluorinated peptides and measured the membrane permeability of the peptides. As a result, we demonstrated that CH₃ to CF₃ substitution is useful for increasing the membrane permeability of di-/tri-peptides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Peptides*

Substances

Peptides