Comparison of the effects of perfluoroalkyl and alkyl groups on cellular uptake in short peptides.

ABSTRACT: The differences in the effects of perfluoroalkyl (R_F) and alkyl (R_H) groups on the cellular uptake of short peptides were evaluated. A facile synthetic method was established to produce Fmoc-protected amino acids bearing R_F and R_H groups on their side chains. The synthesized Fmoc-protected amino acids were successfully incorporated into peptides using solid-phase peptide synthesis. Peptides with an R_F group exhibited higher cellular uptake efficiency compared to peptides with an R_H group of the same side-chain length. Intriguingly, the cytotoxicity of the AF₆₄₇-R_F-tripeptide (R_F = C₈F₁₇) was lower than that of the AF₆₄₇-R_H-tripeptide (R_H

SUBMITTER: Kadota K 

PROVIDER: S-EPMC11912358 | biostudies-literature | 2025 Mar

REPOSITORIES: biostudies-literature