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High-throughput evaluation of relative cell permeability between peptoids and peptides.

Abstract：

:Peptides are limited in their use as drugs due to low cell permeability and vulnerability to proteases. In contrast, peptoids are immune to enzymatic degradation and some peptoids have been shown to be relatively cell permeable. In order to facilitate future design of peptoid libraries for screening experiments, it would be useful to have a high-throughput method to estimate the cell permeability of peptoids containing different residues. In this paper, we report the strengths and limitations of a high-throughput cell-based permeability assay that registers the relative ability of steroid-conjugated peptides and peptoids to enter a cell. A comparative investigation of the physicochemical properties and side chain composition of peptoids and peptides is described to explain the observed higher cell permeability of peptoids over peptides. These data suggest that the conversion of the monomeric residues in peptides to an N-alkylglycine moiety in peptoids reduced the hydrogen-bonding potential of the molecules and is the main contributor to the observed permeability improvement.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Tan NC,Yu P,Kwon YU,Kodadek T

doi

10.1016/j.bmc.2008.04.074

subject

Has Abstract

pub_date

2008-06-01 00:00:00

pages

5853-61

issue

11

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(08)00419-7

journal_volume

16

pub_type

杂志文章

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