Fluorescent Amino Acid Initiated De Novo Cyclic Peptides for the Label-Free Assessment of Cell Permeability

06 May 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The major obstacle in applying peptides to intracellular targets is their low inherent cell permeability. Standard approaches to attach a fluorophore (e.g. FITC, TAMRA) can change the physicochemical properties of the parent peptide and influence their ability to penetrate and localize in cells. We report a label-free strategy for evaluating the cell permeability of cyclic peptide leads. Fluorescent tryptophan analogues 4-cyanotryptophan (4CNW) and beta-(1-azulenyl)-L-alanine (AzAla) were incorporated into in vitro translated macrocyclic peptides by initiator reprogramming. We then demonstrate these efficient blue fluorescent emitters are good tools for monitoring peptide penetration into cells.

Keywords

RaPID
peptides
label-free
cell permeability
fluorescence imaging

Supplementary materials

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SI Walport
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