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

preprint
submitted on 04.05.2021, 10:28 and posted on 06.05.2021, 06:56 by Yuteng Wu, Teresa Bertran Domingo, James Rowley, Ewen D. D. Calder, Dhira Joshi, Louise Walport
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.

Funding

Protein-Protein Interaction Laboratory

Cancer Research UK

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History

Email Address of Submitting Author

l.walport@imperial.ac.uk

Institution

Imperial College London

Country

United Kingdom

ORCID For Submitting Author

0000-0002-3795-8365

Declaration of Conflict of Interest

no conflict of interest

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