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Fluorescent amino acid initiated de novo cyclic peptides for the label-free assessment of cell permeability.

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journal contribution
posted on 03.11.2021, 10:57 by Yuteng Wu, M Teresa Bertran, James Rowley, Ewen DD Calder, Dhira Joshi, Louise J 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

Crick (Grant ID: 10013, Grant title: STP Peptide Chemistry) Crick (Grant ID: 10748, Grant title: Walport FC001748)

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