Please use this identifier to cite or link to this item: http://hdl.handle.net/2440/127446
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Type: Journal article
Title: A bimane‐based peptide staple for combined helical induction and fluorescent imaging
Author: Horsfall, A.J.
Dunning, K.R.
Keeling, K.L.
Scanlon, D.B.
Wegener, K.L.
Abell, A.D.
Citation: ChemBioChem, 2020; 21(23):1-11
Publisher: Wiley
Issue Date: 2020
ISSN: 1439-7633
1439-7633
Statement of
Responsibility: 
Aimee J. Horsfall, Kylie R. Dunning, Kelly L. Keeling, Denis B. Scanlon, Kate L. Wegener, Andrew D. Abell
Abstract: The thiol-selective fluorescent imaging agent, dibromobimane, has been repurposed to crosslink cysteine- and homocysteine- containing peptides, with the resulting bimane linker acting as both a structural constraint and a fluorescent tag. Macro- cyclisation was conducted on nine short peptides containing two cysteines and/or homocysteines, both on-resin and in buffered aqueous solution, to give macrocycles ranging in size from 16 (i,i +2) to 31 (i,i + 7) atoms. The structures were defined by CD, NMR structure calculations by using Xplor-NIH, NMR secondary shift and J HαNH analyses to reveal helical structure in the i,i + 4 (1, 2), and i,i + 3 (5) constrained peptides. Cellular- uptake studies were conducted with three of the macrocycles. Subsequent confocal imaging revealed punctate fluorescence within the cytosol indicative of peptides trapped in endocytic vesicles. These studies demonstrate that dibromobimane is an effective tool for defining secondary structure within short peptides, whilst simultaneously introducing a fluorescent tag suitable for common cell-based experiments.
Keywords: Bimane; fluorescence; helical structures; peptide staple; peptidomimetics
Rights: © 2020 Wiley‐VCH GmbH
RMID: 1000023878
DOI: 10.1002/cbic.202000485
Grant ID: http://purl.org/au-research/grants/arc/CE140100003
Appears in Collections:Medicine publications

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