%0 Journal Article
%A Wu, Yue
%A Tam, Wing-Sze
%A Chau, Ho-Fai
%A Kaur, Simranjeet
%A Thor, Waygen
%A Aik, Wei Shen
%A Chan, Wai Lun
%A Zweckstetter, Markus
%A Wong, Ka-Leung
%T Solid-phase fluorescent BODIPY–peptide synthesis via in situ dipyrrin construction
%J Chemical science
%V 11
%N 41
%@ 2041-6539
%C Cambridge
%I RSC
%M DZNE-2021-00085
%P 11266 - 11273
%D 2020
%X Traditional fluorescent peptide chemical syntheses hinge on the use of limited fluorescent/dye-taggable unnatural amino acids and entail multiple costly purifications. Here we describe a facile and efficient protocol for in situ construction of dipyrrins on the N-terminus with 20 natural and five unnatural amino acids and the lysine's side chain of selected peptides/peptide drugs through Fmoc-based solid-phase peptide synthesis. The new strategy enables the direct formation of boron–dipyrromethene (BODIPY)–peptide conjugates from simple aldehyde and pyrrole derivatives without pre-functionalization, and only requires a single-time chromatographic purification at the final stage. As a model study, synthesized EBNA1-targeting BODIPY1–Pep4 demonstrates intact selectivity in vitro, responsive fluorescence enhancement, and higher light cytotoxicity due to the photo-generation of cytotoxic singlet oxygen. This work offers a novel practical synthetic platform for fluorescent peptides for multifaceted biomedical applications.
%F PUB:(DE-HGF)16
%9 Journal Article
%$ pmid:34094367
%2 pmc:PMC8162834
%R 10.1039/D0SC04849F
%U https://pub.dzne.de/record/154224