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@ARTICLE{Wu:154224,
author = {Wu, Yue and Tam, Wing-Sze and Chau, Ho-Fai and Kaur,
Simranjeet and Thor, Waygen and Aik, Wei Shen and Chan, Wai
Lun and Zweckstetter, Markus and Wong, Ka-Leung},
title = {{S}olid-phase fluorescent {BODIPY}–peptide synthesis via
in situ dipyrrin construction},
journal = {Chemical science},
volume = {11},
number = {41},
issn = {2041-6539},
address = {Cambridge},
publisher = {RSC},
reportid = {DZNE-2021-00085},
pages = {11266 - 11273},
year = {2020},
abstract = {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.},
cin = {AG Zweckstetter},
ddc = {540},
cid = {I:(DE-2719)1410001},
pnm = {342 - Disease Mechanisms and Model Systems (POF3-342)},
pid = {G:(DE-HGF)POF3-342},
typ = {PUB:(DE-HGF)16},
pubmed = {pmid:34094367},
pmc = {pmc:PMC8162834},
doi = {10.1039/D0SC04849F},
url = {https://pub.dzne.de/record/154224},
}