Solid-phase fluorescent BODIPY-peptide synthesis: Via in situ dipyrrin construction

Yue Wu, Wing Sze Tam, Ho Fai Chau, Simranjeet Kaur, Waygen Thor, Wei Shen AIK, Wai Lun Chan*, Markus Zweckstetter, Ka-Leung WONG

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

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. This journal is

Original languageEnglish
Pages (from-to)11266-11273
Number of pages8
JournalChemical Science
Volume11
Issue number41
DOIs
Publication statusPublished - 7 Nov 2020

Scopus Subject Areas

  • Chemistry(all)

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