Spatiotemporal Resolved Live Cell Membrane Tracking through Photo-click Reactions Enriched in Lipid Phase.
bioorthogonal chemistry
cyclic azobenzenes
cycloaddition
photo-click chemistry
supramolecular chemistry
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
16 Aug 2021
16 Aug 2021
Historique:
received:
10
05
2021
pubmed:
1
6
2021
medline:
19
8
2021
entrez:
31
5
2021
Statut:
ppublish
Résumé
A set of photo-switchable monopeptides derived from cis-β-dibenzodiazocine-l-alanine (cis-DBDAA) have been designed and synthesized, which are capable of photo-click reacting with diaryltetrazoles or diarylsydnones in a hydrophobic phospholipid bilayer environment. The DBDAA monopeptides include both a hydrophobic tail on C-terminal, providing high affinity toward lipid membrane, and a modularized functional moiety on N-terminal, enabling rapid optimization of the self-assembly strength to form multifunctional supramolecules. With the cis-DBDAA monopeptides photo-switched into trans-configuration, we were able to disrupt the supramolecular assembly through an efficient photo-click reaction across the lipid bilayer of liposomes. We reveal that the performance of the photo-click reactions between the monopeptides and photo-generated nitrile imine intermediates is significantly enhanced by enrichment of both reactants in the hydrophobic membrane lamel of liposomes. Enrichment of the DBDAA monopeptide in lipid phase serves as a convenient method to introduce bioorthogonal chemical handles on live cell membranes, which enables fluorescence labelling of single cell's membrane with high spatiotemporal resolution to facilitate the studies on cell membrane dynamics.
Identifiants
pubmed: 34057766
doi: 10.1002/chem.202101653
doi:
Substances chimiques
Imines
0
Lipid Bilayers
0
Liposomes
0
Nitriles
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
11957-11965Subventions
Organisme : National Natural Science Foundation of China
ID : 21502130
Organisme : National Natural Science Foundation of China
ID : 22001181
Organisme : National Natural Science Foundation of China
ID : 22077090
Organisme : Fundamental Research Funds for the Central Universities
ID : 20826041D4117
Organisme : Fundamental Research Funds for the Central Universities
ID : 2020SCUNL105
Informations de copyright
© 2021 Wiley-VCH GmbH.
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