Selective Imaging of Late Endosomes with a pH-Sensitive Diazaoxatriangulene Fluorescent Probe

A Wallabregue; D Moreau; P Sherin; P Moneva Lorente; Z Jarolimova; Eric Bakker; E Vauthey; J Gruenberg; J Lacour

doi:10.1021/jacs.5b09972

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Selective Imaging of Late Endosomes with a pH-Sensitive Diazaoxatriangulene Fluorescent Probe

Journal article

Peer reviewed

Selective Imaging of Late Endosomes with a pH-Sensitive Diazaoxatriangulene Fluorescent Probe

A Wallabregue, D Moreau, P Sherin, P Moneva Lorente, Z Jarolimova, Eric Bakker, E Vauthey, J Gruenberg and J Lacour

Journal of the American Chemical Society, Vol.138(6), pp.1752-1755

2016

DOI: https://doi.org/10.1021/jacs.5b09972

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Abstract

Chemical Sciences

acetal resins

chains

fluorophores

molecular biology

pH sensors

quantum theory

Late endosomes are a major trafficking hub in the cell at the crossroads between endocytosis, autophagy, and degradation in lysosomes. Herein is disclosed the first small molecule allowing their selective imaging and monitoring in the form of a diazaoxatriangulene fluorophore, 1a (hexadecyl side chain). The compound is prepared in three steps from a simple carbenium precursor. In nanospheres, this pH-sensitive (pKa = 7.3), photochemically stable dye fluoresces in the red part of visible light (601 and 578 nm, acid and basic forms, respectively) with a quantum yield between 14 and 16% and an excited-state lifetime of 7.7-7.8 ns. Importantly, the protonated form 1a.H+ provokes a specific staining of late endosome compartments (pH 5.0-5.5) after 5 h of incubation with HeLa cells. Not surprisingly, this late endosome marking depends on the intra-organelle pH, and changing the nature of the lipophilic chain provokes a loss of selectivity. Interestingly, fixation of the fluorophore is readily achieved with paraformaldehyde, giving the possibility to image both live and fixed cells. © 2016 American Chemical Society.

Details

Title: Selective Imaging of Late Endosomes with a pH-Sensitive Diazaoxatriangulene Fluorescent Probe
Authors: A Wallabregue (Author) - University of Geneva, Switzerland
D Moreau (Author) - University of Geneva, Switzerland
P Sherin (Author) - University of Geneva, Switzerland
P Moneva Lorente (Author) - University of Geneva, Switzerland
Z Jarolimova (Author) - University of Geneva, Switzerland
Eric Bakker (Author) - University of Geneva, Switzerland
E Vauthey (Author) - University of Geneva, Switzerland
J Gruenberg (Author) - University of Geneva, Switzerland
J Lacour (Author) - University of Geneva, Switzerland
Publication details: Journal of the American Chemical Society, Vol.138(6), pp.1752-1755
Publisher: American Chemical Society
Date published: 2016
DOI: 10.1021/jacs.5b09972
ISSN: 0002-7863
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99449213002621
Output Type: Journal article

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Collaboration types: Domestic collaboration; International collaboration
Web Of Science research areas: Chemistry, Multidisciplinary

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