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

Wallabregue, Antoine; Moreau, Dimitri; Sherin, Petr; Moneva Lorente, Pau; Jarolimova, Zdenka; Bakker, Eric; Vauthey, Eric; Gruenberg, Jean; Lacour, Jérôme

doi:10.1021/jacs.5b09972

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Title		Selective Imaging of Late Endosomes with a pH-Sensitive Diazaoxatriangulene Fluorescent Probe
Authors		Wallabregue, Antoine Moreau, Dimitri Sherin, Petr Moneva Lorente, Pau Jarolimova, Zdenka Bakker, Eric Vauthey, Eric Gruenberg, Jean Lacour, Jérôme show all authors [1 - 9]
Published in		Journal of the American Chemical Society. 2016, vol. 138, no. 6, p. 1752-1755
Abstract		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.
Identifiers		DOI: 10.1021/jacs.5b09972
Full text		Article (Published version) (2.3 MB) - Limited access to UNIGE
Structures		Faculté des sciences / Section de chimie et biochimie / Département de chimie minérale, analytique et appliquée Faculté des sciences / Section de chimie et biochimie / Département de chimie physique Faculté des sciences / Section de chimie et biochimie / Département de chimie organique Faculté des sciences / Section de chimie et biochimie / Département de biochimie
Research groups		Groupe Bakker Groupe Gruenberg Groupe Lacour Groupe Vauthey
Citation (ISO format)		WALLABREGUE, Antoine et al. Selective Imaging of Late Endosomes with a pH-Sensitive Diazaoxatriangulene Fluorescent Probe. In: Journal of the American Chemical Society, 2016, vol. 138, n° 6, p. 1752-1755. doi: 10.1021/jacs.5b09972 https://archive-ouverte.unige.ch/unige:80718