Selective Imaging of Late Endosomes with a pH-Sensitive Diazaoxatriangulene Fluorescent Probe.
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 cha...
| Publicado en: | Journal of the American Chemical Society Vol. 138; no. 6; pp. 1752 - 1756 |
|---|---|
| Autores principales: | , , , , , , , , |
| Formato: | Artículo |
| Publicado: |
American Chemical Society
2/17/2016
|
| Materias: | |
| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=113269302&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 113269302 longDbName: Humanities International Complete uiTag: AN controlInfo: bkinfo: jinfo: jid: 00027863 ACS jtl: Journal of the American Chemical Society issn: 00027863 maglogo: N pubinfo: dt: 2/17/2016 vid: 138 iid: 6 pid: 997 pub: American Chemical Society artinfo: ui: 113269302 10.1021/jacs.5b09972 ppf: 1752 ppct: 4 formats: tig: atl: Selective Imaging of Late Endosomes with a pH-Sensitive Diazaoxatriangulene Fluorescent Probe. aug: au: Wallabregue, Antoine Moreau, Dimitri Sherin, Peter Lorente, Pau Moneva Jarolímová, Zdeňka Bakker, Eric Vauthey, Eric Gruenberg, Jean Lacour, Jérôme affil: Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Genève 4, Switzerland Department of Biochemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Genève 4, Switzerland Department of Physical Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Genève 4, Switzerland International Tomography Center SB RAS, Institutskaya street 3A, 630090 Novosibirsk, Russia Department of Inorganic and Analytical Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Genève 4, Switzerland su: Endosomes Imaging systems pH effect Fluorescent probes Endocytosis Lysosomes sug: subj: Endosomes Imaging systems pH effect Fluorescent probes Endocytosis Lysosomes ab: 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 (pK = 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. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2016 holdings: @attributes: islocal: N |
|---|