Skip to Main content Skip to Navigation
Journal articles

BODIPY with Tuned Amphiphilicity as a Fluorogenic Plasma Membrane Probe

Abstract : Staining of the plasma membrane (PM) is essential in bioimaging, as it delimits the cell surface and provides various information regarding the cell morphology and status. Herein, the lipophilicity of a green emitting BODIPY fluorophore was tuned by gradual functionalization with anchors composed of zwitterionic and aliphatic groups, thus yielding three different amphiphilic dyes. We found that BODIPY bearing one or three anchors failed in efficiently staining the PM: the derivative with one anchor showed low affinity to PM and exhibited strong fluorescence in water due to high solubility, whereas BODIPY with three anchors aggregated strongly in media and precipitated before binding to the PM. In sharp contrast, the BODIPY bearing two anchors (B-2AZ, MemBright-488) formed virtually nonfluorescent soluble aggregates in aqueous medium that quickly deaggregated in the presence of PM, leading to a bright soluble molecular form (quantum yield of 0.92). This fluorogenic response allowed for efficient probing of the PM at low concentration (20 nM) with high signal to background ratio images in mono- as well as two-photon excitation microscopy. B-2AZ proved to selectively stain the PM in a more homogeneous manner than the commercially available fluorescently labeled lectin WGA. Finally, it was successfully used in 3D-imaging to reveal fine intercellular tunneling nanotubes in KB cells and to stain the PM in glioblastoma cells in spheroids.
Document type :
Journal articles
Complete list of metadata

Cited literature [62 references]  Display  Hide  Download
Contributor : Adeline Rege <>
Submitted on : Monday, August 26, 2019 - 11:01:22 PM
Last modification on : Friday, December 18, 2020 - 12:16:02 PM
Long-term archiving on: : Friday, January 10, 2020 - 9:13:20 AM


Files produced by the author(s)




Mayeul Collot, Emmanuel Boutant, Maxime Lehmann, Andrey Klymchenko. BODIPY with Tuned Amphiphilicity as a Fluorogenic Plasma Membrane Probe. Bioconjugate Chemistry, American Chemical Society, 2019, 30 (1), pp.192-199. ⟨10.1021/acs.bioconjchem.8b00828⟩. ⟨hal-02271504⟩



Record views


Files downloads