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Please use this identifier to cite or link to this item: http://hdl.handle.net/1942/21539

Title: A Blue-Light-Emitting BODIPY Probe for Lipid Membranes
Authors: Bacalum, Mihaela
Wang, Lina
Boodts, Stijn
Yuan, Peijia
Leen, Volker
Smisdom, Nick
Fron, Eduard
Knippenberg, Stefan
Fabre, Gabin
Trouillas, Patrick
Beljonne, David
Dehaen, Wim
Boens, Noel
Ameloot, Marcel
Issue Date: 2016
Citation: LANGMUIR, 32 (14), p. 3495-3505
Abstract: Here we describe a new BODIPY-based membrane probe (1) that provides an alternative to dialkylcarbocyanine dyes, such as DiI-C,8, that can be excited in the blue spectral region. Compound 1 has unbranched octadecyl chains at the 3,5 -positions and a meso-amino function. In organic solvents, the absorption and emission maxima of 1 are determined mainly by solvent acidity and dipolarity. The fluorescence quantum yield is high and reaches 0.93 in 2-propanol. The fluorescence decays are well fitted with a single -exponential in pure solvents and in small and giant unilamellar vesicles (GUV) with a lifetime of ca. 4 ns. Probe 1 partitions in the same lipid phase as DiI-C-18(5) for lipid mixtures containing sphingomyelin and for binary mixtures of dipalmitoylphosphatidylcholine (DPPC) and dioleoylphosphatidylcholine (DOPC). The lipid phase has no effect on the fluorescence lifetime but influences the fluorescence anisotropy. The translational diffusion coefficients of 1 in GUVs and OLN-93 cells are of the same order as those reported for DiI-C-18. The directions of the absorption and transition dipole moments of 1 are calculated to be parallel. This is reflected in the high steady-state fluorescence anisotropy of 1 in high ordered lipid phases. Molecular dynamic simulations of 1 in a model of the DOPC bilayer indicate that the average angle of the transition moments with respect to membrane normal is ca. 70 degrees, which is comparable with the value reported for al DiI-C-18.
Notes: [Bacalum, Mihaela; Smisdom, Nick; Knippenberg, Stefan; Ameloot, Marcel] Hasselt Univ, Biomed Res Inst, Agoralaan Bldg C, B-3590 Diepenbeek, Belgium. [Bacalum, Mihaela] Horia Hulubei Natl Inst Phys & Nucl Engn, Dept Life & Environm Phys, Reactorului 30, Magurele 077125, Romania. [Wang, Lina; Boodts, Stijn; Yuan, Peijia; Leen, Volker; Fron, Eduard; Dehaen, Wim; Boens, Noel] Katholieke Univ Leuven, Dept Chem, Celestijnenlaan 200f Bus 02404, B-3001 Louvain, Belgium. [Knippenberg, Stefan] KTH Royal Inst Technol, Sch Biotechnol, Div Theoret Chem & Biol, Roslagstullsbacken 15, S-10691 Stockholm, Sweden. [Fabre, Gabin] Univ Limoges, Fac Pharm, LCSN EA1069, 2 Rue Dr Marcland, F-87025 Limoges, France. [Fabre, Gabin; Trouillas, Patrick] Palacky Univ, Fac Sci, Dept Phys Chem, Reg Ctr Adv Technol & Mat, Tr 17 Listopadu 12, Olomouc 77146, Czech Republic. [Trouillas, Patrick] Univ Limoges, Fac Pharm, INSERM, UMR S850, 2 Rue Docteur Marcland, F-87025 Limoges, France. [Trouillas, Patrick; Beljonne, David] Univ Mons, Serv Chim Mat Nouveaux, Pl Parc 20, B-7000 Mons, Belgium. [Wang, Lina] Qingdao Univ Sci & Technol, Coll Environm & Safety Engn, Qingdao 266042, Shandong, Peoples R China. [Yuan, Peijia] Yale Univ, Dept Chem, 225 Prospect St,POB 208107, New Haven, CT 06520 USA.
URI: http://hdl.handle.net/1942/21539
DOI: 10.1021/acs.langmuir.6b00478
ISI #: 000374196700020
ISSN: 0743-7463
Category: A1
Type: Journal Contribution
Validation: ecoom, 2017
Appears in Collections: Research publications

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