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Originally published In Press as doi:10.1194/jlr.M600459-JLR200 on April 7, 2007

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Journal of Lipid Research, Vol. 48, 1518-1532, July 2007
Copyright © 2007 by American Society for Biochemistry and Molecular Biology

New BODIPY lipid probes for fluorescence studies of membranes

Ivan A. Boldyrev1,*, Xiuhong Zhai1,{dagger}, Maureen M. Momsen{dagger}, Howard L. Brockman{dagger}, Rhoderick E. Brown2,{dagger} and Julian G. Molotkovsky2,*

* Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, 117997 Russia
{dagger} Hormel Institute, University of Minnesota, Austin, MN 55912

Published, JLR Papers in Press, April 7, 2007.

1 I. A. Boldyrev and X. Zhai contributed equally to this work.

2 To whom correspondence should be addressed. e-mail: reb{at}umn.edu (R.E.B.); jgmol{at}ibch.ru (J.G.M.)

Many fluorescent lipid probes tend to loop back to the membrane interface when attached to a lipid acyl chain rather than embedding deeply into the bilayer. To achieve maximum embedding of BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) fluorophore into the bilayer apolar region, a series of sn-2 acyl-labeled phosphatidylcholines was synthesized bearing 4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene-8-yl (Me4-BODIPY-8) at the end of C3-, C5-, C7-, or C9-acyl. A strategy was used of symmetrically dispersing the methyl groups at BODIPY ring positions 1, 3, 5, and 7 to decrease fluorophore polarity. Iodide quenching of the phosphatidylcholine probes in bilayer vesicles confirmed that the Me4-BODIPY-8 fluorophore was embedded in the bilayer. Parallax analysis of Me4-BODIPY-8 fluorescence quenching by phosphatidylcholines containing iodide at different positions along the sn-2 acyl chain indicated that the penetration depth of Me4-BODIPY-8 into the bilayer was determined by the length of the linking acyl chain. Evaluation using monolayers showed minimal perturbation of <10 mol% probe in fluid-phase and cholesterol-enriched phosphatidylcholine. Spectral characterization in monolayers and bilayers confirmed the retention of many features of other BODIPY derivatives (i.e., absorption and emission wavelength maxima near 498 nm and ~506–515 nm) but also showed the absence of the 620–630 nm peak associated with BODIPY dimer fluorescence and the presence of a 570 nm emission shoulder at high Me4-BODIPY-8 surface concentrations. We conclude that the new probes should have versatile utility in membrane studies, especially when precise location of the reporter group is needed.

Supplementary key words spectral properties • monolayers • lipid lateral packing • surface compressional modulus • lipid phase state • fluorophore position • fluorescence quenching • iodide • fluorophore location in bilayers • parallax analysis • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

Abbreviations: AV12-PC, 1-acyl-2-[12-(9-anthryl)-11E-dodecenoyl]-sn-glycero-3-phosphocholine; B3-, B5-, B7-, or B9-PC, phosphatidylcholine bearing at the sn-2 position {omega}-Me4-BODIPY-8-C3-, -C5-, -C7-, or -C9-fatty acid, respectively; DMPC, 1,2-dimyristoyl-sn-glycero-3-phosphocholine; I7- or I11-PC, phosphatidylcholine bearing 7-iodoheptanoic or 11-iodoundecanoic acid, respectively, at the sn-2 position; Ksv, Stern-Volmer quenching constant; Me2-BODIPY-3, 4,4-difluoro-5,7-dimethyl-4-bora-3a,4a-diaza-s-indacene-3-yl; Me4-BODIPY-8, 4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene-8-yl; PB-PC, 1-palmitoyl-2-Me2-BODIPY-3-pentanoyl-sn-glycero-3-phosphocholine; Tm, phase transition temperature


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