Synthesis, spectroscopic properties and protein labeling of water soluble 3,5-disubstituted boron dipyrromethenes

被引:38
作者
Dilek, Oezlem [1 ]
Bane, Susan L. [1 ]
机构
[1] SUNY Binghamton, Dept Chem, Binghamton, NY 13902 USA
关键词
Boron dipyrromethenes; Fluorescence; Protein labeling; FLUORESCENT BODIPY DYES; CRYSTAL-STRUCTURE; FUNCTIONALIZATION; ELECTROCHEMISTRY; PHOTOPHYSICS;
D O I
10.1016/j.bmcl.2009.10.080
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Sulfur-containing 3,5-disubstituted boron dipyrromethene (Bodipy (R)) fluorescent probes with improved water solubility were synthesized. A dicarboxylic acid derivative that can be excited by the 543 nm HeNe laser line is very soluble in aqueous solution and retains high fluorescence quantum yield of the unionizable parent molecule. Conversion of the dicarboxylic acid to the succimidyl or sulfosuccinimidyl diester produces molecules capable of labeling proteins with a bright and stable fluorescence signal. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6911 / 6913
页数:3
相关论文
共 24 条
[1]   BODIPY-based hydroxyaryl derivatives as fluorescent pH probes [J].
Baruah, M ;
Qin, WW ;
Basaric, N ;
De Borggraeve, WM ;
Boens, N .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4152-4157
[2]   Lighting the way ahead with boron dipyrromethene (Bodipy) dyes [J].
Benniston, Andrew C. ;
Copley, Graeme .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2009, 11 (21) :4124-4131
[3]   4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes modified for extended conjugation and restricted bond rotations [J].
Chen, J ;
Burghart, A ;
Derecskei-Kovacs, A ;
Burgess, K .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :2900-2906
[4]   Bidirectional switching of near IR emitting boradiazaindacene fluorophores [J].
Deniz, Erhan ;
Isbasar, G. Ceyda ;
Bozdemir, Oe. Altan ;
Yildirim, Leyla T. ;
Siemiarczuk, Aleksander ;
Akkaya, Engin U. .
ORGANIC LETTERS, 2008, 10 (16) :3401-3403
[5]   Synthesis of boron dipyrromethene fluorescent probes for bioorthogonal labeling [J].
Dilek, Oezlem ;
Bane, Susan L. .
TETRAHEDRON LETTERS, 2008, 49 (08) :1413-1416
[6]   3- and 5-Functionalized BODIPYs via the Liebeskind-Srogl reaction [J].
Han, Junyan ;
Gonzalez, Oswaldo ;
Aguilar-Aguilar, Angelica ;
Pena-Cabrera, Eduardo ;
Burgess, Kevin .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (01) :34-36
[7]  
*INV, 2007, INV MOL PROB
[8]   Syntheses and spectral properties of functionalized, water-soluble BODIPY derivatives [J].
Li, Lingling ;
Han, Junyan ;
Nguyen, Binh ;
Burgess, Kevin .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05) :1963-1970
[9]   Functionalization of the 4,4-difluoro-4-bora-3a, 4a-diaza-s-indacene (BODIPY) core [J].
Li, Lingling ;
Nguyen, Binh ;
Burgess, Kevin .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (10) :3112-3116
[10]   B,O-Chelated Azadipyrromethenes as Near-IR Probes [J].
Loudet, Aurore ;
Bandichhor, Rakeshwar ;
Burgess, Kevin ;
Palma, Aniello ;
McDonnell, Shane O. ;
Hall, Michael J. ;
O'Shea, Donal F. .
ORGANIC LETTERS, 2008, 10 (21) :4771-4774