Convenient synthesis of water-soluble nitrilotriacetic acid (NTA) BODIPY dyes

被引:23
作者
Brellier, Marie [1 ]
Duportail, Guy [2 ]
Baati, Rachid [1 ]
机构
[1] Univ Strasbourg, Fac Pharm, Lab Funct ChemoSyst, CNRS,UMR 7199, F-67401 Illkirch Graffenstaden, France
[2] Univ Strasbourg, Fac Pharm, Lab Biophoton & Pharmacol, CNRS,UMR 7213, F-67401 Illkirch Graffenstaden, France
关键词
Nitrilotriacetic acid (NTA); bis-NTA; BODIPY dyes; Water soluble probes; BORON-DIPYRROMETHENE DYES; ENERGY-TRANSFER; SPECTRAL PROPERTIES; COMPLEX-FORMATION; FLUORESCENT; DERIVATIVES; FUNCTIONALIZATION; CHEMISTRY; ACCEPTOR; CELLS;
D O I
10.1016/j.tetlet.2009.12.126
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mono- and bis-NTA-BODIPY dyes have been efficiently synthesized by amide bond formation between hepta-alkylated meso-aryl-BODIPY derivatives and the free amine of mono- and bis-NTA binder surrogates. These new fluorescent hybrids exhibited valuable photophysical properties under buffered aqueous conditions, thus expanding the arsenal of water-soluble BODIPY dyes for potential labeling and monitoring of biological systems and processes. (C) 2010 Elsevier Ltd All rights reserved.
引用
收藏
页码:1269 / 1272
页数:4
相关论文
共 39 条
[1]   Water soluble distyryl-boradiazaindacenes as efficient photosensitizers for photodynamic therapy [J].
Atilgan, Serdar ;
Ekmekci, Zeynep ;
Dogan, A. Lale ;
Guc, Dicle ;
Akkaya, Engin U. .
CHEMICAL COMMUNICATIONS, 2006, (42) :4398-4400
[2]  
BIELLIER M, 2009, CHEM-EUR J, V46, P12689
[3]   Synthesis, spectral properties and photostability of novel boron-dipyrromethene dyes [J].
Cui, Aijun ;
Peng, Xiaojun ;
Fan, Jiangli ;
Chen, Xiuying ;
Wu, Yunkou ;
Guo, Binchen .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2007, 186 (01) :85-92
[4]   Star-Shaped Multichromophoric Arrays from Bodipy Dyes Grafted on Truxene Core [J].
Diring, Stephane ;
Puntoriero, Fausto ;
Nastasi, Francesco ;
Campagna, Sebastiano ;
Ziessel, Raymond .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (17) :6108-+
[5]   Synthesis and Optical Properties of Red and Deep-Red Emissive Polymeric and Copolymeric BODIPY Dyes [J].
Donuru, Venkat R. ;
Vegesna, Giri K. ;
Velayudham, Singaravelu ;
Green, Sarah ;
Liu, Haiying .
CHEMISTRY OF MATERIALS, 2009, 21 (10) :2130-2138
[6]   BENEXTRAMINE NEUROPEPTIDE-Y RECEPTOR INTERACTIONS - CONTRIBUTION OF THE BENZYLIC MOIETIES TO [H-3] NEUROPEPTIDE-Y DISPLACEMENT ACTIVITY [J].
DOUGHTY, MB ;
CHAURASIA, CS ;
LI, K .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (02) :272-279
[7]   Fluorescence quantum yield of rhodamine 6G in ethanol as a function of concentration using thermal lens spectrometry [J].
Fischer, M ;
Georges, J .
CHEMICAL PHYSICS LETTERS, 1996, 260 (1-2) :115-118
[8]   New Redox Stable Low Band Gap Conjugated Polymer Based on an EDOT-BODIPY-EDOT Repeat Unit [J].
Forgie, John C. ;
Skabara, Peter J. ;
Stibor, Ivan ;
Vilela, Filipe ;
Vobecka, Zuzana .
CHEMISTRY OF MATERIALS, 2009, 21 (09) :1784-1786
[9]   Synthesis and photophysical properties of borondipyrromethene dyes bearing aryl substituents at the boron center [J].
Goze, Christine ;
Ulrich, Gilles ;
Mallon, Laura J. ;
Allen, Ben D. ;
Harriman, Anthony ;
Ziessel, Raymond .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (31) :10231-10239
[10]   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