Effect of binding and conformation on fluorescence quenching in new 2′,7′-dichlorofluorescein derivatives

被引:39
作者
Sparano, BA [1 ]
Shahi, SP [1 ]
Koide, K [1 ]
机构
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
关键词
D O I
10.1021/ol049537y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Symmetrical and unsymmetrical 2',7'-dichlorofluorescein (DCF) derivatives have been synthesized by means of Mannich reactions and an aromatic Claisen rearrangement. NMR and fluorescence spectroscopic studies reveal the correlation between the conformations, the photoinduced electron transfer mechanism, and fluorescent intensities of these DCF derivatives. Two quenching nitrogen atoms cooperatively and reversibly suppress the fluorescence of the chromophore.
引用
收藏
页码:1947 / 1949
页数:3
相关论文
共 10 条
[1]   Fluorescent sensors for Zn2+ based on a fluorescein platform:: Synthesis, properties and intracellular distribution [J].
Burdette, SC ;
Walkup, GK ;
Spingler, B ;
Tsien, RY ;
Lippard, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (32) :7831-7841
[2]   Signaling recognition events with fluorescent sensors and switches [J].
de Silva, AP ;
Gunaratne, HQN ;
Gunnlaugsson, T ;
Huxley, AJM ;
McCoy, CP ;
Rademacher, JT ;
Rice, TE .
CHEMICAL REVIEWS, 1997, 97 (05) :1515-1566
[3]   Specific covalent labeling of recombinant protein molecules inside live cells [J].
Griffin, BA ;
Adams, SR ;
Tsien, RY .
SCIENCE, 1998, 281 (5374) :269-272
[4]  
GRYNKIEWICZ G, 1985, J BIOL CHEM, V260, P3440
[5]   Improvement and biological applications of fluorescent probes for zinc, ZnAFs [J].
Hirano, T ;
Kikuchi, K ;
Urano, Y ;
Nagano, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (23) :6555-6562
[6]   Fluorogenic and chromogenic chemosensors and reagents for anions [J].
Martínez-Máñez, R ;
Sancenón, F .
CHEMICAL REVIEWS, 2003, 103 (11) :4419-4476
[7]   INTRAMOLECULAR FLUORESCENCE SELF-QUENCHING OF FLUORESCEINAMINE [J].
MUNKHOLM, C ;
PARKINSON, DR ;
WALT, DR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (07) :2608-2612
[8]   Derivatives of 8-hydroxy-2-methylquinoline are powerful prototypes for zinc sensors in biological systems [J].
Pearce, DA ;
Jotterand, N ;
Carrico, IS ;
Imperiali, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (21) :5160-5161
[9]   Complexation thermodynamics of cyclodextrins [J].
Rekharsky, MV ;
Inoue, Y .
CHEMICAL REVIEWS, 1998, 98 (05) :1875-1917
[10]   A new cell-permeable fluorescent probe for Zn2+ [J].
Walkup, GK ;
Burdette, SC ;
Lippard, SJ ;
Tsien, RY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (23) :5644-5645