Methylazacalix[4]pyridine:: En route to Zn2+-specific fluorescence sensors

被引:108
作者
Gong, Han-Yuan [1 ]
Zheng, Qi-Yu [1 ]
Zhang, Xiao-Hang [1 ]
Wang, De-Xian [1 ]
Wang, Mei-Xiang [1 ]
机构
[1] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, Biol Chem Lab, Beijing 100080, Peoples R China
关键词
D O I
10.1021/ol061928k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Owing to the electronic nature of the bridging nitrogen atoms which can adopt different hybridizations and form various conjugations with the adjacent pyridine(s), methylazacalix[4] pyridine underwent conformation and cavity preorganization to highly selectively bind the Zn2+ ion. Rigidification and coplanarity of the macrocyclic ring led to a great enhancement of fluorescence of the intrinsic fluorescent host molecule.
引用
收藏
页码:4895 / 4898
页数:4
相关论文
共 41 条
[1]   CHELATION-ENHANCED FLUORESCENCE OF ANTHRYLAZAMACROCYCLE CONJUGATE PROBES IN AQUEOUS-SOLUTION [J].
AKKAYA, EU ;
HUSTON, ME ;
CZARNIK, AW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3590-3593
[2]   Measurement of intracellular free zinc in living neurons [J].
Canzoniero, LMT ;
Sensi, SL ;
Choi, DW .
NEUROBIOLOGY OF DISEASE, 1997, 4 (3-4) :275-279
[3]   ZP8, a neuronal zinc sensor with improved dynamic range; Imaging zinc in hippocampal slices with two-photon microscopy [J].
Chang, CJ ;
Nolan, EM ;
Jaworski, J ;
Okamoto, KI ;
Hayashi, Y ;
Sheng, M ;
Lippard, SJ .
INORGANIC CHEMISTRY, 2004, 43 (21) :6774-6779
[4]   Zinc metabolism in the brain: Relevance to human neurodegenerative disorders [J].
Cuajungco, MP ;
Lees, GJ .
NEUROBIOLOGY OF DISEASE, 1997, 4 (3-4) :137-169
[5]  
Da Silva J. F., 1991, The Biological Chemistry of the Elements-The Inorganic Chemistry of Life
[6]   Aqueous coordination chemistry of quinoline-based fluorescence probes for the biological chemistry of zinc [J].
Fahrni, CJ ;
O'Halloran, TV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) :11448-11458
[7]   The molecular basis for the role of zinc in developmental biology [J].
Falchuk, KH .
MOLECULAR AND CELLULAR BIOCHEMISTRY, 1998, 188 (1-2) :41-48
[8]   Transition metal speciation in the cell: Insights from the chemistry of metal ion receptors [J].
Finney, LA ;
O'Halloran, TV .
SCIENCE, 2003, 300 (5621) :931-936
[9]   CYTOARCHITECTONIC DISTRIBUTION OF ZINC IN THE HIPPOCAMPUS OF MAN AND THE RAT [J].
FREDERICKSON, CJ ;
KLITENICK, MA ;
MANTON, WI ;
KIRKPATRICK, JB .
BRAIN RESEARCH, 1983, 273 (02) :335-339
[10]  
FREDERICKSON CJ, 1989, INT REV NEUROBIOL, V31, P145