The synthesis and fluorescent properties of analogues of the zinc(II) specific fluorophore zinquin ester

被引:61
作者
Kimber, MC [1 ]
Mahadevan, IB [1 ]
Lincoln, SF [1 ]
Ward, AD [1 ]
Tiekink, ERT [1 ]
机构
[1] Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia
关键词
D O I
10.1021/jo000678x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis and fluorescent properties in the absence and presence of zinc(II) of a range of a-substituted derivatives of N-(6-methoxy-2-methyl-8-quinolyl)-4-methylbenzenesulfonamide are described. These analogues formed complexes with zinc(II) as indicated by a bathochromic shift in their UV/vis spectra. Analogues with isobutenyl and isobutyl side chains at the 2-position formed fluorescent complexes whose fluorescence was stronger than that of the 2-methyl-containing parent. These derivatives were converted, via conversion to the phenol with boron tribromide and reaction with ethyl bromoacetate, to systems with ester-containing side chains analogous to zinquin ester, a specific cellular fluorophore for zinc(ll). All of these ester derivatives formed complexes with zinc(II) resulting in a bathochomic shift in their UV/vis spectra. Compounds with isobutyl, isobutenyl, and styryl. side chains exhibited increased fluorescence compared to that of zinquin ester in the presence of zinc(II). The compound with the 2-isobutyl side chain was more selective in its fluorescence for zinc(II) over cadmium(II) compared to zinquin ester.
引用
收藏
页码:8204 / 8209
页数:6
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