LONG-WAVELENGTH CHLORIDE-SENSITIVE FLUORESCENT INDICATORS
LONG-WAVELENGTH CHLORIDE-SENSITIVE FLUORESCENT INDICATORS
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DOI：
10.1006/abio.1994.1242
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发表时间：
1994-05-15
影响因子：
2.9
通讯作者：
VERKMAN, AS
中科院分区：
文献类型：
--
作者：
BIWERSI, J;TULK, B;VERKMAN, AS
本研究的目标是开发长波长荧光 Cl 指示剂，其光学性能优于喹啉化合物。筛选了一系列季铵化三环杂环。我们发现 N,N-二甲基-9,9-双吖啶鎓（光泽精）对于 390 M(-1) (Cl)、585 M(-1) (Br)、750 M(-1) (I) 和 590 M(-1) (SCN) 的碰撞猝灭具有非常高的卤化物敏感性，其 Stern-Volmer 常数远高于参考化合物的敏感性6-甲氧基-N-(3-磺基丙基)喹啉鎓 (SPQ) (118 M(-1) (Cl))；光泽精荧光对磷酸盐、硫酸盐和硝酸盐不敏感。 505 nm 处的光泽精荧光被 34,000 M(-1) cm(-1) (368 nm) 和 7500 M(-1) cm(-1) (455 nm) 的摩尔吸光度激发。为了研究构效关系，合成了五种9-取代的N-甲基吖啶化合物（9-氨基、9-甲醛、9-甲酰胺、9-N,N-二甲基甲酰胺和9-甲基羧酸酯），其中N-甲基吖啶-9-甲酰胺（MACA）具有最好的光学性质。 MACA 在 424 和 500 nm 处具有激发和发射最大值，Stern-Volmer 常数为 225 M(-1) (Cl)、480 M(-1) (Br)、550 M(-1) (I) 和 480 M(-1) (SCN)。光泽精和MACA的量子产率为0.6-0.7。吖啶化合物可用作脂质体和膜囊泡中的 Cl 指示剂，但在细胞质中不稳定。 (C) 1994 年学术出版社
The goal of this study was to develop long-wavelength fluorescent Cl indicators that have improved optical properties over quinolinium compounds. A series of quaternized tricyclic heterocycles was screened. We found that N,N-dimethyl-9,9-bisacridinium (lucigenin) had very high halide sensitivity with Stern-Volmer constants for collisional quenching of 390 M(-1) (Cl), 585 M(-1) (Br), 750 M(-1) (I), and 590 M(-1) (SCN), much higher than those for the reference compound 6-methoxy-N-(3-sulfopropyl)quinolinium (SPQ) (118 M(-1) (Cl)); lucigenin fluorescence was insensitive to phosphate, sulfate, and nitrate. Lucigenin fluorescence at 505 nm was excited with molar absorbances of 34,000 M(-1) cm(-1) (368 nm) and 7500 M(-1) cm(-1) (455 nm). To examine structure-activity relationships, five 9-substituted N-methylacridinium compounds were synthesized (9-amino, 9-carboxaldehyde, 9-carboxamide, 9-N,N-dimethylcarboxamide, and 9-methylcarboxylate), of which N-methylacridinium-9-carboxamide (MACA) had the best optical properties. MACA had excitation and emission maxims at 424 and 500 nm, and Stern-Volmer constants of 225 M(-1) (Cl), 480 M(-1) (Br), 550 M(-1) (I), and 480 M(-1) (SCN). The quantum yields of lucigenin and MACA were 0.6-0.7. The acridinium compounds are useful as Cl indicators in liposomes and membrane vesicles, but are not stable in cell cytoplasm. (C) 1994 Academic Press, Inc.