1-Acyl-5-methoxy-8-nitro-1,2-dihydroquinoline: a biologically useful photolabile precursor of carboxylic acids
1-Acyl-5-methoxy-8-nitro-1,2-dihydroquinoline: a biologically useful photolabile precursor of carboxylic acids
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DOI：
10.1016/j.tetlet.2009.12.081
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发表时间：
2010-03-31
影响因子：
1.8
通讯作者：
Arai, Tatsuo
中科院分区：
文献类型：
--
作者：
Obi, Naoko;Momotake, Atsuya;Arai, Tatsuo
报道了1-酰基-5-甲氧基-8-硝基-1，2-二氢喹啉（MNDQ-笼状羧酸）的合成、光化学及生物学应用。对三种乙酰基衍生物（3a-c）进行了优化实验，确定了最适合应用于谷氨酸笼化的类似物为3c。因此，合成了MNDQ-caged谷氨酸盐（MNDQ-Glu），并且通过NMR、MS和HPLC分析证实了通过MNDQ-Glu的释放的谷氨酸盐的光化学释放。当用海马切片中的锥体神经元测试MNDQ-Glu时，由于L-谷氨酸的释放，全场UV照射导致大的内向电流。一个短的双光子uncaging MNDQ-Glu在单个树突棘诱导的瞬态电流，表现出类似的动力学特性的微型兴奋性突触后电流（mEPSC）。(C)2010爱思唯尔有限公司版权所有。
The synthesis, photochemistry, and biological application of 1-acyl-5-methoxy-8-nitro-1,2-dihydroquinoline (MNDQ-caged carboxylic acid) are described. Optimization experiments were carried out on three acetyl derivatives (3a-c), and the most appropriate analogue for application to the caging of glutamate was determined to be 3c. Thus, a MNDQ-caged glutamate (MNDQ-Glu) was synthesized, and the photochemical release of glutamate by uncaging of MNDQ-Glu was confirmed by NMR, MS, and HPLC analysis. When MNDQ-Glu was tested with pyramidal neurons in hippocampal slices, whole-field UV illumination resulted in a large inward current due to the release Of L-glutamate. A short two-photon uncaging of MNDQ-Glu at single dendritic spines induced a transient current that exhibited similar kinetic properties to miniature excitatory postsynaptic currents (mEPSC). (C) 2010 Elsevier Ltd. All rights reserved.