1-Acyl-5-methoxy-8-nitro-1,2-dihydroquinoline: a biologically useful photolabile precursor of carboxylic acids

被引：11

作者：

Obi, Naoko ^{[1
]}

Momotake, Atsuya ^{[1
]}

Kanemoto, Yuya ^{[2
]}

Matsuzaki, Masanori ^{[2
,3
]}

Kasai, Haruo ^{[2
]}

Arai, Tatsuo ^{[1
]}

机构：

[1] Univ Tsukuba, Grad Sch Pure & Appl Sci, Tsukuba, Ibaraki 3058571, Japan

[2] Univ Tokyo, Grad Sch Med, Lab Struct Physiol, Ctr Dis Biol & Integrat Med, Tokyo 1130033, Japan

[3] Japan Sci & Technol Agcy, PRESTO, Saitama, Japan

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 13期

关键词：

METABOTROPIC SLOW EPSC; CAGED GLUTAMATE; CYCLIC-NUCLEOTIDES; PROTECTING GROUPS; ONE-PHOTON; RELEASE; PHOTOLYSIS; EFFICIENT; CA2+; PHOTOCLEAVAGE;

D O I：

10.1016/j.tetlet.2009.12.081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1642 / 1647

页数：6

共 9 条

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