二硝基吲哚啉笼状神经递质的合成实用指南。
A practical guide to the synthesis of dinitroindolinyl-caged neurotransmitters.
机构信息
Department of Neuroscience, Mount Sinai School of Medicine, New York, New York, USA.
出版信息
Nat Protoc. 2011 Mar;6(3):314-26. doi: 10.1038/nprot.2010.193. Epub 2011 Feb 17.
Abstract
This protocol describes a method for efficient chemical synthesis of dinitroindolinyl derivatives of glutamate and γ-aminobutyric acid. These caged neurotransmitters are currently the most chemically and photochemically efficient probes for two-photon photolysis in living brain slices. The protocol only requires basic organic synthesis equipment, and no silica gel column chromatography or NMR spectroscopy is needed at any stage. HPLC is used to purify the caged transmitters at the end of the syntheses. Thus, the synthesis of dinitroindolinyl-caged neurotransmitters is within the scope of a modestly equipped chemistry laboratory.
摘要
本方案描述了一种高效化学合成谷氨酸和γ-氨基丁酸的二硝基吲哚啉衍生物的方法。这些笼状神经递质是目前用于活体脑切片双光子光解的最具化学和光化学效率的探针。该方案仅需要基本的有机合成设备，并且在任何阶段都不需要硅胶柱层析或 NMR 光谱学。在合成结束时，使用 HPLC 来纯化笼状递质。因此，二硝基吲哚啉笼状神经递质的合成在配备适度的化学实验室范围内。
相似文献
1
A practical guide to the synthesis of dinitroindolinyl-caged neurotransmitters.二硝基吲哚啉笼状神经递质的合成实用指南。
Nat Protoc. 2011 Mar;6(3):314-26. doi: 10.1038/nprot.2010.193. Epub 2011 Feb 17.
2
Improved Synthesis of Caged Glutamate and Caging Each Functional Group.笼状谷氨酸的改进合成和每个功能基团的笼化。
ACS Chem Neurosci. 2018 Nov 21;9(11):2713-2721. doi: 10.1021/acschemneuro.8b00152. Epub 2018 May 25.
3
Photochemical and pharmacological evaluation of 7-nitroindolinyl-and 4-methoxy-7-nitroindolinyl-amino acids as novel, fast caged neurotransmitters.7-硝基吲哚啉基和4-甲氧基-7-硝基吲哚啉基氨基酸作为新型快速笼形神经递质的光化学和药理学评价
J Neurosci Methods. 2001 Nov 15;112(1):29-42. doi: 10.1016/s0165-0270(01)00451-4.
4
Development of Anionically Decorated Caged Neurotransmitters: In Vitro Comparison of 7-Nitroindolinyl- and 2-(p-Phenyl-o-nitrophenyl)propyl-Based Photochemical Probes.阴离子修饰笼形神经递质的开发：基于7-硝基吲哚啉基和2-(对苯基-邻硝基苯基)丙基的光化学探针的体外比较
Chembiochem. 2016 May 17;17(10):953-61. doi: 10.1002/cbic.201600019. Epub 2016 Apr 9.
5
Caged glutamates with π-extended 1,2-dihydronaphthalene chromophore: design, synthesis, two-photon absorption property, and photochemical reactivity.具有π-扩展1,2-二氢萘发色团的笼状谷氨酸：设计、合成、双光子吸收特性及光化学反应性
J Org Chem. 2014 Sep 5;79(17):7822-30. doi: 10.1021/jo501425p. Epub 2014 Aug 13.
6
A protecting group for carboxylic acids that can be photolyzed by visible light.一种可被可见光光解的羧酸保护基团。
Biochemistry. 2005 May 17;44(19):7107-14. doi: 10.1021/bi047665o.
7
Optofluidic control of rodent learning using cloaked caged glutamate.用光流控技术控制啮齿动物学习的隐形笼状谷氨酸。
Proc Natl Acad Sci U S A. 2020 Mar 24;117(12):6831-6835. doi: 10.1073/pnas.1920869117. Epub 2020 Mar 9.
8
Synthesis of a caged glutamate for efficient one- and two-photon photorelease on living cells.用于活细胞上高效单光子和双光子光释放的笼形谷氨酸的合成。
Chem Commun (Camb). 2005 Aug 7(29):3664-6. doi: 10.1039/b504922a. Epub 2005 Jun 13.
9
Synthesis, photochemistry, and biological characterization of photolabile protecting groups for carboxylic acids and neurotransmitters.用于羧酸和神经递质的光不稳定保护基团的合成、光化学及生物学特性研究
Methods Enzymol. 1998;291:30-50. doi: 10.1016/s0076-6879(98)91005-9.
10
4-Carboxymethoxy-5,7-dinitroindolinyl-Glu: an improved caged glutamate for expeditious ultraviolet and two-photon photolysis in brain slices.4-羧甲氧基-5,7-二硝基吲哚啉基谷氨酸：一种用于脑片快速紫外光和双光子光解的改良型笼形谷氨酸。
J Neurosci. 2007 Jun 20;27(25):6601-4. doi: 10.1523/JNEUROSCI.1519-07.2007.
引用本文的文献
1
Seeing and Cleaving: Turn-Off Fluorophore Uncaging and Its Application in Hydrogel Photopatterning and Traceable Neurotransmitter Photocages.可视与裂解：关闭型荧光团光解笼及其在水凝胶光图案化和可追踪神经递质光笼中的应用。
ACS Appl Mater Interfaces. 2024 Oct 5;16(41):55107-17. doi: 10.1021/acsami.4c10861.
2
GluN3A excitatory glycine receptors control adult cortical and amygdalar circuits.GluN3A 兴奋性甘氨酸受体控制成人皮质和杏仁核回路。
Neuron. 2022 Aug 3;110(15):2438-2454.e8. doi: 10.1016/j.neuron.2022.05.016. Epub 2022 Jun 13.
3
Optofluidic control of rodent learning using cloaked caged glutamate.用光流控技术控制啮齿动物学习的隐形笼状谷氨酸。
Proc Natl Acad Sci U S A. 2020 Mar 24;117(12):6831-6835. doi: 10.1073/pnas.1920869117. Epub 2020 Mar 9.
4
Dendrimer Conjugation Enables Multiphoton Chemical Neurophysiology Studies with an Extended π-Electron Caging Chromophore.树枝状聚合物缀合使具有扩展的π-电子笼状发色团的多光子化学神经生理学研究成为可能。
Angew Chem Int Ed Engl. 2019 Aug 26;58(35):12086-12090. doi: 10.1002/anie.201906067. Epub 2019 Jul 19.
5
Caged Proline in Photoinitiated Organocatalysis.笼状脯氨酸在光引发的有机催化中的应用。
J Org Chem. 2019 May 3;84(9):5236-5244. doi: 10.1021/acs.joc.9b00220. Epub 2019 Apr 3.
6
Two-Photon Uncaging of Glutamate.谷氨酸的双光子解笼锁
Front Synaptic Neurosci. 2019 Jan 9;10:48. doi: 10.3389/fnsyn.2018.00048. eCollection 2018.
7
Improved Synthesis of Caged Glutamate and Caging Each Functional Group.笼状谷氨酸的改进合成和每个功能基团的笼化。
ACS Chem Neurosci. 2018 Nov 21;9(11):2713-2721. doi: 10.1021/acschemneuro.8b00152. Epub 2018 May 25.
8
Correlative Light Electron Microscopy: Connecting Synaptic Structure and Function.相关光电子显微镜技术：连接突触结构与功能
Front Synaptic Neurosci. 2016 Aug 23;8:28. doi: 10.3389/fnsyn.2016.00028. eCollection 2016.
9
State-dependent diffusion of actin-depolymerizing factor/cofilin underlies the enlargement and shrinkage of dendritic spines.肌动蛋白解聚因子/丝切蛋白的状态依赖性扩散是树突棘增大和缩小的基础。
Sci Rep. 2016 Sep 6;6:32897. doi: 10.1038/srep32897.
10
Development of Anionically Decorated Caged Neurotransmitters: In Vitro Comparison of 7-Nitroindolinyl- and 2-(p-Phenyl-o-nitrophenyl)propyl-Based Photochemical Probes.阴离子修饰笼形神经递质的开发：基于7-硝基吲哚啉基和2-(对苯基-邻硝基苯基)丙基的光化学探针的体外比较
Chembiochem. 2016 May 17;17(10):953-61. doi: 10.1002/cbic.201600019. Epub 2016 Apr 9.
本文引用的文献
1
A practical guide to the synthesis and use of membrane-permeant acetoxymethyl esters of caged inositol polyphosphates.笼形肌醇多磷酸盐的膜通透乙酰氧甲基酯的合成与应用实用指南。
Nat Protoc. 2011 Mar;6(3):327-37. doi: 10.1038/nprot.2010.194. Epub 2011 Feb 17.
2
Two-photon uncaging of gamma-aminobutyric acid in intact brain tissue.在完整脑组织中对γ-氨基丁酸的双光子光解笼。
Nat Chem Biol. 2010 Apr;6(4):255-257. doi: 10.1038/nchembio.321. Epub 2010 Feb 21.
3
Two-color, two-photon uncaging of glutamate and GABA.双色双光子谷氨酸和 GABA 的光解笼。
Nat Methods. 2010 Feb;7(2):123-5. doi: 10.1038/nmeth.1413. Epub 2009 Dec 27.
4
Experience-dependent structural synaptic plasticity in the mammalian brain.哺乳动物大脑中依赖经验的结构性突触可塑性。
Nat Rev Neurosci. 2009 Sep;10(9):647-58. doi: 10.1038/nrn2699.
5
Dendritic spine dynamics.树突棘动力学
Annu Rev Physiol. 2009;71:261-82. doi: 10.1146/annurev.physiol.010908.163140.
6
Constructing and exploiting the fluorescent protein paintbox (Nobel Lecture).构建与利用荧光蛋白颜料盒（诺贝尔演讲）
Angew Chem Int Ed Engl. 2009;48(31):5612-26. doi: 10.1002/anie.200901916.
7
Connectivity patterns revealed by mapping of active inputs on dendrites of thalamorecipient neurons in the auditory cortex.通过绘制听觉皮层丘脑接受神经元树突上的活跃输入所揭示的连接模式。
J Neurosci. 2009 May 20;29(20):6406-17. doi: 10.1523/JNEUROSCI.0258-09.2009.
8
A genetically encoded calcium indicator for chronic in vivo two-photon imaging.一种用于慢性体内双光子成像的基因编码钙指示剂。
Nat Methods. 2008 Sep;5(9):805-11. doi: 10.1038/nmeth.1243.
9
Single-spike detection in vitro and in vivo with a genetic Ca2+ sensor.利用基因钙传感器在体外和体内进行单峰检测。
Nat Methods. 2008 Sep;5(9):797-804. doi: 10.1038/nmeth.1242.
10
Questioning the role of rebound firing in the cerebellum.质疑小脑回射放电的作用。
Nat Neurosci. 2008 Nov;11(11):1256-8. doi: 10.1038/nn.2195. Epub 2008 Sep 28.
Zotero 插件