2-((4-(carboxy(2-nitrophenyl)methoxy)-4-oxobutyl)amino)-2-(2-nitrophenyl)acetic acid | 1541867-39-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-((4-(carboxy(2-nitrophenyl)methoxy)-4-oxobutyl)amino)-2-(2-nitrophenyl)acetic acid
• 英文别名: bis-CNB-GABA；2-[[4-[Carboxy-(2-nitrophenyl)methoxy]-4-oxobutyl]amino]-2-(2-nitrophenyl)acetic acid；2-[[4-[carboxy-(2-nitrophenyl)methoxy]-4-oxobutyl]amino]-2-(2-nitrophenyl)acetic acid
• CAS: 1541867-39-3
• 化学式: C₂₀H₁₉N₃O₁₀
• 分子量: 461.385
• InChiKey: CENANTMVXUXZTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  205
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-硝基苯乙酸 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 二碳酸二叔丁酯 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 2-((4-(carboxy(2-nitrophenyl)methoxy)-4-oxobutyl)amino)-2-(2-nitrophenyl)acetic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Bis-CNB-GABA, a Photoactivatable Neurotransmitter with Low Receptor Interference and Chemical Two-Photon Uncaging Properties

  摘要：

  Photoactivatable "caged" neurotransmitters allow optical control of neural tissue with high spatial and temporal precision. However, the development of caged versions of the chief vertebrate inhibitory neurotransmitter, gamma-amino butyric acid (GABA), has been limited by the propensity of caged GABAs to interact with GABA receptors. We describe herein the synthesis and application of a practically useful doubly caged GABA analog, termed bis-alpha-carboxy-2-nitrobenzyl-GABA (bis-CNB-GABA). Uncaging of bis-CNB-GABA evokes inward GABAergic currents in cerebellar molecular layer interneurons with rise times of 2 ms, comparable to flash duration. Response amplitudes depend on the square of flash intensity, as expected for a chemical two-photon uncaging effect. Importantly, prior to uncaging, bis-CNB-GABA is inactive at the GABA(A) receptor, evoking no changes in holding current in voltage-clamped neurons and showing an IC50 of at least 2.5 mM as measured using spontaneous GABAergic synaptic currents. Bis-CNB-GABA is stable in solution, with an estimated half-life of 98 days in the light. We expect that bis-CNB-GABA will prove to be an effective tool for high-resolution chemical control of brain circuits.

  DOI：

  10.1021/ja411082f

文献信息

• DOUBLE CAGED GABA COMPOUNDS, BIS-CNB-GABA
  申请人：The Trustees of Princeton University

  公开号：US20150266809A1

  公开（公告）日：2015-09-24

  Double caged GABA compounds and compositions including the same are described. Methods of synthesizing and using double caged GABA compounds are provided.

  描述了双笼式GABA化合物及包括其在内的组合物。提供了合成和使用双笼式GABA化合物的方法。
• US9625448B2
  申请人：——

  公开号：US9625448B2

  公开（公告）日：2017-04-18
• Synthesis and Biological Evaluation of Bis-CNB-GABA, a Photoactivatable Neurotransmitter with Low Receptor Interference and Chemical Two-Photon Uncaging Properties
  作者：Diana D. Shi、Federico F. Trigo、Martin F. Semmelhack、Samuel S.-H. Wang

  DOI：10.1021/ja411082f

  日期：2014.2.5

  Photoactivatable "caged" neurotransmitters allow optical control of neural tissue with high spatial and temporal precision. However, the development of caged versions of the chief vertebrate inhibitory neurotransmitter, gamma-amino butyric acid (GABA), has been limited by the propensity of caged GABAs to interact with GABA receptors. We describe herein the synthesis and application of a practically useful doubly caged GABA analog, termed bis-alpha-carboxy-2-nitrobenzyl-GABA (bis-CNB-GABA). Uncaging of bis-CNB-GABA evokes inward GABAergic currents in cerebellar molecular layer interneurons with rise times of 2 ms, comparable to flash duration. Response amplitudes depend on the square of flash intensity, as expected for a chemical two-photon uncaging effect. Importantly, prior to uncaging, bis-CNB-GABA is inactive at the GABA(A) receptor, evoking no changes in holding current in voltage-clamped neurons and showing an IC50 of at least 2.5 mM as measured using spontaneous GABAergic synaptic currents. Bis-CNB-GABA is stable in solution, with an estimated half-life of 98 days in the light. We expect that bis-CNB-GABA will prove to be an effective tool for high-resolution chemical control of brain circuits.