1,3,3-trimethyl-5-(carboxypropyl)-7'-azidospiro[indoline-2,3'-[3H]naphtho[2,1-b][1,4]oxazine] | 1261460-28-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 1,3,3-trimethyl-5-(carboxypropyl)-7'-azidospiro[indoline-2,3'-[3H]naphtho[2,1-b][1,4]oxazine]
• 英文别名: 5-CO, 7'-N3 NISO；4-(7-Azido-1',3',3'-trimethylspiro[benzo[f][1,4]benzoxazine-3,2'-indole]-5'-yl)butanoic acid；4-(7-azido-1',3',3'-trimethylspiro[benzo[f][1,4]benzoxazine-3,2'-indole]-5'-yl)butanoic acid
• CAS: 1261460-28-9
• 化学式: C₂₆H₂₅N₅O₃
• 分子量: 455.516
• InChiKey: SSMIIGSVGCFGGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  76.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,3,3-trimethyl-5-(carboxypropyl)-7'-azidospiro[indoline-2,3'-[3H]naphtho[2,1-b][1,4]oxazine] 在 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以81%的产率得到1,3,3-trimethyl-5-(carboxypropyl)-7'-aminospiro[indoline-2,3'-[3H]naphtho[2,1-b][1,4]oxazine]
  参考文献：
  名称：

  Synthesis and spectroscopic characterization of red-shifted spironaphthoxazine based optical switch probes

  摘要：

  Spironaphthoxazine (NISO) is an efficient optical switch probe that has applications in high contrast detection of Forster resonance energy transfer (FRET) using optical lock-in detection (OLID). NISO exists in two distinct states, spiro (SP) and merocyanine (MC), that can be independently controlled by using alternate irradiation with near ultraviolet and visible light. Unfortunately, the SP-state of NISO has an absorption centered at 350 nm, which may lead to phototoxic effects when manipulating the probe within a living cell. To overcome this problem we introduce new, red-shifted amino-substituted NISO probes compared to NISO that undergo an efficient SP to MC transition in response to irradiation by using 405-nm light, which is less damaging to living cells. This study details the synthesis of amino-substituted NISO and their N-hydroxysuccinimide ester and maleimide derivatives and their use in generating covalent attached protein conjugates. This study also presents a characterization of the spectroscopic and optical switching properties of these red-shifted NISO probe in solution. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.084
• 作为产物：
  描述：

  5-azido-1-nitroso-2-naphthol 、 1,2,3,3-tetramethyl-5-(3-carboxypropyl)-3H-indoleninium iodide 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以59%的产率得到1,3,3-trimethyl-5-(carboxypropyl)-7'-azidospiro[indoline-2,3'-[3H]naphtho[2,1-b][1,4]oxazine]
  参考文献：
  名称：

  Synthesis and spectroscopic characterization of red-shifted spironaphthoxazine based optical switch probes

  摘要：

  Spironaphthoxazine (NISO) is an efficient optical switch probe that has applications in high contrast detection of Forster resonance energy transfer (FRET) using optical lock-in detection (OLID). NISO exists in two distinct states, spiro (SP) and merocyanine (MC), that can be independently controlled by using alternate irradiation with near ultraviolet and visible light. Unfortunately, the SP-state of NISO has an absorption centered at 350 nm, which may lead to phototoxic effects when manipulating the probe within a living cell. To overcome this problem we introduce new, red-shifted amino-substituted NISO probes compared to NISO that undergo an efficient SP to MC transition in response to irradiation by using 405-nm light, which is less damaging to living cells. This study details the synthesis of amino-substituted NISO and their N-hydroxysuccinimide ester and maleimide derivatives and their use in generating covalent attached protein conjugates. This study also presents a characterization of the spectroscopic and optical switching properties of these red-shifted NISO probe in solution. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.084

文献信息

• Synthesis and spectroscopic characterization of red-shifted spironaphthoxazine based optical switch probes
  作者：Chutima Petchprayoon、Gerard Marriott

  DOI：10.1016/j.tetlet.2010.10.084

  日期：2010.12

  Spironaphthoxazine (NISO) is an efficient optical switch probe that has applications in high contrast detection of Forster resonance energy transfer (FRET) using optical lock-in detection (OLID). NISO exists in two distinct states, spiro (SP) and merocyanine (MC), that can be independently controlled by using alternate irradiation with near ultraviolet and visible light. Unfortunately, the SP-state of NISO has an absorption centered at 350 nm, which may lead to phototoxic effects when manipulating the probe within a living cell. To overcome this problem we introduce new, red-shifted amino-substituted NISO probes compared to NISO that undergo an efficient SP to MC transition in response to irradiation by using 405-nm light, which is less damaging to living cells. This study details the synthesis of amino-substituted NISO and their N-hydroxysuccinimide ester and maleimide derivatives and their use in generating covalent attached protein conjugates. This study also presents a characterization of the spectroscopic and optical switching properties of these red-shifted NISO probe in solution. (C) 2010 Elsevier Ltd. All rights reserved.