5-(2-azidoethyl)-1,3,3-trimethyl-2-methyleneindoline | 1261460-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-(2-azidoethyl)-1,3,3-trimethyl-2-methyleneindoline
• 英文别名: 5-(azidoethyl)-1,3,3-trimethyl-2-methyleneindoline；5-(2-Azidoethyl)-1,3,3-trimethyl-2-methylideneindole；5-(2-azidoethyl)-1,3,3-trimethyl-2-methylideneindole
• CAS: 1261460-38-1
• 化学式: C₁₄H₁₈N₄
• 分子量: 242.324
• InChiKey: NEDSUMKXAHVMGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  17.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(2-azidoethyl)-1,3,3-trimethyl-2-methyleneindoline 在 水 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 26.0h， 生成 1,3,3-trimethyl-5-(2-aminoethyl)spiro[indoline-2,3'-[3H]naphtho[2,1-b][1,4]oxazine]
  参考文献：
  名称：

  Rational design, synthesis, and characterization of highly fluorescent optical switches for high-contrast optical lock-in detection (OLID) imaging microscopy in living cells

  摘要：

  control of cellular processes. These studies require microscope imaging techniques and associated optical probes that provide high-contrast and high-resolution images of specific proteins and their complexes. Auto-fluorescence however, can severely compromise image contrast and represents a fundamental limitation for imaging proteins within living cells. We have previously shown that optical switch probes and optical lock-in detection (OLID) image microscopy improve image contrast in high background environments. Here, we present the design, synthesis, and characterization of amino-reactive and cell permeable optical switches that integrate the highly fluorescent fluorophore, tetramethylrhodamine (TMR) and spironaphthoxazine (NISO), a highly efficient optical switch. The NISO moiety in TMR-NISO undergoes rapid and reversible, excited-state driven transitions between a colorless Spiro (SP)-state and a colored merocyanine (MC)-state in response to irradiation with 365 and >530 nm light. In the MC-state, the TMR (donor) emission is almost completely extinguished by Forster resonance energy transfer (FRET) to the MC probe (acceptor), whereas in the colorless SP-state, the quantum yield for TMR fluorescence is maximal. Irradiation of TMR-NISO with a defined sequence of 365 and 546 nm manipulates the levels of SP and MC with concomitant modulation of FRET efficiency and the TMR fluorescence signal. High fidelity optical switching of TMR fluorescence is shown for TMR-NISO probes in vitro and for membrane permeable TMR-NISO within living cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.015
• 作为产物：
  描述：

  4-氨基苯乙醇 在 盐酸 、 sodium azide 、 偶氮二甲酸二异丙酯 、 硫酸 、 三苯基膦 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 25.0h， 生成 5-(2-azidoethyl)-1,3,3-trimethyl-2-methyleneindoline
  参考文献：
  名称：

  Rational design, synthesis, and characterization of highly fluorescent optical switches for high-contrast optical lock-in detection (OLID) imaging microscopy in living cells

  摘要：

  control of cellular processes. These studies require microscope imaging techniques and associated optical probes that provide high-contrast and high-resolution images of specific proteins and their complexes. Auto-fluorescence however, can severely compromise image contrast and represents a fundamental limitation for imaging proteins within living cells. We have previously shown that optical switch probes and optical lock-in detection (OLID) image microscopy improve image contrast in high background environments. Here, we present the design, synthesis, and characterization of amino-reactive and cell permeable optical switches that integrate the highly fluorescent fluorophore, tetramethylrhodamine (TMR) and spironaphthoxazine (NISO), a highly efficient optical switch. The NISO moiety in TMR-NISO undergoes rapid and reversible, excited-state driven transitions between a colorless Spiro (SP)-state and a colored merocyanine (MC)-state in response to irradiation with 365 and >530 nm light. In the MC-state, the TMR (donor) emission is almost completely extinguished by Forster resonance energy transfer (FRET) to the MC probe (acceptor), whereas in the colorless SP-state, the quantum yield for TMR fluorescence is maximal. Irradiation of TMR-NISO with a defined sequence of 365 and 546 nm manipulates the levels of SP and MC with concomitant modulation of FRET efficiency and the TMR fluorescence signal. High fidelity optical switching of TMR fluorescence is shown for TMR-NISO probes in vitro and for membrane permeable TMR-NISO within living cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.015

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.
• Rational design, synthesis, and characterization of highly fluorescent optical switches for high-contrast optical lock-in detection (OLID) imaging microscopy in living cells
  作者：Chutima Petchprayoon、Yuling Yan、Shu Mao、Gerard Marriott

  DOI：10.1016/j.bmc.2010.07.015

  日期：2011.2

  control of cellular processes. These studies require microscope imaging techniques and associated optical probes that provide high-contrast and high-resolution images of specific proteins and their complexes. Auto-fluorescence however, can severely compromise image contrast and represents a fundamental limitation for imaging proteins within living cells. We have previously shown that optical switch probes and optical lock-in detection (OLID) image microscopy improve image contrast in high background environments. Here, we present the design, synthesis, and characterization of amino-reactive and cell permeable optical switches that integrate the highly fluorescent fluorophore, tetramethylrhodamine (TMR) and spironaphthoxazine (NISO), a highly efficient optical switch. The NISO moiety in TMR-NISO undergoes rapid and reversible, excited-state driven transitions between a colorless Spiro (SP)-state and a colored merocyanine (MC)-state in response to irradiation with 365 and >530 nm light. In the MC-state, the TMR (donor) emission is almost completely extinguished by Forster resonance energy transfer (FRET) to the MC probe (acceptor), whereas in the colorless SP-state, the quantum yield for TMR fluorescence is maximal. Irradiation of TMR-NISO with a defined sequence of 365 and 546 nm manipulates the levels of SP and MC with concomitant modulation of FRET efficiency and the TMR fluorescence signal. High fidelity optical switching of TMR fluorescence is shown for TMR-NISO probes in vitro and for membrane permeable TMR-NISO within living cells. (C) 2010 Elsevier Ltd. All rights reserved.