7-hydroxy-5,5-dimethyl-10-(o-tolyl)dibenzo[b,e]silin-3(5H)-one | 1301205-26-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-hydroxy-5,5-dimethyl-10-(o-tolyl)dibenzo[b,e]silin-3(5H)-one
• 英文别名: Tokyo Magenta；7-Hydroxy-5,5-dimethyl-10-(2-methylphenyl)benzo[b][1]benzosilin-3-one；7-hydroxy-5,5-dimethyl-10-(2-methylphenyl)benzo[b][1]benzosilin-3-one
• CAS: 1301205-26-4
• 化学式: C₂₂H₂₀O₂Si
• 分子量: 344.485
• InChiKey: UCAPVIZVWFANJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-hydroxy-5,5-dimethyl-10-(o-tolyl)dibenzo[b,e]silin-3(5H)-one 在 吡啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.17h， 生成 N-[5,5-dimethyl-10-(2-methylphenyl)-3-oxobenzo[b][1]benzosilin-7-yl]acetamide
  参考文献：
  名称：

  EP2942352

  摘要：

  公开号：
• 作为产物：
  描述：

  间溴苯酚 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 叔丁基锂 、 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 1.5h， 生成 7-hydroxy-5,5-dimethyl-10-(o-tolyl)dibenzo[b,e]silin-3(5H)-one
  参考文献：
  名称：

  A Photoactivatable Formaldehyde Donor with Fluorescence Monitoring Reveals Threshold To Arrest Cell Migration

  摘要：

  Controlled light-mediated delivery of biological analytes can enable the investigation of highly reactivity molecules within living systems. As many biological effects are concentration dependent, it is critical to determine the location, time, and quantity of analyte donation. In this work, we have developed the first photoactivatable donor for formaldehyde (FA). Our optimized photoactivatable donor, photoFAD-3, is equipped with a fluorescence readout that enables monitoring of FA release with a concomitant 139-fold fluorescence enhancement. Tuning of photostability and cellular retention enabled quantification of intracellular FA release through cell lysate calibration. Application of photoFAD-3 uncovered the concentration range necessary for arresting wound healing in live cells. This marks the first report where a photoactivatable donor for any analyte has been used to quantify intracellular release.

  DOI：

  10.1021/jacs.9b11899

文献信息

• FLUORESCENT PROBE
  申请人：Nagano Tetsuo

  公开号：US20130289256A1

  公开（公告）日：2013-10-31

  A compound represented by the formula (I) (R 1 represents hydrogen atom or a monovalent substituent; R 2 and R 3 represent hydrogen atom, an alkyl group, or a halogen atom; R 4 and R 5 represent an alkyl group or an aryl group; R 6 and R 7 represent hydrogen atom, an alkyl group, or a halogen atom; R 8 represent hydroxy group or a dialkoxyboranetriyl group; and X represents silicon atom, germanium atom, or tin atom), which is a novel fluorophore usable as a mother nucleus of an off/on type fluorescent probe not utilizing the intramolecular photoinduced electron transfer.

  由公式(I)表示的化合物（其中R1代表氢原子或单价取代基；R2和R3代表氢原子、烷基或卤素原子；R4和R5代表烷基或芳基；R6和R7代表氢原子、烷基或卤素原子；R8代表羟基或二烷氧基硼三基团；X代表硅原子、锗原子或锡原子），这是一种新型的荧光发光体，可用作不利用分子内光诱导电子转移的off/on型荧光探针的母核。
• Fluorescent probe
  申请人：Nagano Tetsuo

  公开号：US09170266B2

  公开（公告）日：2015-10-27

  A compound represented by the formula (I) (one of substituents represented by R1 is a trapping group for an object substance for measurement; R2 and R3 represent hydrogen, alkyl, or halogen; R4 and R5 represent alkyl or aryl; R6 and R7 represent hydrogen, alkyl, or halogen; R8 represents hydrogen, alkylcarbonyl, or alkylcarbonyloxymethyl, and X represents silicon, germanium, or tin, which can be used as a fluorescent probe that enables red color bioimaging using intramolecular photoinduced electron transfer.

  根据您提供的英文句子，翻译成中文如下： 由公式(I)表示的化合物（其中R1代表的一个取代基是对测量对象的捕捉基团；R2和R3代表氢、烷基或卤素；R4和R5代表烷基或芳基；R6和R7代表氢、烷基或卤素；R8代表氢、烷基羰基或烷基羰基氧甲基，而X代表硅、锗或锡），可作为荧光探针使用，利用分子内光诱导电子转移实现红色生物成像。
• Development of a fluorescein analogue, TokyoMagenta, as a novel scaffold for fluorescence probes in red region
  作者：Takahiro Egawa、Yuichiro Koide、Kenjiro Hanaoka、Toru Komatsu、Takuya Terai、Tetsuo Nagano

  DOI：10.1039/c1cc00078k

  日期：——

  We present a design strategy for fluorescence probes with a high off/on activation ratio in the red wavelength region, based on a novel fluorescein analogue in which the O atom at the 10 position of the xanthene chromophore is replaced with a Si atom. To demonstrate the usefulness of this strategy, we designed and synthesized a red-fluorescent probe for β-galactosidase, and showed that it works in live HEK293 cells.

  我们提出了一种在红色波长区域具有高关/开激活比的荧光探针的设计策略，该策略基于一种新型荧光素类似物，其中位于荧光素发色团 10 位的 O 原子被一个 Si 原子取代。为了证明这一策略的实用性，我们设计并合成了β-半乳糖苷酶的红色荧光探针，并在活的 HEK293 细胞中证明了它的作用。
• Photophysics of a Live-Cell-Marker, Red Silicon-Substituted Xanthene Dye
  作者：Luis Crovetto、Angel Orte、Jose M. Paredes、Sandra Resa、Javier Valverde、Fabio Castello、Delia Miguel、Juan M. Cuerva、Eva M. Talavera、Jose M. Alvarez-Pez

  DOI：10.1021/acs.jpca.5b07898

  日期：2015.11.5

  Dyes with near-red emission are of great interest because of their undoubted advantages for use as probes in living cells. In-depth knowledge of their photophysics is essential for employment of such dyes. In this article, the photophysical behavior of a new silicon-substituted xanthene, 7-hydroxy-5,5-dimethy1-10-(o-toly1)-dibenzo[b,e]silin-3(5H)-one (2-Me TM), was explored by means absorption, steady-state, and time-resolved fluorescence. First, the near-neutral pH, ground-state acidity constant of the dye, K-p(N-A), was determined by absorbance and steady-state fluorescence at very low buffer concentrations. Next, we determined whether the addition of phosphate buffer promoted the excited-state proton-transfer (ESPT) reaction among the neutral and anion form of 2-Me TM in aqueous solutions at near-neutral pH. For this analysis, both the steady-state fluorescence method and time-resolved emission spectroscopy (TRES) were employed. The TRES experiments demonstrated a remarkably favored conversion of the neutral form to the anion form. Then, the values of the excited-state rate constants were determined by global analysis of the fluorescence decay traces recorded as a function of pH, and buffer concentration. The revealed kinetic parameters were consistent with the TRES results, exhibiting a higher rate constant for deprotonation than for protonation, which implies an unusual low value of the excited-state acidity constant pK*(N-A) and therefore an enhanced photoacid behavior of the neutral form. Finally, we determined whether 2-Me TM could be used as a sensor inside live cells by measuring the intensity profile of the probe in different cellular compartments of HeLa 229 cells.