5,5-dimethylluciferin | 73918-30-6

• 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: 5,5-dimethylluciferin
• 英文别名: D-penicilluc；(S)-2-(6-hydroxybenzo[d]thiazol-2-yl)-5,5-dimethyl-4,5-dihydrothiazole-4-carboxylic acid；(S)-2-(6-hydroxy-benzothiazol-2-yl)-5,5-dimethyl-4,5-dihydro-thiazole-4-carboxylic acid；(4S)-4,5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-5,5-dimethyl-4-thiazolecarboxylic Acid；(4S)-2-(6-hydroxy-1,3-benzothiazol-2-yl)-5,5-dimethyl-4H-1,3-thiazole-4-carboxylic acid
• CAS: 73918-30-6
• 化学式: C₁₃H₁₂N₂O₃S₂
• 分子量: 308.382
• InChiKey: XXZCJMWSTWCVLY-VIFPVBQESA-N

物化性质

• 沸点：
  557.1±60.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5,5-dimethylluciferin 在 mercury(II) diacetate 、 sodium phenoxide 作用下， 以 四氢呋喃 为溶剂， 生成 2-(6-hydroxy-benzothiazol-2-yl)-4-isopropylidene-4H-thiazol-5-one
  参考文献：
  名称：

  Chemiluminescence of 2-(6-hydroxy-2-benzothiazolyl)-4-isopropylidene-2-thiazolin-5-one, a by-product formed in the chemiluminescence of a firefly luciferin analog

  摘要：

  DOI：

  10.1021/jo00406a013
• 作为产物：
  描述：

  2-氰基-6-甲氧基苯并噻唑 在 吡啶盐酸盐 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 3.5h， 生成 5,5-dimethylluciferin
  参考文献：
  名称：

  Luciferin and derivatives as a DYRK selective scaffold for the design of protein kinase inhibitors

  摘要：

  D-Luciferin is widely used as a substrate in luciferase catalysed bioluminescence assays for in vitro studies. However, little is known about cross reactivity and potential interference of D-luciferin with other enzymes. We serendipitously found that firefly luciferin inhibited the CDK2/Cyclin A protein kinase. Inhibition profiling of D-luciferin over a 103-protein kinase panel showed significant inhibition of a small set of protein kinases, in particular the DYRK-family, but also other members of the CMGC-group, including ERK8 and CK2. Inhibition profiling on a 16-member focused library derived from D-luciferin confirms that D-luciferin represents a DYRK-selective chemotype of fragment-like molecular weight. Thus, observation of its inhibitory activity and the initial SAR information reported here promise to be useful for further design of protein kinase inhibitors with related scaffolds. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.035

文献信息

• A firefly inspired one-pot chemiluminescence system using n-propylphosphonic anhydride (T3P)
  作者：Dai-ichiro Kato、Daiki Shirakawa、Robin Polz、Mika Maenaka、Masahiro Takeo、Seiji Negoro、Kazuki Niwa

  DOI：10.1039/c4pp00250d

  日期：2014.12

  A simple reaction procedure for chemiluminescence of firefly luciferin (d-luc) using n-propylphosphonic anhydride (T3P) is reported. A luminescent photon is produced as a result of one-pot reaction, only requiring mixing with the substrate carboxylic acid and T3P in the presence of a mild organic base.

  本研究报道了一种利用正丙基膦酸酐（T3P）对萤火虫荧光素（d-luc）进行化学发光的简单反应程序。只需在温和的有机碱存在下将底物羧酸和 T3P 混合，即可通过一次反应产生发光光子。
• Yellow-Green and Red Firefly Bioluminescence from 5,5-Dimethyloxyluciferin
  作者：Bruce R. Branchini、Martha H. Murtiashaw、Rachelle A. Magyar、Nathan C. Portier、Maria C. Ruggiero、Justin G. Stroh

  DOI：10.1021/ja017400m

  日期：2002.3.1

  (including those of the firefly) use the same luciferin substrate to naturally display light ranging in color from green (lambda(max) similar 530 nm) to red (lambda(max) similar 635 nm). The original mechanism of bioluminescence color determination advanced by White and co-workers was based on the concept that the keto and enol tautomers of the emitter oxyluciferin produce red and green light, respectively.

  甲虫荧光素酶（包括萤火虫的荧光素酶）使用相同的荧光素底物自然显示颜色范围从绿色（λ(max) 类似于 530 nm）到红色（λ(max) 类似于 635 nm）的光。White 及其同事提出的生物发光颜色测定的原始机制基于发射体氧化荧光素的酮和烯醇互变异构体分别产生红光和绿光的概念。或者，麦卡普拉提出颜色变化与激发态氧化荧光素的酮形式的构象有关。我们已经制备了 D-5,5-二甲基荧光素的腺苷酸，并表明它在生物发光反应中转化为假定的发射体 5,5-二甲基氧基荧光素，该反应由来自 Photinus pyralis 的荧光素酶和发射绿色的点击甲虫催化。5、5-二甲氧基荧光素被限制以酮形式存在并发出红色荧光。然而，生物发光光谱显示萤火虫酶产生绿光发射，而点击甲虫蛋白则观察到红光。这些结果加上稳态动力学研究，可作为对 McCapra 的萤火虫生物发光颜色机制或任何其他仅需要单一酮形式的氧化荧光素的提议的第一个实验支持。
• LUMINOGENIC AND FLUOROGENIC COMPOUNDS AND METHODS TO DETECT MOLECULES OR CONDITIONS
  申请人：Promega Corporation

  公开号：US20140154716A1

  公开（公告）日：2014-06-05

  A method to detect the presence or amount of at least one molecule in a sample which employs a derivative of luciferin or a derivative of a fluorophore is provided. Compounds and compositions for carrying out the methods of the invention are also provided.

  本发明提供了一种检测样本中至少一种分子存在或数量的方法，该方法采用了luciferin的衍生物或荧光团的衍生物。还提供了用于执行本发明方法的化合物和组合物。
• Luminogenic and fluorogenic compounds and methods to detect molecules or conditions
  申请人：Promega Corporation

  公开号：EP2277872B1

  公开（公告）日：2016-03-23
• US7951550B2
  申请人：——

  公开号：US7951550B2

  公开（公告）日：2011-05-31