萤光素 | 7273-34-9

• 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
• 中文名称: 萤光素
• 英文名称: (+)-cypridina luciferin
• 英文别名: 2-[3-[2-butan-2-yl-6-(1H-indol-3-yl)-3-oxo-7H-imidazo[1,2-a]pyrazin-8-yl]propyl]guanidine
• CAS: 7273-34-9；17297-75-5；89024-30-6
• 化学式: C₂₂H₂₇N₇O
• 分子量: 405.503
• InChiKey: ZWPWSXGBDMGKKS-UHFFFAOYSA-N

物化性质

• 熔点：
  252-254 (HBr salt)
• 沸点：
  598.6±60.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  128.37
• 氢给体数：
  5.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  萤光素 在 potassium hexacyanoferrate(III) 作用下， 以 二甲基亚砜 为溶剂， 生成 Cypridina biluciferyl
  参考文献：
  名称：

  Structure of biluciferyl, a dimer of luciferyl radical having bioluminescent activity

  摘要：

  DOI：

  10.1016/s0040-4039(00)61889-0
• 作为产物：
  描述：

  cypridina luciferinyl methyl ether 在 sodium dithionite 作用下， 以50%的产率得到萤光素
  参考文献：
  名称：

  萤光素荧光素的结构，“可逆氧化的萤光素荧光素”

  摘要：

  赛普拉斯荧光素的结构（可逆氧化的荧光素）是由赛普拉斯荧光素的自氧化或PbO 2氧化而无光产生的，并且可以用Na 2 S 2 O 4或NaBH 4还原为C. luciferin 。

  DOI：

  10.1016/s0040-4039(00)94192-3

文献信息

• Convergent and short-step syntheses of dl-Cypridina luciferin and its analogues based on Pd-mediated cross couplings
  作者：Hideshi Nakamura、Mihoko Aizawa、Daisuke Takeuchi、Akio Murai、Osamu Shimoura

  DOI：10.1016/s0040-4039(00)00131-3

  日期：2000.3

  luciferin and its analogues were synthesized from 2-aminopyrazine by an eight-step method that included two regio-selective Pd-mediated cross couplings, and their chemi- and bioluminescent activities were compared. Analogues having a 3-benzofuranyl or a 3-benzothienyl group in the place of a 3-indolyl group showed luciferase affinities similar to Cypridina luciferase but with a lower luminescent efficiency

  通过八步法从2-氨基吡嗪合成了dl- Cypridina luciferin及其类似物，该方法包括两个区域选择性Pd介导的交叉偶联，并比较了它们的化学发光和生物发光活性。具有3-苯并呋喃基或3-苯并噻吩基取代3-吲哚基的类似物显示出类似于Cypridina luciferase的萤光素酶亲和力，但发光效率较低，这表明NH基对于分子识别并不重要，而吲哚基是对于有效发光至关重要。
• Syntheses and evaluation of the bioluminescent activity of (S)-Cypridina luciferin and its analogs
  作者：Chun Wu、Kosei Kawasaki、Satoru Ohgiya、Yoshihiro Ohmiya

  DOI：10.1016/j.tetlet.2005.11.119

  日期：2006.1

  the presence of Cypridina luciferase was about 1.7 times as active as that of racemic form. Furthermore, several luciferin analogs prepared by the same condensation with different α-ketoacetal derivatives showed moderate light yield with Cypridina luciferase. These readily available Cypridina luciferin and analogs are applicable to the bioluminescent detection of Cypridina luciferase.

  赛氏丝虫萤光素是发光的球形赛氏丝虫（姬菇）hilgendorfii的生物发光的底物。球藻萤光素在仲丁基部分中含有一个手性中心。在这里，我们报告了通过（S）-1,1-二乙氧基-3-甲基戊-2--2-与硫代荧光素的缩合来制备（S）-Cypridina luciferin的简便方法。合成（S荧光素酶荧光素酶的存在下，）-荧光素的活性约为外消旋形式的活性的1.7倍。此外，通过用不同的α-酮缩醛衍生物相同的缩合反应制备的几种荧光素类似物在赛普里迪纳荧光素酶中显示出中等的光产量。这些容易获得的丝藻荧光素和类似物可用于丝藻荧光素酶的生物发光检测。
• IMIDAZO[1,2-ALPHA]PYRAZIN-3(7H)-ONE DERIVATIVES BEARING A NEW ELECTRON-RICH STRUCTURE
  申请人：Giuliani Germano

  公开号：US20120171703A1

  公开（公告）日：2012-07-05

  The present invention relates to compound of formula I: and their use as chemiluminescent and/or bioluminescent reagents.

  本发明涉及化合物I的配方和它们作为化学发光和/或生物发光试剂的用途。
• Method for determining kinetic profiles in drug discovery
  申请人：ENZYMLOGIC, S.L

  公开号：US10261079B2

  公开（公告）日：2019-04-16

  The present invention relates to a reliable, robust and sensitive platform aimed to analyze the massive kinetic profile of new molecules against its main target and also against other potential targets. Thus, the present invention relates to a method for calculating the kinetic profile of a compound of interest against a target protein or polyprotein wherein it is not needed to predetermine the Ki value of the compound of interest against the target protein or polyprotein before starting the assay. The present invention also discloses the use of said method in a high-throughput system for developing a Binding Kinetic Profiling assay of multiple compounds of interest against a unique target, or a Kinetic Selectivity Profiling assay of one selected compound against multiple target proteins or polyproteins to therefore establish multiple clinical profiles of potential drugs.

  本发明涉及一种可靠、稳健和灵敏的平台，旨在分析新分子针对其主要靶标和其他潜在靶标的大量动力学特征。因此，本发明涉及一种计算感兴趣的化合物对靶蛋白或多蛋白的动力学特征的方法，在该方法中，不需要在开始测定前预先确定感兴趣的化合物对靶蛋白或多蛋白的 Ki 值。本发明还公开了上述方法在高通量系统中的应用，该系统用于开发针对一个独特靶点的多种相关化合物的结合动力学剖析检测，或针对多种靶蛋白或多蛋白的一种选定化合物的动力学选择性剖析检测，从而建立多种潜在药物的临床概况。
• METHOD FOR DETERMINING KINETIC PROFILES IN DRUG DISCOVERY
  申请人：ENZYMLOGIC, S.L

  公开号：US20190049441A1

  公开（公告）日：2019-02-14

  The present invention relates to a reliable, robust and sensitive platform aimed to analyze the massive kinetic profile of new molecules against its main target and also against other potential targets. Thus, the present invention relates to a method for calculating the kinetic profile of a compound of interest against a target protein or polyprotein wherein it is not needed to predetermine the K i value of the compound of interest against the target protein or polyprotein before starting the assay. The present invention also discloses the use of said method in a high-throughput system for developing a Binding Kinetic Profiling assay of multiple compounds of interest against a unique target, or a Kinetic Selectivity Profiling assay of one selected compound against multiple target proteins or polyproteins to therefore establish multiple clinical profiles of potential drugs.