(4-(((2-cyanobenzo[d]thiazol-6-yl)oxy)methyl)phenyl)boronic acid | 1421277-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (4-(((2-cyanobenzo[d]thiazol-6-yl)oxy)methyl)phenyl)boronic acid
• 英文别名: 4-((2-cyanobenzo[d]thiazol-6-yloxy)methyl)phenylboronic acid；peroxy caged luciferein-2；4-((2-Cyanobenzo[d]thiazol-6-yloxy)methyl)phenylboronic acid；[4-[(2-cyano-1,3-benzothiazol-6-yl)oxymethyl]phenyl]boronic acid
• CAS: 1421277-81-7
• 化学式: C₁₅H₁₁BN₂O₃S
• 分子量: 310.141
• InChiKey: YVBFNEVBWGYMNK-UHFFFAOYSA-N

物化性质

• 沸点：
  559.8±60.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4-(((2-cyanobenzo[d]thiazol-6-yl)oxy)methyl)phenyl)boronic acid 在 双氧水 作用下， 以 aq. buffer 为溶剂， 生成 2-氰基-6-羟基苯并噻唑
  参考文献：
  名称：

  Strategy for Dual-Analyte Luciferin Imaging: In Vivo Bioluminescence Detection of Hydrogen Peroxide and Caspase Activity in a Murine Model of Acute Inflammation

  摘要：

  In vivo molecular imaging holds promise for understanding the underlying mechanisms of health, injury, aging, and disease, as it can detect distinct biochemical processes such as enzymatic activity, reactive small-molecule fluxes, or post-translational modifications. Current imaging techniques often detect only a single biochemical process, but, within whole organisms, multiple types of biochemical events contribute to physiological and pathological phenotypes. In this report, we present a general strategy for dual-analyte detection in living animals that employs in situ formation of firefly luciferin from two complementary caged precursors that can be unmasked by different biochemical processes. To establish this approach, we have developed Peroxy Caged Luciferin-2 (PCL-2), a H2O2-responsive boronic acid probe that releases 6-hydroxy-2-cyanobenzothiazole (HCBT) upon reacting with this reactive oxygen species, as well as a peptide-based probe, z-Ile-Glu-ThrAsp-D-Cys (IETDC), which releases D-cysteine in the presence of active caspase 8. Once released, HCBT and D-cysteine form firefly luciferin in situ, giving rise to a bioluminescent signal if and only if both chemical triggers proceed. This system thus constitutes an AND-type molecular logic gate that reports on the simultaneous presence of H2O2 and caspase 8 activity. Using these probes, chemoselective imaging of either H2O2 or caspase 8 activity was performed in vitro and in vivo. Moreover, concomitant use of PCL-2 and IETDC in vivo establishes a concurrent increase in both H2O2 and caspase 8 activity during acute inflammation in living mice. Taken together, this method offers a potentially powerful new chemical tool for studying simultaneous oxidative stress and inflammation processes in living animals during injury, aging, and disease, as well as a versatile approach for concurrent monitoring of multiple analytes using luciferin-based bioluminescence imaging technologies.

  DOI：

  10.1021/ja309078t
• 作为产物：
  描述：

  2-氰基-6-甲氧基苯并噻唑 在 吡啶盐酸盐 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 (4-(((2-cyanobenzo[d]thiazol-6-yl)oxy)methyl)phenyl)boronic acid
  参考文献：
  名称：

  Luciferin Derivatives from Bicyclic Reactants and Aminothiol Derivatives and Methods of Use Thereof

  摘要：

  本公开涉及一种可以在生理条件下进行的缩合反应和发光素暴露反应。通常，缩合反应涉及将双环反应物与氨基硫醇衍生物反应，生成发光素或发光素衍生物。发光素可以提供可检测的发光。发光素衍生物可以在发光素暴露反应中被揭示出来，提供可检测的发光。本公开提供适用于缩合反应的双环反应物和氨基硫醇衍生物。缩合和发光素暴露反应在各种应用中有用，这些应用也被提供。

  公开号：

  US20130287699A1

文献信息

• [EN] DETECTION OF HYDROGEN PEROXIDE<br/>[FR] DÉTECTION DE PEROXYDE D'HYDROGÈNE
  申请人：PROMEGA CORP

  公开号：WO2013025885A1

  公开（公告）日：2013-02-21

  The present invention provides compounds of formula (I), (II) or (III) wherein R1and R11are boronic acid or a borate ester useful for detection of hydrogen peroxide and methods of using same.

  本发明提供了式(I)、(II)或(III)的化合物，其中R1和R11为硼酸或硼酸酯，用于检测过氧化氢，并提供了使用方法。
• DETECTION OF HYDROGEN PEROXIDE
  申请人：Klaubert Dieter

  公开号：US20130045497A1

  公开（公告）日：2013-02-21

  The present invention provides compounds useful for detection of hydrogen peroxide and methods of using same.

  本发明提供了用于检测过氧化氢的化合物及其使用方法。
• Detection of hydrogen peroxide
  申请人：Klaubert Dieter

  公开号：US08785652B2

  公开（公告）日：2014-07-22

  The present invention provides compounds useful for detection of hydrogen peroxide and methods of using same.

  本发明提供了用于检测过氧化氢的化合物及其使用方法。
• Luciferin derivatives from bicyclic reactants and aminothiol derivatives and methods of use thereof
  申请人：The Regents of the University of California

  公开号：US09173966B2

  公开（公告）日：2015-11-03

  The present disclosure features a condensation reaction and a luciferin-unmasking reaction that can be carried out under physiological conditions. In general, the condensation reaction involves reacting a bicyclic reactant with an aminothiol derivative, generating a luciferin or luciferin derivative. A luciferin can provide detectable luminescence. A luciferin derivative can be unmasked to provide detectable luminescence in a luciferin-unmasking reaction. The present disclosure provides bicyclic reactants and aminothiol derivatives suitable for use in the condensation reaction. The condensation and luciferin-unmasking reactions find use in a variety of applications, which are also provided.

  本公开涉及一种可以在生理条件下进行的缩合反应和发光素解掩蔽反应。一般来说，缩合反应涉及将一个双环反应物与氨基硫醇衍生物反应，生成发光素或发光素衍生物。发光素可以提供可检测的发光。发光素衍生物可以被解除掩蔽以在发光素解掩蔽反应中提供可检测的发光。本公开提供了适用于缩合反应的双环反应物和氨基硫醇衍生物。缩合和发光素解掩蔽反应在各种应用中得到应用，这些应用也在本公开中提供。
• LUCIFERIN DERIVATIVES FROM BICYCLIC REACTANTS AND AMINOTHIOL DERIVATIVES AND METHODS OF USE THEREOF
  申请人：The Regents of the University of California

  公开号：US20160015835A1

  公开（公告）日：2016-01-21

  The present disclosure features a condensation reaction and a luciferin-unmasking reaction that can be carried out under physiological conditions. In general, the condensation reaction involves reacting a bicyclic reactant with an aminothiol derivative, generating a luciferin or luciferin derivative. A luciferin can provide detectable luminescence. A luciferin derivative can be unmasked to provide detectable luminescence in a luciferin-unmasking reaction. The present disclosure provides bicyclic reactants and aminothiol derivatives suitable for use in the condensation reaction. The condensation and luciferin-unmasking reactions find use in a variety of applications, which are also provided.

  本公开涉及一种可以在生理条件下进行的缩合反应和发光素解掩蔽反应。一般而言，缩合反应涉及将双环反应物与氨硫醇衍生物反应，生成发光素或发光素衍生物。发光素可以提供可检测的发光。发光素衍生物可以在发光素解掩蔽反应中被揭示出来，提供可检测的发光。本公开提供了适用于缩合反应的双环反应物和氨硫醇衍生物。缩合和发光素解掩蔽反应在多种应用中发挥作用，这些应用也被提供。