2-azaniumyl-3-[(4-methoxyphenyl)-diphenylmethyl]sulfanylpropanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2-azaniumyl-3-[(4-methoxyphenyl)-diphenylmethyl]sulfanylpropanoate
• 化学式: C₂₃H₂₃NO₃S
• 分子量: 393.507
• InChiKey: QAINHNNAIDVCEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  97.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-azaniumyl-3-[(4-methoxyphenyl)-diphenylmethyl]sulfanylpropanoate 在 环己烯 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 6.25h， 生成 6-(4-(2-amino-3-((4-methoxyphenyl)diphenylmethylthio)-propanamido)but-1-ynyl)-3,3-difluoro-2-(propan-2-ylidene)-2,3-dihydro[1,2,4,3]triazaborolo[4,5-a]pyridin-2-ium-3-uide
  参考文献：
  名称：

  Design and Synthesis of a New Class of Membrane-Permeable Triazaborolopyridinium Fluorescent Probes

  摘要：

  A new class of fluorescent triazaborolopyridinium compounds was synthesized from hydrazones of 2-hydrazinylpyridine (HPY) and evaluated as potential dyes for live-cell imaging applications. The HPY dyes are small, their absorption/emission properties are tunable through variation of pyridyl or hydrazone substituents, and they offer favorable photophysical characteristics featuring large Stokes shifts and general insensitivity to solvent or pH. The stability, neutral charge, cell membrane permeability, and favorable relative influences on the water solubility of HPY conjugates are complementary to existing fluorescent dyes and offer advantages for the development of receptor-targeted small-molecule probes. This potential was assessed through the development of a new class of cysteine-derived HPY-conjugate imaging agents for the kinesin spindle protein (KSP) that is expressed in the cytoplasm during mitosis and is a promising chemotherapeutic target. Conjugates possessing the neutral HPY or charged Alexa Fluor dyes that function as potent, selective allosteric inhibitors of the KSP motor were compared using biochemical and cell-based phenotypic assays and live-cell imaging. These results demonstrate the effectiveness of the HPY dye moiety as a component of probes for an intracellular protein target and highlight the importance of dye structure in determining the pathway of cell entry and the overall performance of small-molecule conjugates as imaging agents.

  DOI：

  10.1021/ja2005175

文献信息

• US8349899B1
  申请人：——

  公开号：US8349899B1

  公开（公告）日：2013-01-08
• US8765817B1
  申请人：——

  公开号：US8765817B1

  公开（公告）日：2014-07-01
• Design and Synthesis of a New Class of Membrane-Permeable Triazaborolopyridinium Fluorescent Probes
  作者：Sudath Hapuarachchige、Gilbert Montaño、Chinnasamy Ramesh、Delany Rodriguez、Lauren H. Henson、Casey C. Williams、Samuel Kadavakkollu、Dennis L. Johnson、Charles B. Shuster、Jeffrey B. Arterburn

  DOI：10.1021/ja2005175

  日期：2011.5.4

  A new class of fluorescent triazaborolopyridinium compounds was synthesized from hydrazones of 2-hydrazinylpyridine (HPY) and evaluated as potential dyes for live-cell imaging applications. The HPY dyes are small, their absorption/emission properties are tunable through variation of pyridyl or hydrazone substituents, and they offer favorable photophysical characteristics featuring large Stokes shifts and general insensitivity to solvent or pH. The stability, neutral charge, cell membrane permeability, and favorable relative influences on the water solubility of HPY conjugates are complementary to existing fluorescent dyes and offer advantages for the development of receptor-targeted small-molecule probes. This potential was assessed through the development of a new class of cysteine-derived HPY-conjugate imaging agents for the kinesin spindle protein (KSP) that is expressed in the cytoplasm during mitosis and is a promising chemotherapeutic target. Conjugates possessing the neutral HPY or charged Alexa Fluor dyes that function as potent, selective allosteric inhibitors of the KSP motor were compared using biochemical and cell-based phenotypic assays and live-cell imaging. These results demonstrate the effectiveness of the HPY dye moiety as a component of probes for an intracellular protein target and highlight the importance of dye structure in determining the pathway of cell entry and the overall performance of small-molecule conjugates as imaging agents.