N,N'-bis[2-[bis[carboxymethylen]amino]ethyl]-L-S-(2-pyridylthio)cysteine | 1234299-88-7

• 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: N,N'-bis[2-[bis[carboxymethylen]amino]ethyl]-L-S-(2-pyridylthio)cysteine
• 英文别名: (2R)-2-[bis[2-[bis(carboxymethyl)amino]ethyl]amino]-3-(pyridin-2-yldisulfanyl)propanoic acid
• CAS: 1234299-88-7
• 化学式: C₂₀H₂₈N₄O₁₀S₂
• 分子量: 548.595
• InChiKey: XGYDGYFHIRMBFI-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7
• 重原子数：
  36
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  260
• 氢给体数：
  5
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  6-巯基-6-去氧-β-环糊精 、 N,N'-bis[2-[bis[carboxymethylen]amino]ethyl]-L-S-(2-pyridylthio)cysteine 以 水 为溶剂， 生成
  参考文献：
  名称：

  通过磁各向异性提高主客体化学中的手性传感能力

  摘要：

  对映体分子通常在化学、生物学和药理学中发挥不同的功能。手性分析物相似的物理和化学性质给对映体的区分和定量带来了困难。我们在此报告了一种通过磁各向异性提高主客体化学中广泛使用的主体分子β-环糊精（β-CD）手性传感能力的有效方法。将刚性手性镧系元素结合标签附着在β-CD上，以放大主客体识别过程中核磁共振（NMR）信号的变化。与反磁性 β-CD 参考相比，在 β-CD 中安装顺磁性镧系元素离子大大增强了对映体辨别能力，高达 30 倍。此外，顺磁效应的大小可以根据镧系元素顺磁强度的不同范围进行调节。该方法显着提高了β-CD的手性传感能力，可应用于其他主体分子。从主体分子到客体分子的转移顺磁效应、赝接触位移（PCS）和顺磁弛豫增强（PRE）是确定手性分析物的绝对立体化学的有价值的结构限制。该策略不需要对分析物进行修改，并且是对依赖于手性分析物功能化的报道的分析方法的补充。

  DOI：

  10.1007/s11426-024-1989-y
• 作为产物：
  描述：

  N,N-bis[2-[bis[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]ethyl]-L-S-(2-pyridylthio)cysteine 在 三氟乙酸 、 三异丙基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以0.82 g的产率得到N,N'-bis[2-[bis[carboxymethylen]amino]ethyl]-L-S-(2-pyridylthio)cysteine
  参考文献：
  名称：

  Exofacial Protein Thiols as a Route for the Internalization of Gd(III)-Based Complexes for Magnetic Resonance Imaging Cell Labeling

  摘要：

  Four novel MRI Gd(III)-based probes have been synthesized and evaluated for their labeling properties on cultured cell lines K562, C6, and B16. The labeling strategy relies upon the fact that cells display a large number of reactive exofacial protein thiols (EPTs) that can be exploited as anchorage points for suitably activated MRI probes. The probes are composed of a Gd(III) chelate (based on either DO3A or DTPA) connected through a flexible linker to the 2-pyridyldithio chemical function for binding to EPTs. GdDO3A-based chelates could efficiently label cells (up to a level of 1.2 x 10(10) Gd(III) atoms/cell), whereas GdDTPA-based chelates showed poor or no cell labeling ability at all. Among the GdDO3A based compounds, that having the longest spacer (compound GdL1A) showed the best labeling efficacy. The mechanism of EPT mediated cell labeling by GdL1A involves probe internalization without sequestration of the Gd(III) chelate within subcellular structures such as endosomes.

  DOI：

  10.1021/jm901876r

文献信息

• Exofacial Protein Thiols as a Route for the Internalization of Gd(III)-Based Complexes for Magnetic Resonance Imaging Cell Labeling
  作者：Giuseppe Digilio、Valeria Menchise、Eliana Gianolio、Valeria Catanzaro、Carla Carrera、Roberta Napolitano、Franco Fedeli、Silvio Aime

  DOI：10.1021/jm901876r

  日期：2010.7.8

  Four novel MRI Gd(III)-based probes have been synthesized and evaluated for their labeling properties on cultured cell lines K562, C6, and B16. The labeling strategy relies upon the fact that cells display a large number of reactive exofacial protein thiols (EPTs) that can be exploited as anchorage points for suitably activated MRI probes. The probes are composed of a Gd(III) chelate (based on either DO3A or DTPA) connected through a flexible linker to the 2-pyridyldithio chemical function for binding to EPTs. GdDO3A-based chelates could efficiently label cells (up to a level of 1.2 x 10(10) Gd(III) atoms/cell), whereas GdDTPA-based chelates showed poor or no cell labeling ability at all. Among the GdDO3A based compounds, that having the longest spacer (compound GdL1A) showed the best labeling efficacy. The mechanism of EPT mediated cell labeling by GdL1A involves probe internalization without sequestration of the Gd(III) chelate within subcellular structures such as endosomes.