1-[6,11-dioxo-7,10-diaza-14,15-dithia-15(2-pyridyl)pentadecanyl]-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic tris(1,1-dimethylethyl) ester | 1234299-78-5

• 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: 1-[6,11-dioxo-7,10-diaza-14,15-dithia-15(2-pyridyl)pentadecanyl]-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic tris(1,1-dimethylethyl) ester
• 英文别名: Tert-butyl 2-[4,7-bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-10-[6-oxo-6-[2-[3-(pyridin-2-yldisulfanyl)propanoylamino]ethylamino]hexyl]-1,4,7,10-tetrazacyclododec-1-yl]acetate
• CAS: 1234299-78-5
• 化学式: C₄₂H₇₃N₇O₈S₂
• 分子量: 868.216
• InChiKey: MOPZAJUWPCDIEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  59
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  214
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  1-[6,11-dioxo-7,10-diaza-14,15-dithia-15(2-pyridyl)pentadecanyl]-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic tris(1,1-dimethylethyl) ester 在 三氟乙酸 、 三异丙基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以2.25 g的产率得到1-[6,11-dioxo-7,10-diaza-14,15-dithia-15(2-pyridyl)pentadecanyl]-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic acid
  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
• 作为产物：
  描述：

  3-(2-吡啶二硫代)丙酸 、 1-[5-[N-[2-aminoethyl]aminocarbonyl]-pentyl]-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic tris(1,1-dimethylethyl) ester 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以24.5 g的产率得到1-[6,11-dioxo-7,10-diaza-14,15-dithia-15(2-pyridyl)pentadecanyl]-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic tris(1,1-dimethylethyl) ester
  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