N-(pyridin-3-ylmethyl)-12-[1,3,5,7-tetraoxo-2-[12-oxo-12-(pyridin-3-ylmethylamino)dodecyl]pyrrolo[3,4-f]isoindol-6-yl]dodecanamide | 1356860-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(pyridin-3-ylmethyl)-12-[1,3,5,7-tetraoxo-2-[12-oxo-12-(pyridin-3-ylmethylamino)dodecyl]pyrrolo[3,4-f]isoindol-6-yl]dodecanamide
• CAS: 1356860-83-7
• 化学式: C₄₆H₆₀N₆O₆
• 分子量: 793.019
• InChiKey: CIEUKZGTLWLEBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  58
• 可旋转键数：
  28
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  fac-[Re(1,10-phenanthroline)(CO)₃(MeCN)]BF₄ 、 N-(pyridin-3-ylmethyl)-12-[1,3,5,7-tetraoxo-2-[12-oxo-12-(pyridin-3-ylmethylamino)dodecyl]pyrrolo[3,4-f]isoindol-6-yl]dodecanamide 以 氯仿 为溶剂， 以14%的产率得到fac,fac-([Re(CO)3(phen)]2((C5H4NCH2NHCO(CH2)11)2C10H2N2O4))(BF4)2
  参考文献：
  名称：

  Biologically Compatible, Phosphorescent Dimetallic Rhenium Complexes Linked through Functionalized Alkyl Chains: Syntheses, Spectroscopic Properties, and Applications in Imaging Microscopy

  摘要：

  A range of luminescent, dimetallic complexes based upon the rhenium fac-tricarbonyl diimine core, linked by aliphatic chains of varying lengths and functionality, have been synthesized and their photophysical properties examined. Each complex displays characteristic (MReLdiimineCT)-M-3 emission in aerated acetonitrile solution, with long lifetimes in the range of 129-248 ns and corresponding quantum yields in the range 3.2-8.0%. In aqueous solution, as opposed to acetonitrile, the complexes generally show a small hypsochromic shift in lambda(em) and an extension of the (MLCT)-M-3 lifetime, attributed to a hydrophobically driven association of the alkyl chains with the rhenium-bound diimine units. In live cell imaging experiments using MCF7 cells the complexes all show good uptake by non-energy dependent mechanisms without endosomal entrainment, and with varying propensity to localize in organelles. The degrees of uptake and localization properties are discussed in terms of the length and chemical nature of the linkers, and in terms of the likely interactions between these and the various cellular components encountered.

  DOI：

  10.1021/ic201654d
• 作为产物：
  描述：

  ω-phthalimidododecanoyl chloride 在 一水合肼 、 三乙胺 作用下， 以 氯仿 、 乙二醇甲醚 为溶剂， 反应 15.0h， 生成 N-(pyridin-3-ylmethyl)-12-[1,3,5,7-tetraoxo-2-[12-oxo-12-(pyridin-3-ylmethylamino)dodecyl]pyrrolo[3,4-f]isoindol-6-yl]dodecanamide
  参考文献：
  名称：

  Biologically Compatible, Phosphorescent Dimetallic Rhenium Complexes Linked through Functionalized Alkyl Chains: Syntheses, Spectroscopic Properties, and Applications in Imaging Microscopy

  摘要：

  A range of luminescent, dimetallic complexes based upon the rhenium fac-tricarbonyl diimine core, linked by aliphatic chains of varying lengths and functionality, have been synthesized and their photophysical properties examined. Each complex displays characteristic (MReLdiimineCT)-M-3 emission in aerated acetonitrile solution, with long lifetimes in the range of 129-248 ns and corresponding quantum yields in the range 3.2-8.0%. In aqueous solution, as opposed to acetonitrile, the complexes generally show a small hypsochromic shift in lambda(em) and an extension of the (MLCT)-M-3 lifetime, attributed to a hydrophobically driven association of the alkyl chains with the rhenium-bound diimine units. In live cell imaging experiments using MCF7 cells the complexes all show good uptake by non-energy dependent mechanisms without endosomal entrainment, and with varying propensity to localize in organelles. The degrees of uptake and localization properties are discussed in terms of the length and chemical nature of the linkers, and in terms of the likely interactions between these and the various cellular components encountered.

  DOI：

  10.1021/ic201654d

文献信息

• Biologically Compatible, Phosphorescent Dimetallic Rhenium Complexes Linked through Functionalized Alkyl Chains: Syntheses, Spectroscopic Properties, and Applications in Imaging Microscopy
  作者：Rebeca G. Balasingham、Flora L. Thorp-Greenwood、Catrin F. Williams、Michael P. Coogan、Simon J. A. Pope

  DOI：10.1021/ic201654d

  日期：2012.2.6

  A range of luminescent, dimetallic complexes based upon the rhenium fac-tricarbonyl diimine core, linked by aliphatic chains of varying lengths and functionality, have been synthesized and their photophysical properties examined. Each complex displays characteristic (MReLdiimineCT)-M-3 emission in aerated acetonitrile solution, with long lifetimes in the range of 129-248 ns and corresponding quantum yields in the range 3.2-8.0%. In aqueous solution, as opposed to acetonitrile, the complexes generally show a small hypsochromic shift in lambda(em) and an extension of the (MLCT)-M-3 lifetime, attributed to a hydrophobically driven association of the alkyl chains with the rhenium-bound diimine units. In live cell imaging experiments using MCF7 cells the complexes all show good uptake by non-energy dependent mechanisms without endosomal entrainment, and with varying propensity to localize in organelles. The degrees of uptake and localization properties are discussed in terms of the length and chemical nature of the linkers, and in terms of the likely interactions between these and the various cellular components encountered.