coumazin-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: coumazin-1
• 英文别名: 2-[4,5-Bis[[bis(pyridin-2-ylmethyl)amino]methyl]-2,7-dichloro-3-hydroxy-6-oxoxanthen-9-yl]-4-[4-(4-oxo-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,5,7,9(17)-tetraene-5-carbonyl)oxybutylcarbamoyl]benzoic acid；2-[4,5-bis[[bis(pyridin-2-ylmethyl)amino]methyl]-2,7-dichloro-3-hydroxy-6-oxoxanthen-9-yl]-4-[4-(4-oxo-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,5,7,9(17)-tetraene-5-carbonyl)oxybutylcarbamoyl]benzoic acid
• 化学式: C₆₇H₅₈Cl₂N₈O₁₀
• 分子量: 1206.15
• InChiKey: DMLVLSFDACGYND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  87
• 可旋转键数：
  22
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  227
• 氢给体数：
  3
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  coumazin-1 在 porcine liver esterase 作用下， 以 various solvent(s) 为溶剂， 生成 香豆素 343 、 2-{4,5-Bis-[(bis-pyridin-2-ylmethyl-amino)-methyl]-2,7-dichloro-6-hydroxy-3-oxo-3H-xanthen-9-yl}-N-(4-hydroxy-butyl)-terephthalamic acid
  参考文献：
  名称：

  A Novel Two-Fluorophore Approach to Ratiometric Sensing of Zn²⁺

  摘要：

  We present a small molecule ratiometric Zn2+-sensing system based on two fluorophores excited by visible light, a Zn2+-insensitive reporter fluorophore, coumarin 343, and a Zn2+-sensitive fluorescein-based compound, ZPA-1. The two fluorophores are linked by an ester to give Coumazin-1, a membrane-permeable, essentially nonfluorescent compound. Upon exposure to esterases, Coumazin-1 is hydrolyzed to its constituent fluorophores. Measurement of the ratio of coumarin emission at 488 nm (lambdaexc = 445 nm) and comparison with ZPA-1 emission at 534 nm (lambdaexc = 505 nm) affords information about the amount of sensor present as well as the amount of Zn2+ present. A generally applicable synthetic route to amide-functionalized ZP1 sensors is also described. The Zn2+-sensing properties of one member of this class are similar to those of the parent ZP1 sensor, with slightly tighter binding and lower background signal.

  DOI：

  10.1021/ja0364930
• 作为产物：
  描述：

  3',6'-diacetyl-2',7'-dichloro-6-(4-hydroxybutyl)fluoresceinamide 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 27.25h， 生成 coumazin-1
  参考文献：
  名称：

  A Novel Two-Fluorophore Approach to Ratiometric Sensing of Zn²⁺

  摘要：

  We present a small molecule ratiometric Zn2+-sensing system based on two fluorophores excited by visible light, a Zn2+-insensitive reporter fluorophore, coumarin 343, and a Zn2+-sensitive fluorescein-based compound, ZPA-1. The two fluorophores are linked by an ester to give Coumazin-1, a membrane-permeable, essentially nonfluorescent compound. Upon exposure to esterases, Coumazin-1 is hydrolyzed to its constituent fluorophores. Measurement of the ratio of coumarin emission at 488 nm (lambdaexc = 445 nm) and comparison with ZPA-1 emission at 534 nm (lambdaexc = 505 nm) affords information about the amount of sensor present as well as the amount of Zn2+ present. A generally applicable synthetic route to amide-functionalized ZP1 sensors is also described. The Zn2+-sensing properties of one member of this class are similar to those of the parent ZP1 sensor, with slightly tighter binding and lower background signal.

  DOI：

  10.1021/ja0364930

文献信息

• A Novel Two-Fluorophore Approach to Ratiometric Sensing of Zn²⁺
  作者：Carolyn C. Woodroofe、Stephen J. Lippard

  DOI：10.1021/ja0364930

  日期：2003.9.1

  We present a small molecule ratiometric Zn2+-sensing system based on two fluorophores excited by visible light, a Zn2+-insensitive reporter fluorophore, coumarin 343, and a Zn2+-sensitive fluorescein-based compound, ZPA-1. The two fluorophores are linked by an ester to give Coumazin-1, a membrane-permeable, essentially nonfluorescent compound. Upon exposure to esterases, Coumazin-1 is hydrolyzed to its constituent fluorophores. Measurement of the ratio of coumarin emission at 488 nm (lambdaexc = 445 nm) and comparison with ZPA-1 emission at 534 nm (lambdaexc = 505 nm) affords information about the amount of sensor present as well as the amount of Zn2+ present. A generally applicable synthetic route to amide-functionalized ZP1 sensors is also described. The Zn2+-sensing properties of one member of this class are similar to those of the parent ZP1 sensor, with slightly tighter binding and lower background signal.