5,10-di(4-carboxyphenyl)-15,20-diphenylporphyrin-Zn | 259539-57-6

• 分子结构分类: 有机化合物
• 英文名称: 5,10-di(4-carboxyphenyl)-15,20-diphenylporphyrin-Zn
• 英文别名: zinc 5,10-di(4-carboxy)phenylporphyrin
• CAS: 259539-57-6
• 化学式: C₄₆H₂₈N₄O₄Zn
• 分子量: 766.143
• InChiKey: MHIAYCOHHURZCM-CTPWHPEQSA-L

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  吡啶 、 十二羰基三钌 、 5,10-di(4-carboxyphenyl)-15,20-diphenylporphyrin-Zn 以 四氢呋喃 为溶剂， 反应 20.0h， 以21%的产率得到[{Ru2(CO)4(pyridine)2}2(5,10-di-(4-carboxyphenyl)-15,20-diphenyl-porphyrin-Zn(II)-2H)2]
  参考文献：
  名称：

  Photoactive sawhorse-type diruthenium tetracarbonyl complexes

  摘要：

  Sawhorse-type diruthenium tetracarbonyl complexes incorporating carboxyphenyl porphyrin bridges and pyridine axial ligands have been prepared, characterized and evaluated as potential photosensitizing and chemotherapeutic agents in several human cancer cells (A2780, A549, Me300, HeLa). The mono carboxyphenyl porphyrin derivatives, 5-(4-carboxyphenyl)-10,15,20-triphenyl-21,23H-porphyrin (HOOCR1-H2) and 5-(4-carboxyphenyl)-10,15,20-triphenylporphyrin-Zn (HOOCR1-Zn), after reaction with Ru-3(CO)(12) and pyridine, give the dinuclear complexes [Ru-2(CO)(4)(OOCR1-H2)(2)(NC5H5)(2)] (1) and [Ru-2(CO)(4)-(OOCR1-Zn)(2)(NC5H5)(2)] (2), respectively. Under the same reaction conditions, the di-carboxyphenyl porphyrin derivatives, 5,10-di(4-carboxyphenyl)-15,20-diphenyl-21,23H-porphyrin (HOOCR2-H2COOH) and 5,10-di(4-carboxyphenyl)-15,20-diphenylporphyrin-Zn (HOOCR2-ZnCOOH), give rise to the tetranuclear complexes, [{Ru-2(CO)(4)(NC5H5)(2)}(2)(OOCR2-H2COO)(2)] (3) and [{Ru-2(CO)(4)(NC5H5)(2)}(2)(OOCR2-ZnCOO)(2)] (4), in which two sawhorse diruthenium tetracarbonyl units are linked by the di-carboxyphenyl porphyrin ligands. When tested in human cancer cell lines, both Zn(II) metallo-porphyrin derivatives 2 and 4 and the tetranuclear derivative 3 show some degree of cytotoxicity in the dark, but seem to present no phototoxicity upon irradiation at 652 nm. These results demonstrate the effect of the Zn(II) ion insertion into the porphyrin core, resulting in increased cytotoxicity and decreased phototoxicity. On the other hand, complex 1, the less cytotoxic derivative with IC50 > 170 mu M in HeLa cervix and A2780 ovarian cancer cell lines, shows an excellent phototoxicity toward these cancer cell lines with LD50 comprised between 4.5 and 7.5 J/cm(2) (irradiance 30 mW/cm(2)) at 5 mu M concentration (incubation time: 24 h). Overall, an excellent ratio between photo-and cytotoxicity has been found for the metal-free porphyrin derivative [Ru-2(CO)(4)(OOCR1-H2)(2)(NC5H5)(2)] (1). (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.05.026

文献信息

• Sawhorse‐Type Tetracarbonyldiruthenium Tweezers
  作者：Justin P. Johnpeter、John Mohanraj、Nicola Armaroli、Bruno Therrien

  DOI：10.1002/ejic.201200318

  日期：2012.7

  dinuclearruthenium units and carboxyphenyl porphyrin derivatives5-(4-carboxyphenyl)-10,15,20-triphenyl-21H,23H-porphyrin,[5-(4-carboxyphenyl)-10,15,20-triphenylporphyrin]zinc, 5,10-bis(4-carboxyphenyl)-15,20-diphenyl-21H,23H-porphyrin, and [5,10-bis(4-carboxyphenyl)-15,20-diphenylporphyrin]zinc} are presented. Molecular modeling shows that in all cases the two porphyrin moieties are adequately positioned

  由锯木架型双核钌单元和羧基苯基卟啉衍生物5-(4-羧基苯基)-10,15,20-三苯基-21H,23H-卟啉,[5-(4-羧基苯基)-10,15,20]构建的分子镊子-三苯基卟啉]锌、5,10-双(4-羧基苯基)-15,20-二苯基-21H,23H-卟啉和[5,10-双(4-羧基苯基)-15,20-二苯基卟啉]锌}是呈现。分子模型表明，在所有情况下，两个卟啉部分都被充分定位以封装客体分子。因此，锯木架型四羰基二钌镊子与不同客体分子 [富勒烯 (C60)、吡啶 (pyr)、4,4'-联吡啶 (bpy)、1,2-双 (4-吡啶基) 乙烯之间的主客体相互作用(bpe)、5,10-双(4-吡啶基)-15,20-二苯基-21H,23H-卟啉(5,10-dpp)和5,15-双(4-吡啶基)-10,20-二苯基-21H,23H-卟啉 (5,