[(phenyltetramethylcyclopentadienyl)Ir(phpy)Cl] | 1326301-06-7

• 英文名称: [(phenyltetramethylcyclopentadienyl)Ir(phpy)Cl]
• 英文别名: [(Cp^xph)Ir(phpy)Cl]；[(η5-tetramethyl(phenyl)cyclopentadienyl)Ir(2-phenylpyridine(1-))Cl]
• CAS: 1326301-06-7
• 化学式: C₂₆H₂₅ClIrN
• 分子量: 579.164
• InChiKey: JKJZNLMRHAVVIU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  [(phenyltetramethylcyclopentadienyl)Ir(phpy)Cl] 、 水 在 silver nitrate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  环状肽-聚合物纳米管作为有机金属抗癌复合物的高效高效药物递送系统

  摘要：

  功能性药物载体系统具有增加药物溶解度和效力同时减少副作用的潜力。复杂的聚合材料，特别是各向异性结构，由于其长循环时间而特别有吸引力。在这里，我们将环状肽与生物相容性聚合物聚 (2-羟丙基甲基丙烯酰胺) (pHPMA) 结合在一起。所得缀合物用有机铱抗癌复合物官能化。小角度中子散射和静态光散射证实了它们的自组装和细长的圆柱形状。与游离药物或载药聚合物相比，载药纳米管对人类癌细胞表现出更有效的抗增殖活性，而纳米管本身是无毒的。

  DOI：

  10.1021/acs.biomac.7b01491
• 作为产物：
  描述：

  2-苯基吡啶 、 dichloro(tetramethylcyclopentadienylbenzene)iridium(III)dimer 在 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以87.1%的产率得到[(phenyltetramethylcyclopentadienyl)Ir(phpy)Cl]
  参考文献：
  名称：

  二茂铁固定铱（III）配合物：构型调控，抗癌应用和机理研究。

  摘要：

  已设计并合成了一系列二茂铁加成的半夹心铱（III）苯基吡啶配合物。这些复合物显示出比相同条件下临床上广泛使用的顺铂更好的抗癌活性。同时，复合物可以有效抑制细胞迁移和集落形成。复合物可以与蛋白质相互作用并通过血清蛋白质转运，从而有效地催化烟酰胺-腺嘌呤二核苷酸的氧化并诱导活性氧的积累（ROS，1 O 2），证实了氧化的抗癌机制。此外，激光扫描共聚焦检测表明这些复合物可以进入细胞，随后是一种非能量依赖性的细胞摄取机制，有效地积累在溶酶体中（皮尔逊共定位系数：〜0.90），导致溶酶体损伤，并降低了线粒体膜电位（MMP）。综上所述，二茂铁加铱（III）配合物具有成为新型多功能治疗平台的前景，包括靶向溶酶体的成像和抗癌药物。

  DOI：

  10.1021/acs.inorgchem.9b02227

文献信息

• [EN] NOVEL IRIDIUM/RHODIUM ANTI-CANCER COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTICANCÉREUX CONTENANT DE L'IRIDIUM/RHODIUM
  申请人：UNIV WARWICK

  公开号：WO2011148124A1

  公开（公告）日：2011-12-01

  The present invention relates to novel iridium and/or rhodium containing complexes for use as a cytotoxic, such as an anti-cancer agent. There is also provided a method of preparing said compounds.

  本发明涉及用作细胞毒性物质，如抗癌药物的新型含铱和/或铑配合物，还提供了一种制备所述化合物的方法。
• Organometallic Iridium(III) Cyclopentadienyl Anticancer Complexes Containing C,N-Chelating Ligands
  作者：Zhe Liu、Abraha Habtemariam、Ana M. Pizarro、Guy J. Clarkson、Peter J. Sadler

  DOI：10.1021/om2005468

  日期：2011.9.12

  Organometallic Ir(III) cyclopentadienyl complexes [(eta(5)-Cp(x))Ir(C((sic))N)Cl] Cp(x) = Cp*, C((sic))N = 2-(p-tolyl)pyridine (1), 2-phenylquinoline (2), 2-(2,4-difluorophenyl)pyridine (3), Cp(x) = tetramethyl(phenyl)cyclopentadienyl (Cp(xph)), C((sic))N = 2-phenylpyridine (4), and Cp(x) = tetramethyl(biphenyl)cyclopentadienyl (C(pxbiph)), C((sic))N = 2-phenylpyridine (5)} have been synthesized and characterized. The X-ray crystal structures of 2 and 5 have been determined and show typical "piano-stool" geometry. All the complexes hydrolyzed rapidly in aqueous solution (< 5 min) even at 278 K. The plc values of the aqua adducts 1A-5A are in the range 8.31-8.87 and follow the order 1A > 2A > 4A > 5A approximate to 3A. Hydroxo-bridged dimers [eta(5)-Cp(x))Ir](2)(mu-OD)(3)}(+) (Cp(x) = Cp*, 6; Cp(xph), 7; Cp(xbiph), 8) are readily formed during pH titrations at ca. pH 8.7. Complexes I and 3-5 bind strongly to 9-ethylguanine (9-EtG) moderately strongly to 9-methyladenine (9-MeA), and hence preferentially to 9-EtG when in competition with 9-MeA. The extent of guanine and adenine binding to complex 2 was significantly lower for both purines due to steric hindrance from the chelating ligand. All complexes showed potent cytotoxicity, with IC(50) values ranging from 6.5 to 0.7 mu M toward A2780 human ovarian cancer cells. Potency toward these cancer cells increased with additional phenyl substitution on Cp*, Cp(xbiph) > Cp(xph) > Cp*, Cp(xbiph) with complex 5 exhibited submicromolar activity (2X as active as cisplatin). These data demonstrate how the aqueous chemistry, nucleobase binding, and anticancer activity of C,N-bound Ir(III) cyclopentadienyl complexes can be controlled and fine-tuned by the modification of the chelating and cyclopentadienyl ligands.
• Potent Half-Sandwich Iridium(III) Anticancer Complexes Containing C^∧N-Chelated and Pyridine Ligands
  作者：Zhe Liu、Isolda Romero-Canelón、Abraha Habtemariam、Guy J. Clarkson、Peter J. Sadler

  DOI：10.1021/om500644f

  日期：2014.10.13

  We report the synthesis and characterization of eight half-sandwich cyclopentadienyl Ir-III pyridine complexes of the type [(eta(5)-Cpxph)Ir(phpy)Z]PF6, in which Cp-xph = C5Me4C6H5 (tetramethyl(phenyl)cyclopentadienyl), phpy = 2-phenylpyridine as C boolean AND N-chelating ligand, and Z = pyridine (py) or a pyridine derivative. Three X-ray crystal structures have been determined. The monodentate py ligands blocked hydrolysis; however, antiproliferative studies showed that all the Ir compounds are highly active toward A2780, A549, and MCF-7 human cancer cells. In general the introduction of an electron-donating group (e.g., Me, NMe2) at specific positions on the pyridine ring resulted in increased antiproliferative activity, whereas electron-withdrawing groups (e.g., COMe, COOMe, CONEt2) decreased anticancer activity. Complex 5 displayed the highest anticancer activity, exhibiting submicromolar potency toward a range of cancer cell lines in the National Cancer Institute NCI-60 screen, ca. 5 times more potent than the clinical platinum(II) drug cisplatin. DNA binding appears not to be the major mechanism of action. Although complexes [(eta(5)-Cp-xph)Ir(phpy)(py)](+) (1) and [(eta(5)-Cp-xph)Ir(phpy)(+)(4-NMe2-py)](+) (5) did not cause cell apoptosis or cell cycle arrest after 24 h drug exposure in A2780 human ovarian cancer cells at IC50 concentrations, they increased the level of reactive oxygen species (ROS) dramatically and led to a loss of mitochondrial membrane potential (Delta psi m), which appears to contribute to the anticancer activity. This class of organometallic Ir complexes has unusual features worthy of further exploration in the design of novel anticancer drugs.