Gold(I) chloride adducts of 1,3-bis(di-2-pyridylphosphino) propane: synthesis, structural studies and antitumour activity

Humphreys AS; Filipovska A; Berners-Price SJ; Koutsantonis GA; Skelton BW; White AH

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Gold(I) chloride adducts of 1,3-bis(di-2-pyridylphosphino) propane: synthesis, structural studies and antitumour activity

机译：1,3-双（二-2-吡啶基膦基）丙烷的氯化金（I）加合物：合成，结构研究和抗肿瘤活性

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The novel water soluble bidentate phosphine ligand 1,3-bis( di-2-pyridylphosphino) propane (d2pypp) has been synthesized by a convenient route involving treatment of 2-pyridyllithium with Cl2P(CH2)(3)PCl2 and isolation in crystalline form as the hydrochloride salt. The synthesis of the precursor Cl2P(CH2)(3)PCl2 has been optimized by the use of triphosgene as the chlorinating agent. The 2 : 1 and 1 : 2 AuCl : d2pypp adducts have been synthesized and characterized by NMR spectroscopy and single crystal X-ray studies, and shown to be of the form ( AuCl)(2)(mu-d2pypp-P,P ') and [ Au(d2pypp-P,P ')(2)]Cl(.3.75H(2)O), respectively. The latter is more lipophilic than analogous 1 : 2 adducts of gold( I) chloride with the diphosphine ligands 1,2-bis(di-n-pyridylphosphino)ethane(dnpype) for n = 2, 3 and 4, based on measurement of the n-octanol-water partition coefficient ( log P= -0.46). A single crystal structure determination of the 1 : 2 Au( I) complex of the 3-pyridyl ethane ligand shows it to be of the form [ Au( d3pype-P,P ')(2)]Cl center dot 5H(2)O. The in vitro cytotoxic activity of [ Au( d2pypp)(2)]Cl was assessed in human normal and cancer breast cells and selective toxicity to the cancer cells found. The significance of these results to the antitumour properties of chelated 1 : 2 Au( I) diphosphine complexes is discussed.

机译：新型水溶性双齿膦配体1,3-双（二-2-吡啶基膦基）丙烷（d2pypp）是通过一种方便的方法合成的，包括用Cl2P（CH2）（3）PCl2处理2-吡啶基锂并分离成结晶形式作为盐酸盐。通过使用三光气作为氯化剂，可以优化前体Cl2P（CH2）（3）PCl2的合成。已经合成了2：1和1：2 AuCl：d2pypp加合物并通过NMR光谱和单晶X射线研究对其进行了表征，显示为（AuCl）（2）（mu-d2pypp-P，P' ）和[Au（d2pypp-P，P'）（2）] Cl（.3.75H（2）O）。后者的亲脂性比氯化金（I）与二膦配体1,2-双（二-正-吡啶基膦基）乙烷（dnpype）的类似1：2加合物（基于n = 2、3和4）更亲脂。正辛醇-水分配系数（log P = -0.46）。对3-吡啶基乙烷配体的1：2 Au（I）配合物进行单晶结构测定，表明它的形式为[Au（d3pype-P，P'）（2）] Cl中心点5H（2）哦评估了[Au（d2pypp）（2）] Cl在人正常和癌细胞中的体外细胞毒性活性，并发现了对癌细胞的选择性毒性。讨论了这些结果对螯合的1：2 Au（I）二膦配合物的抗肿瘤特性的重要性。

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《Dalton transactions: An international journal of inorganic chemistry》 |2007年第43期|共8页
作者
Humphreys AS; Filipovska A; Berners-Price SJ; Koutsantonis GA; Skelton BW; White AH;
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正文语种 eng
中图分类无机化学;
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MITOCHONDRIAL CELL-DEATH; 4-PYRIDYL PHOSPHINES; CARCINOMA-CELLS; PERMEABILITY TRANSITION; CANCER-THERAPY; TUMOR-CELLS; BIDENTATE 2; COMPLEXES; NMR; LIGANDS;

机译：线粒体死亡;4-吡啶基膦;癌瘤细胞;通透性转变;癌治疗;肿瘤细胞;二齿酸盐2;络合物;NMR;脂质;

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Gold(I) chloride adducts of 1,3-bis(di-2-pyridylphosphino) propane: synthesis, structural studies and antitumour activity

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