Quinoxaline-2-carboxamide as a carrier ligand in two new platinum(ii) compounds: Synthesis, crystal structure, cytotoxic activity and DNA interaction

Marqués-Gallego P.; Gamiz-Gonzalez M.A.; Fortea-Pérez F.R.; Lutz M.; Spek A.L.; Pevec A.; Kozlevar B.; Reedijk J.

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Quinoxaline-2-carboxamide as a carrier ligand in two new platinum(ii) compounds: Synthesis, crystal structure, cytotoxic activity and DNA interaction

机译：喹喔啉-2-羧酰胺作为两种新型铂（ii）化合物的载体配体：合成，晶体结构，细胞毒性活性和DNA相互作用

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The search for platinum compounds structurally different from cisplatin has led to two new platinum(ii) compounds containing quinoxaline-2-carboxamide as a carrier ligand, i.e. cis-[Pt(qnxca)(MeCN)Cl_2] (1) and the [Pt(qnxca_(-H))(dmso)Cl] (2). Both compounds have been synthesized and characterized using different spectroscopic methods. In addition, single-crystal structures have been determined by X-Ray diffraction for both compounds. In each case a square planar Pt(ii) is present; in (1) the qnxca is monodentate and neutral, whereas in (2) the ligand has lost a hydrogen, to form the anionic chelating ligand abbreviated as qnxca_(-H). The biological activity of both compounds has been investigated in a panel of seven human tumour cells, displaying poor cytotoxic activity, compared to cisplatin. The interaction of the new compounds with 1 or 2 equiv. of 9-ethylguanine has been studied using ~1H NMR, ~(195)Pt NMR and ESI-MS spectroscopy, finding poor reactivity of 1 towards the model base, forming only the monosubstituted adduct. Surprisingly, compound 2, which is more sterically crowded, interacts more efficiently with the 9-EtG, forming a bifunctional adduct with two 9-EtG with substitution of the dmso and the chloride ligand. Unwinding studies of pUC19 plasmid DNA by compound 1 show similar unwinding properties to cisplatin.

机译：寻找结构与顺铂不同的铂化合物已导致了两种新的含喹喔啉-2-羧酰胺作为载体配体的铂（ii）化合物，即顺式[Pt（qnxca）（MeCN）Cl_2]（1）和[Pt （qnxca _（-H））（dmso）Cl]（2）。两种化合物均已使用不同的光谱方法合成和表征。另外，已经通过X射线衍射确定了两种化合物的单晶结构。在每种情况下，都存在一个方形的平面Pt（ii）;在（1）中，qnxca是单齿的并且是中性的，而在（2）中，配体失去了氢，形成了阴离子螯合配体，缩写为qnxca _（-H）。与顺铂相比，已经在一组七个人类肿瘤细胞中研究了这两种化合物的生物活性，显示出较弱的细胞毒性活性。新化合物与1或2当量的相互作用。使用〜1H NMR，〜（195）Pt NMR和ESI-MS光谱对9-乙基鸟嘌呤进行了研究，发现1对模型碱基的反应性较差，仅形成单取代的加合物。令人惊讶地，空间上更拥挤的化合物2与9-EtG更有效地相互作用，与两个9-EtG形成双官能加合物，其被dmso和氯化物配体取代。化合物1对pUC19质粒DNA的展开研究显示与顺铂相似的展开性质。

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《Dalton transactions: An international journal of inorganic chemistry》 |2010年第21期|共7页
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Marqués-Gallego P.; Gamiz-Gonzalez M.A.; Fortea-Pérez F.R.; Lutz M.; Spek A.L.; Pevec A.; Kozlevar B.; Reedijk J.;
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Quinoxaline-2-carboxamide as a carrier ligand in two new platinum(ii) compounds: Synthesis, crystal structure, cytotoxic activity and DNA interaction

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