Preparation, characterization, and antitumor activity of new cisplatin analogues with 1-methyl-4-(methylamino)piperidine: crystal structure of [PtII(1-methyl-4-(methylamino) piperidine)(oxalate)].
Preparation, characterization, and antitumor activity of new cisplatin analogues with 1-methyl-4-(methylamino)piperidine: crystal structure of [PtII(1-methyl-4-(methylamino) piperidine)(oxalate)].
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DOI：
10.1016/s0162-0134(02)00614-1
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发表时间：
2003-02
影响因子：
3.9
通讯作者：
U. Mukhopadhyay;John H Thurston;K. Whitmire;Z. Siddik;A. Khokhar
中科院分区：
文献类型：
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作者：
U. Mukhopadhyay;John H Thurston;K. Whitmire;Z. Siddik;A. Khokhar
合成了一系列新的[PtII(Mmap)X](其中mmap，1-甲基-4-(甲氨基)哌啶和X，1，1-环丁二酸二甲酯(CBDCA)，草酸，丙二酸甲酯，甲基丙二酸甲酯，二甲基丙二酸甲酯，乙基丙二酸乙酯，二乙基丙二酸甲酯或2，3-萘二甲酸二甲酯(NDCA))的铂(II)配合物，并用元素分析、红外光谱、~(13)C和~(195)铂核磁共振谱对其结构进行了表征。用单晶X射线衍射法测定了类似物[PtII(Mmap)(草酸)]的晶体结构。根据共收集到的4,964个反射，我们确定该化合物属于单斜晶系P21/c空间群(a=11.890(2)？，b=9.6695(19)？，c=9.875(2)？，β=102.03(3)°，Z=4，R=0.0428)。在这个络合物中，铂具有轻微扭曲的正方形平面构型，相邻的两个角落被mMAP配体的两个氮原子占据，而其余的顺式位置被草酸盐分子的两个氧原子占据。MMAP配体呈舟形构象，形成六元螯合环，草酸分子与铂形成五元螯合环。评估了这些化合物对敏感的A2780肿瘤模型和来自潜在细胞的顺铂耐药克隆的细胞毒性潜力。
A series of new platinum(II) complexes of the type [PtII(mmap)X] (where mmap, 1-methyl-4-(methylamino)piperidine and X, 1,1-cyclobutanedicarboxylato (CBDCA), oxalato, malonato, methylmalonato, dimethylmalonato, ethylmalonato, diethylmalonato or 2,3-naphthalene dicarboxylato (NDCA)) have been synthesized and characterized by elemental analysis, infrared (IR), and13C and195Pt nuclear magnetic resonance (NMR) spectroscopy. The crystal structure of the analogue [PtII(mmap)(oxalate)] was determined using the single crystal X-ray diffraction method. Based upon a total of 4964 collected reflections, we determined that the compound crystallizes in the monoclinic space group P21/c (with a=11.890(2) Å, b=9.6695(19) Å, c=9.875(2) Å, β=102.03(3)°, Z=4, and R=0.0428). In this complex, platinum has a slightly distorted square planar geometry with the two adjacent corners being occupied by two nitrogen atoms of the mmap ligand, whereas the remaining cis positions are occupied by two oxygen atoms of the oxalate molecule. The mmap ligand is in a boat conformation and forms six-membered chelating rings as well as the oxalate molecule forms five-membered chelating rings with platinum. The complexes were evaluated for their cytotoxic potential against the sensitive A2780 tumor model and cisplatin-resistant clone derived in vitro from potential cells.