tetraphenylphosphonium aminotrichloroplatinate(III) | 110790-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tetraphenylphosphonium aminotrichloroplatinate(III)
• CAS: 110790-59-5
• 化学式: C₂₄H₂₀P*Cl₃H₃NPt
• 分子量: 657.866
• InChiKey: COSAFPPKHPOCPD-UHFFFAOYSA-K

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：

  tetraphenylphosphonium aminotrichloroplatinate(III) 、 氮杂-15-冠醚-5 以 甲醇 为溶剂， 以39%的产率得到cis-[PtCl2(NH3)(1,4,7,10,-tetraoxa-13-azacyclooctadecane-N)]
  参考文献：
  名称：

  氧氮杂冠醚作为混合配体顺铂衍生物和双核铂抗癌药物的配体

  摘要：

  在寻找新型铂类抗癌药物的过程中，已制备出顺铂衍生物和含氧杂二氮杂冠醚和氧杂二氮杂冠醚配体的双核铂配合物。顺铂衍生物 cis[PtCl2(NH3)(1,4,7,10,13-pentaoxa-16-azacyclooctadecaneN)] (AO18) 和 cis-[PtCl2(NH3)(1,4,7,10-tetraoxa-13 -氮杂环十五烷-N)] (AO15) 和双核阳离子铂配合物 [{trans-PtCl(NH3)2}2(μ-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-N,N' )](NO3)2 (DAO18) 和 [{trans-PtCl(NH3)2}2(μ-1,4,10-trioxa-7,13-diazacyclopentadecane-N,N')](NO3)2 (DAO15) ) 研究了它们在 A2780 人卵巢癌中的细胞毒性、细胞摄取和细胞内

  DOI：

  10.1002/1099-0682(200209)2002:9<2375::aid-ejic2375>3.0.co;2-b
• 作为产物：
  描述：

  四乙基氯化铵 、 四苯基氯化膦 、 cisplatin 以 N,N-二甲基乙酰胺 为溶剂， 以48%的产率得到tetraphenylphosphonium aminotrichloroplatinate(III)
  参考文献：
  名称：

  Crystal and Molecular Structures of Asymmetric cis- and trans-Platinum(II/IV) Compounds and Their Reactions with DNA Fragments

  摘要：

  The asymmetrically substituted platinum(II) complexes cis-Pt(NH3)(c-C6H11NH2)Cl-2 and trans-Pt(NH3)(c-C6H11NH2)Cl-2 have been synthesized and their crystal structures have been determined. Crystals of cis-Pt(NH3)(c-C6H11NH2)Cl-2 (1) are orthorhombic, space group Pbca (no. 61) with a = 10.1994(12), b = 10.494(2), c = 18.826(2) Angstrom, Z = 8. The structure refinement converged to R1 = 0.0518 and wR2 = 0.1143. Crystals of trans-Pt(NH3)(c-C6H11NH2)Cl-2 (2) are monoclinic, space group P2(1)/c (no. 14) with a = 12.141(3), b = 6.0965(9), c = 19.864(3) Angstrom, beta = 118.71(2)degrees, Z = 4. The structure refinement converged to R1 = 0.0711 and wR2 = 0.1846. In addition, the Pt(IV) analogues with axial hydroxide ligands have been synthesized. Also the corresponding bis(carboxylato)platinum(IV) compound of formula trans,cis,cis-Pt(NH3)(c-C6H11NH2)Cl-2(OOCCH3)(2) has been obtained by conversion of the hydroxide with acetic anhydride. Reactions of these platinum complexes with 9-methylhypoxanthine and guanosine-5'-monophosphate (5'-GMP) have been studied in significant detail. The course of the reactions was followed by NMR spectroscopy, and H-1 and Pt-195 techniques were used to identify the formation of the products. It was found that the Pt(II) compounds easily react with the bases at the N7 position, whereas the Pt(IV) compounds react very slowly (for trans,cis,cis-Pt(NH3)(c-C6H11NH2)Cl-2(OOCCH3)(2)) or not at all (for trans, trans, trans-Pt(NH3)(c-C6H11NH2)Cl-2(OH)(2)), Only in the presence of glutathione does a reaction of the latter with 5'-GMP takes place. In this case a major product was found to be the reduced trans-Pt(II) complex with one molecule of 5'-GMP and one molecule of S-bonded glutathione.

  DOI：

  10.1021/ic960983u

文献信息

• An innovative and efficient route to the synthesis of metal-based glycoconjugates: proof-of-concept and potential applications
  作者：Andrea Pettenuzzo、Diego Montagner、Patrick McArdle、Luca Ronconi

  DOI：10.1039/c8dt01583j

  日期：——

  synthetic strategy was also successfully extended to other metal ions of biomedical interest, such as gold(I) and platinum(II), to obtain [AuI(SSC-Inp-GlcN)(PPh3)] and [PtII(SSC-Inp-GlcN)2], respectively. All compounds were fully characterized by elemental analysis, mid- and far-IR, mono- and multidimensional NMR spectroscopy, and, where possible, X-ray crystallography. Results and potential applications

  为了开发更有效的策略来使金属药物与碳水化合物功能化，我们在此报告了一种创新而有效的合成途径，以高产率和纯度产生金（III）糖缀合物。该方法是基于锌（II）-二硫代氨基甲酸酯中间体[Zn II（SSC-Inp-GlcN）2 ]（Inp =异烟交联部分； GlcN =氨基葡萄糖）的初始合成，然后将葡萄糖二氢吡啶二硫代氨基甲酸酯配体转移至金（III）中心经由所述锌（间金属转移反应II）中间体和K [金III溴4以1∶2的化学计量比，产生相应的葡萄糖官能化的金（III）-二硫代氨基甲酸酯衍生物[Au III Br 2（SSC-Inp-GlcN）]。不需要氨基葡萄糖支架的保护/去保护，也不需要色谱纯化。合成方案针对在C 2或C 6位置具有氨基功能的葡萄糖前体进行了优化，并且适用于α和β异构体。合成策略的应用也成功地扩展到其他具有生物医学意义的金属离子，例如金（I）和铂（II），以获得[Au I（SSC-Inp-GlcN）（PPh
• The synthesis and characterization of dinuclear platinum complexes bridged by the 4,4′-dipyrazolylmethane ligand
  作者：John A. Broomhead、Mark J. Lynch

  DOI：10.1016/0020-1693(95)04644-5

  日期：1995.12

  Abstract Monobridged-dinuclear platinum(II) complexes, where the bridging ligand is 4,4′-dipyrazolylmethane, have been prepared for use as potential anticancer agents. The complexes synthesized include [ cis -PtCl 2 (NH 3 )} 2 ( μ -dpzm)], [ trans -PtCl 2 (Me 2 SO)} 2 ( μ -dpzm)] and [ cis -PtCl 2 (Me 2 SO)} 2 ( μ -dpzm)]. The characterization of these complexes is based on microanalytical, IR and

  摘要制备了桥联配体为4,4'-二吡唑基甲烷的单桥双核铂（II）配合物，作为潜在的抗癌药。合成的配合物包括[顺式-PtCl 2（NH 3）} 2（μ-dpzm）]，[反式-PtCl 2（Me 2 SO）} 2（μ-dpzm）]和[顺式-PtCl 2（ Me 2 SO）} 2（μ-dpzm）]。这些配合物的表征基于微观分析，IR和1 H NMR数据。
• The first examples of platinum(II)-amine complexes containing 1,2-dicarba-closo-dodecaborane(12)
  作者：Jean A. Todd、Louis M. Rendina

  DOI：10.1016/j.inoche.2003.11.027

  日期：2004.2

  Treatment of the labile precursor complexes cis- or trans-[PtCl(dmf)(NH3)2]OTf (dmf=N,N-dimethylformamide; OTf=trifluoromethanesulfonate) with the monodentate 1-aminoalkyl-1,2-carborane ligands NH2(CH2)nC2B10H11 (n=1,3) afforded the moderately-stable species cis- or trans-[PtCl(NH3)2NH2(CH2)nC2B10H11}]OTf, respectively. The novel complexes are the first examples of platinum(II)-amine derivatives containing

  摘要 用单齿 1-氨基烷基-1,2-碳硼烷配体 NH2 处理不稳定的前体配合物顺式或反式 [PtCl(dmf)(NH3)2]OTf（dmf=N,N-二甲基甲酰胺；OTf=三氟甲磺酸盐） (CH2)nC2B10H11 (n=1,3) 分别提供了中等稳定的顺式或反式 [PtCl(NH3)2NH2( )nC2B10H11}]OTf。新型配合物是铂 (II)-胺衍生物的第一个例子，其中包含 1,2-二碳- closo-ddecaborane(12) (closo-1,2-carborane) 配体。
• Platinum Compounds for High-Resolution In Vivo Cancer Imaging
  作者：Miles A. Miller、Bjorn Askevold、Katherine S. Yang、Rainer H. Kohler、Ralph Weissleder

  DOI：10.1002/cmdc.201300502

  日期：2014.6

  model. By using a genetic reporter of single‐cell DNA damage for in vivo imaging, Pt drug accumulation and resultant DNA damage could be monitored in individual tumor cells, at subcellular resolution, and in real time in a live animal model of cancer. These derivatives represent promising imaging tools that will be useful in understanding further the distribution and interactions of platinum within tumors

  铂（II）化合物，主要是顺铂和卡铂，是常用的一线癌症治疗药物。尽管它们被广泛使用并且对开发新衍生物（包括具有改进特性的纳米制剂）的持续兴趣，但很难在活体受试者中实时地以亚细胞分辨率可视化铂化合物。在这里，我们提出了四种新型顺铂和卡铂衍生的荧光成像化合物，用于定量活体癌症成像。我们将 4,4-difluoro-5,7-dimethyl-4-bora-3a,4a-daiza- s - indacene (BODIPY) 与 Pt II共轭复合物以产生具有强大体内荧光并保留 DNA 损伤和细胞毒性特性的衍生物。我们成功地将这些化合物应用于异种移植癌症小鼠模型的药代动力学和肿瘤摄取成像。通过使用单细胞 DNA 损伤的遗传报告基因进行体内成像，可以在单个肿瘤细胞中以亚细胞分辨率实时监测癌症活体动物模型中 Pt 药物的积累和由此产生的 DNA 损伤。这些衍生物代表了很有前景的成像工具，将有助于进一步了解铂在肿瘤内的分布和相互作用。
• Long-Range Distance Constraints in Platinated Nucleotides: Structure Determination of the 5' Orientational Isomer of cis-[Pt(NH3)(4-aminoTEMPO){d(GpG)}]+ from Combined Paramagnetic and Diamagnetic NMR Constraints with Molecular Modeling
  作者：Stephen U. Dunham、Stephen J. Lippard

  DOI：10.1021/ja00148a012

  日期：1995.11

  The compound cis-[Pt(NH3)(4-aminoTEMPO)ClI] (7) is a paramagnetic analogue of the anticancer drug cisplatin and of cis-[Pt(NH3)(C6H11NH2)Cl-2] (1), a major metabolite of a recently developed, orally administered derivative. The bifunctional mixed amine complex 7 and a monofunctional triamine complex, trans-[Pt(NH3)(2)(4-aminoTEMPO)Cl]NO3 (8), were synthesized to provide localized unpaired electron spin density for use in NMR spectral studies of their polynucleotide adducts. Compounds 7 and 8 readily coordinate to the N(7) positions of guanosine nucleosides, as revealed by H-1, P-31, and Pt-195 NMR spectroscopy. The NMR spectra were selectively broadened owing to distance-dependent relaxation from the unpaired electron localized on the nitroxyl radical of the 4-aminoTEMPO ligand. Platination of d(GpG) by the mixed amine complex 7 afforded two orientational isomers which differed with respect to the positioning of the 4-aminoTEMPO group toward either the 3' or 5' side of the phosphodiester linkage. The purified orientational isomers were readily distinguished by selective broadening of the H-1 NMR resonances of the 3' and 5' deoxyribose rings. The minimum energy solution structure for the 5' orientational isomer of the platinated dinucleotide cis-[Pt(NH3)(4-aminoTEMPO)(d(GpG)}](+) (13) was determined by NMR methods including combined diamagnetic (J coupling constants) and paramagnetic (electron-H-1, P-31 distances) constraints. Moreover, with the paramagnetic spin probe, we have been able to obtain the first observable NMR distance constraints for determining the configuration of the zeta or alpha torsion angles in any oligonucleotide. Dynamics trajectories (200 ps) for 13 demonstrated that only computations including paramagnetic distance constraints could determine the zeta(-), alpha(-) conformation of the phosphodiester linkage and the conformation of the 4-aminoTEMPO ligand. These NMR data and computational methods demonstrate the utility of long-range paramagnetic distance constraints in elucidating the NMR solution structures of DNA modified by cisplatin analogues.