Synthesis, Characterization and Cytotoxicity of Diam(m)‐ineplatinum(II) Complexes Containing β‐phenylisosuccinate Ligand

Ye, Qingsong; Lou, Liguang; Liu, Zuoyan; Liu, Weiping; Hou, Shuhua; Chen, Xi-Zhu; Yu, Yanyan

doi:10.1002/ardp.200700114

Cited by 6 publications

(3 citation statements)

References 20 publications

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“…As shown in Figure , the cytotoxicity data obtained in both cell lines showed the classical sigmoidal dose–response curves when they were plotted as a logarithmic function of concentration (μM). Figure a,b illustrates the dose-dependent cytotoxic effect of the reference platinum complexes Pt-NH 3 , Pt-Py , and PtCyDA , which are in the range of those reported with similar compounds, and the ranking is consistent with previous studies: , Pt-NH 3 < Pt-Py < PtCyDA . Overall, the Pt complex with the ligand CyDA is the most cytotoxic of the series with a lower IC 50 value than cisplatin (IC 50 (cisplatin) ≈ 5 μM) .…”

Section: Resultssupporting

confidence: 86%

Synthesis and Anticancer Activity of Gold Porphyrin Linked to Malonate Diamine Platinum Complexes

et al. 2019

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Recently, Gold(III) porphyrins have gained great interest as anticancer drugs not only for stability of gold(III), but also for the functionalization of porphyrin to allow bridging with another metal such as platinum(II). We report here, for the first time, the synthesis of three new bi-metal compounds containing gold(III) porphyrin conjugated to a platinum diamine moiety through malonate bridging to obtain enhanced cytotoxicity from both metals combined to the phototoxicity of the porphyrin. The three complexes differ by type of diamine ligands around platinum(II) which are ammonia (NH3), cyclohexane diamine (CyDA) and pyridine methyl amine (Py). The synthesis was carried out using complexation of activated malonic acid derivatives with aqua diamino-platinum(II) complexes and the products were characterized by IR, NMR, mass spectra and by elementary analysis. Cytotoxic activity of the conjugates was screened in both healthy and cancer cell lines, human fibroblast cells (FS-68) and human breast cancer cells (MCF-7), and was compared to the corresponding platinum(II) complexes. The cyclohexyldiamine (CyDA) derivative exhibited the most cytotoxic effect among the series. The results showed that gold(III)/Pt(II)conjugates are more potent by 2 to 5.6-fold than the corresponding platinum complexes. Moreover, the dyad AuP-PtCyDA is 18% more potent and also more selective towards cancer cells than the parent gold porphyrin substituted with malonic acid. On the other hand, the IC50 of dyad AuP-PtCyDA is 43% lower than that of AuTPP, but more selective towards healthy cells. Singlet oxygen measurements indicated that gold(III) porphyrin derivatives are poor oxygen sensitizers and cell death occurred potentially due to generation of others reactive oxygen species (ROS) upon reductive quenching of the gold porphyrin excited state. In addition, the increase in cancer cell death obtained after light irradiation is totally absent in healthy cells, demonstrating the specificity of this PDT treatment on cancer cells. Our findings imply that the incorporation of two different cytotoxic metals in the same molecule represents a remarkable cytotoxic effect compared to traditional homometallic Pt(II) drugs.

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Section: Resultssupporting

confidence: 86%

Synthesis and Anticancer Activity of Gold Porphyrin Linked to Malonate Diamine Platinum Complexes

et al. 2019

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“…Pt(NH 3 ) 2 (C 2 O 4 ) was prepared by using an extension of Dhara's method [9,10] Triammine(oxalato)platinum(II) crystallized in the form of colorless block crystals of triclinic symmetry. The ORTEP drawing of triammine(oxalato)platinum(II) is shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Synthesis of diammine(oxalato)platinum(II) Diammine(oxalato)platinum(II), Pt(NH 3 ) 2 (C 2 O 4 ), was prepared by using the conventional method [9,10]. Briefly, K 2 PtCl 4 (6.6 g, 16 mmol) was dissolved in water (100 mL) and treated with KI (2.6 g, 96 mmol).…”

Section: Methodsmentioning

confidence: 99%

An unexpected triammine(oxalato)platinum(II) complex obtained from the aqueous solution of tetraammineplatinum(II) oxalate

Chen

Xie

et al. 2011

Res Chem Intermed

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An unexpected complex, triammine(oxalato)platinum(II) in which oxalate anion acts as a monodentate ligand, was isolated in the process of recrystallizing [Pt(NH 3 ) 4 ](C 2 O 4 ). The complex was presumably formed via the loss of one ammonia molecule from [Pt(NH 3 ) 4 ](C 2 O 4 ), followed by the binding of oxalate from the outer coordination sphere. Single crystal X-ray diffraction study revealed that the Pt(II) atom was coordinated on a distorted square by three N atoms of the ammine molecules and one O atom of the oxalate ligand. The crystal packing was stabilized by moderate to strong hydrogen bonds formed between ammine, water molecules and O atoms of oxalate with d(NÁÁÁO) in the range of 2.84(2)-3.29(2) Å , and d(OÁÁÁO) in the range of 2.86(2)-3.37(2) Å . The complex underwent thermal decomposition at 200-231°C in the nitrogen atmosphere, giving rise to Pt, NH 3 and CO 2 .

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Synthesis and In Vitro cytotoxicity of Cis-[Pt(NH3)(NH2OH)Cl2]

Liu

Chen

et al. 2010

Arch. Pharm. Res.

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A novel mixed NH(3)/NH(2)OH platinum(II) complex cis-[Pt(NH(3))(NH(2)OH)Cl(2)] was synthesized and characterized by elemental analysis, FAB-MS, FT-IR and (1)H NMR spectroscopy. This complex was determined to have a good water-solubility and satisfactory stability. The pertinent complex was evaluated for its in vitro cytotoxicity against 3AO, HCT-116, LNcap, A549/ATCC and SGC-7901 human carcinoma cell lines. It shows appreciable cytotoxic activity that is comparable with cisplatin and is much more active than carboplatin.

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Synthesis, Characterization and Cytotoxicity of Diam(m)‐ineplatinum(II) Complexes Containing β‐phenylisosuccinate Ligand

Cited by 6 publications

References 20 publications

Synthesis and Anticancer Activity of Gold Porphyrin Linked to Malonate Diamine Platinum Complexes

Synthesis and Anticancer Activity of Gold Porphyrin Linked to Malonate Diamine Platinum Complexes

An unexpected triammine(oxalato)platinum(II) complex obtained from the aqueous solution of tetraammineplatinum(II) oxalate

Synthesis and In Vitro cytotoxicity of Cis-[Pt(NH3)(NH2OH)Cl2]

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