A rapid method for the synthesis of water-soluble platinum(II) amine and pyridine complexes

Souchard, Jean‐Pierre; Wimmer, Franz Martin; Ha, Tam T. B.; Johnson, Neil P.

doi:10.1039/dt9900000307

Cited by 17 publications

(15 citation statements)

References 3 publications

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“…We verified that the conversion of 1 to 2 in this manner can occur on a bulk scale as had previously been reported for the conversion of 5 to 6 under different reaction conditions [43, 51]. Moreover, we found that the method here is generalizable to the bromo and iodo salts of [Pt(NH 2 C 6 H 11 ) 4 ] 2+ , compounds 3 and 5, respectively, affording compounds 4 and 6 .…”

Section: Resultssupporting

confidence: 88%

Conformational isomerism of trans-[Pt(NH2C6H11)2I2] and the classical Wernerian chemistry of [Pt(NH2C6H11)4]X2 (X=Cl, Br, I)

Johnstone

Lippard

2013

Polyhedron

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X-ray crystallographic analysis of the compound trans-[Pt(NH2C6H11)2I2] revealed the presence of two distinct conformers within one crystal lattice. This compound was studied by variable temperature NMR spectroscopy to investigate the dynamic interconversion between these isomers. The results of this investigation were interpreted using physical (CPK) and computational (molecular mechanics and density functional theory) models. The conversion of the salts [Pt(NH2C6H11)4]X2 into trans-[Pt(NH2C6H11)2X2] (X = Cl, Br, I) was also studied and is discussed here with an emphasis on parallels to the work of Alfred Werner.

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Section: Resultssupporting

confidence: 88%

Conformational isomerism of trans-[Pt(NH2C6H11)2I2] and the classical Wernerian chemistry of [Pt(NH2C6H11)4]X2 (X=Cl, Br, I)

Johnstone

Lippard

2013

Polyhedron

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“…101 An efficient synthesis of cis -[PtL 2 (ONO 2 ) 2 ] is accomplished by treating cis -[PtL 2 I 2 ] with AgNO 3 in acetone. 62,102 The reaction proceeds substantially faster in acetone compared to water. Solid cis -[PtL 2 (ONO 2 ) 2 ] dissolves in water with heating to form the diaqua species described above, which can then be used to install new leaving group ligands.…”

Section: Synthesis Of Platinum(ii) Complexesmentioning

confidence: 99%

Synthetic Methods for the Preparation of Platinum Anticancer Complexes

2013

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“…Platinum compounds, u , c -[Pt(R-NH2)2(N03)2J, where R-NH2 = NH3, methylamine, cyclobutylamine, cyclopentylamine and cyclohexylamine, were synthesized by published methods (Dhara, 1970;Souchard et al, 1990). Compounds purified by recrystallization from toluene or acetone gave satisfactory elemental analysis (Souchard et al, 1990). Platinum-DNA complexes in 10 mM NaClO, (Fluka) were prepared in the dark at 37°C and rb values measured by atomic-absorption spectroscopy.…”

Section: Chemicalsmentioning

confidence: 99%

Effect of the amine non‐leaving group on the structure and stability of DNA complexes with cis‐[Pt(R‐NH₂)₂(NO₃)₂]

Butour

Alvinerie

Souchard

et al. 1991

European Journal of Biochemistry

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The antitumor compound c i~-[ P t ( N H~)~C l~l (cisplatin), conserves two ammine ligands during the reaction with its cellular target DNA. Modifications of these non-leaving groups change the antineoplastic properties of this compound and its genotoxic effects. It is therefore of interest to determine the influence of non-leaving groups on the structure and stability of DNA in vitro. We have investigated platinum-DNA adducts formed by cis-[Pt(R-NH2)2(N03)2] (where R-NH2 = NH3, methylamine, cyclobutylamine, cyclopentylamine and cyclohexylamine) as a function of DNA binding. All compounds quantitatively reacted with DNA in less than 1 h at 37°C. They formed bifunctional adducts with adjacent nucleotides judging from the displacement of the intercalating molecule ethidium bromide, ultraviolet absorption spectroscopy and circular dichroism. Substitution of a H on the NH3 ligand by alkyl groups dramatically destabilized the platinum-DNA complex. Thermal stability decreased progressively with an increasing number of carbon atoms, At,, = -4.4"C for 3 cyclohexylamine-platinum-DNA adducts/ 1000 nucleotides, conditions where cisplatin had no effect. DNA adducts with cyclobutylamine and cyclohexylamine ligdnds inhibited the hydrolysis of platinum-DNA complexes by S1 nuclease. K, for the digestion of DNA containing these lesions was 2.3 times greater than for cisplatin, indicating steric inhibition of enzymesubstrate complex formation. These results show that the non-leaving groups of substituted cis-Pt(1I) compounds may destabilize DNA and interfere with protein-DNA interactions. These perturbations may have consequences for the genotoxic and antitumor activities of platinum compounds.

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A rapid method for the synthesis of water-soluble platinum(II) amine and pyridine complexes

Cited by 17 publications

References 3 publications

Conformational isomerism of trans-[Pt(NH2C6H11)2I2] and the classical Wernerian chemistry of [Pt(NH2C6H11)4]X2 (X=Cl, Br, I)

Conformational isomerism of trans-[Pt(NH2C6H11)2I2] and the classical Wernerian chemistry of [Pt(NH2C6H11)4]X2 (X=Cl, Br, I)

Synthetic Methods for the Preparation of Platinum Anticancer Complexes

Effect of the amine non‐leaving group on the structure and stability of DNA complexes with cis‐[Pt(R‐NH₂)₂(NO₃)₂]

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A rapid method for the synthesis of water-soluble platinum(II) amine and pyridine complexes

Cited by 17 publications

References 3 publications

Conformational isomerism of trans-[Pt(NH2C6H11)2I2] and the classical Wernerian chemistry of [Pt(NH2C6H11)4]X2 (X=Cl, Br, I)

Conformational isomerism of trans-[Pt(NH2C6H11)2I2] and the classical Wernerian chemistry of [Pt(NH2C6H11)4]X2 (X=Cl, Br, I)

Synthetic Methods for the Preparation of Platinum Anticancer Complexes

Effect of the amine non‐leaving group on the structure and stability of DNA complexes with cis‐[Pt(R‐NH2)2(NO3)2]

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Effect of the amine non‐leaving group on the structure and stability of DNA complexes with cis‐[Pt(R‐NH₂)₂(NO₃)₂]