Solvolysis reactions of cis- and trans-diamminedichloroplatinum(II) in dimethyl sulfoxide. Structural characterization and DNA binding of trans-bis(ammine)chloro(DMSO)platinum(1+)

Sundquist, Wesley I.; Ahmed, Kazi J.; Hollis, L. Steven; Lippard, Stephen J.

doi:10.1021/ic00257a013

Cited by 104 publications

(46 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The PtÐCl bond cis to the dimethyl sulfoxide (dmso) ligand is slightly shorter than the trans-PtÐCl bond, in line with the trend generally observed for ligands with a trans in¯uence. While the PtÐS distance is within the range reported for other Pt II ±sulfoxide derivatives (Pasini et al, 1994;Sundquist et al, 1987), it is noteworthy that this bond length of 2.220 (3) A Ê is greater than the value expected when considering the cis in¯uence of related ligands (Belsky et al, 1991). This is likely to be due to the electron-donating ability of the methoxy group in the 2-position of the ring.…”

supporting

confidence: 51%

“…Compound (I) is a square-planar Pt derivative with bond distances and angles at the Pt atom in the normal range (Sundquist et al, 1987;Melanson & Rochon, 1977b). The Pt atom deviates by 0.012 (1) A Ê from the mean plane of the ligand atoms (NÐSÐCl1ÐCl2).…”

Section: Commentmentioning

confidence: 99%

“…This has prompted us to investigate the antitumor activity of both cis and trans isomers of the general formula (N-Het)Pt(dmso)Cl 2 , where N-Het is a nitrogen heterocycle. The title compound, (I), is a member of a series of complexes prepared as part of our study.Compound (I) is a square-planar Pt derivative with bond distances and angles at the Pt atom in the normal range (Sundquist et al, 1987;Melanson & Rochon, 1977b). The Pt atom deviates by 0.012 (1) A Ê from the mean plane of the ligand atoms (NÐSÐCl1ÐCl2).…”

mentioning

confidence: 99%

See 2 more Smart Citations

cis-Dichloro(dimethyl sulfoxide-S)(2-methoxypyridine-N)platinum(II)

et al. 2000

View full text Add to dashboard Cite

The title complex, [PtCl 2 (C 6 H 7 NO)(C 2 H 6 OS)], exhibits square-planar geometry. The plane of the pyridine ring makes a dihedral angle of 67.2 (3) with the square plane of the metal center. The SÐO bond is nearly aligned with the adjacent PtÐ N bond, leaving the methyl groups of the dimethyl sulfoxide ligand to stagger the PtÐCl bond. CommentCisplatin, cis-[Pt(NH 3 ) 2 Cl 2 ], is extensively used in the treatment of a variety of cancers (Kelland et al., 1992). Most of its second generation analogs are simple amines with a cis geometry about the metal, which is in either the +2 or +4 oxidation state. These compounds share a common rationale in their design (Cleare & Hoeschle, 1973). Reports of the biological effects of unusual Pt derivatives (Hambley, 1997), such as triamine complexes (Hollis et al., 1989;Baird et al., 1997) or those with a trans geometry (Van Beusichem & Farrell, 1992), have appeared in the literature. The antitumor activity of sulfoxide derivatives has also been noted (Farrell et al., 1990). This has prompted us to investigate the antitumor activity of both cis and trans isomers of the general formula (N-Het)Pt(dmso)Cl 2 , where N-Het is a nitrogen heterocycle. The title compound, (I), is a member of a series of complexes prepared as part of our study.Compound (I) is a square-planar Pt derivative with bond distances and angles at the Pt atom in the normal range (Sundquist et al., 1987;Melanson & Rochon, 1977b). The Pt atom deviates by 0.012 (1) A Ê from the mean plane of the ligand atoms (NÐSÐCl1ÐCl2). The structure validates 195 Pt NMR chemical shift data, which suggested a cis geometry for the product. The PtÐCl bond cis to the dimethyl sulfoxide (dmso) ligand is slightly shorter than the trans-PtÐCl bond, in line with the trend generally observed for ligands with a trans in¯uence. While the PtÐS distance is within the range reported for other Pt II ±sulfoxide derivatives (Pasini et al., 1994;Sundquist et al., 1987), it is noteworthy that this bond length of 2.220 (3) A Ê is greater than the value expected when considering the cis in¯uence of related ligands (Belsky et al., 1991). This is likely to be due to the electron-donating ability of the methoxy group in the 2-position of the ring.The S atom of the coordinated dmso ligand is tetrahedral. The SÐO distance in Pt±dmso complexes is typically shorter than in the free ligand, and (I) also possesses a shortened bond. A near eclipsing of the PtÐN bond by the SÐO group has been observed in other cis-Pt±dmso complexes (Melanson & Rochon, 1977b;Dyksterhouse et al., 2000) and compound (I) is no exception. The resulting coplanarity of the SÐO bond with the square plane of the metal atom in (I) [torsion angle O2ÐSÐPtÐN 7.3 (4) ] and other cis complexes contrasts with trans derivatives, in which the SÐO bond is perpendicular to the Pt square plane.Another feature of (I) is a weak association of O1 to Pt, with a contact of 2.972 (8) A Ê . Furthermore, the dihedral angle between the pyridine plane and the metal coordination plane is 67.2 (3) . T...

show abstract

supporting

confidence: 51%

Section: Commentmentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

cis-Dichloro(dimethyl sulfoxide-S)(2-methoxypyridine-N)platinum(II)

et al. 2000

View full text Add to dashboard Cite

show abstract

“…concentration 7.5 mM) and then dissolved in the complete culture medium, at concentrations twice those of the final ones, and 1 mL of resulting solution was added per well. The solutions of 2 and CDDP compounds were freshly made before every experiment to avoid the solvolysis [53,54]. Stock solution of 1 was stored refrigerated.…”

Section: Solution Stability Studies: Uv-vis Spectroscopymentioning

confidence: 99%

New Look on 3-Hydroxyiminoflavanone and Its Palladium(II) Complex: Crystallographic and Spectroscopic Studies, Theoretical Calculations and Cytotoxic Activity

et al. 2016

View full text Add to dashboard Cite

This work presents the synthesis, spectroscopic properties and single-crystal X-ray examination of the structure of 3-hydroxyiminoflavanone and its palladium complex. It presents the results of NMR (Nuclear Magnetic Resonance) spectroscopy, electron-density studies based on X-ray wavefunction refinement and theoretical calculations combined with QTAIM (Quantum Theory of Atoms in Molecules) and ELI-D (Electron Localizability Indicator) analyses. These offer an interesting new insight into the structures and behavior of flavanone and its complex, in solid state and in solution. The study also examines the cytotoxicity of the ligand and its complex against three human ovarian and lung cancer cell lines.

show abstract

“…In regard to the dppf containing complexes this assumption is based on a study by Longato et al, 20 in which it was found that for Pt(dppf)Cl 2 (complex I) dissolved in neat DMSO the mono-substituted DMSO product formed only on addition of AgBF 4 and the bis product did not form at all. In the case of cisplatin (complex IV) the first-order rate constant of solvolysis in neat DMSO has been determined as 6.24 × 10 −5 s −1 at 26 • C. 21 Since the solutions of all complexes were freshly prepared for each measurement, the time spent in neat DMSO prior to addition to aqueous solution was less then five minutes (corresponding to less than 3% conversion of cisplatin to the solvolysis product).…”

Section: Kinetic Measurements In Aqueous Solutionmentioning

confidence: 99%

A comparative kinetic study of modified Pt(dppf)Cl2 complexes and their interactions with l-cys and l-met

et al. 2005

View full text Add to dashboard Cite

With the success of cisplatin (cis-diamminedichloroplatinum(II)), strong interest has developed in the application of inorganic metal complexes to the treatment of cancer. Research has focused on platinum(II) complexes with a variety of spectator ligands that provide novel physicochemical properties. In this paper we report a kinetic study of 1 ,1 -bis(diphenylphosphino)ferrocenedichloroplatinum(II) and two related compounds with either an acetate or amide ester substituent attached to the cyclopentadienyl ring. For all compounds the reactivity towards L-cysteine and L-methionine in aqueous solution has been investigated (25 ). The attached substituents were found to have a significant effect upon the reaction kinetics, with the substituted complexes found to have increased reactivity. It is proposed that the increased reactivity stems from hydrogen bonding between the substituent and the entering ligand and subsequent outer-sphere complex stabilisation. Evidence in support of this theory was obtained form measurements in dichloromethane with 1-propanethiol as the entering ligand. The reactivity of the dppf containing complexes was also compared to that of cisplatin (mono adduct: (0.170(1)-0.175(1)) × 10 −3 s −1 , bis adduct: (0.183(1)-0.397(1)) × 10 −4 s −1 ) and found to be significantly enhanced.

show abstract

Solvolysis reactions of cis- and trans-diamminedichloroplatinum(II) in dimethyl sulfoxide. Structural characterization and DNA binding of trans-bis(ammine)chloro(DMSO)platinum(1+)

Cited by 104 publications

References 1 publication

cis-Dichloro(dimethyl sulfoxide-S)(2-methoxypyridine-N)platinum(II)

cis-Dichloro(dimethyl sulfoxide-S)(2-methoxypyridine-N)platinum(II)

New Look on 3-Hydroxyiminoflavanone and Its Palladium(II) Complex: Crystallographic and Spectroscopic Studies, Theoretical Calculations and Cytotoxic Activity

A comparative kinetic study of modified Pt(dppf)Cl2 complexes and their interactions with l-cys and l-met

Contact Info

Product

Resources

About