Manifestation of redox duality of 2-propanone oxime: Pt(II)-assisted reduction versus Pt(IV)-mediated oxidation of Me2CNOH species

Silva, M.Fátima C. Guedes da; Izotova, Youlia A.; Pombeiro, Armando J. L.; Kukushkin, Vadim Yu.

doi:10.1016/s0020-1693(97)06126-4

Cited by 13 publications

(7 citation statements)

References 12 publications

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“…its oxidative addition to an electron-rich rhenium(I) center, [10] (iii) the oxime N atom, e.g. its oxidation to give (nitrosoalkane)Pt complexes [11,12] or its reduction in a strongly acidic solution, [13] (iv) the CϭN group, e.g. its metal-mediated hydrolysis [14] and the conversion into aldoximato ligands remained intact.…”

Section: Introductionmentioning

confidence: 99%

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Chlorination of Platinum-Bound Salicylaldoxime. The First Example of a Structurally Characterized Monodentate Salicylaldoxime-Type Ligand

Kaplan

Kukushkin

Shova

et al. 2001

Eur. J. Inorg. Chem.

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Section: Introductionmentioning

confidence: 99%

“…its metal-mediated hydrolysis [14] and the conversion into aldoximato ligands remained intact. All complexes were characterized by C, H, N, Cl and Pt elemental analyses, FAB + mass spectrometry, IR and 1 H, 13 C{ 1 H} and 195 Pt NMR spectroscopy. Compounds 1, 3 and 5 were analyzed by X-ray crystallography.…”

Section: Introductionmentioning

confidence: 99%

Chlorination of Platinum-Bound Salicylaldoxime. The First Example of a Structurally Characterized Monodentate Salicylaldoxime-Type Ligand

Kaplan

Kukushkin

Shova

et al. 2001

Eur. J. Inorg. Chem.

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“…Moreover, apart from the data analyzed in the review, new interesting examples, e.g. stepwise deprotonation accompanied by self-assembly of oxime/oximato species formed, oxidation of coordinated oximes to give nitrosoalkanes, nitrosylation of metal centers, the redox duality of oxime species toward one and the same metal, observation of N−O bond cleavage in oxidative addition of oximes, and facile dehydration and formation of coordinated nitriles, have been reported in the last 3 years.…”

Section: Introductionmentioning

confidence: 99%

Iminoacylation. 1. Addition of Ketoximes or Aldoximes to Platinum(IV)-Bound Organonitriles

et al. 1998

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The metal-mediated iminoacylation reaction of ketoximes or aldoximes upon treatment with the organonitrile platinum(IV) complexes trans-[PtCl(4)(RCN)(2)] proceeds under relatively mild conditions in acetonitrile (R = Me) or in chloroform (R = CH(2)Ph, Ph) to give trans-[PtCl(4)(NH=C(R)ON=CR(1)R(2))(2)] (R(1) = R(2) = Me; R(1)R(2) = C(4)H(8), R(1)R(2) = C(5)H(10), R(1)R(2) = (H)Ph, R(1)R(2) = (H)C(6)H(4)(OH)-o; 1-14) in 90-95% yield. All these compounds were characterized by elemental analyses (C, H, N, Cl, Pt), FAB mass spectrometry, and IR and (1)H, (13)C{(1)H}, and (195)Pt NMR spectroscopies. X-ray structure determinations of [PtCl(4)(NH=C(Me)ON=CMe(2))(2)] (1) and [PtCl(4){NH=C(Me)ON=C(C(5)H(10))}(2)] (3) disclosed their overall trans-configuration and the amidine one-end rather than N,N-bidentate coordination mode of the N-donor ligands. The iminoacyl species are in E-conformation which is held by a rather weak N-H.N hydrogen bond between the amidine =NH atom and the oxime nitrogen with the following observed distances and angles for 1 and [3]: N(1).N(2), and N(1)-H, N(1)H.N(2) are 2.605 [2.592], 0.74 [0.71], and 2.20 [2.25] Å; N(1)-H.N(2) is 115 degrees [111 degrees ]. No evidence of the Z-conformation in solution was obtained by NMR spectroscopy. Compounds trans-[PtCl(4)(NH=C(R)ON=CR(1)R(2))(2)] are unexpectedly stable toward hydrolysis both in the solid state and in solutions.

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“…Platinum (II) complexes are relatively important in the treatment of cancer. For anti-cancer platinum-based drugs, mainly experimental studies have quite extensive and there are major economic losses in these studies [14][15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Hidroksi- ve Sülfonamid- Azobenzen Platin (II) Komplekslerinin Yapısal, Spektroskopik ve Anti-Kanser Özellikleri: DFT ve Moleküler Yerleştirme Çalışmaları

Erkan

2018

Cumhuriyet Science Journal

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The three platinum (II) complexes ([Pt(L1)(DMSO)Cl], [Pt(L2)(DMSO)Cl] and [Pt(L2) 2 ]) bearing the bidentate ligands sulphonamide-((E)-2-(4-methylphenylsulfonamido)-2′,6′-difluoroazobenzene, HL1) and hydroxy-azo-2,6-difluorobenzene ((E)-2-((2,6-difluorophenyl)diazenyl)phenol, HL2) were optimized with the optimum levels of B3LYP/6-31+G(d) and B3LYP/LANL2DZ/6-31+G(d) level. The structural parameters (bond lengths and ligand angles), IR and 1 H, 13 C and 19 F-NMR spectra obtained from the optimized structures were compared with the experimental data and the results were found to be consistent with the experimental results. Experimental inhibition activities against A2780 and A2780CP70 cancer cells were compared with quantum chemical parameters such as HOMO energy (E HOMO ), LUMO energy (E LUMO ), LUMO-HOMO energy vacancy (E), hardness (), softness (), electronegativity () and chemical potential (). The relationship between the molecular structure with the biological activity was examined and E LUMO order was found to be compatible with the experimental inhibition efficiency ranking. Molecular electrostatic potential (MEP) maps were studied of ligands and complexes exhibiting anti-cancer properties and for ligands and complexes, regions of attachment to cancer cells were determined. In addition, electrostatic potential (ESP) charges obtained from MEP maps of ligands and complexes were ranked according to their ease of binding to the cancer cell. The obtained ranking was found to be in accordance with the experimental inhibition efficiency order. For studied ligands and complexes, molecular docking studies were carried out with the Hex.8.0.0 program. The target proteins (PDB ID: 4M5W and 5FI4, respectively) corresponding to the A2780 and A2780CP70 cell lines were selected in the literature. The interaction energies of 4M5W and 5FI4 target proteins with HL1 and HL2 ligands were calculated to be -300.02, -240.80 and -336.64, -247.04 kJ/mol, respectively. The binding energies between the complexes and 4M5W and 5FI4 target proteins were calculated to be -387.52, -285.44, -364.88 and -399.63, -297.8, -385.323 kJ/mol. According to these results, the experimental and calculated inhibition efficiency order was found to be compatible.

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Manifestation of redox duality of 2-propanone oxime: Pt(II)-assisted reduction versus Pt(IV)-mediated oxidation of Me2CNOH species

Cited by 13 publications

References 12 publications

Chlorination of Platinum-Bound Salicylaldoxime. The First Example of a Structurally Characterized Monodentate Salicylaldoxime-Type Ligand

Chlorination of Platinum-Bound Salicylaldoxime. The First Example of a Structurally Characterized Monodentate Salicylaldoxime-Type Ligand

Iminoacylation. 1. Addition of Ketoximes or Aldoximes to Platinum(IV)-Bound Organonitriles

Hidroksi- ve Sülfonamid- Azobenzen Platin (II) Komplekslerinin Yapısal, Spektroskopik ve Anti-Kanser Özellikleri: DFT ve Moleküler Yerleştirme Çalışmaları

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