Synthesis, structure and antitumor properties of platinum complexes of vitamin C

Hollis, L. Steven; Amundsen, Alan R.; Stern, Eric

doi:10.1021/ja00287a062

Cited by 106 publications

(45 citation statements)

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“…A plausible explanation of these differences is that the primary amine groups were less constrained during optimizations, giving rise to a significant degree of movement away from the central Pt(II) ion. The experimental structures of some related Pt(II)-complexes with biological relevance have been elucidated via both theoretical methods using effective core potential (ECP) and a variety of basis sets [23], as well as with experimental X-ray methods [24][25][26][27][28][29]. The principal difference between the structures studied previously and the tetraamine investigated here is that the tetraamine is a single multidentate ligand that provides all the chelating moieties, while the previously reported structures comprised multiple ligands.…”

Section: Geometry Of the Coordination Complexmentioning

confidence: 95%

“…Despite the availability of ab initio [23] and X-ray crystallography data for other biologically active Pt(II)-amine complexes [24][25][26][27][28][29], to the best of our knowledge this is the first systematic characterization of the conformational landscape of metalpolyamine complexes of this type. Employing density functional theory methods we computed the potential energy surfaces of five diastereoisomers and determined their relative stabilities.…”

Section: Introductionmentioning

confidence: 99%

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Conformational landscape of platinum(II)-tetraamine complexes: DFT and NBO studies

Yongye

Giulianotti

Nefzi

et al. 2010

J Comput Aided Mol Des

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The potential energy surfaces of chiral tetraamine Pt(II) coordination complexes were computed at the B3LYP/LANL2DZ level of theory by a systematic variation of two dihedral angles: C12-C15-C34-C37 (theta) and C24-C17-C31-C48 (psi) employing a grid resolution of 30 degrees . Potential energy surfaces calculated using density functional theory methods and Boltzmann-derived populations revealed strong preference for one diasteromer of each series studied. In addition, natural bond orbital analysis show that the minima are stabilized predominantly by a combination of electronic interactions between two phenyl groups, the phenyl groups and the Pt(2+) ion, as well as with the amine groups. Additional experimental characterization of the diasteroisomers studied here is in progress and will permit further molecular modeling studies with the appropriate stereochemistry.

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Section: Geometry Of the Coordination Complexmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

Conformational landscape of platinum(II)-tetraamine complexes: DFT and NBO studies

Yongye

Giulianotti

Nefzi

et al. 2010

J Comput Aided Mol Des

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show abstract

“…[4,12] This coordination mode seems to be precluded with phosphanic precursors, probably because of steric interactions. [4] On the contrary, any attempts to obtain the O2,O3 coordination with amine-Pt precursors invariably gave C2,O5 complexes.…”

Section: C2o5 Coordination -Known Complexmentioning

confidence: 99%

New Coordination Modes of L‐Ascorbic Acid and Dehydro‐L‐ascorbic Acid as Dianionic Chelating Ligand for Platinum

et al. 2008

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A variety of coordination modes of L-ascorbic acid as an anionic bidentate ligand has been exploited to prepare platinum(II) complexes 1-7 that contain phosphanes or R,R-dach (1R,2R-diaminocyclohexane) as neutral ligands in which O2, O3, O5, O6 and C2 act as anionic donating functionalities. An alternative synthetic route to known O2,O3 complexes is proposed, and their solubility in water has been enhanced by introducing PTA (1,3,5-triaza-7-phosphaadamantane) as a neutral ligand. A new coordination mode of ascorbic acid (O2 and O3 protected) as an O5,O6-diolate chelating ligand has been characterised in solution by NMR spectroscopy and in

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“…It also has clinical importance, e.g., prevention of scurvy [1], and is vital to immune response and wound healing [2]. Recently, the anticancer and antitumor properties of organometallic ascorbic acid were also investigated [3,4]. This vital component in the diet of human is widely distributed in fruits, vegetables and beverages especially derived from fruit juices and also present in animal liver, leukocytes, anterior pituitary lobe and human nervous system [5].…”

Section: Introductionmentioning

confidence: 99%

Electrooxidation and Amperometric Detection of Ascorbic Acid at GC Electrode Modified by Electropolymerization of N,N‐Dimethylaniline

et al. 2004

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The polymer film of N,N-dimethylaniline (DMA) is deposited on the electrochemically pretreated glassy carbon (GC) electrode by continuous electrooxidation of the monomer. This poly N,N-dimethylaniline (PDMA) film-coated electrode can be used as an amperometric sensor of ascorbic acid (AA). The polymer film (thickness (f): 0.3 AE 0.02 mm) having positive charge in its backbone attracts the anionic species AA. Thus, the anodic peak potential (350 mV vs. Ag j AgCl j NaCl (sat) ) for the oxidation of AA at the bare electrode is largely shifted to the negative value (150 mV) at this electrode. The PDMA film-coated electrode is stable in acidic, alkaline and neutral media and can sense AA at different pH×s. The diffusion coefficients of AA in solution (D) and in film (D s ) were estimated by rotating disk electrode voltammetry:, (6.0 AE 0.2) Â 10 À8 and (4.7 AE 0.2) Â 10 À8 cm 2 s À1 for 0.5, 1.5 and 3.0 mM AA, respectively. A permeability of AA through the PDMA film was found to decrease with increasing the concentration of AA in the solution. In the chronoamperometry, the current response for the oxidation of AA at different times elapsed after potential-step application is linearly increased with the increase in AA concentration in a wide range of its concentration from 25 mM to 1.65 mM. In the hydrodynamic amperometry, a successive addition of 10 mM AA caused the successive increase in current response with equal amplitude and the sensitivity was calculated as 0.178 mA cm À2 mM À1. So, the fouling of the electrode surface caused by the oxidized product of AA is markedly eliminated at this PDMA film-coated electrode. A flow injection analysis based on the present electrode was performed to estimate the concentration of vitamin C in fruit juice.

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Synthesis, structure and antitumor properties of platinum complexes of vitamin C

Cited by 106 publications

References 0 publications

Conformational landscape of platinum(II)-tetraamine complexes: DFT and NBO studies

Conformational landscape of platinum(II)-tetraamine complexes: DFT and NBO studies

New Coordination Modes of L‐Ascorbic Acid and Dehydro‐L‐ascorbic Acid as Dianionic Chelating Ligand for Platinum

Electrooxidation and Amperometric Detection of Ascorbic Acid at GC Electrode Modified by Electropolymerization of N,N‐Dimethylaniline

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