Synthesis, characterization, solution equilibria and DNA binding of some mixed-ligand palladium(II) complexes. Thermodynamic models for carboplatin drug and analogous compounds

Tercero, J. M.; Matilla, Ángel J.; Sanjuán, Míriam; Moreno, C.; Martín, Jacobo Cambil; Walmsley, Judith A.

doi:10.1016/s0020-1693(02)01071-x

Cited by 37 publications

(25 citation statements)

References 29 publications

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“…All of these agree well with the data of related palladium complexes [1,2]. The C1-O1 and C2-O2 bond length are 1.289(3) and 1.291(3) Å,r espectively, while the C1-O3 and C2-O4 bond length are 1.222(3) and 1.217(3) Å,respectively, which indicate a monodentate coordination mode for the carboxylates [3,4]. The crystal packing of the title complex is stablilized by extensive hydrogen bonds formed between ammonium cations, water molecules and Oatoms of the oxalates with d(O···O) of 2.951(3) Å and 2.888(3) Å,a nd d(N···O) of 2.910(3), 2.983(3), 2.935(3), 2.865(3) and 2.871(3) Å (figure, bottom).…”

supporting

confidence: 87%

Crystal structure of diammonium bis(oxalato)palladium(II) dihydrate, (NH4)2[Pd(C2O4)2] · 2H2O

Ye¹,

Pan²,

Xie³

et al. 2010

Zeitschrift Für Kristallographie - New Crystal Structures

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C 4 H 12 N 2 O 10 Pd, monoclinic, P12 1 /c1(no. 14), a =6.7795(7) Å, b =14.377(2) Å, c =6.1774(7) Å, b =111.052(1)°, V =561.9 Å 3 , Z =2,Rgt(F) =0.018, wRref (F 2 ) =0.048, T =298 K. Source of materialTo asolution of palladium(II) chloride (0.89 g, 5.0 mmol) in dilute hydrochloric acid (2 M, 6mL), ammonium oxalate (1.86 g, 15.0 mmol) in 10 mL of distilled water was added. The resulting solution was stirred for 1hat60°C, and then the pH was adjusted to 5.5 by adding dilute sodium hydroxide solution. After cooling to room temperature, ayellow prodct precipitated from the solution. The product was filtrated, washed with ice-cold water, and dried under vaccuum at 70°C. The crystals suitable for crystallographic studies were obtained by slow evaporation from the aqueous solution of the product at room temperature. Experimental detailsAll Hatoms were found in difference Fourier maps and refined independently. DiscussionThe crystal structure of the title complex comprises discrete ammonium cations, [Pd(C 2 O 4 )] 2-anions and water molecules (figure, top). The Pd atom occupying the inversion centre is coordinated in as lightly distorted square manner by the four oxygen atoms of two oxalate ligands. The average Pd-Od istance is 2.000(2) Å,w hile the angles O1-Pd-O2 and the O1-Pd-O2A are 83.64(6)°and 96.36(6)°,r espectively. All of these agree well with the data of related palladium complexes [1,2]. The C1-O1 and C2-O2 bond length are 1.289(3) and 1.291(3) Å,r espectively, while the C1-O3 and C2-O4 bond length are 1.222(3) and 1.217(3) Å,respectively, which indicate a monodentate coordination mode for the carboxylates [3,4]. The crystal packing of the title complex is stablilized by extensive hydrogen bonds formed between ammonium cations, water molecules and Oatoms of the oxalates with d(O···O) of 2.951(3) Å and 2.888(3) Å,a nd d(N···O) of 2.910(3), 2.983(3), 2.935(3), 2.865(3) and 2.871(3) Å (figure, bottom). The mean planes defined by the four coordinated Oatoms are parallel to each other along [001] with adistance of 3.356 Å between the nearest neighbors, and the distance Pd···Pd is 6.177 Å.

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supporting

confidence: 87%

Crystal structure of diammonium bis(oxalato)palladium(II) dihydrate, (NH4)2[Pd(C2O4)2] · 2H2O

Ye¹,

Pan²,

Xie³

et al. 2010

Zeitschrift Für Kristallographie - New Crystal Structures

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“…The mechanisms of action for these coordination complexes are closely tied to their hydrolysis products, and these products and mechanisms are poorly understood, partly due to the possibility of multiple equilibria with similar energetics [11,12]. It is for these reasons that coordination complexes of Ni(II), Pd(II), and Pt(II) in aqueous solutions have been the focus of a number of investigations [13][14][15][16][17].Electrospray mass spectrometry (ESMS) is particularly well suited for the study of metal-containing aqueous solutions, and a variety of such studies have been conducted [18,19]. We recently reported the results of one such study into aqueous solutions of dibromo(ethylenediamine)palladium(II) [20].…”

mentioning

confidence: 99%

mentioning

confidence: 99%

Complexes of dichloro(ethylenediamine)palladium(II) observed from aqueous solutions by electrospray mass spectrometry

Bach

Green

Nagore

et al. 2007

J. Am. Soc. Mass Spectrom.

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Aqueous solutions of dichloro(ethylenediamine)palladium(II) were investigated using electrospray mass spectrometry (ESMS). The most abundant peak (m/z 436.8) was attributed to the dimeric Pd(en)Cl 2 ·Pd(en)Cl ϩ ion. We conjecture that the structures of the observed ions arise from the clustering of the hydrolysis products of the parent compound. This hypothesis was tested experimentally by carrying out a series of collision-induced dissociation (CID) experiments and deuterium exchange reactions. It was also assessed by performing density functional theory (DFT) calculations, from which optimized structures and reaction energetics were obtained. These results were compared with our earlier ESMS study of an aqueous Pd(en)Br 2 solution. Calculations were also carried out on the Pd(en)Br 2 system to facilitate the comparisons. Conclusions are drawn regarding the species present in the two aqueous solutions. (J Am Soc Mass Spectrom 2007, 18, 769 -777) © 2007 American Society for Mass Spectrometry T he last decade has seen a resurgence of interest in the coordination chemistry of transition metals. This is due in large part to their therapeutic value as antitumor agents. Many of these agents are platinum(II) complexes, the four best known being cisplatin, carboplatin, oxaliplatin, and nedaplatin [1][2][3]. Palladium(II) complexes have also attracted attention for similar reasons [4][5][6][7].In vivo, hydrolysis of these compounds occurs, and it is these hydrolytic products that yield their medicinal activity [8,9]. The hydrolytic products are also strongly linked to issues of renal toxicity [10]. The mechanisms of action for these coordination complexes are closely tied to their hydrolysis products, and these products and mechanisms are poorly understood, partly due to the possibility of multiple equilibria with similar energetics [11,12]. It is for these reasons that coordination complexes of Ni(II), Pd(II), and Pt(II) in aqueous solutions have been the focus of a number of investigations [13][14][15][16][17].Electrospray mass spectrometry (ESMS) is particularly well suited for the study of metal-containing aqueous solutions, and a variety of such studies have been conducted [18,19]. We recently reported the results of one such study into aqueous solutions of dibromo(ethylenediamine)palladium(II) [20]. When the solution was electrosprayed into a quadrupole ion-trap mass spectrometer, a number of previously unreported species were detected, the principle one being a dimeric ion formed from the Pd(en)Br 2 parent compound and the Pd(en)Br ϩ ion. The dimeric ion was subjected to collision-induced dissociation (CID), and these MS n experiments revealed a series of ions formed through the sequential loss of HBr molecules. Complexes observed from the electrospray process are not necessarily a reflection of those complexes in solution, but they may instead simply represent species in solution from which the complexes are produced in the electrospray desolvation process. This has been observed previously in solutions containi...

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“…Selected bond lengths and angles (Table 4) are similar to those reported for analogous compounds. 30,44 The palladium atom and the four donor atoms are coplanar with Pd located 0.0072 Å from the mean plane of the four donors atoms. The metal atom and the dapol ligand form a six-membered chelate ring adopting a chair conformation.…”

Section: Crystal Structure Of Pd(dapol)clmentioning

confidence: 99%

Cyclic Tetranuclear and Hexanuclear Palladium(II) Complexes and Their Host−guest Chemistry

et al. 2007

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Cyclic tetrameric complexes have been prepared by the reaction of Pd(en)Cl 2 or Pd(dapol)Cl 2 , or their nitrato analogs, with Na 2 (5′GMP) in aqueous solution, where en = 1,2-diaminoethane, dapol = 1,3-diamino-2-propanol, 5′-GMP = guanosine 5′-monophosphate. Addition of certain small molecules containing hydrophobic groups resulted in the expansion of the tetramer to a cyclic hexamer with strong bonding of one guest per hexameric host. At pH 5-6, the guest molecule can be a cation, anion, or neutral, and those species containing trimetylsilyl and t-butyl groups bonded the most strongly. The size of the central cavity of the [Pd(en)(5′GMP)] 6 host has been estimated to be 5.2 Ǻ. Formation of the host-guest complex caused a large upfield shift (Δδ) of 2.5-2.9 ppm in the 1 H NMR spectrum of the most highly affected guest protons, which were those in closest proximity to the guanine nucleobases. NOESY spectra were used to determine the interaction sites between the host and the guest. Apparent association constants determined at 26 °C and pD 5.4 for the [Pd(en)(5′GMP)] 6 -DSS and [Pd(en)(5′GMP)] 6 -t-butanol systems, where DSS is 3-(trimethylsilyl)-1-propanesulfonate anion, were 1.36 ± 0.11 × 10 4 and 2.74 ± 0.95 × 10 4 M −3/2 , respectively. The Pd(dapol)-5′GMP system forms hexameric host-guest complexes, similar in nature to those of the Pd(en)-5′-GMP system. The molecular and crystal structures of Pd(dapol)Cl 2 are also reported.

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Synthesis, characterization, solution equilibria and DNA binding of some mixed-ligand palladium(II) complexes. Thermodynamic models for carboplatin drug and analogous compounds

Cited by 37 publications

References 29 publications

Crystal structure of diammonium bis(oxalato)palladium(II) dihydrate, (NH4)2[Pd(C2O4)2] · 2H2O

Crystal structure of diammonium bis(oxalato)palladium(II) dihydrate, (NH4)2[Pd(C2O4)2] · 2H2O

Complexes of dichloro(ethylenediamine)palladium(II) observed from aqueous solutions by electrospray mass spectrometry

Cyclic Tetranuclear and Hexanuclear Palladium(II) Complexes and Their Host−guest Chemistry

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