Synthesis and preliminary DNA-binding studies of diimineplatinum(ii) complexes containing 3- or 4-pyridineboronic acid

Ching, H. Y. Vincent; Clegg, Jack K.; Rendina, Louis M.

doi:10.1039/b618668h

Cited by 10 publications

(9 citation statements)

References 26 publications

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“…These results were interpreted by the conformation of the rings seen in the X-ray crystal structure of [Pt(py) 2 (AtC2)](NO 3 ) 2 . The structures of platinum complexes containing pyridine have been investigated by many workers (Ching et al, 2007;Cavigliasso et al, 2013) and, in many cases, the two pyridine rings show a symmetrical orientation. However, in (I), the N3-Pt1-N1-C1 torsion angle is 110.2 (2) , whereas that of N4-Pt1-N2-C10 is À60.1 (3) , indicating an asymmetrical orientation (Table 2).…”

Section: Resultsmentioning

confidence: 99%

Asymmetric structure of cis-[N-(9-anthracenylmethyl)-1,2-ethanediamine]dipyridineplatinum(II) dinitrate

et al. 2017

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Platinum antitumour agents, containing aromatic rings, which are used for targeting DNA in effective therapies for the treatment of cancer. We have synthesized the title metallocomplex with an aromatic ligand and determined its crystal structure. In many cases, complexes of platinum and other metals have a symmetrical structure. In contrast, the platinum(II) complex with pyridine and N-(9-anthracenylmethyl)-1,2-ethanediamine as ligands (systematic name: cis-{N-[(anthracen-9-yl)methyl]ethane-1,2-diamine-κN,N'}bis(pyridine-κN)platinum(II) dinitrate), [Pt(CHN)(CHN)](NO), is asymmetric. Of the two pyridine ligands, only one is π-stacked with anthracene, resulting in an asymmetric structure. Moreover, the angle of orientation of each pyridine ligand is variable. Further examination of the packing motif confirms an intermolecular edge-to-face interaction.

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Section: Resultsmentioning

confidence: 99%

Asymmetric structure of cis-[N-(9-anthracenylmethyl)-1,2-ethanediamine]dipyridineplatinum(II) dinitrate

et al. 2017

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“…It is known that the speciation of free 3-and 4-pyB and their platinum(II)-diimine complexes is highly pH dependent. 26,12 The resonances assigned to the pyB protons, H2¢¢¢ and H3¢¢¢ (for 4-pyB) and H2¢¢¢ (for 3-pyB), were found to shift substantially as a function of pH. At pH > 5, hydroxylation of the boronic acid functionality occurs to afford the tetrahedral boronate species, and at this pH…”

Section: Synthesis and Variable Ph Measurementsmentioning

confidence: 99%

“…195 Pt{ 1 H} NMR spectroscopy was used to confirm the coordination environment of 1•2NO 3 , 2•2NO 3 , and 3•3NO 3 : the presence of single resonances at -2752, -2750, and -2660 ppm, respectively, is consistent with a PtN 4 core in each complex. 23,12 In contrast, a PtN 3 S coordination geometry. 24, 25 The results of 11 B{ 1 H} NMR spectroscopy confirmed the presence of the boronic acid group with a singlet observed at ca.…”

Section: Synthesis and Variable Ph Measurementsmentioning

confidence: 99%

“…Preliminary DNA-binding studies with diimineplatinum(II) complexes containing either 3-or 4-pyridineboronic acid revealed only minimal interactions with calf-thymus DNA, an effect that was directly attributed to hydroxylation of the boronic acid groups at biological pH. 12 The consequent loss of cationic charge from the complexes resulted in significantly reduced DNA-binding due to the absence of favourable electrostatic interactions between the complexes and the polyanion.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, carbohydrate- and DNA-binding studies of cationic 2,2′:6′,2′′-terpyridineplatinum(ii) complexes containing N- and S-donor boronic acid ligands

et al. 2011

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A series of platinum(II) complexes of the type [Pt(trpy)L](NO(3))(n) (L = 3- or 4-pyridineboronic acid (3- or 4-pyB, respectively), n = 2; HL = 4-mercaptophenylboronic acid (HmpB), n = 1; trpy = 2,2':6',2''-terpyridine) and [{Pt(trpy)}(2)(μ-pzB)](NO(3))(3) (HpzB = 4-pyrazoleboronic acid) were synthesized and fully characterized by means of multinuclear ((1)H, (13)C, (11)B, and (195)Pt) 1D- and 2D-NMR spectroscopy and elemental analysis. The triflate derivatives [Pt(trpy)(4-pyB)](OTf)(2) and [{Pt(trpy)}(2)(μ-pzB)](OTf)(3) were also prepared, and their molecular structures were confirmed by X-ray crystallography. Variable pH (1)H NMR spectroscopy showed that hydroxylation of the boronic acid group occurs in aqueous solution at pH > 5 and the pK(a) values for the complexes were determined. In buffered aqueous solution (pH 7.4), the complexes bind strongly to simple diols such as catechol and monosaccharides including D-fructose, D-ribose, D-sorbitol and D-mannitol, as determined by isothermal titration calorimetry (ITC). The equilibrium binding constants for these reactions were determined and were found to exceed those of organic boronic acids such as phenylboronic acid by an order of magnitude or greater, an effect that can be directly attributed to the cationic charge of the complexes. 2D-NMR methods (HSQC and HMBC) were used to elucidate the structures of the carbohydrate adducts [Pt(trpy)(3-pyB)]·D-fructose·NO(3) and [Pt(trpy)(4-pyB)]·D-fructose·NO(3) in aqueous solution. DNA-binding experiments with calf-thymus DNA (CT-DNA) indicate an avid DNA-binding interaction by the mononuclear complexes, as determined using thermal melting methods and ITC, but the behaviour of the dinuclear species [{Pt(trpy)}(2)(μ-pzB)](NO(3))(3) is complicated and could not be modeled adequately; higher ionic strength solutions and lower temperatures resulted in a similar DNA binding interaction to the mononuclear complexes. The presence of excess d-fructose did not significantly affect the binding of the platinum(II)-trpy complexes to CT-DNA.

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“…In contrast, our group has shown that ligands containing the thermodynamically stable 1,12-carborane cluster do not degrade upon complexation to gold(I) (Ioppolo et al, 2007a,b). Boron-containing ligands and their respective complexes are of interest for potential application in boron neutron capture therapy (BNCT) (Crossley et al, 2005(Crossley et al, , 2007Todd et al, 2005;Ioppolo et al, 2007a,b;Ching et al, 2007). For the synthesis of the precursor gold compound, see: Uson et al (1989).…”

Section: Related Literaturementioning

confidence: 99%

[1,2-Bis(diphenylphosphino)-1,2-dicarba-closo-dodecaborane-κ²P,P′][7,8-bis(diphenylphosphino)-7,8-dicarba-nido-undecaborato-κ²P,P′]gold(I)–dichloromethane–water (2/1/1)

2009

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[1,2-Bis(diphenylphosphino)-1,2-dicarbacloso-dodecaborane-j Key indicators: single-crystal X-ray study; T = 150 K; mean (C-C) = 0.010 Å; Hatom completeness 99%; disorder in main residue; R factor = 0.044; wR factor = 0.094; data-to-parameter ratio = 14.8.The title compound, [Au(C 26 H 30 B 10 P 2 )(C 26 H 30 B 9 P 2 )]Á-0.5CH 2 Cl 2 Á0.5H 2 O, contains two independent complex molecules in the asymmetric unit. The gold(I) centres display a distorted tetrahedral geometry. The complex is stablized through weak intramolecular -stacking (CgÁ Á ÁCg = 4.17 Å ) and edge-to-face interactions (HÁ Á ÁCg = 3.21 Å ). Adjacent molecules interact through C-HÁ Á Á (HÁ Á ÁCg = 2.88 Å ) and B-HÁ Á Á (HÁ Á ÁCg = 3.15 Å ) contacts, forming a threedimensional network, with solvent molecules occupying the cavities. One of the phenyl groups was disordered over two sites with occupancy factors of 0.65 and 0.35. Related literatureThe chelating P-donor ligand 1,2-bis(diphenylphosphino)-1,2-dicarba-closo-carborane has been used to prepare 2-, 3-and 4-coordinate complexes of gold(I) (Crespo et al., 1992(Crespo et al., , 1994 AlBaker et al., 1985). Coordination of this ligand has often led to deboronation of the closo-carborane cage to afford the corresponding nido-carborane in polar solvents (Teixidor et al., 1995(Teixidor et al., , 1996. A non-solvated crystal structure of the title compound has been reported previously (Crespo et al., 1997). Facile deboronation of the carborane cage in polar solvents has also been observed when substituents to the cage are electron withdrawing (Shaeck & Kahl, 1999; Ioppolo et al., 2007a,b). In contrast, our group has shown that ligands containing the thermodynamically stable 1,12-carborane cluster do not degrade upon complexation to gold(I) (Ioppolo et al., 2007a,b

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Synthesis and preliminary DNA-binding studies of diimineplatinum(ii) complexes containing 3- or 4-pyridineboronic acid

Cited by 10 publications

References 26 publications

Asymmetric structure of cis-[N-(9-anthracenylmethyl)-1,2-ethanediamine]dipyridineplatinum(II) dinitrate

Asymmetric structure of cis-[N-(9-anthracenylmethyl)-1,2-ethanediamine]dipyridineplatinum(II) dinitrate

Synthesis, carbohydrate- and DNA-binding studies of cationic 2,2′:6′,2′′-terpyridineplatinum(ii) complexes containing N- and S-donor boronic acid ligands

[1,2-Bis(diphenylphosphino)-1,2-dicarba-closo-dodecaborane-κ²P,P′][7,8-bis(diphenylphosphino)-7,8-dicarba-nido-undecaborato-κ²P,P′]gold(I)–dichloromethane–water (2/1/1)

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Synthesis and preliminary DNA-binding studies of diimineplatinum(ii) complexes containing 3- or 4-pyridineboronic acid

Cited by 10 publications

References 26 publications

Asymmetric structure of cis-[N-(9-anthracenylmethyl)-1,2-ethanediamine]dipyridineplatinum(II) dinitrate

Asymmetric structure of cis-[N-(9-anthracenylmethyl)-1,2-ethanediamine]dipyridineplatinum(II) dinitrate

Synthesis, carbohydrate- and DNA-binding studies of cationic 2,2′:6′,2′′-terpyridineplatinum(ii) complexes containing N- and S-donor boronic acid ligands

[1,2-Bis(diphenylphosphino)-1,2-dicarba-closo-dodecaborane-κ2P,P′][7,8-bis(diphenylphosphino)-7,8-dicarba-nido-undecaborato-κ2P,P′]gold(I)–dichloromethane–water (2/1/1)

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[1,2-Bis(diphenylphosphino)-1,2-dicarba-closo-dodecaborane-κ²P,P′][7,8-bis(diphenylphosphino)-7,8-dicarba-nido-undecaborato-κ²P,P′]gold(I)–dichloromethane–water (2/1/1)