New routes for the synthesis of chloro(diethylenetriamine) platinum(II) chloride and chloro(2,2′ : 6′,2″-terpyridine) platinum(II) chloride dihydrate

Annibale, Giuliano; Brandolisio, Matilde; Pitteri, Bruno

doi:10.1016/0277-5387(94)00408-7

Cited by 132 publications

(79 citation statements)

References 12 publications

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“…45. [34] The pK a values given above (average 4.45) thus imply that Pt II bonded to N1 acidifies the rare tautomer, hence N7H, by around 1 log unit.…”

Section: Crystal Structure Analysis Of {Trans-mentioning

confidence: 94%

“…The following compounds were prepared as described in the literature: [Pt-A C H T U N G T R E N N U N G (dien)I]I, [44] [PtA C H T U N G T R E N N U N G (dien)Cl]Cl, [45] trans-[PtA C H T U N G T R E N N U N G (NH 3 ) 2 Cl 2 ], [46] trans-[Pt-A C H T U N G T R E N N U N G (MeNH 2 ) 2 Cl 2 ], [47] [Pd(en)Cl 2 ], [48] [PtA C H T U N G T R E N N U N G (NH 3 ) 3 Cl]Cl, [49] and [PtA C H T U N G T R E N N U N G (dien)(9-MeGH-N7)]A C H T U N G T R E N N U N G (ClO 4 ) 2 .…”

Section: Methodsmentioning

confidence: 99%

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Pt^II Coordination to N1 of 9‐Methylguanine: Why it Facilitates Binding of Additional Metal Ions to the Purine Ring

Müller¹,

Shen²,

Miguel³

et al. 2011

Chemistry A European J

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The preparation and X-ray crystal structure analysis of {trans-[Pt(MeNH(2))(2)(9-MeG-N1)(2)]}⋅{3 K(2)[Pt(CN)(4)]}⋅6 H(2)O (3 a) (with 9-MeG being the anion of 9-methylguanine, 9-MeGH) are reported. The title compound was obtained by treating [Pt(dien)(9-MeGH-N7)](2+) (1; dien=diethylenetriamine) with trans-[Pt(MeNH(2))(2)(H(2)O)(2)](2+) at pH 9.6, 60 °C, and subsequent removal of the [(dien)Pt(II)] entities by treatment with an excess amount of KCN, which converts the latter to [Pt(CN)(4)](2-). Cocrystallization of K(2)[Pt(CN)(4)] with trans-[Pt(MeNH(2))(2)(9-MeG-N1)(2)] is a consequence of the increase in basicity of the guanine ligand following its deprotonation and Pt coordination at N1. This increase in basicity is reflected in the pK(a) values of trans-[Pt(MeNH(2))(2)(9-MeGH-N1)(2)](2+) (4.4±0.1 and 3.3±0.4). The crystal structure of 3 a reveals rare (N7,O6 chelate) and unconventional (N2,C2,N3) binding patterns of K(+) to the guaninato ligands. DFT calculations confirm that K(+) binding to the sugar edge of guanine for a N1-platinated guanine anion is a realistic option, thus ruling against a simple packing effect in the solid-state structure of 3 a. The linkage isomer of 3 a, trans-[Pt(MeNH(2))(2)(9-MeG-N7)(2)] (6 a) has likewise been isolated, and its acid-base properties determined. Compound 6 a is more basic than 3 a by more than 4 log units. Binding of metal entities to the N7 positions of 9-MeG in 3 a has been studied in detail for [(NH(3))(3)Pt(II)], trans-[(NH(3))(2)Pt(II)], and [(en)Pd(II)] (en=ethylenediamine) by using (1)H NMR spectroscopy. Without exception, binding of the second metal takes place at N7, but formation of a molecular guanine square with trans-[(Me(2)NH(2))Pt(II)] cross-linking N1 positions and trans-[(NH(3))(2)Pt(II)] cross-linking N7 positions could not be confirmed unambiguously, despite the fact that calculations are fully consistent with its existence.

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“…45. [34] The pK a values given above (average 4.45) thus imply that Pt II bonded to N1 acidifies the rare tautomer, hence N7H, by around 1 log unit.…”

Section: Crystal Structure Analysis Of {Trans-mentioning

confidence: 94%

Section: Methodsmentioning

confidence: 99%

Pt^II Coordination to N1 of 9‐Methylguanine: Why it Facilitates Binding of Additional Metal Ions to the Purine Ring

Müller¹,

Shen²,

Miguel³

et al. 2011

Chemistry A European J

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“…Chloro(diethylenetriamine)platinum(II)chloride (hereafter abbreviated as either [Pt(H 2 NCH 2 CH 2 ) 2 NHCl]Cl or ([Pt(dien)Cl]Cl)), and its methylated analog were synthesized via standard literature procedures. 10 Deuterium oxide (D 2 O, 99.9%) was purchased from Cambridge Isotope Laboratories (Woburn, MA, USA). CH 3 OH, CH 3 CN and pyridine (AR grade) were purchased from Ajax Chemical (Auburn, NSW, Australia).…”

Section: Methodsmentioning

confidence: 99%

“…With recent attention focused on the use of mass spectrometry to examine non-covalent complexes, especially those of biological relevance, 10 we were interested in examining the potential for ion-molecule reactions as structural probes. We were attracted to gas phase H/D exchange reactions since: (i) these can be readily carried out and (ii) a considerable amount of work has been carried out on the H/D exchange reactions of protonated biomolecules, especially peptides.…”

Section: Gas Phase H/d Exchange Reactions Of Non-covalent Complexes Omentioning

confidence: 99%

Gas phase ion-molecule reactions in a modified ion trap: H/D exchange of non-covalent complexes and coordinatively unsaturated platinum complexes

Reid

O’Hair

Styles

et al. 1998

Rapid Commun. Mass Spectrom.

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A commercially available electrospray ionization ion trap mass spectrometer has been modified to carry out gas phase ion-molecule reactions. The ability to study gas phase ion-molecule reactions in conjunction with collision induced dissociation (CID) based methods and the multistage trapping capabilities of the ion trap have been exploited in two ways: (i) gas phase H/D exchange reactions inside the ion trap, coupled with CID tandem mass spectrometry have been used to provide insights into the reactivity of non covalent complexes of amino acids and simple peptides, and (ii) CID prior to performing ion-molecule reactions has been used to synthesize and examine the reactivity of coordinatively unsaturated platinum complexes. # 1998 John

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“…[75,76] The synthesis is complicated by a tendency to form insoluble tetrachloroplatinate salts [75] and further complicated by different solid-state packing motifs that are believed to be responsible for dramatic differences in colour (yellow through red) and solubility. Moreover, no one synthetic route has been identified which is suitable for all differently substituted terpyridines.…”

Section: Synthesis and Characterization Ofmentioning

confidence: 99%

An Estrogen–Platinum Terpyridine Conjugate: DNA and Protein Binding and Cellular Delivery

Hannon

Green

Fisher

et al. 2006

Chemistry A European J

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A platinum metal complex in which terpyridine joins estradiol (via an ethynyl link) to a platinum with a labile ligand (chloride) has been designed, synthesised and its X-ray crystal structure determined. The aim of this work was to link a targeting motif (in this case estrogen) to a metal-based biomolecule recognition unit (the platinum moiety). The target molecule: 17alpha-[4'-ethynyl-2,2':6',2'-terpyridine]-17beta-estradiol platinum(II) chloride (PtEEtpy) has been shown to bind to both human and bovine serum albumin (SA) and to DNA. FTICR mass spectrometry shows that the bimolecular units are in each case linked through coordination to the platinum with displacement of the chloride ligand. Circular dichroism indicates that a termolecular entity involving PtEEtpy, SA and DNA is formed. A range of electrospray mass spectrometry experiments showed that the PtEEtpy complex breaks and forms coordination bonds relatively easily. A whole cell estrogen receptor assay in an estrogen receptor positive cell (MCF-7) confirms binding of both EEtpy and PtEEtpy to the estrogen receptor in cells. The work demonstrates the concept of linking a targeting moiety (in this case estrogen) to a DNA binding agent.

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New routes for the synthesis of chloro(diethylenetriamine) platinum(II) chloride and chloro(2,2′ : 6′,2″-terpyridine) platinum(II) chloride dihydrate

Cited by 132 publications

References 12 publications

Pt^II Coordination to N1 of 9‐Methylguanine: Why it Facilitates Binding of Additional Metal Ions to the Purine Ring

Pt^II Coordination to N1 of 9‐Methylguanine: Why it Facilitates Binding of Additional Metal Ions to the Purine Ring

Gas phase ion-molecule reactions in a modified ion trap: H/D exchange of non-covalent complexes and coordinatively unsaturated platinum complexes

An Estrogen–Platinum Terpyridine Conjugate: DNA and Protein Binding and Cellular Delivery

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New routes for the synthesis of chloro(diethylenetriamine) platinum(II) chloride and chloro(2,2′ : 6′,2″-terpyridine) platinum(II) chloride dihydrate

Cited by 132 publications

References 12 publications

PtII Coordination to N1 of 9‐Methylguanine: Why it Facilitates Binding of Additional Metal Ions to the Purine Ring

PtII Coordination to N1 of 9‐Methylguanine: Why it Facilitates Binding of Additional Metal Ions to the Purine Ring

Gas phase ion-molecule reactions in a modified ion trap: H/D exchange of non-covalent complexes and coordinatively unsaturated platinum complexes

An Estrogen–Platinum Terpyridine Conjugate: DNA and Protein Binding and Cellular Delivery

Contact Info

Product

Resources

About

Pt^II Coordination to N1 of 9‐Methylguanine: Why it Facilitates Binding of Additional Metal Ions to the Purine Ring

Pt^II Coordination to N1 of 9‐Methylguanine: Why it Facilitates Binding of Additional Metal Ions to the Purine Ring