The crystal structures of four models for the binding to DNA of cisplatinum derivatives containing a bidentate tertiary diamine

Orbell, John D.; Taylor, Max R.; Birch, S.L.; Lawton, S. E.; Vilkins, L. M.; Keefe, Lisa J.

doi:10.1016/s0020-1693(00)83344-7

Cited by 41 publications

(47 citation statements)

References 10 publications

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“…[16,22,23,27,28] However, two DHT subforms, which differ only in the canting direction (either righthanded (R) or left-handed (L) Figure 8) are possible. For a right-hand canted DHT rotamer (b in Figure 8), the sixmembered ring of each guanine leans towards the cis-guanine.…”

Section: Discussionmentioning

confidence: 99%

X‐ray Structure and Circular Dichroism of Pure Rotamers of Bis[guanosine‐5′‐monophosphate(−1)](N,N,N′,N′‐tetramethylcyclohexyl‐1,2‐diamine)platinum(II) Complexes That Have R,R and S,S Configurations at the Asymmetric Diamine

Benedetti

Tamasi

Cini

et al. 2003

Chemistry A European J

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The use of a sterically hindered diamine ligand (Me(4)DACH) has allowed for the first time, the isolation and characterization, both in the solid state (X-ray crystallography) and in solution (circular dichroism), of pure DeltaHT rotamers of [Pt(Me(4)dach)(5'-GMP)(2)] (compounds 1 and 2 for R,R and S,S configurations of the Me(4)DACH ligand, respectively). Comparison of the CD spectra obtained for each rotamer, which differ only in the chirality of the Me(4)DACH ligand (R,R or S,S) or in the chirality of the HT conformation (Delta or Lambda), allowed us to conclude that, in the 200-350 nm range, the contributions to the overall CD spectrum that stem from diamine chirality and diamine-induced chirality of platinum d--d transitions or from sugar chirality are negligible relative to the exciton chiral coupling that occurs for pi-pi* transitions of the cis guanines. Accurate molecular structures of 1.10 D(2)O and 2.14 D(2)O (conventional crystallographic agreement indexes R(1) convergent to 2.07 % and 2.18 %, respectively) revealed that the crystallized rotamers have a DeltaHT conformation that is in agreement with all previously reported X-ray structures of [Pt(diamine)(nucleos(t)ide)(2)] complexes. This conformation allows the 5'-phosphate to be located in proximity to the Me(4)DACH ligand so that (P)O...HC(N) hydrogen-bond interactions exists in both complexes. For both structures, the canting of the guanine planes on the coordination plane is right-handed (R; canting angle (Phi) of 80.9 degrees and 73.2 degrees, respectively); this indicates that the canting direction is driven by the HT conformation chirality (Delta for both compounds) and not by the chirality of the carrier ligand (different for the two compounds). Density functional theory analysis of the conformational space as a function of Phi indicated a good agreement between the computed and experimental structures. The increase in energy for Phi values below 65 degrees and 55 degrees (for 1 and 2, respectively) is mainly due to the short intramolecular contacts between C(8)H and the cis N-Me groups on the same side of the platinum coordination plane.

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Section: Discussionmentioning

confidence: 99%

X‐ray Structure and Circular Dichroism of Pure Rotamers of Bis[guanosine‐5′‐monophosphate(−1)](N,N,N′,N′‐tetramethylcyclohexyl‐1,2‐diamine)platinum(II) Complexes That Have R,R and S,S Configurations at the Asymmetric Diamine

Benedetti

Tamasi

Cini

et al. 2003

Chemistry A European J

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“…The activity of cis-PtA 2 X 2 compounds was found to decrease in the series A = NH 3 > RNH 2 > R 2 NH. 11 This correlation with the number of amine hydrogens led to speculation about hydrogen-bond formation between the amine NH's and a nucleotide-phosphate or a guanine-O6 of the cross-link. [10][11][12] In order to investigate the effect of substituents on the amine carrier ligand upon the interaction of platinum drugs with DNA bases, diamine ligands having C 2 symmetry and one alkyl substituent and one hydrogen on each coordinated nitrogen, were selected.…”

Section: Introductionmentioning

confidence: 99%

“…11 This correlation with the number of amine hydrogens led to speculation about hydrogen-bond formation between the amine NH's and a nucleotide-phosphate or a guanine-O6 of the cross-link. [10][11][12] In order to investigate the effect of substituents on the amine carrier ligand upon the interaction of platinum drugs with DNA bases, diamine ligands having C 2 symmetry and one alkyl substituent and one hydrogen on each coordinated nitrogen, were selected. Moreover, the stereochemistry of the carrier ligand was preorganized by introducing chiral carbon centres in the chain linking the two nitrogens.…”

Section: Introductionmentioning

confidence: 99%

Chiral discrimination in the formation reaction and at equilibrium for N,N,N′,N′-tetramethyl-1,2-diaminocyclohexane–PtG2 complexes

et al. 2003

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“…(Orbell, Taylor, Birch, Lawton, Vilkins & Keefe, 1988). In the perchlorate salt of the [PtCI(H2C--CH2)(tmen)] cation, the Pt--N bond distance trans to the C1 atom is 2-084 (2)A and the other Pt--N distance is 2.119(2)A (Gervasio, Mason, Maresca & Natile, 1986).…”

mentioning

confidence: 99%

Structure of potassium thiosaccharinate monohydrate

Penavić¹,

Grupče²,

Jovanovski³

1991

Acta Crystallogr C

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The crystal structures of four models for the binding to DNA of cisplatinum derivatives containing a bidentate tertiary diamine

Cited by 41 publications

References 10 publications

X‐ray Structure and Circular Dichroism of Pure Rotamers of Bis[guanosine‐5′‐monophosphate(−1)](N,N,N′,N′‐tetramethylcyclohexyl‐1,2‐diamine)platinum(II) Complexes That Have R,R and S,S Configurations at the Asymmetric Diamine

X‐ray Structure and Circular Dichroism of Pure Rotamers of Bis[guanosine‐5′‐monophosphate(−1)](N,N,N′,N′‐tetramethylcyclohexyl‐1,2‐diamine)platinum(II) Complexes That Have R,R and S,S Configurations at the Asymmetric Diamine

Chiral discrimination in the formation reaction and at equilibrium for N,N,N′,N′-tetramethyl-1,2-diaminocyclohexane–PtG2 complexes

Structure of potassium thiosaccharinate monohydrate

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