Crystal packing and hydrogen bonding in platinum(II) nucleotide complexes: X-ray crystal structure of [Pt(MeSCH2CH2SMe)(5′-GMP-N7)2]·6H2O

Djuran, Miloš I.; Milinković, Snežana U.; Habtemariam, Abraha; Parsons, Simon; Sadler, Peter J.

doi:10.1016/s0162-0134(01)00351-8

Cited by 14 publications

(20 citation statements)

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“…One of the imidazolyl rings is tilted by 19.1° and the other ring by 10.0°. The Pt–N7( G ) bond of 2.007(8) Å in 5 falls within the typical Pt–N7( G ) bond distance ranges reported for mono adducts − (1.99–2.07 Å) and for bis adducts ,− (2.02–2.08 Å). The metric parameters and conformational features of the 3′-GMPH ligand are normal and are described in the Supporting Information.…”

Section: Resultssupporting

confidence: 80%

“…An analysis by Yao et al of crystallographic data for cis -[PtL 2 G 2 ] type structures available at the time demonstrated a linear correlation (R = 0.897) between the rocking angle and the Pt–O6 non bonded distance . The linear correlation also accounts for the Pt–O6 distance in 5 (3.40 Å) and in all relevant structures published after the report by Yao et al and discussed here. ,− ,− …”

Section: Resultsmentioning

confidence: 56%

“…The typical range of the rocking angle, identified some years ago as being about −2 to +11°, indicates that the Pt–N7–C8 angle is normally smaller than the Pt–N7–C5 angle. Rocking angles in more recent structures also almost always fall in this range. ,,,,− Mono adducts tend to be at the lower end of this range. Small rocking angles usually are observed when the structure has no clear intramolecular interactions, as in [Pt( N (H)-1,1′-Me 2 dma)(3′-GMPH)] + ( 5 ), which has a positive rocking angle of 1.4°.…”

Section: Resultsmentioning

confidence: 83%

“…The molecular structure of [Pt( N (H)-1,1′-Me 2 dma)(3′-GMPH)]NO 3 ·5H 2 O ( 5 ) allows us to compare the proximity of the phosphate group to Pt(II) and N7 to such distances in structurally characterized 5′-GMP complexes, all of which are bis adducts. − , Nonbonded distances were obtained from crystallographically determined molecular structures by using Mercury 3.7 software. For our purposes, we use the central P atom to gauge the distance of the phosphate group to the other atoms.…”

Section: Resultsmentioning

confidence: 99%

“…Other relevant structures with one Pt–N7 bond do not contain a nucleotide; these are [Pt(dien)(guanosine)](ClO 4 ) 2 , [Pt(dien)(inosine)](NO 3 ) 2 ·H 2 O, [Pt(NH 3 ) 3 (9-methylhypoxanthine)]Cl(NO 3 )·1.5H 2 O, [Pt(NH 3 ) 3 (9-ethylhypoxanthine)]Cl(NO 3 )·H 2 O, and cis -[Pt(NH 3 ) 2 ( N 2 , N 2 -dimethyl-9-methylguanine)Cl]PF 6 . In contrast, there are many reported structures of complexes with two cis Pt–N7 bonds to G ligands, quite often 5′-GMP. ,− …”

Section: Introductionmentioning

confidence: 99%

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A Very Rare Example of a Structurally Characterized 3′-GMP Metal Complex. NMR and Synthetic Assessment of Adducts Formed by Guanine Derivatives with [Pt(L^tri)Cl]Cl Complexes with an N,N′,N″ Tridentate Ligand (L^tri) Terminated by Imidazole Rings

et al. 2017

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[Pt(N(R)-1,1'-Medma)Cl]Cl complexes with tridentate ligands (bis(1-methyl-2-methylimidazolyl)amine, R = H; N-(methyl)bis(1-methyl-2-methylimidazolyl)amine, R = Me) were prepared in order to investigate Pt(N(R)-1,1'-Medma)G adducts (G = monodentate N9-substituted guanine or hypoxanthine derivative). Solution NMR spectroscopy is the primary tool for studying metal complexes of nucleosides and nucleotides because such adducts rarely crystallize. However, [Pt(N(H)-1,1'-Medma)(3'-GMPH)]NO·5HO (5) was crystallized, allowing, to our knowledge, the first crystallographic molecular structure determination for a 3'-GMP platinum complex. The structure is one of only a very few structures of a 3'-GMP complex with any metal. Complex 5 has the syn rotamer conformation, with 3'-GMP bound by N7. All Pt(N(R)-1,1'-Medma)G adducts exhibit two new downfield-shifted G H8 signals, consistent with G bound to platinum by N7 and a syn/anti rotamer mixture. Anticancer-active monofunctional platinum(II) complexes have bulky carrier ligands that cause DNA adducts to be distorted. Hence, understanding carrier-ligand steric effects is key in designing new platinum drugs. Ligand bulk can be correlated with the degree of impeded rotation of the G nucleobase about the Pt-N7 bond, as assessed by the observation of rotamers. The signals of syn and anti rotamers are connected by EXSY cross-peaks in 2D ROESY spectra of Pt(N(H)-1,1'-Medma)G adducts but not in spectra of Pt(N(H)dpa)G adducts (N(H)dpa = bis(2-picolyl)amine), indicating that rotamer interchange is more facile and carrier-ligand bulk is lower in Pt(N(H)-1,1'-Medma)G than in Pt(N(H)dpa)G adducts. The lower steric hindrance is a direct consequence of the greater distance of the G nucleobase from the H4/4' protons in the N(R)-1,1'-Medma carrier ligand in comparison to that from the H6/6' protons in the N(H)dpa carrier ligand. Although in 5 the nucleotide is 3'-GMP (not the usual 5'-GMP) and the N(H)-1,1'-Medma carrier ligand is very different from those typically present in structurally characterized Pt(II) G complexes, the rocking and canting angles in 5 adhere to long-recognized trends.

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Section: Resultssupporting

confidence: 80%

Section: Resultsmentioning

confidence: 56%

Section: Resultsmentioning

confidence: 83%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

A Very Rare Example of a Structurally Characterized 3′-GMP Metal Complex. NMR and Synthetic Assessment of Adducts Formed by Guanine Derivatives with [Pt(L^tri)Cl]Cl Complexes with an N,N′,N″ Tridentate Ligand (L^tri) Terminated by Imidazole Rings

et al. 2017

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Nucleic Acid-Metal Ion Interactions in the Solid State

Aoki

Murayama

2011

Metal Ions in Life Sciences

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Metal ions play a key role in nucleic acid structure and activity. Elucidation of the rules that govern the binding of metal ions is therefore an essential step for better understanding of the nucleic acid functions. This review is as an update to a preceding one (Metal Ions Biol. Syst., 1996, 32, 91-134), in which we offered a general view of metal ion interactions with mono-, di-, tri-, and oligonucleotides in the solid state, based on their crystal structures reported before 1994. In this chapter, we survey all the crystal structures of metal ion complexes with nucleotides involving oligonucleotides reported after 1994 and we have tried to uncover new characteristic metal bonding patterns for mononucleotides and oligonucleotides with A-RNA and A/B/Z-DNA fragments that form duplexes. We do not cover quadruplexes, duplexes with metal-mediated base-pairs, tRNAs, rRNAs in ribosome, ribozymes, and nucleic acid-drug and -protein complexes. Factors that affect metal binding to mononucleotides and oligonucleotide duplexes are also dealt with.

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Supramolecular Chemistry of Organoplatinum(IV) Complexes Bearing Ligands with Remote Carboxylic Acid Substituents

Abo-Amer

Puddephatt

2013

J Inorg Organomet Polym

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Crystal packing and hydrogen bonding in platinum(II) nucleotide complexes: X-ray crystal structure of [Pt(MeSCH2CH2SMe)(5′-GMP-N7)2]·6H2O

Cited by 14 publications

References 20 publications

A Very Rare Example of a Structurally Characterized 3′-GMP Metal Complex. NMR and Synthetic Assessment of Adducts Formed by Guanine Derivatives with [Pt(L^tri)Cl]Cl Complexes with an N,N′,N″ Tridentate Ligand (L^tri) Terminated by Imidazole Rings

A Very Rare Example of a Structurally Characterized 3′-GMP Metal Complex. NMR and Synthetic Assessment of Adducts Formed by Guanine Derivatives with [Pt(L^tri)Cl]Cl Complexes with an N,N′,N″ Tridentate Ligand (L^tri) Terminated by Imidazole Rings

Nucleic Acid-Metal Ion Interactions in the Solid State

Supramolecular Chemistry of Organoplatinum(IV) Complexes Bearing Ligands with Remote Carboxylic Acid Substituents

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Crystal packing and hydrogen bonding in platinum(II) nucleotide complexes: X-ray crystal structure of [Pt(MeSCH2CH2SMe)(5′-GMP-N7)2]·6H2O

Cited by 14 publications

References 20 publications

A Very Rare Example of a Structurally Characterized 3′-GMP Metal Complex. NMR and Synthetic Assessment of Adducts Formed by Guanine Derivatives with [Pt(Ltri)Cl]Cl Complexes with an N,N′,N″ Tridentate Ligand (Ltri) Terminated by Imidazole Rings

A Very Rare Example of a Structurally Characterized 3′-GMP Metal Complex. NMR and Synthetic Assessment of Adducts Formed by Guanine Derivatives with [Pt(Ltri)Cl]Cl Complexes with an N,N′,N″ Tridentate Ligand (Ltri) Terminated by Imidazole Rings

Nucleic Acid-Metal Ion Interactions in the Solid State

Supramolecular Chemistry of Organoplatinum(IV) Complexes Bearing Ligands with Remote Carboxylic Acid Substituents

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A Very Rare Example of a Structurally Characterized 3′-GMP Metal Complex. NMR and Synthetic Assessment of Adducts Formed by Guanine Derivatives with [Pt(L^tri)Cl]Cl Complexes with an N,N′,N″ Tridentate Ligand (L^tri) Terminated by Imidazole Rings

A Very Rare Example of a Structurally Characterized 3′-GMP Metal Complex. NMR and Synthetic Assessment of Adducts Formed by Guanine Derivatives with [Pt(L^tri)Cl]Cl Complexes with an N,N′,N″ Tridentate Ligand (L^tri) Terminated by Imidazole Rings