Hydrogen bonding patterns of 7,9-dimethylguanine and its transplatinum(II) complexes

Sigel, Roland K. O.; Freisinger, Eva; Abbate, Michele; Lippert, Bernhard

doi:10.1016/s0020-1693(02)00962-3

Cited by 13 publications

(5 citation statements)

References 130 publications

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“…All these geometric details make this fragment of the imidazole ring more regular in (II) than in (I). The N7-C8 and N9-C8 bond lengths are also unequal in the recently reported 7,9-dimethylpurinium salts (Hocek et al, 2005;Nasiri et al, 2005;Sigel et al, 2002) represented by structures (III)-(V), respectively (the differences in N-C bond lengths are in the range 0.016-0.025 Å ). As the N7-C8 bond is shorter by 0.017 Å in salt (II), double-bond character can be assigned to this bond and the resonance structure is represented by formula (IIB).…”

Section: Commentmentioning

confidence: 79%

“…Recently, the structures of a few 7,9-dialkylpurinium salts (where the anion is iodide, bromide or perchlorate) have been analyzed (Sigel et al, 2002;Nasiri et al, 2005;Hocek et al, 2005;Fu & Lam, 2005;Torii et al, 2006). We have now determined the crystal structure of 2,6-dimethoxy-7,9dimethylpurinium iodide as its hemihydrate, (II), to obtain information about the positions and conformations of the methoxy groups and the geometry of the imidazole ring in comparison with (I) (Kowalska et al, 1999) in an attempt to explain some results of the internal thermal O-N and N-N migrations of the alkyl groups (Kowalska & Maślankiewicz, 1997).…”

Section: Commentmentioning

confidence: 99%

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2,6-Dimethoxy-7,9-dimethylpurinium iodide hemihydrate

2008

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In the title compound, C(9)H(13)N(4)O(2)(+) x I(-) x 0.5 H(2)O, the non-H atoms of the ionic components lie on a mirror plane in Cmca, with the O atom of the partial water molecule lying on a twofold rotation axis. Whereas one of the methoxy methyl groups is directed away from the adjacent N-methyl group, the other methoxy methyl group is directed towards its adjacent N-methyl group. The conformation of the methoxy methyl groups provides an explanation for the outcomes of intramolecular thermal rearrangements of 2,6-dialkoxy-7,9-dimethylpurinium salts.

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Section: Commentmentioning

confidence: 79%

Section: Commentmentioning

confidence: 99%

2,6-Dimethoxy-7,9-dimethylpurinium iodide hemihydrate

2008

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“…However, studies have shown that due to blockage of N7 of the purine ring, the same hydrogen bonding patterns occur on the minor groove binding face in this nucleobase ( Sigel et al, 2002 ). To further demonstrate the universality of this strategy, we chose bpda (11.2 Å) with larger molecular length as the bridging ligand, and fortunately obtained the single crystal structure of 4.…”

Section: Resultsmentioning

confidence: 99%

The Research of G–Motif Construction and Chirality in Deoxyguanosine Monophosphate Nucleotide Complexes

Zhu

Wang

et al. 2021

Front. Chem.

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A detailed understanding of the mismatched base-pairing interactions in DNA will help reveal genetic diseases and provide a theoretical basis for the development of targeted drugs. Here, we utilized mononucleotide fragment to simulate mismatch DNA interactions in a local hydrophobic microenvironment. The bipyridyl-type bridging ligands were employed as a mild stabilizer to stabilize the GG mismatch containing complexes, allowing mismatch to be visualized based on X-ray crystallography. Five single crystals of 2′-deoxyguanosine–5′–monophosphate (dGMP) metal complexes were designed and obtained via the process of self-assembly. Crystallographic studies clearly reveal the details of the supramolecular interaction between mononucleotides and guest intercalators. A novel guanine–guanine base mismatch pattern with unusual (high anti)–(high anti) type of arrangement around the glycosidic angle conformations was successfully constructed. The solution state 1H–NMR, ESI–MS spectrum studies, and UV titration experiments emphasize the robustness of this g–motif in solution. Additionally, we combined the methods of single-crystal and solution-, solid-state CD spectrum together to discuss the chirality of the complexes. The complexes containing the g–motif structure, which reduces the energy of the system, following the solid-state CD signals, generally move in the long-wave direction. These results provided a new mismatched base pairing, that is g–motif. The interaction mode and full characterizations of g–motif will contribute to the study of the mismatched DNA interaction.

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“…7,9-Dimethylguanine is a rare nucleobase in the cap of message RNA (mRNA) and transfer RNA (tRNA) [26,27] 7,9-Dimethylguanine is converted from N 7 -methylguanine [28], which has various functions in an organism. N 7 -Methylguanine in the 5' cap of mature mRNAs mediates cap-related biological functions and functions as an identifier of self RNA in the innate immune system, then ensures cap-dependent protein synthesis [29].…”

Section: Discussionmentioning

confidence: 99%

Metabolic Analysis of Nucleosides/Bases in the Urine and Serum of Patients with Alcohol-Associated Liver Disease

Vatsalya

et al. 2022

Metabolites

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Accumulating evidence supports the important role of RNA modifications in liver disease pathogenesis. However, RNA modifications in alcohol-associated liver disease (ALD) have not yet been reported. Modified ribonucleosides/bases are products of RNA degradation; therefore, we investigated whether modified ribonucleosides/bases in human urine and serum are changed and whether these changes are associated with the severity of ALD. Human urine and serum samples from patients with ALD and appropriate controls were collected. Free nucleosides/bases were extracted from these samples and quantified using untargeted and targeted metabolomic approaches. Thirty-nine and forty free nucleosides/bases were respectively detected in human urine and serum samples. Twelve and eleven modified nucleosides are significantly changed in patients’ urine and serum (q < 0.05 and fold-change > 20%). The abundance of modified nucleobase and ribonucleoside, 7,9-dimethylguanine in urine and 2-methylthio-N6-threonylcarbamoyladenosine (ms2t6A) in serum are strongly associated with the severity of ALD. Spearman’s rank correlation coefficient of these two metabolites with the Model for End-stage Liver Disease (MELD) score are 0.66 and 0.74, respectively. Notably, the abundance changes in these two metabolites are sufficiently large to distinguish severe alcohol-associate hepatitis (AH) from non-severe ALD and non-severe ALD from healthy controls.

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Hydrogen bonding patterns of 7,9-dimethylguanine and its transplatinum(II) complexes

Cited by 13 publications

References 130 publications

2,6-Dimethoxy-7,9-dimethylpurinium iodide hemihydrate

2,6-Dimethoxy-7,9-dimethylpurinium iodide hemihydrate

The Research of G–Motif Construction and Chirality in Deoxyguanosine Monophosphate Nucleotide Complexes

Metabolic Analysis of Nucleosides/Bases in the Urine and Serum of Patients with Alcohol-Associated Liver Disease

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