Co-ordination chemistry of adenine (HAde): synthesis and characterization of [CuII(tren)(nucleobase)]X2[tren = tris-(2-aminoethyl)amine, X = Cl or NO3] complexes and crystal structure of [CuII(tren)(Ade)]Cl·2H2O

Marzotto, A.; Ciccarese, Antonella; Clemente, D. A.; Valle, G.

doi:10.1039/dt9950001461

Cited by 47 publications

(28 citation statements)

References 35 publications

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“…4 • . 48 For comparison, these angles are 103.5 and 105.6 • in the compound (9H-adenine)•2H 2 O. 49 It is now well-documented that DNA bases can undergo proton shifts while keeping their neutrality and form different tautomers.…”

Section: Description Of Structures [Mn(l-ox)(h 2 O)(7h-pur-jn 9 )] N ...mentioning

confidence: 99%

Supramolecular architectures assembled by the interaction of purine nucleobases with metal-oxalato frameworks. Non-covalent stabilization of the 7H-adenine tautomer in the solid-state

et al. 2006

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The synthesis, crystal structure and variable-temperature magnetic measurements of the compounds [Mn(mu-ox)(H2O)(7H-pur-kappaN9)]n (1), {[Mn(mu-ox)(H2O)2].(7H-ade).(H2O)}n (2) and {[Cu(mu-ox)(H2O)(7H-ade-kappaN9)][Cu(mu-ox)(mu-H2O)(7H-ade-kappaN9)]. approximately 10/3H2O}n (3), (where ox: oxalato dianion, pur: purine, and ade: adenine) are reported. Compounds 1and 2 contain one-dimensional chains in which manganese(II) atoms are bridged by bis-bidentate oxalato ligands. The distorted octahedral geometry around each metal centre is completed in compound 1 by one water molecule and the imidazole N9 donor site of the purine ligand, which is a rare example of direct binding between the Mn(II) ion and the N donor site of an isolated nucleobase. Unlike 1, the adenine moiety in compound 2 is not bonded to manganese atoms and the metal coordination polyhedron is filled by two water molecules in a cis-arrangement. Its crystal building is constructed from pi-stacked layers of Watson-Crick hydrogen-bonded adenine...(H2O2)...adenine aggregates and zig-zag Mn(II)-oxalato chains held together by means of a strong network of hydrogen bonding interactions. The nucleobase exists in the lattice as the 7H-adenine tautomer which represents an unprecedented solid-state characterization of this minor tautomer as free molecule (without metal coordination) stabilized through non-covalent interactions. Compound consists of two slightly different [Cu(ox)(H2O)(7H-ade-kappaN9)] units in which the nucleobase coordinates through the imidazole N9 atom. The planar complex entities are parallel stacked and joined by means of long Cu-O bonds involving oxygen atoms from the oxalato and the aqua ligands, giving one-dimensional chains with a [4 + 1] square-planar pyramidal and a [4 + 2] octahedral coordination around the metal centre, respectively. Self-assembled process of compound 3 is further driven by an in-plane network of hydrogen bonding interactions to generate a porous 3D structure containing parallel channels filled by guest water molecules. Variable-temperature magnetic susceptibility measurements of all the complexes show the occurrence of antiferromagnetic interactions between the paramagnetic centres. DFT calculations have been performed to check the influence of packing in the stability of the 7H-amino tautomer of 2 and in the complex geometry of 3.

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Section: Description Of Structures [Mn(l-ox)(h 2 O)(7h-pur-jn 9 )] N ...mentioning

confidence: 99%

Supramolecular architectures assembled by the interaction of purine nucleobases with metal-oxalato frameworks. Non-covalent stabilization of the 7H-adenine tautomer in the solid-state

et al. 2006

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“…It is well-known that the protonation at N sites in similar cycles, such as nucleobases, does not modify substantially the bond distances, but it enlarges the endocyclic C–N–C angles up to 4° as a consequence of the absence of the lone pair in those N atoms. , In the present case, those angles may be compared to N–N–C angles of the pyrazole ring. In good agreement with the last argument, a systematic enlargement of the latter angle is observed for the three ligands [110.8 vs 107.2° (A ligand), 110.4 vs 106.9° (B ligand), and 110.6 vs 107.8° (C ligand) for C5–N1–N2 and N1–N2–C3 angles, respectively], thus confirming the location of those hydrogen atoms.…”

Section: Resultsmentioning

confidence: 64%

Modulating Anticancer Potential by Modifying the Structural Properties of a Family of Zinc Metal–Organic Chains Based on 4-Nitro-1H-pyrazole

Fernández

Cepeda

et al. 2017

Crystal Growth & Design

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We have synthesized a novel family of metal−organic chains based on 4-nitro-1H-pyrazole linker and zinc as metal center. We report the formation of these coordination polymers using hydrothermal routes with water as solvent. These materials display one-dimensional structures with major structural modifications from minimal synthetic variations. What is more interesting, we have carried out antitumor measurements, and we have related these properties with the structural networks. To the best of our knowledge, these materials constitute the first examples of polymeric structures for 4-NO 2pz ligands. NMR and MS spectrometry were used to verify the characterization of the metal complexes in solution to corroborate that these materials are present in the biological assays.

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“…These copper conjugates showed significant growth inhibition in both cell lines (IC 50 values of 3-26 μM). Binuclear copper(II) complexes with 6-(2-chlorobenzylamino)purine, 6-(3-chlorobenzylamino)purine and chloride ions are found to be several times more potent than the mononuclear complex against human malignant melanoma G361 and human osteogenic sarcoma HOS cell lines with IC 50 values ranging from 20 to 88 μM [58].…”

Section: In Vitro Cytotoxic Activitymentioning

confidence: 98%

Preparation and pharmacochemical evaluation of mixed ligand copper(II) complexes with triethanolamine and thiophenyl-2 saturated carboxylic acids

Boulsourani

Geromichalos

Repana

et al. 2011

Journal of Inorganic Biochemistry

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Co-ordination chemistry of adenine (HAde): synthesis and characterization of [Cu^II(tren)(nucleobase)]X₂[tren = tris-(2-aminoethyl)amine, X = Cl or NO₃] complexes and crystal structure of [Cu^II(tren)(Ade)]Cl·2H₂O

Cited by 47 publications

References 35 publications

Supramolecular architectures assembled by the interaction of purine nucleobases with metal-oxalato frameworks. Non-covalent stabilization of the 7H-adenine tautomer in the solid-state

Supramolecular architectures assembled by the interaction of purine nucleobases with metal-oxalato frameworks. Non-covalent stabilization of the 7H-adenine tautomer in the solid-state

Modulating Anticancer Potential by Modifying the Structural Properties of a Family of Zinc Metal–Organic Chains Based on 4-Nitro-1H-pyrazole

Preparation and pharmacochemical evaluation of mixed ligand copper(II) complexes with triethanolamine and thiophenyl-2 saturated carboxylic acids

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