Extent of intramolecular pi stacks in aqueous solution in mixed-ligand copper(II) complexes formed by heteroaromatic amines and the anticancer and antivirally active 9[2-(phosphonomethoxy)ethyl]guanine (PMEG). A comparison with related acyclic nucleotide analogues

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F16%3A00458528" target="_blank" >RIV/61388963:_____/16:00458528 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1016/j.poly.2015.02.022" target="_blank" >http://dx.doi.org/10.1016/j.poly.2015.02.022</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.poly.2015.02.022" target="_blank" >10.1016/j.poly.2015.02.022</a>

Result language

angličtina

Original language name

Extent of intramolecular pi stacks in aqueous solution in mixed-ligand copper(II) complexes formed by heteroaromatic amines and the anticancer and antivirally active 9[2-(phosphonomethoxy)ethyl]guanine (PMEG). A comparison with related acyclic nucleotide analogues

Original language description

The acyclic nucleoside phosphonate (ANP(2-))9-[2-(phosphonomethoxy)ethyliguanine (PMEG) is anticancer and antivirally active. The acidity constants of the threefold protonated H-3(PMEG)(+) were determined by potentiometric pH titrations (aq. sol.; 25 degrees C; I = 0.1 M, NaNO3). Under the same conditions and by the same method, the stability constants of the binary Cu(H;PMEG)(+) and Cu(PMEG) complexes as well as those of the ternary ones containing a heteroaromatic N ligand (Arm), that is, of Cu(Arm)(H;PMEG)(+) and Cu(Arm)(PMEG), where Arm = 2,2'-bipyridine (Bpy) or 1,10-phenanthroline (Phen), were measured. The corresponding equilibrium constants, taken from our earlier work for the systems with 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) and 9[2-(phosphonomethoxy)ethyl]-2,6-diaminopurine (PMEDAP) as well as those for Cu(PME) and Cu(Arm)(PME), where PME2- = (phosphonomethoxy)ethane = (ethoxymethyl)phosphonate, were used for comparisons. These reveal that in the monoprotonated ternary Cu(Arm)(H;PE)(+) complexes, the proton and Cu(Arm)(2+) are at the phosphonate group; the ether oxygen of the -CH2-O-CH2-P(O)(2)(-)(OH) residue also participates to some extent in Cu(Arm)(2+). coordination. Furthermore, the coordinated Cu(Arm)(2+) forms a bridge with the purine moiety undergoing pi-pi stacking which is more pronounced with H center dot PMEDAP(-) than with H center dot PMEA(-). Most intense is pi stack formation (st) with the guanine residue of H center dot PMEG(-); here the bridged form Cu(Arm)(H.PMEG)(st)(+) occurs next to an open (op), unbridged (binary) stack, formulated as Cu(Arm)(2+)/(H.PMEG)(op)(-). The unprotonated and neutral ternary Cu(Arm)(PE) complexes are considerably more stable than the corresponding Cu(Arm)(R-PO3) species, where R-PO32- represents a phosph(on)ate ligand with a group R that is unable to participate in any intramolecular interaction.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

—

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2016

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Polyhedron

ISSN

0277-5387

e-ISSN

—

Volume of the periodical

103

Issue of the periodical within the volume

Jan 8

Country of publishing house

GB - UNITED KINGDOM

Number of pages

13

Pages from-to

248-260

UT code for WoS article

000367761400008

EID of the result in the Scopus database

2-s2.0-84949088279