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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2016

Kód důvěrnosti údajů

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

Název periodika

Polyhedron

ISSN

0277-5387

e-ISSN

—

Svazek periodika

103

Číslo periodika v rámci svazku

Jan 8

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

13

Strana od-do

248-260

Kód UT WoS článku

000367761400008

EID výsledku v databázi Scopus

2-s2.0-84949088279