About: Solution properties of metal ion complexes formed with the antiviral and cytostatic nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]-2-amino-6-dimethylaminopurine (PME2A6DMAP)

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About: Solution properties of metal ion complexes formed with the antiviral and cytostatic nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]-2-amino-6-dimethylaminopurine (PME2A6DMAP) Goto Sponge NotDistinct Permalink

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Description	The acidity constants of protonated 9-[2-(phosphonomethoxy) ethyl]-2-amino-6-dimethylaminopurine (H-3(PME2A6DMAP)(+)) are considered, and the stability constants of the M(H;PME2A6DMAP)(+) and M(PME2A6DMAP) complexes (M2+ = Mg2+, Ca2+, Sr2+, Ba2+, Mn2+, Co2+, Ni2+, Cu2+, Zn2+, or Cd2+) were measured by potentiometric pH titrations in aqueous solution (25 degrees C; I = 0.1 mol/L, NaNO3). In the M(H;PME2A6DMAP)(+) species, H+ and M2+ (mainly outersphere) are at the phosphonate group; this is relevant for phosphoryl-diester bridges in nucleic acids because, in the present system, there is no indication for a M2+-purine binding. This contrasts, for example, with the complexes formed by 9-[2-(phosphonomethoxy) ethyl] adenine, M(H;PMEA)(+), where M2+ is mainly situated at the adenine residue. Application of log K-M(R-PO3)(M) vs center dot pK(H(R-PO3))(H) plots for simple phosph(on) ate ligands, R-PO32- (R being a residue that does not affect M2+ binding), proves that all M(PME2A6DMAP) complexes have larger stabilities than what would be expected for a M2+-phosphonate coordination. Comparisons with M(PME-R) complexes, where R is a noncoordinating residue of the (phosphonomethoxy) ethane chain, allow one to conclude that the increased stability is due to the formation of five-membered chelates involving the ether-oxygen of the -CH2-O-CH2-PO32- residue: the percentages of formation of these M(PME2A6DMAP)(cl/O) chelates, which occur in intramolecular equilibria, vary between 20% (Sr2+, Ba2+) and 50% (Zn2+, Cd2+), up to a maximum of 67% (Cu2+). Any M2+ interaction with N3 or N7 of the purine moiety, as in the parent M(PMEA) complexes, is suppressed by the (C2)NH2 and (C6)N(CH3)(2) substituents. This observation, together with the previously determined stacking properties, offers an explanation why PME2A6DMAP(2-) has remarkable therapeutic effects. The acidity constants of protonated 9-[2-(phosphonomethoxy) ethyl]-2-amino-6-dimethylaminopurine (H-3(PME2A6DMAP)(+)) are considered, and the stability constants of the M(H;PME2A6DMAP)(+) and M(PME2A6DMAP) complexes (M2+ = Mg2+, Ca2+, Sr2+, Ba2+, Mn2+, Co2+, Ni2+, Cu2+, Zn2+, or Cd2+) were measured by potentiometric pH titrations in aqueous solution (25 degrees C; I = 0.1 mol/L, NaNO3). In the M(H;PME2A6DMAP)(+) species, H+ and M2+ (mainly outersphere) are at the phosphonate group; this is relevant for phosphoryl-diester bridges in nucleic acids because, in the present system, there is no indication for a M2+-purine binding. This contrasts, for example, with the complexes formed by 9-[2-(phosphonomethoxy) ethyl] adenine, M(H;PMEA)(+), where M2+ is mainly situated at the adenine residue. Application of log K-M(R-PO3)(M) vs center dot pK(H(R-PO3))(H) plots for simple phosph(on) ate ligands, R-PO32- (R being a residue that does not affect M2+ binding), proves that all M(PME2A6DMAP) complexes have larger stabilities than what would be expected for a M2+-phosphonate coordination. Comparisons with M(PME-R) complexes, where R is a noncoordinating residue of the (phosphonomethoxy) ethane chain, allow one to conclude that the increased stability is due to the formation of five-membered chelates involving the ether-oxygen of the -CH2-O-CH2-PO32- residue: the percentages of formation of these M(PME2A6DMAP)(cl/O) chelates, which occur in intramolecular equilibria, vary between 20% (Sr2+, Ba2+) and 50% (Zn2+, Cd2+), up to a maximum of 67% (Cu2+). Any M2+ interaction with N3 or N7 of the purine moiety, as in the parent M(PMEA) complexes, is suppressed by the (C2)NH2 and (C6)N(CH3)(2) substituents. This observation, together with the previously determined stacking properties, offers an explanation why PME2A6DMAP(2-) has remarkable therapeutic effects. (en)
Title	Solution properties of metal ion complexes formed with the antiviral and cytostatic nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]-2-amino-6-dimethylaminopurine (PME2A6DMAP) Solution properties of metal ion complexes formed with the antiviral and cytostatic nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]-2-amino-6-dimethylaminopurine (PME2A6DMAP) (en)
skos:prefLabel	Solution properties of metal ion complexes formed with the antiviral and cytostatic nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]-2-amino-6-dimethylaminopurine (PME2A6DMAP) Solution properties of metal ion complexes formed with the antiviral and cytostatic nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]-2-amino-6-dimethylaminopurine (PME2A6DMAP) (en)
skos:notation	RIV/61388963:_____/14:00435258!RIV15-AV0-61388963
http://linked.open...avai/riv/aktivita	I
http://linked.open...avai/riv/aktivity	I
http://linked.open...iv/cisloPeriodika	8
http://linked.open...vai/riv/dodaniDat	2015
http://linked.open...aciTvurceVysledku	Holý, Antonín
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	45920
http://linked.open...ai/riv/idVysledku	RIV/61388963:_____/14:00435258
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	acyclic nucleoside phosphonates; antivirals; intramolecular equilibria; metal-ion complexes; nucleotide analogues; stability constants (en)
http://linked.open.../riv/klicoveSlovo	antivirals nucleotide analogues acyclic nucleoside phosphonates stability constants intramolecular equilibria metal-ion complexes
http://linked.open...odStatuVydavatele	CA - Kanada
http://linked.open...ontrolniKodProRIV	[E193E2D1873F]
http://linked.open...i/riv/nazevZdroje	Canadian Journal of Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	5 (xsd:int)
http://linked.open...UplatneniVysledku	2014
http://linked.open...v/svazekPeriodika	92
http://linked.open...iv/tvurceVysledku	Holý, Antonín Gómez-Coca, R. B. Operschall, B. P. Sigel, A. Sigel, H.
http://linked.open...ain/vavai/riv/wos	000343117300013
issn	0008-4042
number of pages	10 (xsd:int)
http://bibframe.org/vocab/doi	10.1139/cjc-2014-0041

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