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Statements

Subject Item
n2:RIV%2F61388963%3A_____%2F12%3A00385302%21RIV13-AV0-61388963
rdf:type
skos:Concept n15:Vysledek
dcterms:description
The acidity constants of twofold protonated, antivirally active, acyclic nucleoside phosphonates (ANPs), 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA), 2-amino-9-[2-(phosphonomethoxy)ethyl]purine (PME2AP), 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine (PMEDAP), or 2-amino-6-(dimethylamino)-9-[2-(phosphonomethoxy)ethyl]purine (PME(2A6DMAP), as well as the stability constants of the corresponding ternary Cu complexes are compared. The constants for the systems containing PMEDAP and PME(2A6DMAP) have been determined now by potentiometric pH titrations in aqueous solution at I=0.1M (NaNO3) and 25 degrees; the corresponding results for the other ANPs were taken from our earlier work. The basicity of the terminal phosphonate group is very similar for all the ANP species, whereas the addition of a second amino substituent at the pyrimidine ring of the purine moiety significantly increases the basicity of the N(1) site. Detailed stability-constant comparisons for mixed-ligand Cu(II) complexes and the role of pi-pi stacking between the aromatic rings and the purine moiety are discussed. There are indications that ternary Cu(Arm)(2+)-bridged stacks as well as unbridged (binary) stacks are formed. The 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 kind of intramolecular interaction within the complexes. The observed stability enhancements are mainly attributed to intramolecular-stack formation in the Cu(Arm)(PE) complexes and also, to a smaller extent, to the formation of five-membered chelates involving the ether O-atom present in the -CH2-O-CH2-PO3 residue. Comparison of the various formation degrees of the species formed reveals that, in the Cu(phen)(PE) complexes, intramolecular-stack formation is more pronounced than in the Cu(bpy)(PE) species. The acidity constants of twofold protonated, antivirally active, acyclic nucleoside phosphonates (ANPs), 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA), 2-amino-9-[2-(phosphonomethoxy)ethyl]purine (PME2AP), 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine (PMEDAP), or 2-amino-6-(dimethylamino)-9-[2-(phosphonomethoxy)ethyl]purine (PME(2A6DMAP), as well as the stability constants of the corresponding ternary Cu complexes are compared. The constants for the systems containing PMEDAP and PME(2A6DMAP) have been determined now by potentiometric pH titrations in aqueous solution at I=0.1M (NaNO3) and 25 degrees; the corresponding results for the other ANPs were taken from our earlier work. The basicity of the terminal phosphonate group is very similar for all the ANP species, whereas the addition of a second amino substituent at the pyrimidine ring of the purine moiety significantly increases the basicity of the N(1) site. Detailed stability-constant comparisons for mixed-ligand Cu(II) complexes and the role of pi-pi stacking between the aromatic rings and the purine moiety are discussed. There are indications that ternary Cu(Arm)(2+)-bridged stacks as well as unbridged (binary) stacks are formed. The 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 kind of intramolecular interaction within the complexes. The observed stability enhancements are mainly attributed to intramolecular-stack formation in the Cu(Arm)(PE) complexes and also, to a smaller extent, to the formation of five-membered chelates involving the ether O-atom present in the -CH2-O-CH2-PO3 residue. Comparison of the various formation degrees of the species formed reveals that, in the Cu(phen)(PE) complexes, intramolecular-stack formation is more pronounced than in the Cu(bpy)(PE) species.
dcterms:title
Extent of Intramolecular p-Stacks in Aqueous Solution in Mixed-Ligand Copper(II) Complexes Formed by Heteroaromatic Amines and Several 2-Aminopurine Derivatives of the Antivirally Active Nucleotide Analog 9-[2-(Phosphonomethoxy)ethyl]adenine (PMEA) Extent of Intramolecular p-Stacks in Aqueous Solution in Mixed-Ligand Copper(II) Complexes Formed by Heteroaromatic Amines and Several 2-Aminopurine Derivatives of the Antivirally Active Nucleotide Analog 9-[2-(Phosphonomethoxy)ethyl]adenine (PMEA)
skos:prefLabel
Extent of Intramolecular p-Stacks in Aqueous Solution in Mixed-Ligand Copper(II) Complexes Formed by Heteroaromatic Amines and Several 2-Aminopurine Derivatives of the Antivirally Active Nucleotide Analog 9-[2-(Phosphonomethoxy)ethyl]adenine (PMEA) Extent of Intramolecular p-Stacks in Aqueous Solution in Mixed-Ligand Copper(II) Complexes Formed by Heteroaromatic Amines and Several 2-Aminopurine Derivatives of the Antivirally Active Nucleotide Analog 9-[2-(Phosphonomethoxy)ethyl]adenine (PMEA)
skos:notation
RIV/61388963:_____/12:00385302!RIV13-AV0-61388963
n15:predkladatel
n16:ico%3A61388963
n3:aktivita
n14:Z n14:P
n3:aktivity
P(1M0508), Z(AV0Z40550506)
n3:cisloPeriodika
9
n3:dodaniDat
n6:2013
n3:domaciTvurceVysledku
n12:9587217
n3:druhVysledku
n18:J
n3:duvernostUdaju
n13:S
n3:entitaPredkladatele
n11:predkladatel
n3:idSjednocenehoVysledku
135924
n3:idVysledku
RIV/61388963:_____/12:00385302
n3:jazykVysledku
n17:eng
n3:klicovaSlova
copper complexes; nucleotides; acyclic nucleoside phosphonates; ANPs; antiviral activity
n3:klicoveSlovo
n10:copper%20complexes n10:ANPs n10:acyclic%20nucleoside%20phosphonates n10:antiviral%20activity n10:nucleotides
n3:kodStatuVydavatele
DE - Spolková republika Německo
n3:kontrolniKodProRIV
[1E005C6E88A2]
n3:nazevZdroje
Chemistry & Biodiversity
n3:obor
n19:CE
n3:pocetDomacichTvurcuVysledku
1
n3:pocetTvurcuVysledku
6
n3:projekt
n9:1M0508
n3:rokUplatneniVysledku
n6:2012
n3:svazekPeriodika
9
n3:tvurceVysledku
Sigel, H. Gómez-Coca, R. B. Operschall, B. P. Sigel, A. Holý, Antonín Blindauer, C. A.
n3:wos
000308715800032
n3:zamer
n20:AV0Z40550506
s:issn
1612-1872
s:numberOfPages
27
n8:doi
10.1002/cbdv.201200022