Properties of the Ternary (Dien)Pt(PMEA-N7) Complex Containing Diethylenetriamine (Dien) and the Antiviral 9-[2-(Phosphonomethoxy)ethyl]adenine (PMEA). Synthesis, Biological Screening, Acid-Base Behaviour, and Metal Ion-Binding in Aqueous Solution
-
Gunnar Kampf
,
Bernhard Lippert
The synthesis of (Dien)Pt(PMEA-N7), where Dien = diethylenetriamine and PMEA2- = dianion of 9-[2-(phosphonomethoxy)ethyl]adenine, is described. No useful biological activity could be discovered for this complex which is in contrast to the known antiviral properties of PMEA itself. The acidity constants of the twofold protonated H2[(Dien)Pt(PMEA-N7)]2+ complex were determined (UV spectrophotometry and potentiometric pH titration): The release of the proton from the -P(O)2(OH)- group is only slightly affected by the N7-coordinated (Dien)Pt2+ unit, whereas the acidity of the (N1)H+ site is strongly enhanced. The stability constants of the M[(Dien)Pt(PMEA-N7)]2+ complexes with the metal ions M2+ = Mg2+, Ca2+, Mn2+, Co2+, Ni2+, Cu2+, Zn2+, and Cd2+ were measured by potentiometric pH titrations in aqueous solution at 25 °C and I = 0.1 M (NaNO3). Application of previously determined straightline plots of log KM(R-PO3)M versus KH(R-PO3)H for simple phosph(on)ate ligands, R-PO32- where R represents a non-inhibiting residue without an affinity for metal ions, proves that the primary binding site of the complex-ligand, (Dien)Pt(PMEA-N7), with all the metal ions studied is the phosphonate group; in most instances the expected stability is actually reduced by about 0.4 log units due to the N7-bound (Dien)Pt2+ unit. Only for the Cu[(Dien)Pt(PMEA-N7)]2+ and the Zn[(Dien)Pt(PMEA-N7)]2+ systems the formation of some 5-membered chelates involving the ether oxygen atom of the -CH2-O-CH2-PO32- residue could be detected; the formation degrees are 52 ± 9% and 32 ± 14%, respectively. The metal ion-binding properties of (Dien)Pt(PMEA-N7) differ considerably from those of PMEA2-, yet they are relatively similar to those of pyrimidine-nucleoside 5'-monophosphates. The structures of the various complex species in solution are discussed and compared.
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Articles in the same Issue
- Wechselwirkungen in Molekülkristallen, 160 [1,2]. Kristallzüchtung und Strukturbestimmung der verschiedenartigen Polyphenyl-Kontaktionenmultipel [p-Quaterphenylee⊖⊖][Na⊕(DME)3]2, [p-Quaterphenyl⊖⊖(Na⊕(THF)3)2] und [p-Terphenyl⊖⊖Na⊕(DME)2Na⊕(DME)]2 / Interaction in Molecular Crystals, 160 [1, 2]. Crystallization and Structure Determination of the Different Polyphenyl Contact Ion Multiples [p-Quaterphenylee⊖⊖][Na⊕(DME)3]2, [p-Quaterphenyl⊖⊖(Na⊕(THF)3)2] und [p-Terphenyl⊖⊖Na⊕(DME)2Na⊕(DME)]2
- Synthesis and Structure of the Substituted Lithium Benzyl [Li(tmeda)2]+[C(PMe2)(SiMe3)C6H3-3,5-Me2]-. The First Metal Phosphinomethanide Consisting of Solvent-Separated Ion Pairs
- Optical Outer-Sphere Charge Transfer in Ion Pairs with Peroxoborate as Donor
- Enantioselektive Gewinnung und Kristallstruktur des Ecstasy-Analogons N-Ethyl-3,4-methylendioxyamphetamin-HCl (MDE) und seiner beiden Hauptmetaboliten MDA und HME / Enantioselective Production and Crystal Structure of the Ecstasy Analogue N-Ethyl-3,4- methylenedioxyamphetamine-HCl (MDE) and its Major Metabolites MDA and HME
- Synthesis, Crystal Structure and Magnetic Properties of a Novel GdIII -CuII Heterodinuclear Complex
- Atomvolumen und Packungsdichte der Atome in metallischen Elementen Atomic Volume and Packing Density of Atoms in Metallic Elements
- Properties of the Ternary (Dien)Pt(PMEA-N7) Complex Containing Diethylenetriamine (Dien) and the Antiviral 9-[2-(Phosphonomethoxy)ethyl]adenine (PMEA). Synthesis, Biological Screening, Acid-Base Behaviour, and Metal Ion-Binding in Aqueous Solution
- Photochemical Synthesis and Identification of Tetracarbonyl-bis(olefin)metal(0) Complexes of Group VI B Elements
- Structural and Spectroscopic Characterization of Two New Cu(II)-Dipeptide Complexes
- Wechselwirkungen in Molekülkristallen, 163 [1, 2]. Einfluß der Alkalimetall-Reduktionspotentiale auf die Bildung ihrer Kontaktionenmultipel mit Tetracen- und Decacylen-Polyanionen / Interaction in Molecular Crystals, 163 [ 1,2]. The Influence of Alkaline Metal Reduction Potentials on the Formation of their Contaction Multiples with Tetracene and Decacyclene Polyanions
- Reactivity of Cobalt(III) Amine-Thiolate Complexes with Terminal and Bridging Thiolate Functions towards Hydrogen Peroxide
- Monosubstituierte Derivate des Halbsandwich-Komplexes Cp*Ta(CO)4 - Vergleich mit den analogen Vanadiumverbindungen Cp*V(CO)3L und Röntgenstrukturanalyse des γ-Picolin-Komplexes Cp*V(CO)3(NC5H4-Me(4)) / Monosubstituted Derivatives of the Halfsandwich Complex Cp*Ta(CO)4 - Comparison with the Analogous Vanadium Compounds Cp*V(CO)3L and X-Ray Structural Analysis of the γ-Picoline Complex Cp*V(CO)3(NC5H4-Me(4))
- Formation of Methylchloroaluminium Alkanethiolates, MeAl(SR)Cl, and Dichloroaluminium Alkanethiolates, Cl2AlSR, from Methylaluminium Dichloride and Trimethylsilyl Alkanethiolates, Me3SiSR
- Chemischer Transport intermetallischer Phasen III: Das System Co-Si / Chemical Vapour Transport of Intermetallic Phases III: The System Co -Si
- Triterpenes from Mimusops elengi
- Studies with 2-Arylhydrazono-3-oxopropanaIs: A Novel Route to 4-Aroyl-2-aryl-1,2,3-triazoIes, 3-Substituted 4-Arylazopyrazoles, 2-Substituted Glyoxalonitrile and 3-Oxoalkanonitriles
- Furanoid and Furofuranoid Lignans from Daphne oleoides
- Subject Index
- Authors Index
Articles in the same Issue
- Wechselwirkungen in Molekülkristallen, 160 [1,2]. Kristallzüchtung und Strukturbestimmung der verschiedenartigen Polyphenyl-Kontaktionenmultipel [p-Quaterphenylee⊖⊖][Na⊕(DME)3]2, [p-Quaterphenyl⊖⊖(Na⊕(THF)3)2] und [p-Terphenyl⊖⊖Na⊕(DME)2Na⊕(DME)]2 / Interaction in Molecular Crystals, 160 [1, 2]. Crystallization and Structure Determination of the Different Polyphenyl Contact Ion Multiples [p-Quaterphenylee⊖⊖][Na⊕(DME)3]2, [p-Quaterphenyl⊖⊖(Na⊕(THF)3)2] und [p-Terphenyl⊖⊖Na⊕(DME)2Na⊕(DME)]2
- Synthesis and Structure of the Substituted Lithium Benzyl [Li(tmeda)2]+[C(PMe2)(SiMe3)C6H3-3,5-Me2]-. The First Metal Phosphinomethanide Consisting of Solvent-Separated Ion Pairs
- Optical Outer-Sphere Charge Transfer in Ion Pairs with Peroxoborate as Donor
- Enantioselektive Gewinnung und Kristallstruktur des Ecstasy-Analogons N-Ethyl-3,4-methylendioxyamphetamin-HCl (MDE) und seiner beiden Hauptmetaboliten MDA und HME / Enantioselective Production and Crystal Structure of the Ecstasy Analogue N-Ethyl-3,4- methylenedioxyamphetamine-HCl (MDE) and its Major Metabolites MDA and HME
- Synthesis, Crystal Structure and Magnetic Properties of a Novel GdIII -CuII Heterodinuclear Complex
- Atomvolumen und Packungsdichte der Atome in metallischen Elementen Atomic Volume and Packing Density of Atoms in Metallic Elements
- Properties of the Ternary (Dien)Pt(PMEA-N7) Complex Containing Diethylenetriamine (Dien) and the Antiviral 9-[2-(Phosphonomethoxy)ethyl]adenine (PMEA). Synthesis, Biological Screening, Acid-Base Behaviour, and Metal Ion-Binding in Aqueous Solution
- Photochemical Synthesis and Identification of Tetracarbonyl-bis(olefin)metal(0) Complexes of Group VI B Elements
- Structural and Spectroscopic Characterization of Two New Cu(II)-Dipeptide Complexes
- Wechselwirkungen in Molekülkristallen, 163 [1, 2]. Einfluß der Alkalimetall-Reduktionspotentiale auf die Bildung ihrer Kontaktionenmultipel mit Tetracen- und Decacylen-Polyanionen / Interaction in Molecular Crystals, 163 [ 1,2]. The Influence of Alkaline Metal Reduction Potentials on the Formation of their Contaction Multiples with Tetracene and Decacyclene Polyanions
- Reactivity of Cobalt(III) Amine-Thiolate Complexes with Terminal and Bridging Thiolate Functions towards Hydrogen Peroxide
- Monosubstituierte Derivate des Halbsandwich-Komplexes Cp*Ta(CO)4 - Vergleich mit den analogen Vanadiumverbindungen Cp*V(CO)3L und Röntgenstrukturanalyse des γ-Picolin-Komplexes Cp*V(CO)3(NC5H4-Me(4)) / Monosubstituted Derivatives of the Halfsandwich Complex Cp*Ta(CO)4 - Comparison with the Analogous Vanadium Compounds Cp*V(CO)3L and X-Ray Structural Analysis of the γ-Picoline Complex Cp*V(CO)3(NC5H4-Me(4))
- Formation of Methylchloroaluminium Alkanethiolates, MeAl(SR)Cl, and Dichloroaluminium Alkanethiolates, Cl2AlSR, from Methylaluminium Dichloride and Trimethylsilyl Alkanethiolates, Me3SiSR
- Chemischer Transport intermetallischer Phasen III: Das System Co-Si / Chemical Vapour Transport of Intermetallic Phases III: The System Co -Si
- Triterpenes from Mimusops elengi
- Studies with 2-Arylhydrazono-3-oxopropanaIs: A Novel Route to 4-Aroyl-2-aryl-1,2,3-triazoIes, 3-Substituted 4-Arylazopyrazoles, 2-Substituted Glyoxalonitrile and 3-Oxoalkanonitriles
- Furanoid and Furofuranoid Lignans from Daphne oleoides
- Subject Index
- Authors Index
