Binary and ternary complexes of metal ions, nucleoside 5′-monophosphates, and amino acids

Orenberg, J. B.; Fischer, Beda E.; Sigel, Helmut

doi:10.1016/0022-1902(80)80232-6

Cited by 33 publications

(18 citation statements)

References 35 publications

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“…The value, however, is smaller than that obtained by Orenberg et al (1980) in potentiometric titration where log KNI (AMI') = 2.61 + 0.05. The explanation for this difference is that in the latter study KNO 3 was used as the supporting electrolyte, while in the present study NaC1 (and NiC12) is utilized and Ni2+/chloro complexes are formed.…”

Section: Resultscontrasting

confidence: 71%

“…Frey and Stueher (1972) postulated the formation of this type of complex with two 5'-AMP molecules (ML 2" 2n) coordinated to a single metal cation in their study of the Ni2+-5'-AMP system. This was most recently corroborated by Orenberg et al (1980) in a potentiometric study. As demonstrated in the latter study, the concentration of ML~" 2n species was very small.…”

Section: Resultsmentioning

confidence: 52%

“…This approximation was invoked because the value of the acid dissociation constant, H+ ~ 6.30 PKH(NMV)- (Orenberg et al 1980), for the protonated nucleotide species H(NMP)" is large einough that some competition between H + and Ni 2+ for coordination at the nucleotide phosphate group still exists. This competition may be taken into account in calculation of a revised Kapp for tM Ni2+-5'-AMP complex as shown (Scheller et al 1980 …”

Section: Resultsmentioning

confidence: 99%

“…where L is the nucleotide, nucleoside, or base ligand (Orenberg et al 1980). At the pH of these studies, 7.0, nucleoside 5'-monophosphates exist almost completely as the dianion, that is, the phosphate moiety is in essence completely deprotonated.…”

Section: Introductionmentioning

confidence: 99%

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Binding of nickel (II) to 5′-nucleoside monophosphates and related compounds

et al. 1982

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The interactions of Ni(II) cation with a representative suite of purine bases and the respective nucleosides and nucleotides have been studied by ultraviolet difference spectroscopy. Apparent association constants, Kapp, were determined for each system at pH 7.0, using computer linear regression coupled with an iteration technique. The specificity of binding of Ni2+ for the purine nucleotides studied at pH 7.0 was 5'-GMP greater than 5'-IMP greater than 5'-AMP; a similar ordering was also found for the respective nucleosides and bases. In this study binding was not observed for the suite of pyramidines used, although a Ni2+ - cytidine complex has been observed (Fiskin and Beer, 1965). It was also found that Ni2+ bound more strongly to the purine 5'-nucleotides than to the respective nucleosides and bases. These trends are explained in terms of metal-ligand bonds and available bonding positions on the ligands. A role for metal-ion-nucleotide types of complexes is suggested in the processes that might have given rise to the origin of life.

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Section: Resultscontrasting

confidence: 71%

Section: Resultsmentioning

confidence: 52%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Binding of nickel (II) to 5′-nucleoside monophosphates and related compounds

et al. 1982

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“…Later, the position of the intramolecular equilibrium 9 (9) was determined with Zn 2+ as metal ion and it was concluded [67] that the stacked species occurs with a formation degree of approximately 75 %. Other metal ions were studied as well [67][68][69][70], and the occurrence of intramolecular stacks in M(ATP)(Trp) 3-complexes was confirmed by several groups [71,72]. Related complexes containing phenyl and imidazole residues have also been investigated [73][74][75].…”

Section: Solution Structures Of Mixed Ligand Complexes Containing Atp 4-mentioning

confidence: 95%

Adenosine 5'-triphosphate (ATP4-): Aspects of the coordination chemistry of a multitalented biological substrate

Sigel

2004

Pure and Applied Chemistry

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Firstly, the self-stacking properties of ATP 4-and the effects of metal ions and protons on these properties are described. Some examples involving macrochelate formation between phosphate-coordinated metal ions (M 2+ ) and N7 of the adenine residue in M(ATP) 2-are discussed, and this is followed by considerations on mixed ligand complexes consisting of ATP 4-, M 2+ , and amino acid anions with side chains that allow either aromatic-ring stacking or hydrophobic interactions with the adenine moiety; this gives rise to selectivity. Next, the properties of diphosphorylated 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA 2-; Adefovir), i.e., of PMEApp 4-, are compared with those of (2′-deoxy)ATP 4-with regard to their metal ion-binding qualities, and in this way it can be explained why PMEApp 2-is initially an excellent substrate for nucleic acid polymerases. Of course, after incorporation of the PMEA residue into the growing nucleic acid chain, this is terminated and this is how PMEA exerts its antiviral properties [its bis(pivaloyloxymethyl)ester, Adefovir dipivoxil, was recently approved for use in hepatitis B therapy]. Finally, the change in free energy connected with (macro)chelate formation or intramolecular stacking interactions and the effect of a reduced dielectric constant of the solvent on the stability of complexes and their structures in solution is considered.

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