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Metal Ion-Coordinating Properties in Solution of Purine-Nucleoside 5’-Monophosphates and Some Analogues

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Bioinorganic Chemistry

Part of the book series: NATO ASI Series ((ASIC,volume 459))

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Abstract

The stability constants of the 1:1 complexes formed between Mg2+, Ca2+, Sr2+, Ba2+, Mn2+, Co2+, Ni2+, Cu2+, Zn2+, or Cd2+ and adenosine 5’-monophosphate (AMP2-), inosine 5’-monophosphate (IMP2-), or guanosine 5’- monophosphate (GMP2-) as well as the AMP analogue 9-[2-(phosphonomethoxy)ethyl)]adenine (PMEA2-), which owns antiviral properties, are analyzed with regard to the structures of the complexes formed in solution. Based on log K MM (R-PO3) versus PK HH (R-PO3) straight-line plots, where R-PO 2-3 represents simple phosphate monoester or phosphonate ligands that can only undergo a -PO 2-3 -M2+ coordination, the stabilities of the M(AMP), M(IMP), M(GMP), and M(PMEA) complexes are evaluated. By including tubercidin 5’-monophosphate (= 7-deaza-AMP2-; i.e., N-7 is replaced by a CH unit) into the study it is proven that an increased stability of the M(AMP) complexes is due to macroche- late formation of a phosphate-coordinated metal ion with N-7 of the adenine residue. This macrochelate formation is quantified for the M(AMP), M(IMP), and M(GMP) complexes. Plots of the log stability increases versus the negative log of the micro acidity constants of the H+(N-7) site of the monoprotonated nucleosides reveal that the extent of macrochelate formation is mainly determined by the basicity of N-7. In the case of the M(PMEA) complexes the also observed stability increase has to be attributed to the formation of five-membered chelates involving the ether oxygen present in the -CH2-O-CH2-PO 2-3 residue of PMEA for the complexes with Mg2+, Ca2+, Sr2+, Ba2+, Mn2+, Co2+, Zn2+, and Cd2+; only in the case of Cu2+, and possibly also Ni2+, an interaction with the adenine residue (probably with N-3) occurs in addition. The equilibrium scheme for the three isomers of Cu(PMEA) is elaborated and the formation degree of the various isomers is quantified. Finally, the properties of the M(PMEA) and M(AMP) complexes are compared and it is emphasized that the ether oxygen, which influences so much the stability and structure of the M(PMEA) complexes in solution, is also crucial for the antiviral properties of PMEA.

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Authors and Affiliations

  1. Institute of Inorganic Chemistry, University of Basel, Spitalstrasse 51, CH-4056, Basel, Switzerland

    Helmut Sigel

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  1. Helmut Sigel
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Editors and Affiliations

  1. Department of General and Inorganic Chemistry, Aristotle University of Thessaloniki, Thessaloniki, 54006, Greece

    Dimitris P. Kessissoglou

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Sigel, H. (1995). Metal Ion-Coordinating Properties in Solution of Purine-Nucleoside 5’-Monophosphates and Some Analogues. In: Kessissoglou, D.P. (eds) Bioinorganic Chemistry. NATO ASI Series, vol 459. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-0255-1_14

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  • DOI: https://doi.org/10.1007/978-94-011-0255-1_14

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-4113-3

  • Online ISBN: 978-94-011-0255-1

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