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Pure Appl. Chem., 1998, Vol. 70, No. 4, pp. 845-854

http://dx.doi.org/10.1351/pac199870040845

The effects of N7-coordinated cis-diammine-platinum(ii) on the acid-base properties of guanine derivatives

H. Sigel and B. Lippert

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  • Çelebi Bekir, Gökaltun Aslıhan, Arman Esra, Evirgen Oğulcan A., Tuncel Ali: Polyethylenimine attached-poly(3-chloro-2-hydroxypropyl methacrylate-co-ethylene dimethacrylate) monosized-porous microspheres as a new separation medium for polar compounds. Colloids and Surfaces A: Physicochemical and Engineering Aspects 2014, 441, 629. <http://dx.doi.org/10.1016/j.colsurfa.2013.10.030>
  • Blindauer Claudia A., Sigel Astrid, Operschall Bert P., Holý Antonin, Sigel Helmut: Extent of Intramolecular π Stacks in Aqueous Solution in Mixed-Ligand Copper(II) Complexes Formed by Heteroaromatic Amines and 1-[2-(Phosphonomethoxy)ethyl]cytosine (PMEC), a Relative of Antivirally Active Acyclic Nucleotide Analogues (Part 72) [1, 2]. Z. anorg. allg. Chem. 2013, 639, 1661. <http://dx.doi.org/10.1002/zaac.201300095>
  • Gómez-Coca Raquel B., Blindauer Claudia A., Sigel Astrid, Operschall Bert P., Holý Antonín, Sigel Helmut: Extent of Intramolecular π-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). Chemistry & Biodiversity 2012, 9, 2008. <http://dx.doi.org/10.1002/cbdv.201200022>
  • Sigel Astrid, Operschall Bert P., Sigel Helmut: Steric guiding of metal ion binding to a purine residue by a non-coordinating amino group: Examplified by 9-[(2-phosphonomethoxy)ethyl]-2-aminopurine (PME2AP), an isomer of the antiviral nucleotide analogue 9-[(2-phosphonomethoxy)ethyl]adenine (PMEA), and by related compounds. Coord Rev 2012, 256, 260. <http://dx.doi.org/10.1016/j.ccr.2011.06.030>
  • Marrubini Giorgio, Mendoza Bolivar Enrique Castillo, Massolini Gabriella: Separation of purine and pyrimidine bases and nucleosides by hydrophilic interaction chromatography. J Sep Science 2010, 33, 803. <http://dx.doi.org/10.1002/jssc.200900672>
  • Gupta Deepali, Nowak Ralf, Lippert Bernhard: Pt(ii) complexes of unsubstituted guanine and 7-methylguanine. Dalton Trans 2010, 39, 73. <http://dx.doi.org/10.1039/b912701a>
  • Fernández-Botello Alfonso, Operschall Bert P., Holy Antonín, Moreno Virtudes, Sigel Helmut: Metal ion-binding properties of 9-[(2-phosphonomethoxy)ethyl]-2-aminopurine (PME2AP), an isomer of the antiviral nucleotide analogue 9-[(2-phosphonomethoxy)ethyl]adenine (PMEA). Steric guiding of metal ion-coordination by the purine-amino group. Dalton Trans 2010, 39, 6344. <http://dx.doi.org/10.1039/c005238h>
  • Fernández-Botello Alfonso, Holý Antonín, Moreno Virtudes, Operschall Bert P., Sigel Helmut: Intramolecular π–π stacking interactions in aqueous solution in mixed-ligand copper(II) complexes formed by heteroaromatic amines and the nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]-2-aminopurine (PME2AP), an isomer of the antivirally active 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA). Inorg Chim Ada 2009, 362, 799. <http://dx.doi.org/10.1016/j.ica.2008.02.035>
  • Operschall Bert P., Bianchi Emanuela M., Griesser Rolf, Sigel Helmut: Influence of decreasing solvent polarity (1,4-dioxane/water mixtures) on the stability and structure of complexes formed by copper(II), 2,2′-bipyridine or 1,10-phenanthroline and guanosine 5′-diphosphate: evaluation of isomeric equilibria† ‡. J Coord Chem 2009, 62, 23. <http://dx.doi.org/10.1080/00958970802474888>
  • Hartinger Christian G., Keppler Bernhard K.: CE in anticancer metallodrug research – an update. Eletrophoresis 2007, 28, 3436. <http://dx.doi.org/10.1002/elps.200700114>
  • Freisinger Eva, Sigel Roland K.O.: From nucleotides to ribozymes—A comparison of their metal ion binding properties. Coord Chem Rev - 2007, 251, 1834. <http://dx.doi.org/10.1016/j.ccr.2007.03.008>
  • Sigel Helmut, Massoud Salah S., Song Bin, Griesser Rolf, Knobloch Bernd, Operschall Bert P.: Acid–Base and Metal-Ion-Binding Properties of Xanthosine 5′-Monophosphate (XMP) in Aqueous Solution: Complex Stabilities, Isomeric Equilibria, and Extent of Macrochelation. Chem Eur J 2006, 12, 8106. <http://dx.doi.org/10.1002/chem.200600160>
  • Natile Giovanni, Marzilli Luigi G.: Non-covalent interactions in adducts of platinum drugs with nucleobases in nucleotides and DNA as revealed by using chiral substrates. Coord Chem Rev - 2006, 250, 1315. <http://dx.doi.org/10.1016/j.ccr.2005.12.004>
  • Knobloch Bernd, Suliga Danuta, Okruszek Andrzej, Sigel Roland K. O.: Acid-Base and Metal-Ion Binding Properties of the RNA Dinucleotide Uridylyl-(5′→3′)-[5′]uridylate (pUpU3−). Chem Eur J 2005, 11, 4163. <http://dx.doi.org/10.1002/chem.200500013>
  • Bianchi Emanuela M., Griesser Rolf, Sigel Helmut: Influence of Decreasing Solvent Polarity (1,4-Dioxane/Water Mixtures) on the Acid-Base and Copper(II)-Binding Properties of Guanosine 5′-Diphosphate. HCA 2005, 88, 406. <http://dx.doi.org/10.1002/hlca.200590026>
  • Roitzsch Michael, Añorbe Marta Garijo, Miguel Pablo J. Sanz, Müller Barbara, Lippert Bernhard: The role of intramolecular hydrogen bonding on nucleobase acidification following metal coordination: possible implications of an “indirect” role of metals in acid–base catalysis of nucleic acids. J Biol Inorg Chem 2005, 10, 800. <http://dx.doi.org/10.1007/s00775-005-0030-4>
  • Gómez-Coca Raquel B., Kapinos Larisa E., Holý Antonín, Vilaplana Rosario A., González-Vílchez Francisco, Sigel Helmut: Quantification of isomeric equilibria formed by metal ion complexes of 8-[2-(phosphonomethoxy)ethyl]-8-azaadenine (8,8aPMEA) and 9-[2-(phosphonomethoxy)ethyl]-8-azaadenine (9,8aPMEA). Derivatives of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA). J Biol Inorg Chem 2004, 9, 961. <http://dx.doi.org/10.1007/s00775-004-0591-7>