Characterization and Elucidation of Coordination Requirements of Adenine Nucleotides Complexes with Fe(II) Ions

References

• Sigel , A. and Sigel , H. 1996 . Metal Ions in Biological Systems Vol. 32 , 1 – 814 . New York : Dekker Inc. .
   Google Scholar
• Bronk , J.R. and Kielley , W.W. 1957 . Ionic requirements for oxidative phosphorylation, adenosine triphosphate-phosphorus-32 exchange, and adenosine triphosphatase . Biochim. Biophys. Acta , 24 : 440 – 441 .
   Google Scholar
• Kaye , M.A.G. 1955 . Effect of zinc on 5-nucleotidase of cobra venom and the interference of other nucleotides . Biochim. Biophys. Acta , 18 : 456 – 458 .
   PubMed Web of Science ®Google Scholar
• McCornik , W.G. and Levedahl , B.H. 1959 . Rotatory dispersion of inosine triphosphate and the influence of metals on inosine triphosphate and adenosine triphosphate . Biochim. Biophys. Acta , 34 : 303 – 308 .
   Google Scholar
• Smith , R.M. , Martell , A.E. and Chen , Y. 1991 . Critical evaluation of stability constants for nucleotide complexes with protons and metal ions and the accompanying enthalpy changes . Pure Appl. Chem. , 63 ( 7 ) : 1015 – 1080 .
   Google Scholar
• Sigel , H. 1999 . Bioinorganic studies on the structure and reactivity of metal-ion complexes of nucleotides and related compounds . Chimia , 53 ( 5 ) : 224 – 225 .
   Google Scholar
• Terrón , A. 1993 . X-ray structural studies of metal-nucleoside and metal-nucleoside monophosphate complexes: new perspectives . Comments Inorg. Chem. , 14 ( 2–3 ) : 63 – 88 .
   Google Scholar
• Bertini , I. , Gray , H.B. , Lippard , S.J. and Valentine , J.S. 1994 . Bioinorganic Chemistry 2 Sausalito, CA : University Science Books .
   Google Scholar
• Weaver , J. and Pollack , S. 1989 . Low-Mr iron isolated from guinea pig reticulocytes as AMP-Fe and ATP-Fe complexes . Biochem. J. , 261 ( 3 ) : 787 – 792 .
   Google Scholar
• Pippard , M.J. , Johnson , D.K. and Finch , C.A. 1982 . Hepatocyte iron kinetics in the rat explored with an iron chelator . Br. J. Haematol. , 52 ( 2 ) : 211 – 224 .
   Google Scholar
• Anghileri , L. , Mayayo , E. , Domingo , J.L. and Thouvenot , P. 2002 . Toxic and carcinogenic effects of parenteral and percutaneous ATP and its iron complex . Drug Chem. Toxic. , 25 ( 3 ) : 267 – 279 .
   PubMed Web of Science ®Google Scholar
• Anghileri , L. and Thouvenot , P. 1998 . ATP in cellular calcium-overload by trivalent metal ions . Biological Trace Element Research Biol. Trace Elem. Res. , 62 ( 1–2 ) : 115 – 122 .
   Google Scholar
• Hermes-Lima , M. , Castilho , R.F. , Meinicke , A.R. and Vercesi , A.E. 1995 . Characteristics of Fe(II)-ATP complex-induced damage to the rat liver mitochondrial membrane . Mol. Cell Biochem. , 14 ( 1 ) : 53 – 60 .
   Google Scholar
• Singh , V. , Ahmad , S. and Rao , G.S. 1994 . Prooxidant and antioxidant properties of iron-hydroquinone and iron-1,2,4-benzenetriol complex. Implications for benzene toxicity . Toxcicology , 89 ( 1 ) : 25 – 33 .
   Google Scholar
• Thomas , C. , Vile , G.F. and Winterbourn , C.C. 1993 . The hydrolysis product of ICRF-187 promotes iron-catalysed hydroxyl radical production via the Fenton reaction . Biochem. Pharmacol. , 45 ( 10 ) : 1967 – 1972 .
   Google Scholar
• Jonas , S.K. and Riley , P.A. 1992 . Modification of the in vitro cytotoxicity of hydrogen peroxide by iron complexes . Free Rad. Res. Commun. , 17 ( 6 ) : 407 – 419 .
   Web of Science ®Google Scholar
• Jonas , S.K. and Riley , P.A. 1991 . The effect of ligands on the uptake of iron by cells in culture . Cell Biochem. Funct. , 9 ( 4 ) : 245 – 253 .
   Google Scholar
• Tadolini , B. 1989 . Oxygen toxicity. The influence of adenine-nucleotides and phosphate on iron autoxidation . Free Rad. Res. Commun. , 5 ( 4–5 ) : 237 – 43 .
   PubMedGoogle Scholar
• Vile , G.F. , Winterbourn , C.C. and Sutton , H.C. 1987 . Radical-driven fenton reactions: studies with paraquat, adriamycin, and anthraquinone 6-sulfonate and citrate, ATP, ADP, and pyrophosphate iron chelates . Arch. Biochem. Biophys. , 259 ( 2 ) : 616 – 626 .
   Google Scholar
• Rajan , K.S. , Davis , J.M.R. and Colburn , W. 1971 . Metal chelates in the storage and transport of neurotransmitters: interactions of metal ions with biogenic amines . J. Neurochem. , 18 ( 3 ) : 345 – 364 .
   Google Scholar
• Rajan , K.S. and Mainer , S. 1978 . Studies on chelation of L-DOPA with metal ions and metal-ATP systems . Bioinorg. Chem. , 9 ( 3 ) : 187 – 203 .
   Google Scholar
• Rabinowitz , I.N. , Davis , F.F. and Herber , R.H. 1966 . Moessbauer-effect studies on metal binding in purine compounds . J. Am. Chem. Soc. , 88 ( 19 ) : 4346 – 4354 .
   Google Scholar
• Zhelyaskov , V. and Yue , T.K. 1992 . A Raman study of the binding of Fe(III) to ATP and AMP . Biochem. J. , 287 : 561 – 566 .
   PubMed Web of Science ®Google Scholar
• Du , F. , Mao , X.-A , Li , D.F. and Liao , Z.R. 2001 . Binding site of Fe3+ at purine of ATP as studied by NMR . J. Inorg. Biochem. , 83 ( 2–3 ) : 101 – 105 .
   Google Scholar
• Capparelli , M.V. , Goodgame , D.M.L. , Hayman , P.B. , Skapski , A.C. and Hatway , D.E. 1983 . The site of metal binding in an iron(II) derivative of inosine 5′-monophosphate. An x-ray and spectral study . FEBS Lett. , 163 ( 2 ) : 241 – 244 .
   Google Scholar
• Goodgame , D.M.L. , Hayman , P.B. and Sayer , I. 1984 . Correlation of iron-57 Moessbauer spectra and molecular structure for an iron(II) complex with inosine 5′-monophosphate . Inorg. Chim. Acta , 92 ( 2 ) : L13 – L15 .
   Google Scholar
• Terron , A. and Moreno , V. 1981 . Some new complexes with adenine nucleotides . Inorg. Chim. Acta , 56 ( 4 ) : L57 – L59 .
   Google Scholar
• Vogel , A.I. 1961 . Quantitative Inorganic Analysis , Third 309 London : Longmans .
   Google Scholar
• UV spectrum of ATP:Fe(II) complex is identical with that of free ATP
   Google Scholar
• McConnell , H.M. 1958 . Reaction rates by nuclear magnetic resonance . J. Chem. Phys. , 28 : 430 – 431 .
   Web of Science ®Google Scholar
• Pearson , R.G. , Palmer , J. , Anderson , M.M. and Allred , A.L. 1960 . Exchange reactions in complex ions by nuclear magnetic resonance . Z. Elektrochemie , 64 : 110 – 115 .
   Google Scholar
• Major , D.T. , Laxer , A. and Fischer , B. 2002 . Protonation studies of modified adenine and adenine nucleotides by theoretical calculations and 15N NMR . J. Org. Chem. , 67 ( 3 ) : 790 – 802 .
   Google Scholar
• Saenger , W. 1984 . Principles of Nucleic Acid Structure 107 – 110 . NY : Springer Verlag .
   Google Scholar
• Watanabe , S. , Evenson , L. and Gulz , I. 1963 . Effect of magnesium and calcium ions on the fluorescence of the protonated ring of adenine, adenosine, adenosine 5′-phosphate, adenosine diphosphate, and adenosine triphosphate . J. Biol. Chem. , 238 : 324 – 327 .
   Google Scholar
• Sysoeva , S.G. , Utyanskaya , E.Z. and Vinnik , M.I. 1983 . Study of primary ionization of the terminal phosphate group in adenosine 5′-triphosphate by potentiometric titration . Izves. Akad. Nauk SSSR. Seriya. Khim. , 7 : 1505 – 1511 .
   Google Scholar
• Raszka , M. 1974 . Mononucleotides in aqueous solution. Proton magnetic resonance studies of amino groups . Biochemistry , 13 ( 22 ) : 4616 – 4622 .
   Google Scholar
• Sigel , H. , Scheller , K.H. and Milburn , R.M. 1984 . Stability and structure for monomeric cadmium(II) and zinc(II) complexes of the 5′-triphosphates of adenosine and cytidine in aqueous solution: isomeric equilibria in binary and ternary complexes . Inorg. Chem. , 23 ( 13 ) : 1933 – 1938 .
   Google Scholar
• Lister , J.H. 1971 . Fused Pyrimidines 444 NY
   Google Scholar
• Buechner , P. , Maurer , W. and Ruterjans , H. 1978 . Nitrogen-15 nuclear magnetic resonance spectroscopy of nitrogen-15-labeled nucleotides . J. Magn. Res. , 29 ( 1 ) : 45 – 63 .
   Google Scholar
• Tribolet , R. and Sigel , H. 1987 . Self-association and protonation of adenosine 5′-monophosphate in comparison with its 2′- and 3′-analogs and tubercidin 5′-monophosphate (7-deaza-AMP) . Eur. J. Biochem. , 163 ( 2 ) : 353 – 363 .
   Google Scholar
• Tribolet , R. and Sigel , H. 1988 . Influence of the protonation degree on the self-association properties of adenosine 5′-triphosphate (ATP) . Eur. J. Biochem. , 170 ( 3 ) : 617 – 626 .
   Google Scholar
• Gilligan , T.J. III and Schwarz , G. 1976 . The self-association of adenosine-5′-triphosphate studied by circular dichroism at low ionic strengths . Biophys. Chem. , 4 ( 1 ) : 55 – 63 .
   Google Scholar
• Sigel , H. , Tibolet , R. , Malini-Balakrishnan , R. and Martin , R.B. 1987 . Comparison of the stabilities of monomeric metal ion complexes formed with adenosine 5′-triphosphate (ATP) and pyrimidine-nucleoside 5′-triphosphate (CTP, UTP, TTP) and evaluation of the isomeric equilibria in the complexes of ATP and CTP . Inorg. Chem. , 26 ( 13 ) : 2149 – 2157 .
   Google Scholar
• Goucher , C.R. and Taylor , J.F. 1964 . Compounds in ferric iron and adenosine triphosphate (ATP) and other nucleoside phosphates . J. Biol. Chem. , 239 ( 7 ) : 2251 – 2255 .
   Google Scholar
• Sajadi , S.A.A. , Song , B. , Gregan , F. and Sigel , H. 1999 . Acid-Base and metal ion-coordinating properties of pyrimidine-nucleoside 5′-diphosphates (CDP, UDP, dTDP) and of several simple diphosphate monoesters. Establishment of relations between complex stability and diphosphate basicity . Inorg. Chem. , 38 ( 3 ) : 439 – 448 .
   Google Scholar
• Summers , J.S. , Roe , D. , Boyle , P.D. , Colvin , M. and Shaw , B.R. 1998 . Structural studies of a borane-modified phosphate diester linkage: Ab initio calculations on the dimethylboranophosphate anion and the single-crystal X-ray structure of its diisopropylammonium salt . Inorg. Chem. , 37 ( 17 ) : 4158 – 4159 .
   PubMedGoogle Scholar
• Tetas , M. and Lowenstein , J.M. 1963 . The effect of bivalent metal ions on the hydrolysis of adenosine di- and triphosphates . Biochemistry , 2 : 350 – 357 .
   PubMed Web of Science ®Google Scholar
• Sigel , H. 1992 . Have adenosine 5′-triphosphate (ATP4-) and related purine-nucleotides played a role in early evolution? ATP, its own ‘enzyme’ in metal ion facilitated hydrolysis! . Inorg. Chim. Acta , 198–200 : 1 – 11 .
   Web of Science ®Google Scholar
• Cohn , M. and Hughes , T.R. Jr. 1962 . Nuclear magnetic resonance spectra of adenosine di- and triphosphate. II. Effect of complexing with divalent metal ions . J. Biol. Chem. , 237 : 176 – 181 .
   PubMed Web of Science ®Google Scholar
• Sigel , H. and Song , B. 1996 . Metal Ions in Biological Systems Vol. 32 , 135 New York : Dekker Inc .
   Google Scholar
• Sigel , R.K.O. , Song , B. and Sigel , H. 1997 . Stabilities and structures of metal ion complexes of adenosine 5′-O-thiomonophosphate (AMPS2-) in comparison with those of its parent nucleotide (AMP2-) in aqueous solution . J. Am. Chem. Soc. , 119 ( 4 ) : 744 – 755 .
   Google Scholar
• Halbfinger , E. , Major , D.T. , Ritzmann , M. , Ubl , J. , Reiser , G. , Boyer , J.L. , Harden , K.T. and Fischer , B. 1999 . Molecular recognition of modified adenine nucleotides by the P2Y1-receptor. 1. A synthetic, biochemical, and NMR approach . J. Med. Chem. , 42 ( 26 ) : 5325 – 5337 .
   Google Scholar
• Hovinen , J. , Glemarec , C. , Sandström , A. , Sund , C. and Chattopadhyaya , J. 1991 . Spectroscopic, kinetic and semiempirical molecular orbital studies on 8-amino-, 8-methylamino- and 8-dimethylaminoadenosines . Tetrahedron , 47 ( 26 ) : 4693 – 4708 .
   Google Scholar
• Ikehara , M. , Uesugi , S. and Yoshida , K. 1972 . Studies on the conformation of purine nucleosides and their 5′-phosphates . Biochemistry , 11 ( 5 ) : 830 – 836 .
   Google Scholar
• Shohan , M. and Steitz , T.A. 1980 . Crystallographic studies and model building of ATP at the active site of hexokinase . J. Mol. Biol. , 140 ( 1 ) : 1 – 14 .
   Google Scholar
• Hillaire-Buys , D. , Shahar , L. , Fischer , B. , Chulkin , A. , Linck , N. , Chapal , J. , Loubatieres-Mariani , M.M. and Petit , P. 2001 . Pharmacological evaluation and chemical stability of 2-benzylthioether-5′-O-(1-thiotriphosphate)-adenosine, a new insulin secretagogue acting through P2Y receptors . Drug Dev. Res. , 53 ( 1 ) : 33 – 43 .
   Google Scholar
• Nahum , V. , Ubl , J. , Reiser , G. , Levesque , S. , Beaudoin , A.R. and Fischer , B. 2002 . 5′-O-(1-Boranotriphosphate)-adenosine derivatives as novel P2Y1-receptor agonists . J. Med. Chem. , 45 ( 24 ) : 5384 – 5396 .
   Google Scholar
• Charlot , G. 1961 . Les Methodes de la Chimie Analytique Edited by: Quatrienne . 737 – 738 . Paris : Masson ET Editeurs .
   Google Scholar