Coordination modes between copper(II) and N-acetylneuraminic (Sialic) acid from a 2D-simulation analysis of EPR spectra. Implications for copper mediation of sialoglycoconjugate chemistry relevant to human biology

Inorganic Chemistry

Volumn 44, Issue 7, 2005, Pages 2531-2543

  Fainerman Melnikova, Marina ^a   Szabó Plánka, Terézia ^b   Rockenbauer, Antal ^c   Codd, Rachel ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

^b UNIVERSITY OF SZEGED   (Hungary)

^c CHEMICAL RESEARCH CENTER   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

AMYLOID PRECURSOR PROTEIN; CARBOXYLIC ACID; CHELATE; COPPER ION; GLYCEROL; GLYCOCONJUGATE; HYDROXYL GROUP; N ACETYLNEURAMINIC ACID; OXYGEN; SIALIC ACID DERIVATIVE;

ALZHEIMER DISEASE; ARTICLE; BIOCHEMISTRY; COMPLEX FORMATION; ELECTRON SPIN RESONANCE; MASS SPECTROMETRY; PH; PKA; SIALYLATION; SIMULATION; TEMPERATURE;

COMPUTER SIMULATION; COPPER; ELECTRON SPIN RESONANCE SPECTROSCOPY; HUMANS; MOLECULAR STRUCTURE; N-ACETYLNEURAMINIC ACID; ORGANOMETALLIC COMPOUNDS;

EID: 16244403611     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic049126d     Document Type: Article

References (64)

1. Angata, T.; Varki, A. Chem. Rev. 2002, 102, 439-469.
2. Schauer, R.; Kelm, S.; Reuter, G.; Roggentin, P.; Shaw, L. In Biology of the Sialic Acids; Rosenberg, A., Ed.; Plenum Press: New York, 1995; pp 7-67.
3. Traving, C.; Schauer, R. Cell. Mol. Life Sci. 1998, 54, 1330-1349.
4. Varghese, J. N.; McKimm-Breschkin, J. L.; Caldwell, J. B.; Kortt, A. A.; Colman, P. M. Proteins 1992, 14, 327-332.
5. Kiefel, M. J.; von Itzstein, M. Chem. Rev. 2002, 102, 471-490.
6. Sillanaukee, P.; Pönniö, M.; Jääskeläinen, I. P. Eur. J. Clin. Invest. 1999, 29, 413-425.
7. Codd, R.; Lay, P. A. J. Am. Chem. Soc. 2001, 123, 11799-11800.
8. Codd, R.; Lay, P. A. Chem. Res. Toxicol. 2003, 7, 881-892.
9. Codd, R. Chem. Commun. 2004, 2653-2655.
10. Saladini, M.; Menabue, L.; Ferrari, E. J. Inorg. Biochem. 2002, 88, 61-68.
11. Jaques, L. W.; Brown, E. B.; Barrett, J. M.; Brey, J. W. S.; Weltner, J. W. J. Biol. Chem. 1977, 252, 4533-4538.
12. Daman, M. E.; Dill, K. Carbohydr. Res. 1982, 102, 47-57.
13. Sillerud, L. O.; Prestegard, J. H.; Yu, R. K.; Schafer, D. E; Konigsberg, W. H. Biochemistry 1978, 17, 2619-2628.
14. Zeitler, R.; Banzer, J.-P.; Bauer, C.; Reutter, W. BioMetals 1992, 5, 103-109.
15. Yamashita, K.; Liang, C. J.; Funakoshi, S.; Kobata, A. J. Biol. Chem. 1981, 256, 1283-1289.
16. Zaitseva, I.; Zaitsev, V.; Card, G.; Moshkov, K.; Bax, B.; Ralph, A.; Lindley, P. JBIC, J. Biol. Inorg. Chem. 1996, 1, 15-23.
17. McFarlane, I.; Georgopoulou, N.; Coughlan, C. M.; Gillian, A. M.; Breen, K. C. Neuroscience 1999, 90, 15-25.
18. Warita, H.; Murakami, T.; Manabe, Y.; Sato, K.; Hayashi, T.; Seki, T.; Abe, K. Neurosci. Lett. 2001, 300, 75-78.
19. Brown, D. R.; Kozlowski, H. J. Chem. Soc., Dalton Trans. 2004, 1907-1917.
20. Barnham, K. J.; McKinstry, W. J.; Multhaup, G.; Galatis, D.; Morton, C. J.; Curtain, C. C.; Williamson, N. A.; White, A. R.; Hinds, M. G.; Norton, R. S.; Beyreuther, K.; Masters, C. L.; Parker, M. W.; Cappai, R. J. Biol. Chem. 2003, 278, 17401-17407.
21. Karr, J. W.; Kaupp, L. J.; Szalai, V. A. J. Am. Chem. Soc. 2004, 126, 13534-13538.
22. Carroll, M. C.; Girouard, J. B.; Ulloa, J. L.; Subramaniam, J. R.; Wong, P. C.; Valentine, J. S.; Culotta, V. C. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5964-5969.
23. Bush, A. I.; Masters, C. L.; Tanzi, R. E. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 11193-11194.
24. Rockenbauer, A.; Szabó-Plánka, T.; Árkosi, Z.; Korecz, L. J. Am. Chem. Soc. 2001, 123, 7646-7654.
25. Nagy, N. V.; Szabó-Plánka, T.; Rockenbauer, A.; Peintler, G.; Nagypál, I.; Korecz, L. J. Am. Chem. Soc. 2003, 125, 5227-5233.
26. Arkosi, Z.; Szabó-Plánka, T.; Rockenbauer, A.; Nagy, N. V.; Lázár, L.; Fülöp, F. Inorg. Chem. 2003, 42, 4842-4848.
27. Szabó-Plánka, T.; Rockenbauer, A.; Korecz, L. Magn. Reson. Chem. 1999, 37, 484-492.
28. Rockenbauer, A.; Korecz, L. Appl. Magn. Reson. 1996, 10, 29-43.
29. Micera, G.; Dessi, A.; Sanna, D. Inorg. Chem. 1996, 35, 6349-6352.
30. Barba-Behrens, N.; Salazar-Garcia, F.; Bello-Ramirez, A. M.; Garcia-Baez, E.; Rosales-Hoz, M. J.; Contreras, R.; Flores-Parra, A. Transition Met. Chem. (London) 1994, 19, 575-581.
31. Bkouche-Waksman, I. Acta Crystallogr., Sect. C 1994, C50, 62-64.
32. Noack, M.; Kokoszka, G. F.; Gordon, G. J. Chem. Phys. 1971, 54, 1342-1350.
33. Yordadov, N. D.; Shopov, D. Dokl. Bulg. Akad. Nauk 1969, 22, 691-694.
34. Fawcett, J.; Laurie, S. H.; Simpson, C.; Symons, M. C. R.; Taiwo, F. A.; Hawkins, I. Inorg. Chim. Acta 2001, 312, 245-248.
35. Howes, B. D.; Kuhlmeyer, C.; Pogni, R.; Basosi, R. Magn. Reson. Chem. 1999, 37, 538-544.
36. Peisach, J.; Blumberg, W. E. Arch. Biochem. Biophys. 1974, 165, 691-708.
37. Lesniak, W.; Harris, W. R.; Kravitz, J. Y.; Schacht, J.; Pecoraro, V. L. Inorg. Chem. 2003, 42, 1420-1429.
38. Gyurcsik, B.; Nagy, L. Coord. Chem. Rev. 2000, 203, 81-149.
39. Whitfield, D. M.; Stojkovski, S.; Sarkar, B. Coord. Chem. Rev. 1993, 122, 171-225.
40. Farkas, E.; Sóvágó, I. In Amino Acids, Peptides and Proteins; Davies, J. S., Ed.; Royal Soceity of Chemistry: Cambridge, U.K., 1998; pp 324-386.
41. Antolini, L.; Menabue, L.; Saladini, M.; Battaglia, L. P.; Corradi, A. B.; Micera, G. J. Chem. Soc., Dalton Trans. 1988, 909-912.
42. Corradi Bonamartini, A.; Bruni, S.; Cariati, F.; Battaglia, L. P.; Pelosi, G. Inorg. Chim. Acta 1993, 205, 99-104.
43. Casolaro, M.; Chelli, M.; Ginanneschi, M.; Laschi, F.; Messori, L.; Muniz-Miranda, M.; Papini, A. M.; Kowalik-Jankowska, T.; Kozlowski, H. J. Inorg. Biochem. 2002, 89, 181-190.
44. Nagy, L.; Yamashita, S.; Yamaguchi, T.; Sipos, P.; Wakita, H.; Nomura, M. J. Inorg. Biochem. 1998, 72, 49-55.
45. Dabrowski, U.; Friebolin, H.; Brossmer, R.; Supp, M. Tetrahedron Lett. 1979, 20, 4637-4640.
46. Deiana, S.; Gessa, C.; Manunza, B.; Piu, P.; Seeber, R. J. Inorg. Biochem. 1990, 39, 25-32.
47. Aruga, R. Bull. Chem. Soc. Jpn. 1981, 54, 1233-1235.
48. Michaud, E.; Pivert, G.; Duc, G.; Petit-Ramel, M.; Thomas-David, G. Can. J. Chem. 1982, 60, 1063-1066.
49. Erlenmeyer, H.; Griesser, R.; Prijs, B.; Sigel, H. Helv. Chim. Acta 1968, 51, 339-348.
50. Halcrow, M. A. J. Chem. Soc., Dalton Trans. 2003, 4375-4384.
51. Hathaway, B. J. Struct. Bonding (Berlin) 1984, 57, 55-118.
52. Shestavin, A. I.; Bolotin, S. N.; Volynkin, V. A.; Panyuskhin, V. T. J. Mol. Liq. 2003, 107, 69-75.
53. Saladini, M.; Candini, M.; Iacopino, D.; Menabue, L. Inorg. Chim. Acta 1999, 292, 189-197.
54. Micera, G.; Dessi, A.; Kozlowski, H.; Radomska, B.; Urbanska, J.; Decock, P.; Dubois, B.; Olivier, I. Carbohydr. Res. 1989, 188, 25-34.
55. Escandar, G.; Sala, L. F. Can. J. Chem. 1992, 70, 2053-2057.
56. Bunting, J. W.; Kain Men, T. Can. J. Chem. 1970, 48, 1654-1656.
57. Hurd, C. D. J. Chem. Educ. 1970, 47, 481-482.
58. New, E. J.; Jolliffe, K. A.; Codd, R. Work in progress.
59. Hausmann, J.; Jameson, G. B.; Brooker, S. Chem. Commun. 2003, 2992-2993.
60. Funahashi, Y.; Kato, C.; Yamauchi, O. Bull. Chem. Soc. Jpn. 1999, 72, 415-424.
61. Koenig, M. K.; McLean, R. J. C. BioMetals 1999, 12, 47-52.
62. Casadesus, G.; Smith, M. A.; Zhu, X.; Aliev, G.; Cash, A. D.; Honda, K.; Petersen, R. B.; Perry, G. J. Alzheimer's Dis. 2004, 6, 165-169.
63. Finney, L. A.; O'Halloran, T. V. Science 2003, 300, 931-936.
64. Culotta, V. C.; Gitlin, J. D. In The Metabolic & Molecular Bases of Inherited Disease; Scriver, C. R., Beaudet, A. L., Sly, W. S., Valle, D., Eds.; McGraw-Hill: New York, 2001; pp 3105-3126.