Complex formation of divalent metal ions with uridine 5′-O-thiomonophosphate or methyl thiophosphate: Comparison of complex stabilities with those of the parent phosphate ligands

ChemBioChem

Volumn 4, Issue 7, 2003, Pages 593-602

  Da Costa, Carla P ^a   Okruszek, Andrzej ^b   Sigel, Helmut ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

^b CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

Metal ion complexes; Nucleotides; Phosphorothioates; Ribozymes; Stability constants

Indexed keywords

5' O THIOPHOSPHATE; ALKALINE EARTH METAL; BARIUM ION; CADMIUM; CALCIUM ION; COBALT; DIVALENT CATION; ESTER; LIGAND; MAGNESIUM ION; MANGANESE; METHYL THIOPHOSPHATE; NICKEL; NUCLEIC ACID; PHOSPHATE; PHOSPHONIC ACID DERIVATIVE; PROTON; RIBOZYME; SODIUM NITRATE; STRONTIUM; UNCLASSIFIED DRUG; URIDINE PHOSPHATE; ZINC ION;

ALKALINITY; AQUEOUS SOLUTION; ARTICLE; ATOM; BINDING SITE; CHEMICAL BOND; COMPLEX FORMATION; ISOMER; MOLECULAR INTERACTION; PH; POTENTIOMETRY; PRIORITY JOURNAL; PROTON TRANSPORT; TITRIMETRY;

CATIONS, DIVALENT; DRUG STABILITY; HYDROGEN-ION CONCENTRATION; KINETICS; LIGANDS; METALS; ORGANOMETALLIC COMPOUNDS; PHOSPHATES; PHOSPHORIC ACID ESTERS; URIDINE; URIDINE MONOPHOSPHATE;

EID: 0042872995     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/cbic.200200551     Document Type: Article

References (71)

1. R. K. O. Sigel, B. Song, H. Sigel, J. Am. Chem. Soc. 1997, 119, 744-755.
2. H. Sigel, Pure Appl. Chem. 1999, 71, 1727-1740.
3. C. P. Da Costa, D. Krajewska, A. Okruszek, W. J. Stec, H. Sigel, J. Biol. Inorg. Chem. 2002, 7, 405-415.
4. F. Eckstein, J. Am. Chem. Soc. 1966, 88, 4292-4294.
5. V. L. Pecoraro, J. D. Hermes, W. W. Cleland, Biochemistry 1984, 23, 5262-5271.
6. a) J. R. Knowles, Annu. Rev. Biochem. 1980, 49, 877-919;
7. b) F. Eckstein, Annu. Rev. Biochem. 1985, 54, 367-402.
8. a) C. Klevickis, C. M. Grisham, Met. Ions Biol. Syst. 1996, 32, 1-26;
9. b) A. C. Bergman, P. O. Nyman, G. Larsson, FEBS Lett. 1998, 441, 327-330;
10. c) J. Liu, M.-D. Tsai, Biochemistry 2001, 40, 9014-9022;
11. d) M. Koziołkiewicz, A. Owczarek, M. Wójcik, K. Domański, P. Guga, W. J. Stec, J. Am. Chem. Soc. 2002, 124, 4623-4627.
12. a) W. S. Marshall, M. H. Caruthers, Science 1993, 259, 1564-1570;
13. b) A. De Mesmaeker, R. Häner, P. Martin, H. E. Moser, Acc. Chem. Res. 1995, 28, 366-374.
14. a) S. Spitzer, F. Eckstein, Nucleic Acids Res. 1988, 16, 11691-11704;
15. b) M. Gilar, A. Belenky, Y. Budman, D. L. Smisek, A. S. Cohen, Antisense Nucleic Acid Drug Dev. 1998, 8, 35-42.
16. F. Eckstein, Antisense Nucleic Acid Drug Dev. 2000, 10, 117-121.
17. a) S. T. Crooke, Biochem. Biophys. Acta 1999, 1489, 31-44;
18. b) U. Galderisi, A. Cascino, A. Giordano, J. Cell. Physiol. 1999, 181, 251-257;
19. c) S. Agrawal, Q. Zhao, Curr. Opin. Chem. Biol. 1998, 2, 519-528;
20. d) Y. Tamura, M. Tao, N. Miyano-Kurosaki, K. Takai, H. Takaku, Antisense Nucleic Acid Drug Dev. 2000, 10, 87-96.
21. Websites: http://www.isispharm.com or http://www.vitravene.com; information downloaded in July and December 2002.
22. a) M. Koziolkiewicz, E. Gendaszewska, M. Maszewska, C. A. Stein, W. J. Stec, Blood 2001, 98, 995-1002;
23. b) M. Koziolkiewicz, M. Wójcik, A. Kobylańska, B. Karwowski, B. Rebowska, P. Guga, W. J. Stec, Antisense Nucleic Acid Drug Dev. 1997, 7, 43-48;
24. c) J. L. Vaerman, P. Moureau, F. Deldime, P. Lewalle, C. Lammineur, F. Morschhauser, P. Martiat, Blood 1997, 90, 331-339.
25. a) A. M. Pyle, Met. Ions Biol. Syst. 1996, 32, 479-520;
26. b) A. L. Feig, Met. Ions Biol. Syst. 2000, 37, 157-182;
27. c) R. K. O. Sigel, A. M. Pyle, Met. Ions Biol. Syst. 2003, 40, 477-512.
28. a) E. C. Scott, O. C. Uhlenbeck, Nucleic Acids Res. 1999, 27, 479-484;
29. b) L. M. Hunsicker, V. J. DeRose, J. Inorg. Biochem. 2000, 80, 271-281;
30. c) T. E. Horton, M. Maderia, V. J. DeRose, Biochemistry 2000, 39, 8201-8207.
31. a) M. Maderia, L.M. Hunsicker, V.J. DeRose, Biochemistry 2000, 39, 12113-12120;
32. b) S.-o. Shan, A. V. Kravchuk, J. A. Piccirilli, D. Herschlag, Biochemistry 2001, 40, 5161-5171.
33. IUPAC Stability Constants Database, Release 5, Version 5.16 (compiled by L.D. Pettit, H.K.J. Powell), Academic Software, Timble, Otley, West Yorkshire, UK, 2001.
34. NIST Critically Selected Stability Constants of Metal Complexes, Reference Database 46, Version 6.0 (compiled by R. M. Smith, A. E. Martell), US Department of Commerce, National Institute of Standards and Technology, Gaithersburg, MD, USA, 2001.
35. Joint Expert Speciation System (JESS), Version 6.4 (joint venture by K. Murray, P. M. May), Division of Water Technology, CSIR, Pretoria, South Africa, and School of Mathematical and Physical Sciences, Murdoch University, Murdoch, Western Australia, 2001.
36. B. Song, R. K. O. Sigel, H. Sigel, Chem. Eur. J. 1997, 3 29-33.
37. L. L. Slavin, E. H. Cox, R. N. Bose, Bioconjugate Chem. 1994, 5, 316-320.
38. N. A. Kratochwil, J. A. Parkinson, C. Sacht, P. del Socorro Murdoch, T. Brown, P. J. Sadler, Eur. J. Inorg. Chem. 2001, 2743-2746.
39. I. E. Catrina, A. C. Hengge, J. Am. Chem. Soc. 1999, 121, 2156-2163.
40. a) D. B. Davies, P. Rajani, H. Sadikot, J. Chem. Soc. Perkin Trans. 2 1985, 279-285;
41. b) K. Aoki, Met. Ions Biol. Syst. 1996, 32, 91-134.
42. S. S. Massoud, H. Sigel, Inorg. Chem. 1988, 27, 1447-1453.
43. A. Saha, N. Saha, L.-n. Ji, J. Zhao, F. Gregáň, S. A. A. Sajadi, B. Song, H. Sigel, J. Biol. Inorg. Chem. 1996, 1, 231-238.
44. a) P. A. Frey, R. D. Sammons, Science 1985, 228, 541-545;
45. b) P. A. Frey, Adv. Enzymol. Relat. Areas Mol. Biol. 1989, 62, 119-201.
46. C. F. Moreno-Luque, R. Griesser, J. Ochocki, H. Sigel, Z Anorg. Allg. Chem. 2001, 627, 1882-1887.
47. M. Bastian, H. Sigel, J. Coord. Chem. 1991, 23, 137-154.
48. a) M. S. Lüth, L. E. Kapinos, B. Song, B. Lippert, H. Sigel, J. Chem. Soc. Dalton Trans. 1999, 357-365;
49. b) H. Sigel, S. S. Massoud, R. Tribolet, J. Am. Chem. Soc. 1988, 110, 6857-6865.
50. H. Sigel, D. Chen, N. A. Corfû, F. Gregán̂, A. Holý, M. Strašák, Helv. Chim. Acta 1992, 75, 2634-2656.
51. C. P. Da Costa, H. Sigel, J. Biol. Inorg. Chem. 1999, 4, 508-514.
52. H. Sigel, B. Song, Met. Ions Biol. Syst. 1996, 32, 135-205.
53. H. Sigel, Coord. Chem. Rev. 1995, 144, 287-319.
54. H. Sigel, L. E. Kapinos, Coord. Chem. Rev. 2000, 200-202, 563-594.
55. D. E. Volk, T. D. Power, D. G. Gorenstein, B. A. Luxon, Tetrahedron Lett. 2002, 43, 4443-4447.
56. H. Sigel, R. B. Martin, Chem. Soc. Rev. 1994, 23, 83-91.
57. B. Knobloch, C. P. Da Costa, W. Linert, H. Sigel, Inorg. Chem. Commun. 2003, 6, 90-93.
58. S. A. A. Sajadi, B. Song, F. Gregáň, H. Sigel, Inorg. Chem. 1999, 38, 439-448.
59. R. B. Martin, H. Sigel, Comments Inorg. Chem. 1988, 6, 285-314.
60. H. Sigel, Pure Appl. Chem. 1989, 61, 923-932.
61. E. A. Doherty, J. A. Doudna, Annu. Rev. Biochem. 2000, 69, 597-615.
62. J. F. Curley, C. M. Joyce, J. A. Piccirilli, J. Am. Chem. Soc. 1997, 119, 12691-12692.
63. a) C. A. Brautigam, T. A. Steitz, J. Mol. Biol. 1998, 277, 363-377;
64. b) C. A. Brautigam, S. Sun, J. A. Piccirilli, T. A. Steitz, Biochemistry 1999, 38, 696-704.
65. a) G. Parkin, Met. Ions Biol. Syst. 2001, 38, 411-460;
66. b) D. S. Auld in Handbook on Metalloproteins (Eds.: I. Bertini, A. Sigel, H. Sigel), Marcel Dekker, Inc., New York, 2001, pp. 881-959.
67. H. Sigel, A. D. Zuberbühler, O. Yamauchi, Anal. Chim. Acta 1991, 255, 63-72.
68. a) L.-n. Ji, N. A. Corfù, H. Sigel, J. Chem. Soc. Dalton Trans. 1991, 1367-1375;
69. b) H. Sigel, Chimia 1967, 21, 489-500.
70. a) R. Griesser, H. Sigel, Inorg. Chem. 1970, 9, 1238-1243;
71. b) H. Sigel, R. Griesser, B. Prijs, Z. Naturforsch. 1972, 27b, 353-364.