Aspects of the co-ordination chemistry of the antiviral nucleotide analogue, 9-[2-(phosphonomethoxy)ethyl]-2,6-diaminopurine (PMEDAP)

Journal of the Chemical Society - Dalton Transactions

Volumn , Issue 21, 1999, Pages 3661-3671

  Blindauer, Claudia A ^a   Sjåstad, Trond I ^b   Holý, Antonín ^c   Sletten, Einar ^b   Sigel, Helmut ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

^b UNIVERSITY OF BERGEN   (Norway)

^c INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748487591     PISSN: 03009246     EISSN: None     Source Type: Journal    
DOI: 10.1039/a904838c     Document Type: Article

References (85)

1. 2- are separated by a semicolon to facilitate reading, yet they appear within the same parenthesis to indicate that the proton is at the ligand without defining its location (see also Section 3).
2. L. Naesens, R. Snoeck, G. Andrei, J. Balzarini, J. Neyts and E. De Clercq, Antiviral Chem. Chemother., 1997, 8, 1.
3. A. Holý, E. De Clercq and I. Votruba, ACS Symp. Ser., 1989, 401, 51.
4. (a) A. Holý, I. Votruba, A. Merta, J. Černý, J. Veselý, J. Vlach, K. Šedivá, I. Rosenberg, M. Otmar, H. Hřebabecký, M. Trávniček, V. Vonka, R. Snoeck and E. De Clercq, Antiviral Res., 1990, 13, 295;
5. (b) E. De Clercq, T. Sakuma, M. Baba, R. Pauwels, J. Balzarini, I. Rosenberg and A. Holý, Antiviral Res., 1987, 8, 261.
6. E. De Clercq, Biochem. Pharmacol., 1991, 42, 963.
7. E. De Clercq, Collect. Czech. Chem. Commun., 1998, 63, 480.
8. E. De Clercq, Collect. Czech. Chem. Commun., 1998, 63, 449.
9. P. Barditch-Crovo, J. Toole, C. W. Hendrix, K. C. Cundy, D. Ebeling, H. S. Jaffe and P. S. Lietman, J. Infect. Dis., 1997, 176, 406.
10. J. Balzarini, Z. Hao, P. Herdewijn, D. G. Johns and E. De Clercq, Proc. Natl. Acad. Sci. USA, 1991, 88, 1499.
11. A. Merta, I. Votruba, J. Jindřich, A. Holý, T. Cihlář, I. Rosenberg, M. Otmar and T. Y. Herve, Biochem. Pharmacol., 1992, 44, 2067.
12. B. L. Robbins, J. Greenhaw, M. C. Connelly and A. Fridland, Antimicrob. Agents Chemother., 1995, 39, 2304.
13. T. Cihlář and M. S. Chen, Mol. Pharmacol., 1996, 50, 1502.
14. S. A. Foster, J. Černý and Y.-c. Cheng, J. Biol. Chem., 1991, 266, 238.
15. (a) P. Kramata, I. Votruba, B. Otová and A. Holý, Mol. Pharmacol., 1996, 49, 1005;
16. (b) J. Neyts and E. De Clercq, Biochem. Pharmacol., 1994, 47, 39.
17. I. Votruba, R. Bernaerts, T. Sakuma, E. De Clercq, A. Merta, I. Rosenberg and A. Holý, Mol. Pharmacol., 1987, 23, 524.
18. C. A. Blindauer, A. Holý, H. Dvořáková and H. Sigel, J. Chem. Soc., Perkin Trans. 2, 1997, 2353.
19. H. Sigel, D. Chen, N. A. Corfù, F. Gregáň, A. Holý and M. Strašák, Helv Chim. Acta, 1992, 75, 2634.
20. C. A. Blindauer, A. H. Emwas, A. Holý, H. Dvořáková, E. Sletten and H. Sigel, Chem. Eur. J., 1997, 3, 1526.
21. C. A. Blindauer, A. Holý, H. Dvořáková and H. Sigel, J. Biol. Inorg. Chem., 1998, 3, 423.
22. H. Sigel, (a) Coord. Chem. Rev., 1995, 144, 287;
23. (b) J. Indian Chem. Soc., 1997, 74, 261 (P. Ray Award Lecture).
24. (a) H. Sigel, S. S. Massoud and R. Tribolet, J. Am. Chem. Soc., 1988, 110, 6857;
25. (b) S. S. Massoud and H. Sigel, Eur. J. Biochem., 1989, 179, 451;
26. (c) H. Sigel, S. S. Massoud and N. A. Corfù, J. Am. Chem. Soc., 1994, 116, 2958.
27. (a) H. Sigel, Chem. Soc. Rev., 1993, 22, 255;
28. (b) H. Sigel and B. Song, Met. Ions Biol. Syst., 1996, 32, 135 [see ref. 24(a)].
29. (a) A. S. Mildvan, Magnesium, 1987, 6, 28;
30. (b) Compendium on Magnesium and Its Role in Biology, Nutrition, and Physiology, vol. 26 of Metal Ions in Biological Systems, eds. H. Sigel and A. Sigel, Dekker, New York, 1990, pp. 1-744.
31. (a) Interactions of Metal Ions with Nucleotides, Nucleic Acids and Their Constituents, vol. 32 of Metal Ions in Biological Systems, eds. H. Sigel and A. Sigel, Dekker, New York, 1996, pp. 1-814;
32. (b) Interrelations among Metal Ions, Enzymes, and Gene Expression, vol. 25 of Metal Ions in Biological Systems, eds. H. Sigel and A. Sigel, Dekker, New York, 1989, pp. 1-557.
33. H. Pelletier, M. R. Sawaya, W. Wolfle, S. H. Wilson, and J. Kraut, Biochemistry, 1996, 35, 12742; 12762.
34. C. A. Blindauer, A. Holý and H. Sigel, Collect. Czech. Chem. Commun., 1999, 64, 613.
35. B. Song, S. A. A. Sajadi, F. Gregáň, N. Prónayová and H. Sigel, Inorg. Chim. Acta, 1998, 273, 101.
36. B. Song, J. Zhao, F. Gregáň, N. Prónayová, S. A. A. Sajadi and H. Sigel, Metal-Based Drugs, 1999, 6, in the press.
37. H. Sigel, B. Song, C. A. Blindauer, L. E. Kapinos, F. Gregáň and N. Prónayová, Chem. Commun., 1999, 743;
38. H. Sigel, Pure Appl. Chem., 2000, 72, in the press.
39. L. Naesens, J. Balzarini, I. Rosenberg, A. Holý and E. De Clercq, Eur. J. Clin. Microbiol. Infect. Dis., 1989, 8, 1043;
40. E. De Clercq, Drugs Exptl. Clin. Res., 1990, 16, 319;
41. T. Yokota, S. Mochizuki, K. Konno, S. Mori, S. Shigeta and E. De Clercq, Antimicrob. Agents Chemother., 1991, 35, 394;
42. J. Neyts, F. Stals, C. Bruggeman and E. De Clercq, Eur. J. Clin. Microbiol. Infect. Dis., 1993, 12, 437.
43. J. Balzarini, S. Aquaro, C.-F. Perno, M. Witvrouw, A. Holý and E. De Clercq, Biochem. Biophys. Res. Commun., 1996, 219, 337.
44. J. Veselý, A. Merta, I. Votruba, I. Rosenberg and A. Holý, Neoplasma, 1990, 37, 105;
45. F. Franek, A. Holý, I. Votruba and T. Eckschlager, Int. J. Oncol., 1999, 14, 745.
46. A. Holý, J. Günter, H. Dvořáková, M. Masojídková, G. Andrei, R. Snoeck, J. Balzarini and E. De Clercq, J. Med. Chem., 1999, 42, 2064;
47. A. Holý, I. Rosenberg and H. Dvořáková, Collect. Czech. Chem. Commun., 1989, 54, 2190.
48. H. Sigel, A. D. Zuberbühler and O. Yamauchi, Anal. Chim. Acta, 1991, 255, 63.
49. H. M. Irving, M. G. Miles and L. D. Pettit, Anal. Chim. Acta, 1967, 38, 475.
50. V. Sklenář, M. Piotto, R. Leppik and V. Saudek, J. Magn. Reson. Ser. A, 1993, 102, 241.
51. O. Yamauchi, A. Odani, H. Masuda and H. Sigel, Met. Ions Biol. Syst., 1996, 32, 207 [see ref. 24(a)].
52. (a) R. L. Benoit and M. Fréchette, Can. J. Chem., 1984, 62, 995;
53. (b) C. Meiser, B. Song, E. Freisinger, M. Peilert, H. Sigel and B. Lippert, Chem. Eur. J., 1997, 3, 388.
54. H. Reinert and R. Weiss, Hoppe-Seyler's Z. Physiol. Chem., 1969, 350, 1310.
55. B. M. Lynch, R. K. Robins and C. C. Cheng, J. Chem. Soc., 1958, 2973.
56. (a) R. B. Martin, Met. Ions Biol. Syst., 1996, 32, 61 [see ref. 24(a)];
57. (b) R. B. Martin and Y. H. Mariam, Met. Ions Biol. Syst., 1979, 8, 57.
58. A. Saha, N. Saha, L.-n. Ji, J. Zhao, F. Gregáň, S. A. A. Sajadi, B. Song and H. Sigel, J. Biol. Inorg. Chem., 1996, 1, 231.
59. R. Tribolet and H. Sigel, Eur. J. Biochem., 1987, 163, 353.
60. (a) D. Banerjea, T. A. Kaden and H. Sigel, Inorg. Chem., 1981, 20, 2586;
61. (b) M. S. Sun and D. G. Brewer, Can. J. Chem., 1967, 45, 2729.
62. a > 5, which cannot be the case; the latter argument applies also for the N7 site.
63. (a) H. Sigel and D. B. McCormick, Acc. Chem. Res., 1970, 3, 201;
64. (b) H. Sigel, K. Beckerand D. B. McCormick, Biochem. Biophys. Acta, 1967, 148, 655.
65. H. Irving and R. J. P. Williams, Nature (London), 1948, 162, 746;
66. J. Chem.Soc., 1953, 3192.
67. M. S. Lüth, L. E. Kapinos, B. Song, B. Lippert and H. Sigel, J. Chem. Soc., Dalton Trans., 1999, 357.
68. (a) IUPAC Stability Constants Database, Version 3.02 (compiled by L. D. Pettit and H. K. J. Powell), Academic Software, Timble, Otley, UK, 1998;
69. (b) NIST Critically Selected Stability Constants of Metal Complexes, Reference Database 46, Version 5.0 (data collected and selected by R. M. Smith and A. E. Martell), U.S. Department of Commerce, National Institute of Standards and Technology, Gaithersburg, USA, 1998;
70. (c) Joint Expert Speciation System (JESS), Version 5.1 (joint venture by K. Murray and P. M. May), Division of Water Technology, CSIR, Pretoria, South Africa, and School of Mathematical and Physical Sciences, Murdoch University, Murdoch, Western Australia, 1996.
71. (a) R. B. Martin, Met. Ions Biol. Syst., 1979, 9, 1;
72. (b) B. Song, D. Chen, M. Bastian, R. B. Martin and H. Sigel, Helv. Chim. Acta, 1994, 77, 1738;
73. (c) R. K. O. Sigel, B. Song and H. Sigel, J. Am. Chem. Soc., 1997, 119, 744.
74. H. Sigel, N. A. Corfù, L.-n. Ji and R. B. Martin, Comments Inorg. Chem., 1992, 13, 35.
75. L. E. Kapinos, B. Song and H. Sigel, Inorg. Chim. Acta (M. E. Vol'pin Memorial Issue), 1998, 280, 50;
76. Chem. Eur. J., 1999, 5, 1794.
77. R. B. Martin and H. Sigel, Comments Inorg. Chem., 1988, 6, 285.
78. S. S. Massoud and H. Sigel, Inorg. Chem., 1988, 27, 1447.
79. L.-n. Ji, N. A. Corfu and H. Sigel, J. Chem. Soc., Dalton Trans., 1991, 1367.
80. 2 group.
81. (a) H. Sigel, F. Hofstetter, R. B. Martin, R. M. Milburn, V. Scheller-Krattiger and K. H. Scheller, J. Am. Chem. Soc., 1984, 106, 7935;
82. (b) H. Sigel, Coord. Chem. Rev., 1990, 100, 453, see pp. 529-532;
83. (c) H. Pelletier, Science, 1994, 266, 2025;
84. (d) T. A. Steitz, Nature (London), 1998, 391, 231.
85. D. Villemin and F. Thibault-Starzyk, Synth. Commun., 1993, 23, 1053.