Comparison of the surprising metal-ion-binding properties of 5- and 6-uracilmethylphosphonate (SUmpa2- and 6Umpa2-) in aqueous solution and crystal structures of the dimethyl and di(isopropyl) esters of H2(6Umpa)

Chemistry - A European Journal

Volumn 14, Issue 32, 2008, Pages 10036-10046

  Freisinger, Eva ^a   Griesser, Rolf ^b   Lippert, Bernhard ^c   Moreno Luque, Cristóbal E ^b,d   Niclós Gutiérrez, Juan ^d   Ochocki, Justyn ^e   Operschall, Bert P ^b   Sigel, Helmut ^b  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b UNIVERSITY OF BASEL   (Switzerland)

^c TU DORTMUND UNIVERSITY   (Germany)

^d UNIVERSITY OF GRANADA   (Spain)

^e MEDICAL UNIVERSITY OF LODZ   (Poland)

Author keywords

Chelates; Constants; Equilibrium; Isomeric equilibria; Metal ion binding; Nucleotide analogues; Transition metals

Indexed keywords

5 URACILMETHYLPHOSPHONATE; 5-URACILMETHYLPHOSPHONATE; 6 URACILMETHYLPHOSPHONATE; 6-URACILMETHYLPHOSPHONATE; ANTINEOPLASTIC AGENT; DRUG DERIVATIVE; ESTER; URACIL; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; DRUG STABILITY; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; CRYSTALLOGRAPHY, X-RAY; DRUG STABILITY; ESTERS; MODELS, MOLECULAR; THERMODYNAMICS; URACIL; WATER;

EID: 55449129489     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800998     Document Type: Article

References (47)

1. H. Sigel, Pure Appl. Chem. 1999, 71, 1727-1740.
2. H. Sigel, Chem. Soc. Rev. 2004, 33, 191-200.
3. J. Ochocki, J. Graczyk, Pharmazie 1998, 53, 884-885.
4. K. Matlawska, U. Kalinowska, A. Erxleben, R. Osiecka, J. Ochocki, Eur. J. Inorg. Chem. 2005, 3109-3117.
5. A. Holý, Curr. Pharm. Des. 2003, 9, 2567-2592.
6. Chem. Rundsch. (1942-2002) 2002, issue no. 19, p 68.
7. http://www.emea.eu.mt/humandocs/PDFs/EPAR/hepsera/610202en1.pdf
8. R. Krejcova, K. Horska, I. Votruba, A. Holý Coll. Czech. Chem. Commun. 2000, 65, 1653-1668.
9. a) P. Barditch-Crovo, J. Toole, C. W. Hendrix, K. C. Cundy, D. Ebeling, H. S. Jaffe, P. S. Lietman, J. Infect. Dis. 1997, 176, 406-413;
10. b) J.-P. Shaw, M. S. Louie, V. V. Krishnamurthy, M. N. Arimilli, R. J. Jones, A. M. Bidgood, W. A. Lee, K. C. Cundy, Drug Metab. Dispos. 1997, 25, 362-366.
11. A. Holy, I. Votruba, M. Masojfdková, G. Andrei, R. Snoek, L. Naesens, E. De Clercq, J. Balzarini, J. Med. Chem. 2002, 45, 1918-1929.
12. H. Sigel, R. Griesser, Chem. Soc. Rev. 2005, 34, 875-900.
13. C. F. Moreno-Luque, E. Freisinger, B. Costisella, R. Griesser, J. Ochocki, B. Lippert, H. Sigel, J. Chem. Soc. Perkin Trans. 2 2001, 2005-2011.
14. H. Sigel, C. P. Da Costa, B. Song, P. Carloni, F. Gregáň, J. Am. Chem. Soc. 1999, 121, 6248-6257.
15. A. Fernández-Botello, R. Griesser, A. Holý, V. Moreno, H. Sigel, Inorg. Chem. 2005, 44, 5104-5117.
16. B. Knobloch, C. P. Da Costa, W. Linert, H. Sigel, Inorg. Chem. Commun. 2003, 6, 90-93.
17. B. Lippert, Prog. Inorg. Chem. 2005, 54, 385-447.
18. Y. H. Jang, L. C. Sowers, T. Çaǧin, W. A. Goddard III, J. Phys. Chem. A 2001, 105, 274-280.
19. R. K. O. Sigel, H. Sigel, Met. Ions Life Sci. 2007, 2, 109-180.
20. C. F. Moreno-Luque, R. Griesser, J. Ochocki, H. Sigel, Z. Anorg. Allg. Chem. 2001, 627, 1882-1887.
21. H. Sigel, D. B. McCormick, Acc. Chem. Res. 1970, 3, 201-208.
22. H. Sigel, L. E. Kapinos, Coord. Chem. Rev. 2000, 200-202, 563-594.
23. a) H. Irving, R. J. P. Williams, Nature 1948, 162, 746-747;
24. b) H. Irving, R. J. P. Williams, J. Chem. Soc. 1953, 3192-3210.
25. H. Sigel, B. Song, Met Ions Biol. Syst. 1996, 32, 135-205.
26. S. S. Massoud, H. Sigel, Inorg. Chem. 1988, 27, 1447-1453.
27. H. Sigel, D. Chen, N. A. Corfù, F. Gregáň, A. Holý, M. Strašák, Helv. Chim. Acta 1992, 75, 2634-2656.
28. H. Sigel, Coord. Chem. Rev. 1995, 144, 287-319.
29. R. B. Martin, H. Sigel, Comments Inorg. Chem. 1988, 6, 285-314.
30. B. Knobloch, W. Linert, H. Sigel, Proc. Natl. Acad. Sci. USA 2005, 102, 7459-7464.
31. H. Sigel, S. S. Massoud, N. A. Corfù, J. Am. Chem. Soc. 1994, 116, 2958-2971.
32. H. Sigel, R. B. Martin, Chem. Rev. 1982, 82, 385-426.
33. B. Knobloch, H. Sigel, J. Biol. Inorg. Chem. 2004, 9, 365-373.
34. H. Sigel, C. P. Da Costa, J. Inorg. Biochem. 2000, 79, 247-251.
35. K. Aoki, Met. Ions Biol. Syst. 1996, 32, 91-134.
36. K. Aoki, J. Chem. Soc. Chem. Commun. 1976, 748-749.
37. J. Deng, Y. Xiong, M. Sundaralingam, Proc. Natl. Acad. Sci. USA 2001, 98, 13665-13670.
38. J. Ochocki, A. Erxleben, B. Lippert, J. Heterocycl. Chem. 1997, 34, 1179-1184.
39. a) H. Sigel, A. D. Zuberbühler, O. Yamauchi, Anal. Chim. Acta 1991, 255, 63-72;
40. b) M. Bastian, H. Sigel, J. Coord. Chem. 1991, 23, 137-154.
41. a) C. A. Blindauer, T. I. Sjåstad, A. Holý, E. Sielten, H. Sigel, 7. Chem. Soc. Dalton Trans. 1999, 3661-3671;
42. b) G. Kampf, L. E. Kapinos, R. Griesser, B. Lippert, H. Sigel, J. Chem. Soc. Perkin Trans. 2 2002, 1320-1327.
43. KappaCCD package, Nonius, Delft (The Netherlands), 1997.
44. DENZO and SCALEPACK: Z. Otwinowsky, W. Minor, Methods Enzymol. 1997, 276, 307-326.
45. G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473.
46. G. M. Sheldrick, SHELXTL-PLUS (VMS), Madison, WI (USA), 1990.
47. G. M. Sheldrick, SHELX-97, Program for Crystal Structure Refinement, University of Göttingen, Göttingen (Germany), 1997.