1,4,7,10-Tetraazacyclododecane metal complexes as potent promoters of phosphodiester hydrolysis under physiological conditions

Inorganic Chemistry

Volumn 47, Issue 11, 2008, Pages 4661-4668

  Subat, Michael ^a   Woinaroschy, Kristina ^a   Gerstl, Corinna ^a   Sarkar, Biprajit ^b   Kaim, Wolfgang ^b   König, Burkhard ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b UNIVERSITY OF STUTTGART   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BIS(4 NITROPHENYL) PHOSPHATE; BIS(4-NITROPHENYL)PHOSPHATE; NITROPHENOL; ORGANOMETALLIC COMPOUND; WATER;

ARTICLE; CHEMISTRY; HYDROLYSIS; KINETICS; PH; TEMPERATURE;

HYDROGEN-ION CONCENTRATION; HYDROLYSIS; KINETICS; NITROPHENOLS; ORGANOMETALLIC COMPOUNDS; TEMPERATURE; WATER;

EID: 46749089712     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic702413q     Document Type: Article

References (80)

1. Da Silva, J. J. R. Fraústo, Williams, R. J. P. The biological chemistry of elements; Clarendon Press: Oxford, 1991; Chapter 11.
2. Aoki, S.; Kimura, E. Rev. Mol. Biol. 2002, 90, 129-155.
3. Williams, N. H.; Takasaki, B.; Wall, M.; Chin, J. Acc. Chem. Res. 1999, 32, 485-493.
4. For some reviews, see Wilcox, D. E. Chem. Rev. 1996, 96, 2435-2458.
5. (b) Sträter, N.; Lipscomb, W. N.; Klabunde, T.; Krebs, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2024-2055.
6. (c) Lipscomb, W. N.; Sträter, N. Chem. Rev. 1996, 96, 2375-2433.
7. (d) Cowan, J. A. Chem. Rev. 1998, 98, 1067-1087.
8. (e) Jedrjezas, M. J.; Setlow, P. Chem. Rev. 2001, 101, 607-618.
9. (a) For reviews, see Chin, J. Acc. Chem. Res. 1991, 24, 145-152.
10. (b) Liu, C.; Wang, M.; Zhang, T.; Sun, H. Coord. Chem. Rev. 2004, 248, 147-168.
11. (c) Kruppa, M.; König, B. Chem. Rev. 2006, 106, 3520-3560.
12. (a) Hegg, E. L.; Burstyn, J. N. Coord. Chem. Rev. 1998, 173, 133-165.
13. (b) Suh, J. Acc. Chem. Res. 1992, 25, 273-279.
14. Göbel, M. W. Angew. Chem., Int. Ed. Engl. 1994, 33, 1141-1143.
15. (a) Kovbasyuk, L.; Krämer, R. Chem. Rev. 2004, 104, 3161-3187.
16. (b) Feng, G.; Mareque-Rivas, J. C.; de Rosales, R. T. M.; Williams, N. H. J. Am. Chem. Soc. 2005, 127, 13470-13471.
17. (c) O'Donoghue, A. M.; Pyun, S. Y.; Yang, M.-Y.; Morrow, J. R.; Richard, J. P. J. Am. Chem. Soc. 2006, 128, 1615-1621.
18. (a) Breslow, R.; Berger, D.; Huang, D.-L. J. Am. Chem. Soc. 1990, 112, 3686-3687.
19. (b) Morrow, J. R.; Aures, H.; Epstein, D. J. Chem. Soc., Chem. Commun. 1995, 2431-2432.
20. (c) Young, M. J.; Wahnon, D.; Hynes, R. C.; Chin, J. J. Am. Chem. Soc. 1995, 117, 9441-9447.
21. (d) Chu, F.; Smith, J.; Lynch, V. M.; Anslyn, E. V. Inorg. Chem. 1995, 34, 5689-5690. (the authors propose that in a Zn complex either imidazole or imidazolium might act as an auxiliary group, providing an 1.5-fold increase in RNA cleavage rate),
22. (e) See, also: Hsu, C.-M.; Cooperman, B. S. J. Am. Chem. Soc. 1976, 98, 5657-5663.
23. (f) Koike, T.; Inoue, M.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 3091-3099.
24. (g) Kimura, E.; Kodama, Y.; Koike, T.; Shiro, M. J. Am. Chem. Soc. 1995, 117, 8304-8311.
25. Kövari, E.; Krämer, R. J. Am. Chem. Soc. 1996, 118, 12704-12709.
26. Subat, M.; Woinaroschy, K.; Anthofer, S.; Malterer, B.; König, B. Inorg. Chem. 2007, 46, 4336-4356.
27. Walenzyk, T.; König, B. Inorg. Chim. Acta 2005, 358, 2269-2274.
28. (a) Logan, S. R. Grundlagen der Chemischen Kinetik; Wiley-VCH: Weinheim, 1997; Chapter 1-3.
29. (b) Perkampus, H.-H.; Kaufmann, R. Kinetische Analyse mit Hilfe der UV/VIS-Spektrometrie; Wiley-VCH: Weinheim, 1991.
30. The association constant of Zn2L2 with phenylphosphate in neutral aqueous solution was determined by an indicator displacement assay using pyrocatechol violet to be K = 104 L/mol. The association constant of 4-nitrophenylphosphate to Zn2L2 is expected to be even lower in the millimolar range because of the reduced basicity of this phosphate. This excludes a significant product inhibition under the experimental conditions used (less than 5% conversion; typical initial concentrations of BNPP 0.1-1 mM).
31. 4: Fabrizzi, L.; Micheloni, M.; Paoletti, P. Inorg. Chem. 1980, 19, 535-538.
32. (b) Fabrizzi, L. Inorg. Chem. 1977, 16, 2667-2668.
33. (c) Bencini, A.; Bianchi, A.; Garcia-Espana, E.; Jeannin, Y.; Julve, M.; Marcelino, V.; Philoche-Levisalles, M. Inorg. Chem. 1990, 29, 963-970.
34. (a) The comparison of UV and IR spectra with literature values indicate a square pyramidal complex with one molecule of water as the fifth ligand: Styka, M. C.; Smierciak, R. C.; Blinn, E. L.; DeSimone, R. E.; Passariello, J. V. Inorg. Chem. 1978, 17, 82-86.
35. (b) Thöm, V. J.; Hosken, G. D.; Hancock, R. D. Inorg. Chem. 1985, 24, 3378-3381.
36. (c) Thöm, V. J.; Fox, C. C.; Boeyens, J. C. A.; Hancock, R. D. J. Am. Chem. Soc. 1984, 106, 5947-5955.
37. Koike, T.; Kimura, E. J. Am. Chem. Soc. 1991, 113, 8935-8941.
38. Norman, P. R. Inorg. Chim. Acta 1987, 130, 1-4.
39. Norman, P. R.; Tate, A.; Rich, P. Inorg. Chim. Acta 1988, 145, 211-217.
40. (a) Deal, K. A.; Burstyn, J. N. Inorg. Chem. 1996, 35, 2792-2798.
41. (b) Hegg, E. L.; Mortimore, S. H.; Cheung, C. L.; Huyett, J. E.; Powell, D. R.; Burstyn, J. N. Inorg. Chem. 1999, 38, 2961-2968.
42. (a) Fry, F. H.; Fischmann, A. J.; Belousoff, M. J.; Spiccia, L.; Brügger, J. Inorg. Chem. 2005, 44, 941-950; and reference therein.
43. (b) Belousoff, M. J.; Duriska, M. B.; Graham, B.; Batten, S. R.; Moubaraki, B.; Murray, K. S.; Spiccia, L. Inorg. Chem. 2006, 45, 3746-3755.
44. (c) Bonora, G. M.; Drioli, S.; Felluga, F.; Mancin, F.; Rossi, P.; Scrimin, P.; Tecilla, P. Tetrahedron Lett. 2003, 44, 535-538.
45. (a) Vichard, C.; Kaden, T. A. Inorg. Chim. Acta 2002, 337, 173-180.
46. (b) Vichard, C.; Kaden, T. A. Inorg. Chim. Acta 2004, 357, 2285-2293.
47. The reactivity increases from pH 7 to pH 9 because of increasing amounts of the active species in solution (0.007% at pH 7, 0.07% at pH 8, and 0.7% at pH 9). Previously reported azamacrocyclic Ni(II) complexes (see ref 22) were also active only at pH > 9.
48. Kimura, E.; Hashimoto, H.; Koike, T. J. Am. Chem. Soc. 1996, 118, 10963-10970.
49. (a) Gellman, S. H.; Petter, R.; Breslow, R. J. Am. Chem. Soc. 1986, 108, 2388-2394.
50. (b) Bonfa, L.; Gatos, M.; Mancin, F.; Tecilla, P.; Tonellato, U. Inorg. Chem. 2003, 42, 3943-3949.
51. a), binding of the substrate to the metal complex (K), intracomplex nucleophilic attack of the hydroxide (k′) with simultaneous departure of the leaving group and, eventually, deprotonation and decomplexation of the substrate to restore the catalyst. The reaction rate is pH dependent and saturation behavior by formation of the substrate-catalyst complex is expected. However, the affinities of phosphate diesters to Zn(II) complexes are very low and the curvature of the plot is not detectable in the exploitable concentration range. This is common to all reports on metal complexes hydrolyzing phosphate diesters.
52. (a) Costas, M.; Anda, C.; Llobet, A.; Parella, T.; Evans, H. S.; Pinilla, E. Eur. J. Inorg. Chem. 2004, 857-865.
53. (b) Gross, F.; Vahrenkamp, H. Inorg. Chem. 2005, 44, 3321-3329.
54. (a) Li, S.-A.; Xia, J.; Yang, D.-X.; Xu, Y.; Li, D.-F.; Wu, M.-F.; Tang, W.-X. Inorg. Chem. 2002, 41, 1807-1815.
55. (b) Xia, J.; Li, S.-A.; Shi, Y.-B.; Yu, K.-B.; Tang, W.-X. J. Chem. Soc., Dalton Trans. 2001, 2109-2115.
56. (c) Li, S.-A.; Li, D.-F.; Yang, D. X.; Huang, J.; Xu, Y.; Tang, W.-X. Inorg. Chem. Commun. 2003, 6, 221-224.
57. (a) Koike, T.; Gotoh, T.; Aoki, S; Kimura, E.; Shiro, M. Inorg. Chim. Acta 1998, 270, 424-432.
58. (b) Aoki, S.; Kagata, D.; Shiro, M.; Takeda, K.; Kimura, E. J. Am. Chem. Soc. 2004, 126, 13377-13390.
59. Shionoya, M.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1993, 115, 6730-6737.
60. Bazzicalupi, C.; Bencini, A.; Bianchi, A.; Fusi, V.; Giorgi, C.; Paoletti, P.; Valtancoli, B.; Zanchi, D. Inorg. Chem. 1997, 36, 2784-2790.
61. Bazzicalupi, C.; Bencini, A.; Berni, E.; Bianchi, A.; Fornasari, P.; Giorgi, C.; Valtancoli, B. Inorg. Chem. 2004, 43, 6255-6265.
62. Kimura, E.; Gotoh, T.; Koike, T.; Shiro, M. J. Am. Chem. Soc. 1999, 121, 1267-1274.
63. The higher Lewis acidic character of the metal ion in Zn[12]aneN3 complexes leads to a stronger interaction between the metal complex and the phosphodiester, as proposed by Kimura. In the carboxylic ester hydrolysis promoted by mononuclear complexes, the simple nucleophilic mechanism is predominant and the Zn(II)-bound hydroxides act as nucleophile to the carbonyl group. Therefore, the Zn[12]aneN3 complexes with higher Lewis acidic character of the metal ion, but also lower nucleophilic character of the Zn-L-OH- species, have lower reaction rates in the hydrolysis of carboxyesters than the Zn[12]aneN4 system.
64. (a) Fujioka, H.; Koike, T.; Yamada, N.; Kimura, E. Heterocycles 1996, 42, 775-787.
65. (b) Koike, T.; Takashige, M.; Kimura, E.; Fujioka, H.; Shiro, M. Chem. - Eur. J. 1996, 2, 617-623.
66. (c) Kimura, E.; Aoki, S.; Koike, T.; Shiro, M. J. Am. Chem. Soc. 1997, 119, 3068-3076.
67. (d) Aoki, S.; Kimura, E. J. Am. Chem. Soc. 2000, 122, 4542-4548.
68. (a) Yoo, C. E.; Chae, P. S.; Kim, J. E.; Jeong, E. J.; Suh, J. J. Am. Chem. Soc. 2003, 125, 14580-14589.
69. (b) Aoki, S.; Kimura, E. Rev. Mol. Biotechnol. 2002, 90, 129-155; and references therein.
70. 2L2. Their low activity and the concentrations of metal complex and substrate required to reach acceptable experimental errors lead to kinetic data that do not allow a more extended analysis.
71. (a) Jang, B.-B.; Lee, K.-P.; Min, D.-H.; Suh, J. J. Am. Chem. Soc. 1998, 120, 12008-12016.
72. (b) Yoo, C. E.; Chae, P. S.; Kim, J. E.; Jeong, E. J.; Suh, J. J. Am. Chem. Soc. 2003, 125, 14580-14589.
73. (c) Yoo, S. H.; Lee, B. J.; Kim, H.; Suh, J. J. Am. Chem. Soc. 2005, 127, 9593-9602.
74. 2L2 complex have only one coordination site available each and do not act cooperatively. Iranzo, O.; Richard, J. P.; Morrow, J. P. Inorg. Chem. 2004, 43, 1743-1750.
75. (b) Iranzo, O.; Elmer, T.; Richard, J. P.; Morrow, J. P. Inorg. Chem. 2003, 42, 7737-7746.
76. (a) For previous reports of BNPP hydrolysis by di- or trinuclear Zn(II) macrocyclic complexes, see Arca, M.; Bencini, A.; Berni, E.; Caltagirone, C.; Devillanova, F. A.; Isaia, F.; Garau, A.; Giorgi, C.; Lippolis, V.; Perra, A.; Tei, L.; Valtancoli, B. Inorg. Chem. 2003, 42, 6929-6939.
77. (b) Bazzicalupi, C.; Bencini, A.; Berni, E.; Giorgi, C.; Maoggi, S.; Valtancoli, B. J. Chem. Soc., Dalton Trans. 2003, 3574-3580.
78. (c) Bauer-Siebenlist, B.; Meyer, F.; Farkas, E.; Vidovic, D.; Cuesta-Seijo, J. A.; Herbst-Irmer, R.; Pritzkow, H. Inorg. Chem. 2004, 43, 4189-4202.
79. Bazzicalupi, C.; Bencini, A.; Berni, E.; Bianchi, A.; Giorgi, G.; Paoletti, P.; Valtancoli, B. Inorg. Chem. 1999, 38, 6323-6325.
80. The hydrolytic activity of the complexes given in Table 7 were determined at 35.1°C, whereas the hydrolytic activity of the dinuclear complexes reported in this paper was determined at 25°C.