A theoretical analysis of the coordination modes of CuII with penicillins: Activation of the β-lactam C-N bond

ChemPhysChem

Volumn 6, Issue 2, 2005, Pages 344-351

  Campomanes, Pablo ^a   Menéndez, M Isabel ^a   López, Ramón ^a   Sordo, Tomás L ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

C N activation; Coordination modes; Copper; Density functional calculations; Lactams

Indexed keywords

ACTIVATION ANALYSIS; AMIDES; ANTIBIOTICS; CARBOXYLATION; CHEMICAL ACTIVATION; COPPER; DENSITY FUNCTIONAL THEORY; MOLECULES; SEWAGE TREATMENT PLANTS;

CARBOXYLATE GROUPS; COORDINATION MODES; EXPERIMENTAL EVIDENCE; LACTAMS; REACTION COORDINATES; SQUARE-PLANAR COORDINATION; STABLE COMPLEXES; TETRAHEDRAL INTERMEDIATES;

COORDINATION REACTIONS;

2 AZETIDINONE DERIVATIVE; 6 ACETYLAMINO 3ALPHA CARBOXYPENAM; 6 FORMYLAMINO 3ALPHA CARBOXYPENAM; BETA LACTAM ANTIBIOTIC; CARBOXYLIC ACID DERIVATIVE; COORDINATION COMPOUND; COPPER; PENAM DERIVATIVE; PENICILLIN DERIVATIVE; UNCLASSIFIED DRUG; WATER; ANTIINFECTIVE AGENT; BETA LACTAM; NITROGEN;

ARTICLE; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL MODEL; CHEMICAL STRUCTURE; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; DRUG DEGRADATION; REACTION ANALYSIS; THEORETICAL MODEL; THERMODYNAMICS; CHEMISTRY; COMPUTER PROGRAM; CONFORMATION; HYDROGEN BOND; METHODOLOGY; PHYSICAL CHEMISTRY; TEMPERATURE;

ANTI-INFECTIVE AGENTS; BETA-LACTAMS; CHEMISTRY, PHARMACEUTICAL; CHEMISTRY, PHYSICAL; COPPER; HYDROGEN BONDING; MODELS, CHEMICAL; MODELS, MOLECULAR; MODELS, THEORETICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NITROGEN; PENICILLINS; SOFTWARE; TEMPERATURE; THERMODYNAMICS; WATER;

EID: 15044361926     PISSN: 14394235     EISSN: None     Source Type: Journal    
DOI: 10.1002/cphc.200400280     Document Type: Article

References (62)

1. The Chemistry of β-Lactams (Ed.: M. I. Page), Blackie Academic & Professional, London, 1992.
2. S. G. Waley, β-Lactamase: Mechanism of Action in The Chemistry of β-Lactams (Ed.: M. I. Page), Blackie Academics Professional, London, 1992, pp. 199-228.
3. M. I. Page, Chem. Commun. 1998, 1609-1617.
4. Z. Wang, W. Fast, A. M. Valentine, S. J. Benkovic, Curr. Opin. Chem. Biol. 1999, 3, 614-622.
5. W. A. Cressman, E. T. Sugita, J. T. Doluisio, P. J. Niebergall, J. Pharm. Sci. 1969, 58, 1471-1476, and references therein.
6. N. P. Gensmantel, E. W. Gowling, M. I. Page, J. Chem. Soc. Perkin Trans. 2 1978, 335-342.
7. N. P. Gensmantel, P. Proctor, M. I. Page, J. Chem. Soc. Perkin Trans. 2 1980, 1725-1732.
8. H. Tomida, M. A. Schwartz, J. Pharm. Sci. 1983, 72, 331-335.
9. M. I. Page, Acc. Chem. Res. 1984, 17, 144-151.
10. R. W. Hay, A. K. Basak, M. P. Pujari, A. Perotti, J. Chem. Soc. Dalton Trans. 1989, 197-201.
11. J. Martin, R. Méndez, F. Salto, J. Chem. Soc. Perkin Trans. 2 1989, 227-231.
12. J. Martin, R. Méndez, M. Castillo, F. Salto, J. Chem. Soc. Perkin Trans. 2 1990, 43-46.
13. T. J. Przystas, T. H. Fife, J. Chem. Soc. Perkin Trans. 2 1990, 393-399.
14. R. Méndez, T. Alemany, J. Martin-Villacorta, Chem. Pharm. Bull. 1992, 40, 3228-3233.
15. A. Sher, M. Veber, M. Marolt-Gomiscek, S. Gomiscek, Int. J. Pharm. 1993, 90, 181-186.
16. T. Koike, M. Takamura, E. Kimura, J. Am. Chem. Soc. 1994, 116, 8443-8449.
17. a) G. L. Eichhorn, Nature, 1962, 194, 474-479; b) W. Szer, S. Ochoa, J. Mol. Biol. 1964, 8, 823-834.
18. a) G. L. Eichhorn, Nature, 1962, 194, 474-479; b) W. Szer, S. Ochoa, J. Mol. Biol. 1964, 8, 823-834.
19. Metal Ions in Biological Systems, Vol. 19 (Ed.: H. Sigel), Marcel Dekker, New York, 1985.
20. Handbook of Metal-Ligand Interactions in Biological Fluids, Vol. 2 (Ed.: G. Berthon), Marcel Dekker, New York, 1995.
21. H. Dugas, Bioorganic Chemistry. A Chemical Approach to Enzyme Action, 3rd Ed., Springer, Berlin, 1996, Chap. 6, p. 388.
22. R. B. Davies, E. P. Abraham, Biochem. J. 1974, 143, 129-135.
23. A. Kucers, N. McBennet, The Use of Antibiotics, Medical Books, London, 1988.
24. G. V. Fazakerley, G. E. Jackson, J. Chem. Soc. Perkin Trans. 2 1975, 567-571.
25. A. Sher, M. Veber, M. Marolt-Gomiscek, S. Gomiscek, Int. J. Pharm. 1993, 99, 119-123.
26. A. Sher, M. Veber, M. Marolt-Gomiscek, S. Gomiscek, Int. J. Pharm. 1997, 148, 191-199.
27. G. G. Mohamed, Spectrochim. Acta Part A 2001, 57, 1643-1648.
28. T. Grochowski, K. Samochocka, Polyhedron 1991, 10, 1473-1477.
29. A. Pasquarello, I. Petri, P. S. Salmon, O. Parisel, R. Car, E. Tóth, D. H. Powell, H. E. Fischer, L. Helm, A. E. Merbach, Science 2001, 291, 856-859.
30. L. Rulisek, Z. Havlas, J. Am. Chem. Soc. 2000, 122, 10428-10439.
31. To confirm C-N activation in solution we reoptimized 3 S with a continuum model (Poisson-Boltzmann) implemented in the Jaguar program (Jaguar, 5.0 edit., Schrödinger, Inc., Portland, OR, 2003). This optimization failed with the PCM method implemented in Gaussian 98. In solution the C-N bond (1.521 Å) is even more stretched than in the gas phase (1.487 Å).
32. N. Díaz, D. Suárez, T. L. Sordo, I. Tuñón, E. Silla, Chem. Eur. J. 2002, 8, 859-867.
33. J. Pitarch, M. F. Ruiz López, J. L. Pascual-Ahuir, E. Silla, I. Tuñón, J. Phys. Chem. B 1997, 101, 3581-3588.
34. M. Noguera, J. Bertran, M. Sodupe, J. Phys. Chem. A 2004, 108, 333-341.
35. J. L. M. Abboud, T. Cañada, H. Homan, R. Notario, C. Cativiela, M. D. Díaz de Villegas, M. C. Bordejé, O. Mó, M. Yáñez, J. Am. Chem. Soc. 1992, 114, 4728-4736.
36. Gaussían 98 (Revísíon A.7), M. J. Frísch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.
37. a) A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100;
38. b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789;
39. c) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
40. a) W. J. Hehre, L. Radom, J. A. Pople, P. von R. Schleyer, Ab Initio Molecular Orbital Theory, Wiley, New York, 1986;
41. b) V. A. Rassolov, J. A. Pople, M. A. Ratner, T. L. Windus, J. Chem. Phys. 1998, 109, 1223-1228.
42. a) A. J. H. Wachters, J. Chem. Phys. 1970, 52, 1033-1036;
43. b) P. J. Hay, J. Chem. Phys. 1977, 66, 4377-4384;
44. c) R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650-654;
45. d) A. D. McLean, G. S. Chandler, J. Chem. Phys. 1980, 72, 5639-5648;
46. e) K. Raghavachari, G. W. Trucks, J. Chem. Phys. 1989, 91, 1062-1065.
47. H. B. Schlegel, J. Comput. Chem. 1982, 3, 214-218.
48. Th. J. M. de Bruin, A. T. M. Marcelis, H. Zuilhof, E. J. R. Sudhölter, Phys. Chem. Chem. Phys. 1999, 1, 4157.
49. II, and the largest discrepancy between UMP2 and UB3LYP is 0.027 Å for the C6-C7 bond.
50. D. A. McQuarrie, Statistical Mechanics, Harper & Row, New York, 1976.
51. J. Tomasi, M. Persico, Chem. Rev. 1994, 94, 2027-2094.
52. a) S. Miertus, E. Scrocco, J. Tomasi, Chem. Phys. 1981, 55, 117;
53. b) R. Cammi, J. Tomasi, J. Comput. Chem. 1995, 16, 1449-1458;
54. c) M. Cossi, V. Barone, R. Cammi, J. Tomasi, Chem. Phys. Lett. 1996, 255, 327-331;
55. d) V. Barone, M. Cossi, J. Tomasi, J. Chem. Phys. 1997, 107, 3210-3221;
56. e) C. Amovilli, V. Barone, R. Cammi, E. Cancès, M. Cossi, B. Menucci, C. S. Pomelli, J. Tomasi, Adv. Quantum. Chem. 1998, 32, 227-240.
57. a) R. F. W. Bader, Atoms in Molecules. A Quantum Theory, Oxford University Press, Oxford, 1990.;
58. b) R. F. W. Bader, P. L. A. Popelier, T. A. Keith, Angew. Chem. 1994, 106; Angew. Chem. Int. Ed. Engl. 1994, 33, 620-631.
59. b) R. F. W. Bader, P. L. A. Popelier, T. A. Keith, Angew. Chem. 1994, 106; Angew. Chem. Int. Ed. Engl. 1994, 33, 620-631.
60. F. W. Biegler-Konig, R. F. W. Bader, T. Hua-Tang, J. Comput. Chem. 1982, 3, 317.
61. a) A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899-926;
62. b) F. Weinhold, J. E. Carpenter in The Structure of Small Molecules and Ions (Eds.: R. Naaman, Z. Vager), Plenum Press, New York, 1988, pp. 227-236.