Ribonucleotide reductases: Radical chemistry and inhibition at the active site

Nucleosides, Nucleotides and Nucleic Acids

Volumn 22, Issue 5-8, 2003, Pages 519-534

  Robins, Morris J ^a  

^a Brigham Young University   (United States)

Author keywords

Anion vs. radical elimination; Fenton chemistry; Free radical chemistry; Mechanism based inactivation of RDPR; Reduction of ribonucleotides to 2 deoxynucleotides; Ribonucleoside 5 diphosphate reductase (RDPR); Ribonucleotide reductase

Indexed keywords

2' DEOXYNUCLEOSIDE; ACETAL; FREE RADICAL; RIBONUCLEOSIDE DIPHOSPHATE REDUCTASE; RIBONUCLEOTIDE; RIBONUCLEOTIDE REDUCTASE; THIOHEMIACETAL; UNCLASSIFIED DRUG;

BINDING SITE; BIOMIMETICS; CHEMISTRY; COMPLEX FORMATION; CONFERENCE PAPER; CRYSTAL STRUCTURE; ENZYME ACTIVE SITE; ENZYME INHIBITION; FENTON REACTION; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

BINDING SITES; CRYSTALLOGRAPHY, X-RAY; KINETICS; RIBONUCLEOSIDES; RIBONUCLEOTIDE REDUCTASES;

EID: 0141425760     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-120021952     Document Type: Conference Paper

References (71)

1. Hogenkamp, H.P.C.; Sando, G.N. In Structure and Bonding; Dunitz, J.D., Hemmerich, P., Holm, R.H., Ibers, J.A., Jorgensen, C.K., Neilands, J.B., Reinen, D., Williams, R.J.P., Eds.; Springer-Verlag: Heidelberg, 1974; 23-58.
2. Follmann, H. Agnew. Chem. Int. Ed. Engl. 1974, 13, 569-579.
3. (a) Thelander, L.; Reichard, P. Annu. Rev. Biochem. 1979, 48, 133-158;
4. (b) Reichard, P. Science 1993, 260, 1773-1777;
5. (c) Sjöberg, B.-M. In Nucleic Acids and Molecular Biology; Eckstein, F., Lilley, D.M.J., Eds.; Springer-Verlag: Berlin, 1995; Vol. 9, 192-221;
6. (d) Sjöberg, B.-M. Struct. Bonding (Berlin) 1997, 88, 139-173;
7. (e) Jordan, A.; Reichard, P. Annu. Rev. Biochem. 1998, 67, 71-98;
8. (f) Eklund, H.; Uhlin, U.; Färnegardh, M.; Logan, D.T.; Nordlund, P. Prog. Biophys. Molecular Biol. 2001, 77, 177-268.
9. (a) Ashley, G.W.; Stubbe, J. In Inhibitors of Ribonucleoside Diphosphate Reductase Activity; Cory, J.G., Cory, A.H., Eds.; Pergamon Press: New York, 1989; 55-87;
10. (b) Stubbe, J.; Adv. Enzymol. Relat. Areas Mol. Biol. 1990, 63, 349-419;
11. (c) Stubbe, J.; van der Donk, W.A., Chem. Biol. 1995, 2, 793-801;
12. (d) Stubbe, J.; van der Donk, W.A, Chem Rev. 1998, 98, 705-762.
13. (a) Robins, M.J.; Samano, M.C.; Samano, V. Nucleosides Nucleotides 1995, 14, 485-493;
14. (b) Robins, M.J. Nucleosides Nucleotides 1999, 18, 779-793.
15. (a) Walling, C.; Johnson, R.A. J. Amer. Chem. Soc. 1975, 97, 2405-2407;
16. (b) Walling, C. Acc. Chem. Res. 1998, 31, 155-157.
17. MacFaul, P.A.; Wayner, D.D.M.; Ingold, K.U. Acc. Chem. Res. 1998, 31, 159-162.
18. (a) Mao, S.S.; Holler, T.P.; Bollinger, J.M., Jr.; Yu, G.X.; Johnston, M.I.; Stubbe, J. Biochemistry 1992, 31, 9744-9751;
19. (b) Mao, S.S.; Yu, G.X.; Chalfoun, D.; Stubbe, J. Biochemistry 1992, 31, 9752-9759.
20. (a) Nordlund, P.; Sjöberg, B.-M.; Eklund, H. Nature 1990, 345, 593-598;
21. (b) Uhlin, U.; Eklund, H. Nature 1994, 370, 533-539;
22. (c) Uhlin, U.; Eklund, H.J. Mol. Biol. 1996, 262, 358-369;
23. (d) Kauppi, B.; Nielsen, B.B.; Ramaswamy, S.; Larsen, I.K.; Thelander, M.; Thelander, L.; Eklund, H. J. Mol. Biol. 1996, 262, 706-720;
24. (e) Logan, D.T.; Su, X.-D.; Aberg, A.; Regnström, K.; Hajdu, J.; Eklund, H.; Nordlund, P. Structure 1996, 4, 1053-1064;
25. (f) Eriksson, M.; Uhlin, U.; Ramaswamy, S.; Ekberg, M.; Regnström, K.; Sjöberg, B.-M.; Eklund, H. Structure 1997, 5, 1077-1092.
26. Siegbahn, P.E.M. J. Amer. Chem. Soc. 1998, 120, 8417-8429.
27. Samano, V.; Robins, M.J. J. Org. Chem. 1990, 55, 5186-5188.
28. Thelander, L.; Larsson, B.J.; Hobbs, J.; Eckstein, F. J. Biol. Chem. 1976, 251, 1398-1405.
29. Hertel, L.W.; Kroin, J.S.; Misner, J.W.; Tustin, J.M. J. Org. Chem. 1998, 53, 2406-2409.
30. (a) Plunkett, W.; Huang, P.; Searcy, C.E.; Gandhi, V. Semin. Oncol. 1996, 23, 3-15 (Suppl. 10);
31. (b) Peters, G.J.; Ruiz van Haperen, V.W.T.; Bergman, A.M.; Veerman, G.; Smitskamp-Wilms, E.; van Moorsel, C.J.A.; Kuiper, C.M.; Braakhuis, B.J.M. Semin. Oncol. 1996, 23, 16-24 (Suppl. 10);
32. (c) Abbruzzese, J.L. Semin. Oncol. 1996, 23, 25-31 (Suppl. 10);
33. (d) Cheng, X.-M. In Annual Reports in Medicinal Chemistry; Bristol, J.A., Ed.; Academic Press: San Diego, 1996; Vol. 31, 337-355.
34. Huang, P.; Chubb, S.; Hertel, L.W.; Grindey, G.B.; Plunkett, W. Cancer Res. 1991, 51, 6110-6117.
35. (a) Baker, C.H.; Banzon, J.; Bollinger, J.M.; Stubbe, J.; Samano, V.; Robins, M.J.; Lippert, B.; Jarvi, E.; Resvick, R. J. Med. Chem. 1991, 34, 1879-1884;
36. (b) van der Donk, W.A.; Yu, G.; Pérez, L.; Sanchez, R.J.; Stubbe, J.; Samano, V. Robins, M.J. Biochemistry 1998, 37, 6419-6426.
37. (a) Takenuki, K.; Matsuda, A.; Ueda, T.; Sasaki, T.; Fujii, A.; Yamagami, K. J. Med. Chem. 1988, 31, 1063-1064;
38. (b) Yamagami, K.; Fujii, A.; Arita, M.; Okumoto, T.; Sakata, S.; Matsuda, A.; Ueda, T.; Sasaki, T. Cancer Res. 1991, 51, 2319-2323.
39. (a) Samano, V.; Robins, M.J. Synthesis 1991, 283-288;
40. (b) Robins, M.J.; Samano, V.; Zhang, W.; Balzarini, J.; De Clercq, E.; Borchardt, R.T.; Lee, Y.; Yuan, C.-S. J. Med. Chem. 1992, 35, 2283-2293.
41. (a) McCarthy, J.R.; Matthews, D.P.; Stemerick, D.M.; Huber, E.W.; Bey, P.; Lippert, B.J.; Snyder, R.D.; Sunkara, P.S. J. Amer. Chem. Soc. 1991, 113, 7439-7440;
42. (b) Bitonti, A.J.; Dumont, J.A.; Bush, T.L.; Cashman, E.A.; Cross-Doersen, D.E.; Wright, P.S.; Matthews, D.P.; McCarthy, J.R.; Kaplan, D.A. Cancer Res. 1994, 54, 1485-1490;
43. (c) Takahashi, T.; Nakashima, A.; Kanazawa, J.; Yamaguchi, K.; Akinaga, S.; Tamaoki, T.; Okabe, M. Cancer Chemother. Pharmacol. 1998, 41, 268-274.
44. (a) Gerfen, G.J.; van der Donk, W.A.; Yu, G.; McCarthy, J.R.; Jarvi, E.T.; Matthews, D.P.; Farrar, C.; Griffin, R.G.; Stubbe, J. J. Amer. Chem. Soc. 1998, 120, 3823-3835;
45. (b) van der Donk, W.A.; Gerfen, G.J.; Stubbe, J. J. Amer. Chem. Soc. 1998, 120, 4252-4253.
46. Zhou, Y.; Achanta, G.; Pelicano, H.; Gandhi, V.; Plunkett, W.; Huang, P. Mol. Pharmacol. 2002, 61, 222-229.
47. van der Donk, W.A.; Yu, G.; Silva, D.J.; Stubbe, J.; McCarthy, J.R.; Jarvi, E.T.; Matthews, D.P.; Resvick, R.J.; Wagner, E. Biochemistry 1996, 35, 8381-8391.
48. Samano, V.; Robins, M.J. J. Amer. Chem. Soc. 1992, 114, 4007-4008.
49. (a) Griller, D.; Ingold, K.U. Acc. Chem. Res. 1980, 13, 317-323;
50. (b) Suckling, C.J. Angew. Chem., Int. Ed. Engl. 1988, 27, 537-552.
51. Stubbe, J., unpublished data. We thank Professor Stubbe for helpful discussions.
52. Harris, G.; Ashley, G.W.; Robins, M.J.; Tolman, R.L.; Stubbe, J. Biochemistry 1987, 26, 1895-1902.
53. (a) Hattori, H.; Tanaka, M.; Fukushima, M.; Sasaki, T.; Matsuda, A. J. Med. Chem. 1996, 39, 5005-5011;
54. (b) Azuma, A.; Matsuda, A.; Sasaki, T.; Fukushima, M. Nucleosides, Nucleotides Nucleic Acids 2001, 20, 609-619.
55. Lenz, R.; Giese, B. J. Amer. Chem. Soc. 1997, 119, 2784-2794.
56. Cai, Y.; Roberts, B.P. Chem. Commun. 1998, 1145-1146.
57. Robins, M.J.; Sporns, P.; Muhs, W.H. Can. J. Chem. 1979, 57, 274-282.
58. (a) Wagner, P.J.; Sedon, J.H.; Lindstrom, M.J. J. Amer. Chem. Soc 1978, 100, 2579-2580;
59. (b) Wagner, P.J.; Lindstrom, M.J.; Sedon, J.H.; Ward, D.R. J. Amer. Chem. Soc. 1981, 103, 3842-3849.
60. Robins, M.J.; Wnuk, S.F.; Hernández-Thirring, A.E.; Samano, M.C. J. Amer. Chem. Soc. 1996, 118, 11,341-11,348.
61. Barton, D.H.R.; Beaton, J.M.; Geller, L.E.; Pechet, M.M. J. Amer. Chem. Soc. 1961, 83, 4076-4081.
62. (a) Vite, G.D.; Fraser-Reid, B. Synth. Commun. 1988, 18, 1339-1342;
63. (b) Lopez, J.C.; Alonso, R.; Fraser-Reid, B. J. Amer. Chem. Soc. 1989, 111, 6471-6473.
64. (a) Robins, M.J.; Guo, Z.; Samano, M.C.; Wnuk, S.F. J. Amer. Chem. Soc. 1996, 118, 11,317-11,318;
65. (b) Robins, M.J.; Guo, Z.; Wnuk, S.F. J. Amer. Chem. Soc. 1997, 119, 3637-3638;
66. (c) Robins, M.J.; Guo, Z.; Samano, M.C.; Wnuk, S.F. J. Amer. Chem. Soc. 1999, 121, 1425-1433.
67. Zipse, H. J. Amer. Chem. Soc. 1995, 117, 11,798-11,806.
68. (a) Robins, M.J.; MacCoss, M.; Wilson, J.S. J. Amer. Chem. Soc. 1977, 99, 4660-4666;
69. (b) Robins, M.J.; Wilson, J.S.; Hansske, F. J. Amer. Chem. Soc. 1983, 105, 4059-4065.
70. Guo, Z.; Samano, M.C.; Krzykawski, J.W.; Wnuk, S.F.; Ewing, G.J.; Robins, M.J. Tetrahedron 1999, 55, 5705-5718.
71. Robins, M.J.; Ewing, G.J. J. Amer. Chem. Soc. 1999, 121, 5823-5824.