Transient species in the stepwise interconversion of NADH and NAD +

Accounts of Chemical Research

Volumn 37, Issue 6, 2004, Pages 379-386

  Gȩbicki, Jerzy ^a   Marcinek, Andrzej ^a   Zielonka, Jacek ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; NICOTINAMIDE ADENINE DINUCLEOTIDE; PYRIDINIUM DERIVATIVE; RADICAL; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE;

CHEMICAL REACTION; CYTOTOXICITY; ELECTRON TRANSPORT; ENZYME MECHANISM; HYDRIDE TRANSFER; INTERCONVERSION; ISOMER; PROTON TRANSPORT; REACTION ANALYSIS; REVIEW; TAUTOMER;

ANIMALS; CATIONS; FREE RADICALS; HUMANS; NAD;

EID: 2942637485     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar030171j     Document Type: Review

References (55)

1. Stryer, L. Biochemistry; Freeman: New York, 1995.
2. Abeles, R. H.; Hutton, R. F.; Westheimer, F. H. The Reduction of Thioketones by a Model for a Coenzyme. J. Am. Chem. Soc. 1957, 79, 712-716.
3. Powell, M. F.; Bruice, T. C. Hydride vs Electron Transfer in the Reduction of Flavin and Flavin Radical by 1,4-Dihydropyridines. J. Am. Chem. Soc. 1983, 105, 1014-1021.
4. Carlson, B. W.; Miller, L. L. Mechanism of the Oxidation of NADH by Quinones. Energetics of One-Electron and Hydride Routes. J. Am. Chem. Soc. 1985, 107, 479-485.
5. + Analogues. J. Org. Chem. 1985, 50, 4206-4211.
6. + Analogues. J. Am. Chem. Soc. 1988, 110, 524-530.
7. + Analogues. J. Am. Chem. Soc. 1997, 119, 2722-2728.
8. Bunting, J. Merged Mechanisms for Hydride Transfer from 1,4-Dihydronicotinamide. Bioorg. Chem. 1991, 19, 456-491.
9. Taylor, K. E.; Jones, J. B. Nicotinamide Coenzyme Regeneration by Dihydropyridine and Pyridinium Compounds. J. Am. Chem. Soc. 1976, 98, 5689-5694.
10. (a) Morton, R. K. Enzymic Synthesis of Coenzyme I in Relation to Chemical Control of Cell Growth. Nature 1958, 181, 540-542.
11. (b) Boulton, S.; Kyle, S.; Durkacz, B. W. Low Nicotinamide Mononucleotide Adenylyltransferase Activity in a Tiazofurin-resistant Cell Line: Effects on NAD Metabolism and DNA Repair. Br. J. Cancer 1997, 76, 845-851.
12. Powell, M. F.; Bruice, T. C. Effect of Isotope Scrambling and Tunneling on the Kinetic and Product Isotope Effects for Reduced Nicotinamide Adenine Dinucleotide Model Hydride Transfer Reactions. J. Am. Chem. Soc. 1983, 105, 7139-7149.
13. Cheng, J.-P.; Lu, Y.; Zhu, X.; Mu, L. Energetics of Multistep versus One-step Hydride Transfer Reactions of Reduced Nicotinamide Adenine Dinucleotide (NADH) Models with Organic Cations and p-Quinones. J. Org. Chem. 1998, 63, 6108-6114.
14. ./NADH. J. Phys. Chem. 1983, 87, 3135-3138.
15. (b) Carlson, B. W.; Miller, L. L.; Neta, P.; Grodkowski, J. Oxidation of NADH Involving Rate-Limiting One-Electron Transfer. J. Am. Chem. Soc. 1984, 106, 7233-7239.
16. (c) Powell, M. F.; Wu, J. C.; Bruice, T. C. Ferricyanide Oxidation of Dihydropyridines and Analogues. J. Am. Chem. Soc. 1984, 106, 3850-3856.
17. (d) Miller, L. L.; Valentine, J. R. On the Electron-Proton-Electron Mechanism for 1-Benzyl-1,4-Dihydronicotinamide Oxidations. J. Am. Chem. Soc. 1988, 110, 3982-3989.
18. (e) Brewster, M. E.; Kaminski, J. J.; Gabanyi, Z.; Czako, K.; Simay, A.; Bodor, N. Reactivity of Biologically Important Reduced Pyridines VI. Lack of Through-Resonance Stabilization in the Ferricyanide-mediated Oxidation of Substituted 1-Phenyl-1,4-Dihydronicotinamides. Tetrahedron 1990, 46, 319-324.
19. Almarsson, Ö.; Sinha, A.; Gopinath, E.; Bruice, T. C. Mechanism of One-Electron Oxidation of NAD(P)H and Function of NADPH Bound to Catalase. J. Am. Chem. Soc. 1993, 115, 7093-7102.
20. Czochralska, B.; Lindqvist, L. Biphotonic One-Electron Oxidation of NADH on Laser Excitation at 353 nm. Chem. Phys. Lett. 1983, 101, 297-299.
21. +, and Analogues. In Photoinduced Electron Transfer; Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988; Part C., pp 578-635.
22. Fukuzumi, S. Catalysis on Electron Transfer and the Mechanistic Insight into Redox Reactions. Bull. Chem. Soc. Jpn. 1997, 70, 1-28.
23. Gȩbicki, J.; Marcinek, A. Radical Ions: Generation, Characterization and Reactions. In General Aspects of the Chemistry of Radicals, Alfassi, Z. B., Ed.; Wiley: Chichester, U.K., 1999; pp 175-208.
24. Marcinek, A.; Adamus, J.; Huben, K., Gȩbicki, J.; Bartczak, T. J.; Bednarek, P.; Bally, T. Hydrogen-Transferred Radical Cations of NADH Model Compounds. 1. Spontaneous Tautomerization. J. Am. Chem. Soc. 2000, 122, 437-443.
25. Zielonka, J.; Marcinek, A.; Adamus, J.; Gȩbicki, J. Direct Observation of NADH Radical Cation Generated in Reactions with One-electron Oxidants. J. Phys. Chem. A 2003, 107, 9860-9864.
26. Marcinek, A.; Rogowski, J.; Adamus, J.; Gȩbicki, J.; Platz, M. S. Sequential Electron-Proton-Electron Transfer in the Radiolytic Oxidation of Thioxanthene and Xanthene. J. Phys. Chem. 1996, 100, 13539-13543.
27. Marcinek, A.; Zielonka, J.; Adamus, J.; Gȩbicki, J.; Platz, M. S. Direct Characterization of Radical Species Generated on One-Electron Oxidation of 3,6-Diamino-10-methylacridan. J. Phys. Chem. A 2001, 105, 875-879.
28. Schmittel, M. Umpolung of Ketones via Enol Radical Cations. Top. Curr. Chem. 1994, 169, 183-230.
29. (a) Marcinek, A.; Michalak, J.; Rogowski, J.; Tang, W.; Bally, T.; Gȩbicki, J. Enolization in Radical Cations of o-Methylacetophenone and Related Species under Cryogenic Conditions. J. Chem. Soc., Perkin Trans. 2 1992, 1353-1357.
30. (b) Gȩbicki, J.; Bally, T. Spontaneous Hydrogen Atom Transfer on Ionization: Characterization of Enol Radical Cations in Cryogenic Matrices. Acc. Chem. Res. 1997, 30, 477-485.
31. Gȩbicki, J.; Marcinek, A.; Adamus, J.; Paneth, P.; Rogowski, J. Structural Aspects and Rearrangement of Radical Cations Generated from NADH Analogues. J. Am. Chem. Soc. 1996, 118, 691-692.
32. Fukuzumi, S., Inada, O.; Suenobu, T. Mechanisms of Electron-Transfer Oxidation of NADH Analogues and Chemiluminescence. Detection of the Keto and Enol Radical Cations. J. Am. Chem. Soc. 2003, 125, 4808-4816.
33. (a) Oppenheimer, N. J.; Handlon, A. L. Mechanism of NAD-Dependent Enzymes. In The Enzymes; Sigman, D. S., Ed.; Academic Press: San Diego, CA, 1992; Vol. 20, pp 453-505.
34. + and NADH Analogues: Protonated Nicotinamide and 1,4-Dihydronicotinamide. J. Org. Chem. 1993, 58, 2043-2045.
35. Bordwell, F. G.; Cheng, J.-P. Radical-Cation Acidities in Solution and in the Gas Phase. J. Am. Chem. Soc. 1989, 111, 1792-1795.
36. (a) Anne, A.; Hapiot, P.; Moiroux, J.; Neta, P.; Savéant, J.-M. Oxidation of 10-Methylacridan, a Synthetic Analogue of NADH, and Deprotonation of Its Cation Radical. Convergent Application of Laser Flash Photolysis and Direct and Redox Catalyzed Electrochemistry to the Kinetics of Deprotonation of the Cation Radical. J. Phys. Chem. 1991, 95, 2370-2377.
37. (b) Anne, A.; Hapiot, P.; Moiroux, J.; Neta, P.; Savéant, J.-M. Dynamics of Proton Transfer from Cation Radicals. Kinetic and Thermodynamic Acidities of Cation Radicals of NADH Analogues. J. Am. Chem. Soc. 1992, 114, 4694-4701.
38. (a) Land, E. J.; Swallow, A. J. One-Electron Reactions in Biochemical Systems as Studied by Pulse Radiolysis. IV. Oxidation of Dihydronicotinamide- Adenine Dinucleotide. Biochim. Biophys. Acta 1971, 234, 34-42.
39. (b) Moiroux, J.; Elving, P. J. Mechanistic Aspects of the Electrochemical Oxidation of Dihydronicotinamide Adenine Dinucleotide (NADH). J. Am. Chem. Soc. 1980, 102, 6533-6538.
40. + Analogues. A Detailed Mechanistic Kinetic and Thermodynamic Analysis of the 10-Methylacridan/ 10-Methylacridinium Couple in Acetonitrile. J. Am. Chem. Soc. 1990, 112, 1337-1343.
41. (d) Adamus, J.; Rogowski, J.; Michalak, J.; Paneth, P.; Gȩbicki, J.; Marcinek, A.; Platz, M. S. Photochemical and Radiolytic Cleavage of 10-Methylacridine Dimer in Solution and Cryogenic Glasses. J. Phys. Org. Chem. 1993, 6, 254-256.
42. +. J. Phys. Chem. A 2000, 104, 718-723.
43. Marcinek, A.; Adamus, J.; Gȩbicki, J.; Platz, M. S.; Bednarek, P. Hydrogen-Transferred Radical Cations of NADH Model Compounds. 3. 1,8-Acridinediones. J. Phys. Chem. A 2000, 104, 724-728.
44. (a) Land, E. J.; Swallow, A. J. One-Electron Reactions in Biochemical Systems as Studied by Pulse Radiolysis. I. Nicotinamide-Adenine Dinucleotide and Related Compounds. Biochim. Biophys. Acta 1968, 162, 327-337.
45. 5) and Related Compounds. J. Am. Chem. Soc. 1974, 96, 6169-6175.
46. (c) Neta, P.; Patterson, L. K. Substituted Pyridinyl Radicals in Aqueous Solutions. Formation, Reactivity, and Acid-Base Equilibria. J. Phys. Chem. 1974, 78, 2211-2217.
47. +-NADH Dehydrogenase Reactions. J. Am. Chem. Soc. 1978, 100, 5185-5190.
48. Marcinek, A.; Zielonka, J.; Gȩbicki, J.; Gordon, C. M.; Dunkin, I. R. Ionic Liquids: Novel Media for Characterization of Radical Ions. J. Phys. Chem. A 2001, 105, 9305-9309.
49. (a) Dean, A. C. R. The Antibacterial Action of Acridines. In Acridines, 2nd ed.; Acheson, R. M., Ed.; Interscience Publishers: New York, 1973; pp 789-813.
50. (b) Nikaido, H. Prevention of Drug Access to Bacterial Targets: Permeability Barriers and Active Efflux. Science 1994, 264, 382-388.
51. Adamus, J.; Gȩbicki, J.; Ciebiada, I.; Korczak, E.; Denys, A. 3,6-Diamino-10-methylacridan: Uncharged Precursor of Acriflavine and Its Unique Antimicrobial Activity. J. Med. Chem. 1998, 41, 2932-2933.
52. Wieczorkowska, M.; Adamnus, J.; Zielonka, J.; Marcinck, A.; Gȩbicki, J., manuscript in preparation.
53. Wieczorkowska, M.; Zielonka, J.; Celińska, J.; Adamus, J.; Ciesielska, E.; Marcinek, A.; Szmigiero, L.; Gȩbicki, J. 1-Methyl-3-nitropyridine: An Efficient Oxidant of NADH in Nonenzymatic and Enzyme-mediated Processes. Free Radical Res. 2003, 37, 1157-1162.
54. Harrison, R. Xanthine oxidoreductase. In Free Radicals and Inflammation, Winyard, P. G., Blake, D. R., Evans, C. H., Eds.; Birkhäuser: Basel, Switzerland, 2000; pp 65-81.
55. Ciesielska, E.; Studzian, K.; Zyner, E.; Ochocki, J.; Szmigiero, L. DNA Damage and Apoptosis Induction in L1210 Cells by Cis-Diaminedichloroplatinum(II) and Its New Aminoflavone Analogue. Cell. Mol. Biol. Lett. 2000, 5, 441-450.