Drugs of abuse that mediate advanced glycation end product formation: A chemical link to disease pathology

Accounts of Chemical Research

Volumn 42, Issue 5, 2009, Pages 659-669

  Treweek, Jennifer B ^a   Dickerson, Tobin J ^a,b   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b Department of Chemistry ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADVANCED GLYCATION END PRODUCT; DRUG DERIVATIVE; METHAMPHETAMINE; NICOTINE; NORNICOTINE;

ALZHEIMER DISEASE; ARTICLE; ATHEROSCLEROSIS; CHEMICAL STRUCTURE; CHEMISTRY; DIABETES MELLITUS; GENERAL ASPECTS OF DISEASE; HUMAN; METABOLISM; NEOPLASM; PATHOPHYSIOLOGY; RETINA MACULA DEGENERATION;

ALZHEIMER DISEASE; ATHEROSCLEROSIS; DIABETES MELLITUS; DISEASE; GLYCOSYLATION END PRODUCTS, ADVANCED; HUMANS; MACULAR DEGENERATION; METHAMPHETAMINE; MOLECULAR STRUCTURE; NEOPLASMS; NICOTINE;

EID: 66149083940     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar800247d     Document Type: Article

References (53)

1. Davis, V. E.; Walsh, M. J.; Yamanaka, Y. Augmentation of alkaloid formation from dopamine by alcohol and acetaldehyde in vitro. J. Pharmacol. EXD. Ther. 1970, 174, 401-412.
2. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry, Pergamon: Oxford, U.K., 1994.
3. Fessner, W.-D.; Walter, C. Top. Curr. Chem. 1996, 184, 98-183.
4. List, B.; Lerner, R. A.; Barbas, C. F., III. Proline-catalyzed direct asymmetric aldol reactions. J. Am. Chem. Soc. 2000, 122, 2395-2396.
5. Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Asymmetric enamine catalysis. Chem. Rev. 2007, 107, 5471-5569.
6. List, B. Biocatalysis and organocatalysis: Asymmetric synthesis inspired by nature. Asymmetric Synth. 2007, 161-165.
7. Dickerson, T. J.; Janda, K. D. Aqueous aldol catalysis by a nicotine metabolite. J. Am. Chem. Soc. 2002, 124, 3220-3221.
8. Chu, F. L.; Yaylayan, V. A. FTIR monitoring of oxazolidinone formation and decomposition in a glycoaldehyde-phenylalanine model system by isotope labeling techniques. Carbohydr. Res. 2008, in press.
9. Maillard, L. C.; Gautier, M. Action des acides amines sur les sucres: formation des melanoidines par voie methodique. C. R. Seances Acad. Sci. III 1912, 154, 66-68.
10. Brownlee, M.; Cerami, A.; Vlassara, H. Advanced glycosylation end products in tissue and the biochemical basis of diabetic complications. N. Enal. J. Med. 1988, 318, 1315-1321.
11. Monnier, V. M.; Cerami, A. Nonenzymatic browning in vivo: Possible process for aging of long-lived proteins. Science 1981, 211, 491-493.
12. Vlassara, H.; Brownlee, M.; Manogue, K. R.; Dinarello, C. A.; Pasagian, A. Cachectin/TNF and IL-1 induced by glucose-modified proteins: role in normal tissue remodeling. Science 1988, 240, 1546-1548.
13. Monnier, V. M.; Kohn, R. R.; Cerami, A. Accelerated age-related browning of human collagen in diabetes mellitus. Proc. Natl. Acad. Sci. U.S.A. 1984, 91, 583-587.
14. Stopper, H.; Schinzel, R.; Sebekova, K.; Heidland, A. Genotoxicity of advanced glycation end products in mammalian cells. Cancer Lett. 2003, 190, 151-160.
15. Vitek, M. P.; Bhattacharya, K.; Glendening, J. M.; Stopa, E.; Vlassara, H.; Bucala, R.; Manogue, K.; Cerami, A. Advanced glycation end products contribute to amyloidosis in Alzheimer disease. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4766-4770.
16. Ishibashi, T.; Murata, T.; Hangai, M.; Nagai, R.; Horiuchi, S.; Lopez, P. F.; Hinton, D. R.; Ryan, S. J. Advanced glycation end products in age-related macular degeneration. Arch. Ophthalmol. 1998, 116, 1629-1632.
17. Bierhaus, A.; Hofmann, M. A.; Ziegler, R.; Nawroth, P. P. AGE and their interaction with AGE-receptors in vascular disease and diabetes. I. The AGE concept. Cardiovasc. Res. 1998, 37, 586-600.
18. Lo, T. W.; Westwood, M. E.; McLellan, A. C.; Selwood, T.; Thornalley, P. J. Binding and modification of proteins by methylglyoxal under physiological conditions. A kinetic and mechanistic study with N alpha-acetylarginine, N alpha-acetylcysteine, and N alpha-acetyllysine, and bovine serum albumin. J. Biol. Chem. 1994, 269, 32299-32305.
19. Wells-Knecht, K. J.; Zyzak, D. V.; Litchfield, J. E.; Thorpe, S. R.; Baynes, J. W. Identification of glyoxal and arabinose as intermediates in the autoxidative modification of proteins by glucose. Biochemistry 1995, 34, 3702-3709.
20. Singh, R.; Barden, A.; Mori, T.; Beilin, L. Advanced glycation end-products: a review. Diabetologia 2001, 44, 129-146.
21. Monnier, V. M.; Sell, D. R.; Dai, Z.; Nemet, I.; Collard, F.; Zhang, J. The role of the Amadori product in the complications of diabetes. Ann. N Y. Acad. Sci. 2008, 1126, 81-88.
22. Khalifah, R. G.; Todd, P.; Booth, A. A.; Yang, S. X.; Mott, J. D.; Hudson, B. G. Kinetics of nonenzymatic glycation of ribonuclease A leading to advanced glycation end products. Paradoxical inhibition by ribose leads to facile isolation of protein intermediate for rapid post-Amadori studies. Biochemistry 1996, 35, 4645-4654.
23. Bunn, H. F.; Higgins, P. J. Reaction of monosaccharides with proteins: Possible evolutionary significance. Science 1981, 213. 222-224.
24. Booth, A. A.; Khalifah, R. G.; Todd, P.; Hudson, B. G. In vitro kinetic studies of formation of antigenic advanced glycation end products (AGEs). Novel inhibition of post-Amadori glycation pathways. J. Biol. Chem. 1997, 272, 5430-5437.
25. McPherson, J. D.; H., S. B.; Walton, D. J. Role of fructose in glycation and cross-linking of proteins. Biochemistry 1988, 27, 1901-1907.
26. Yan, S. D.; Schmidt, A. M.; Anderson, G. M.; Zhang, J.; Brett, J.; Zou, Y. S.; Pinsky, D.; Stern, D. Enhanced cellular oxidant stress by the interaction of advanced glycation end products with their receptors/binding proteins. J. Biol. Chem. 1994, 269, 9889-9897.
27. Turk, Z.; Ljubic, S.; Turk, N.; Benko, B. Detection of autoantibodies against advanced glycation endproducts and AGE-immune complexes in serum of patients with diabetes mellitus. Clin. Chim. Acta 2001, 303, 105-115.
28. Kislinger, T.; Fu, C.; Huber, B.; Qu, W.; Taguchi, A.; Du Yan, S.; Hofmann, M.; Yan, S. F.; Pischetsrieder, M.; Stern, D.; Schmidt, A. M. N(epsilon)-(carboxymethyl)lysine adducts of proteins are ligands for receptor for advanced glycation end products that activate cell signaling pathways and modulate gene expression. J. Biol. Chem. 1999, 274, 31740-31749.
29. Cerami, C.; Founds, H.; Nicholl, I.; Mitsuhashi, T.; Giordano, D.; Vanpatten, S.; Lee, A.; Al-Abed, Y.; Vlassara, H.; Bucala, R.; Cerami, A. Tobacco smoke is a source of toxic reactive glycation products. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 13915-13920.
30. Dickerson, T. J.; Janda, K. D. A previously undescribed chemical link between smoking and metabolic disease. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 15084-15088.
31. Isomura, S.; Wirsching, P.; Janda, K. D. An immunotherapeutic program for the treatment of nicotine addiction: Hapten design and synthesis. J. Org. Chem. 2001, 66, 4115-4121.
32. Kyerematen, G. A.; Morgan, M.; Chattopadhyay, B.; DeBethizy, J. D.; Vesell, E. S. Disposition of nicotine and eight metabolites in smokers and nonsmokers: Identification in smokers of two metabolites that are longer lived than cotinine. Clin. Pharmacol. Ther. 1998, 48, 641-651.
33. Salomon, A. R.; Marcinowski, K. J.; Friedland, R. P.; Zagorski, M. G. Nicotine inhibits amyloid formation by the beta-peptide. Biochemistry 1996, 35, 13568-13578.
34. Sisodia, S. S.; Price, D. J. Role of the beta-amyloid protein in Alzheimer's disease. FASEB J. 1995, 9, 366-370.
35. Zeng, H.; Zhang, Y.; Peng, L.; Shao, H.; Menon, N. K.; Yang, J.; Salomon, A. R.; Freidland, R. P.; Zagorski, M. G. Nicotine and amyloid formation. Biol. Psychiatry 2001, 49, 248-257.
36. Tjernberg, L. O.; Näslund, J.; Lindqvist, F.; Johansson, J.; Karlström, A. R.; Thyberg, J.; Terenius, L.; Nordstedt, C. Arrest of β-amyloid fibril formation by a pentapeptide ligand. J. Biol. Chem. 1996, 271, 8545-8548.
37. Dickerson, T. J.; Janda, K. D. Glycation of the amyloid β-protein by a nicotine metabolite: A fortuitous chemical dynamic between smoking and Alzheimer's disease. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 8182-8187.
38. Barr, A. M.; Panenka, W. J.; MacEwan, G. W.; Thornton, A. E.; Lang, D. J.; Honer, W. G.; Lecomte, T. The need for speed: An update on methamphetamine addiction. J. Psychiatry Neurosci. 2006, 31, 301-313.
39. Saunders, C.; Ferrer, J. V.; Shi, L.; Chen, J.; G., M.; Lamb, M. E.; Leeb-Lundberg, L. M.; Carvelli, L.; Javitch, J. A.; Galli, A. Amphetamine-induced loss of human dopamine transporter activity: An internalization-dependent and cocaine-sensitive mechanism. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 6850-6855.
40. Itzhak, Y.; Achat-Mendes, C. Methamphetamine and MDMA (ecstasy) neurotoxicity: "Of mice and men". lUBMB Life 2004, 56, 249-255.
41. Melega, W. P.; Jorgensen, M. J.; acutean, G. L.; Way, B. M.; Pham, J.; Morton, G.; Cho, A. K.; Fairbanks, L. A. Long-term methamphetamine administration in the Vervet monkey models aspects of a human exposure: Brain neurotoxicity and behavioral profiles. Neuropsvchopharmacoloay 2008, 33, 1441-1452.
42. Gu, X.; Meer, S. G.; Miyagi, M.; Rayborn, M. E.; Hollyfield, J. G.; Crabb, J. W.; Salomon, R. G. Carboxyethylpyrrole protein adducts and autoantibodies, biomarkers for age-related macular degeneration. J. Biol. Chem. 2003, 278, 42027-42035.
43. Kitamura, O.; Wee, S.; Specio, S. E.; Koob, G. F.; Pulvirenti, L. Escalation of methamphetamine self-administration in rats: A dose-effect function. Psvchopharmacologv (Serf). 2006, 186, 48-53.
44. Wee, S.; Wang, Z.; Woolverton, W. L.; Pulvirenti, L.; Koob, G. F. Effect of aripiprazole, a partial dopamine D2 receptor agonist, on increased rate of methamphetamine self-administration in rats with prolonged session duration. Neuropsvchopharmacology 2007, 32, 2238-2247.
45. Treweek, J.; Wee, S.; Koob, G. F.; Dickerson, T. J.; Janda, K. D. Self-vaccination by methamphetamine glycation products chemically links chronic drug abuse and cardiovascular disease. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 11580-11584.
46. Segal, D. S.; Kuczenski, R.; O'Neil, M. L.; Melega, W. P.; Cho, A. K. Escalating dose methamphetamine pretreatment alters the behavioral and neurochemical profiles associated with exposure to a high-dose methamphetamine binge. Neuropsychopharmacology 2003, 28, 1730-1740.
47. Asanuma, M.; Miyazaki, I.; Higashi, Y.; Tsuji, T.; Ogawa, N. Specific gene expression and possible involvement of inflammation in methamphetamine- induced neurotoxicity. Ann. N.Y. Acad. Sci. 2004, 1025, 69-75.
48. In, S.-W.; Son, E.-W.; Rhee, D.-K.; Pyo, S. Methamphetamine administration produces immunomodulation in mice. J. Toxicol. Environ. Health A. 2005, 68, 2133-2145.
49. He, S. Y.; Matoba, R.; Fujitani, N.; Sodesaki, K.; Onishi, S. Cardiac muscle lesions associated with chronic administration of methamphetamine in rats. Am. J. Forensic Med. Pathol. 1996, 17, 155-62.
50. Schaiberger, P. H.; Kennedy, T. C.; Miller, F. C.; Gal, J.; Petty, T. L. Pulmonary hypertension associated with long-term inhalation of "crank" methamphetamine. Chest 1993, 104, 614-616.
51. Tanaka, N.; Yonekura, H.; Yamagishi, S.; Fujimori, H.; Yamamoto, Y.; Yamamoto, H. The receptor for advanced glycosylation end products is induced by the glycation product themselves and TNF-alpha through nuclear factor kappa B and by 17-beta-estradiol through Sp1 in human vascular endothelial cells. J. Biol. Chem. 2000, 275, 25781-25790.
52. Treins, C.; Giorgetti-Peraldi, S.; Murdaca, J.; Van Obberghen, E. Regulation of vascular endothelial growth factor expression by advanced glycation end products. J. Biol. Chem. 2001, 276, 43836-43841.
53. Yamagishi, S.-L.; Inagaki, Y.; Okamoto, T.; Amano, S.; Koga, K.; Takeuchi, M.; Makita, Z. Advanced glycation end product-induced apoptosis and overexpression of vascular endothelial growth factor and monocyte chemoattractant protein-1 in human-cultured mesangial cells. J. Biol. Chem. 2002, 277, 20309-20315.