Ocular drug metabolism of the bioactivating antioxidant N-acetylcarnosine for vision in ophthalmic prodrug and codrug design and delivery

Drug Development and Industrial Pharmacy

Volumn 34, Issue 10, 2008, Pages 1071-1089

  Babizhayev, Mark A ^a,b  

^a Innovative Vision Products   (United States)

^b MOSCOW HELMHOLTZ RESEARCH INSTITUTE OF EYE DISEASES   (Russian Federation)

Author keywords

Age related cataracts; Corneal disorders; Lipid peroxides; Membrane derangement; N acetylcarnosine; Prodrug and codrug ophthalmic formulations; Tissue buffering

Indexed keywords

AGENTS ACTING ON THE EYE; ANTIOXIDANT; CAN C; CARNOSINE; CELLULOSE; DIPEPTIDE DERIVATIVE; ENZYME INHIBITOR; EYE DROPS; LUBRICATING AGENT; N ACETYLCARNOSINE; PEPTIDASE; PRODRUG; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; AQUEOUS HUMOR; ARTICLE; CONJUNCTIVA; CONTROLLED STUDY; CORNEA; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG FORMULATION; DRUG HYDROLYSIS; DRUG METABOLISM; DRUG PENETRATION; DRUG RETENTION; MALE; MOUSE; NONHUMAN; RABBIT; SENILE CATARACT; SUSTAINED DRUG RELEASE; SUSTAINED RELEASE FORMULATION; TIMED DRUG RELEASE;

AMIDES; ANIMALS; ANTIOXIDANTS; CARNOSINE; CATARACT; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CORNEA; DRUG DESIGN; EYE; HUMANS; LENS, CRYSTALLINE; LIPID PEROXIDATION; LIPOSOMES; MICE; MICE, INBRED C57BL; MICE, INBRED CBA; PRODRUGS; RABBITS;

EID: 52949119196     PISSN: 03639045     EISSN: 15205762     Source Type: Journal    
DOI: 10.1080/03639040801958413     Document Type: Article

References (50)

1. Abe, H. (2000). Role of histidine-related compounds as intracellular proton buffering constituents in vertebrate muscle. Biochemistry (Moscow), 65, 757-765.
2. Aldini, G., Carini, M., Beretta, G., Bradamante, S., & Facino, R. M. (2002). Carnosine is a quencher of 4-hydroxy-nonenal: Through what mechanism of reaction? Biochem. Biophys. Res. Commun., 298(5), 699-706.
3. Al-Ghananeem, A. M., & Crooks, P. A. (2007). Phase I and phase II ocular metabolic activities and the role of metabolism in ophthalmic prodrug and codrug design and delivery. Molecules, 12, 373-388.
4. Anderson, J. A., Davis, W. L., & Wei, C. (1980). Site of ocular hydrolysis of a prodrug, dipivefrin, and a comparison of its ocular metabolism with that of the parent compound, epinephrine. Invest. Ophthalmol. Vis. Sci., 19, 817-823.
5. Aruoma, O. I., Laughton, M. J., & Halliwell, B. (1989). Carnosine, homocarnosine and anserine: Could they act as antioxidants in vivo? Biochem. J., 264, 863-869.
6. Babizhayev, M. A. (1989a). Accumulation of lipid peroxidation products in human cataracts. Acta Ophthalmol. (Copenh.), 67, 281-287.
7. Babizhayev, M. A. (1989b). Antioxidant activity of L-carnosine, a natural histidine-containing dipeptide in crystalline lens. Biochim. Biophys. Acta, 1004, 363-371.
8. Babizhayev, M. A. (1989c). Lipid fluorophores of the human crystalline lens with cataract. Graefe's Arch. Clin. Exp. Ophthalmol., 227, 384-391.
9. Babizhayev, M. A. (1996). Failure to withstand oxidative stress induced by phospholipid hydroperoxides as a possible cause of the lens opacities in systemic diseases and ageing. Biochim. Biophys. Acta, 1315, 87-99.
10. Babizhayev, M. A. (2004a). Method for topical treatment of eye disease and composition and device for said treatment. PCT Patent application. International Publication Number WO 2004/028536 A1. International Publication Date 8 April 2004.
11. Babizhayev, M. A. (2004b). Rejuvenation of visual functions in older adult drivers and drivers with cataract during a short-term administration of N-acetylcarnosine lubricant eye drops. Rejuvenation Res., 7, 186-198.
12. Babizhayev, M. A. (2006). Ophthalmic pharmacology of N-acetylcarnosine lubricant eye drops. J Pharmacol. Toxicol., 1(3), 201-233.
13. Babizhayev, M. A., & Bozzo Costa, E. (1994). Lipid peroxide and reactive oxygen species generating systems of the crystalline lens. Biochim. Biophys. Acta, 1225, 326-337.
14. Babizhayev, M. A., & Deev, A. I. (1986). Free radical oxidation of lipids and thiol groups in the formation of a cataract. Biofizika, 31(1), 109-114.
15. Babizhayev, M. A., & Deyev, A. I. (1989). Lens opacity induced by lipid peroxidation products as a model of cataract associated with retinal disease. Biochim. Biophys. Acta, 1004, 124-133.
16. Babizhayev, M. A., & Meguro, K. (2004). Combined use of carnosinase inhibitor with l-carnosines and composition. WO 2004/064866 PCT/JP2004/000351. Filed 20 January 2003.
17. Babizhayev, M. A., Deyev, A. I., & Chernikov, A. V. (1992). Peroxide-metabolizing systems of the crystalline lens. Biochim. Biophys. Acta, 1138, 11-19.
18. Babizhayev, M. A., Deyev, A. I., & Derevyagin, V. I. (1989). Morphometric evaluation of human lens opacification. J. Microsc. (Oxford), 154(2), 115-127.
19. Babizhayev, M. A., Deyev, A. I., & Linberg, L. F. (1988). Lipid peroxidation as a possible cause of cataract. Mech. Ageing Dev., 44, 69-89.
20. Babizhayev, M. A., Deyev, A. I., Yermakova, V. N., Brikman, I. V., & Bours, J. (2004). Lipid peroxidation and cataracts: N-acetylcarnosine as a therapeutic tool to manage age-related cataracts in human and in canine eyes. Drugs R&D, 5(3), 125-139.
21. Babizhayev, M. A., Deyev, A. I., Yermakova, V. N., Remenshchikov, V. V., & Bours, J. (2006). Revival of the lens transparency with N-acetylcarnosine. Curr. Drug Ther., 1, 91-116.
22. Babizhayev, M. A., Deyev, A. I., Yermakova, V. N., Semiletov, Yu. A., Davydova, N. G., Kurysheva, N. I., Zhukotskii, A. V., & Goldman, I. M. (2001). N-Acetylcarnosine, a natural histidine-containing dipeptide, as a potent ophthalmic drug in treatment of human cataracts. Peptides, 22, 979-994.
23. Babizhayev, M. A., Deyev, A. I., Yermakova, V. N., Semiletov, Yu. A., Davydova, N. G., Doroshenko, V. S., Zhukotskü, A. V., & Goldman, I. M. (2002). Efficacy of N-acetylcarnosine in the treatment of cataracts. Drugs R&D, 3(2), 87-103.
24. Babizhayev, M. A., Seguin, M-C., Gueyne, J., Evstigneeva, R. P., Ageyeva, E. A., & Zheltukhina, G. A. (1994). L-carnosine (beta-alanyl-L-histidine) and carcinine (beta-alanylhistamine) act as natural antioxidants with hydroxyl-radical-scavenging and lipid-peroxidase activities. Biochem. J., 304, 509-516.
25. Babizhayev, M. A., Yermakova, V. N., Deyev, A. I., & Seguin, M-C. (2000). Imidazole-containing peptidomimetic NACA as a potent drug for the medicinal treatment of age-related cataract in humans. J. Anti-Aging Med., 3, 43-62.
26. Babizhayev, M. A., Yermakova, V. N., Sakina, N. L., Evstigneeva, R. P., Rozhkova, E. A., & Zheltukhina, G. A. (1996). N-acetylcarnosine is a pro-drug of L-carnosine in ophthalmic application as antioxidant. Clin. Chim. Acta, 254, 1-21.
27. Babizhayev, M. A., Yermakova, V. N., Semiletov, Yu, A., & Deyev, A. I. (2000). The natural histidine-containing dipeptide N-acetylcarnosine as an antioxidant for ophthalmic use. Biochemistry (Moscow), 65, 588-598.
28. Barbu, E., Verestiuk, L., Nevell, T. G., & Tsibouklis, J. (2006). Polymeric materials for ophthalmic drug delivery: Trends and perspectives. J. Mater. Chem., 16, 3439-3443.
29. Bhuyan, K. C., & Bhuyan, D. K. (1984). Molecular mechanism of cataractogenesis: III. Toxic metabolites of oxygen as initiators of lipid peroxidation and cataract. Curr. Eye Res., 3, 67-81.
30. Boldyrev, A. A. (1998). Carnosine. Biological significance and possibilities for application in medicine (p. 319). Moscow: Moscow State University.
31. Boldyrev, A. A., Dupin, A. M., Bunin, A. Ya., Babizhayev, M. A., & Severin, S. E. (1987). The antioxidative properties of carnosine, a natural histidine containing dipeptide. Biochem. Int., 15, 1105-1113.
32. Bolland, J. L., & Koch, H. P. (1945). The course of autooxidation reactions in polyisoprenes and allied compounds. Part IX. The primary thermal oxidation products of ethyl linoleate. J. Chem. Soc., 7, 445-447.
33. Bonanno, J. A. (1996). Contact lens induced corneal acidosis. CLAO J., 22, 70-74.
34. Chen, P. S., Toribara, T. Y., & Warner, H. (1956). Microdetermination of phosphurus. Anal. Chem., 28, 1756-1758.
35. Chio, K. S., & Tappel, A. L. (1969). Synthesis and characterization of the fluorescent products derived from malonaldehyde and amino acids. Biochemistry (Wash), 8, 2821-2827.
36. Deejing, S., Yoshimune, K., Lumyong, S., & Moriguchi, M. (2005). Purification and characterization of hyperthermotolerant leucine aminopeptidase from Geobacillus thermoleovorans 47b. J. Ind. Microbiol. Biotechnol., 32(7), 269-276.
37. Folch, J., Lee, M., & Sloane-Stanely, G. H. S. (1957). A simple method for the isolation and purification of total lipids from animal tissues. J. Biol. Chem., 226, 497-509.
38. Halliwell, B., & Gutteridge, J. M. C., (1985). Free radicals in biology and medicine. Oxford: Clarendon.
39. Hobart, L. J., Seibel, I., Yeargans, G. S., & Seidler, N. W. (2004). Anti-crosslinking properties of carnosine: Significance of histidine. Life Sci., 75(11), 1379-1389.
40. Huang, L., Tang, D., Yappert, M. C., & Borchman, D. (2006). Oxidation-induced changes in human lens epithelial cells 2. Mitochondria and the generation of reactive oxygen species. Free Radic. Biol. Med., 41(6), 926-936. Epub 2006 May 26.
41. Jay, J. L., Miller, D. J., Morrison, J. D., & O'Dowd, J. J. (1990). Histidyl derivatives in rabbit lens and their diminution in human cataract. Meeting Abstr. J. Physiol. Lond., 420, 155.
42. Kashi, S. D., & Lee, V. H. (1986). Hydrolysis of enkephalins in homogenates of anterior segment tissues of the albino rabbit eye. Invest. Ophthalmol. Vis. Sci., 27(8), 1300-1333.
43. Robertson, J. M. (1990). Cataract prevention: Time for a clinical trial? Br. J. Clin. Pract., 44, 475-476.
44. Sasaki, H., Tei, C., Nishida, K., & Nakamura, J. (1995). Effect of ophthalmic preservatives on serum concentration and local irritation of ocularly applied insulin. Biol. Pharm. Bull., 18(1), 169-171.
45. Sasaki, H., Yamamura, K., Mukai, T., Nishida, K., Nakamura, J., Nakashima, M., & Ichikawa, M. (2000). Modification of ocular permeability of peptide drugs by absorption promoters. Bio. Pharm. Bull., 23(12), 1524-1527.
46. Seidler, N. W., Yeargans, G. S., & Morgan, T. G. (2004). Carnosine disaggregates glycated alpha-crystallin: An in vitro study. Arch. Biochem. Biophys., 427(1), 110-115.
47. Sharma, K. K., & Ortwerth, B. J. (1987). Purification and characterization of an aminopeptidase from bovine cornea. Exp. Eye Res., 45(1), 117-126.
48. Stewart, J. J. (1989b). MOPAC. Ver.6, QCPE Bull. 9,10. Revised as Ver. 6.01 by T. Hirano, University of Tokyo, for HITAC and UNIX machines (JCPE Newsletter, 1989. 1,10).
49. Stewart, J. J. P. (1989a). MOPAC. F. J. Seiler Research Laboratory. US Air Force Academy, Boulder, CO80840 USA.
50. Testa, M., Iuliano, G., Morton, P., & Longoni, A. (1987). Topical benzyl alcohol reduces cataract surgery need: two long-term double blind studies. J. Ocul. Pharmacol., 3(3), 211-225.