Spectroscopic properties and reactivity of free radical forms of A2E

Free Radical Biology and Medicine

Volumn 38, Issue 8, 2005, Pages 1037-1046

  Broniec, Agnieszka ^a   Pawlak, Anna ^a   Sarna, Tadeusz ^a   Wielgus, Albert ^b   Roberts, Joan E ^c   Land, Edward J ^d   Truscott, T George ^d   Edge, Ruth ^e,f   Navaratnam, Suppiah ^e,g  

^a JAGIELLONIAN UNIVERSITY   (Poland)

^b NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

^c FORDHAM UNIVERSITY   (United States)

^d KEELE UNIVERSITY   (United Kingdom)

^e DARESBURY LABORATORY   (United Kingdom)

^f GLYNDWR UNIVERSITY   (United Kingdom)

^g UNIVERSITY OF SALFORD   (United Kingdom)

Author keywords

A2E; A2E radicals; Free radicals; Oxidative stress; Phototoxicity; Pulse radiolysis; Retinal lipofuscin; Retinal pigment epithelium

Indexed keywords

BENZENE; FREE RADICAL; LIPOFUSCIN; METHANOL; SUPEROXIDE;

ABSORPTION; ARTICLE; DISSOCIATION; ELECTRON; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; OXIDATION; PHOTOREACTIVITY; PHOTOTOXICITY; PRIORITY JOURNAL; PULSE RADIOLYSIS; REDUCTION; SEMICONDUCTOR; SPECTROSCOPY;

EID: 15244353819     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2004.12.023     Document Type: Article

References (65)

1. R.W. Young Solar radiation and age-related macular degeneration Surv. Ophthalmol. 32 1988 252 269
2. L. Feeney-Burns, E.S. Hilderbrand, and S. Eldridge Aging human RPE: morphometric analysis of macular, equatorial, and peripheral cells Invest. Ophthalmol. Visual Sci. 25 1984 195 200
3. C.K. Dorey, G. Wu, D. Ebenstein, A. Garsd, and J.J. Weiter Cell loss in the aging retina: relationship to lipofuscin accumulation and macular degeneration Invest. Ophthalmol. Visual Sci. 30 1989 1691 1699
4. C.J. Kennedy, P.E. Rakoczy, and I.J. Constable Lipofuscin of the retinal pigment epithelium: a review Eye 9 1995 763 771
5. J.J. Weiter, F.C. Delori, G.L. Wing, and K.A. Fitch Retinal pigment epithelium lipofuscin and melanin and choroidal melanin in human eyes Invest. Ophthalmol. Visual Sci. 27 1986 145 152
6. R.W. Young Pathophysiology of age-related macular degeneration Surv. Ophthalmol. 31 1987 291 306
7. R. Klein, B.E. Klein, S.C. Tomany, S.M. Meuer, and G.H. Huang Ten-year incidence and progression of age-related maculopathy: the Beaver Dam eye study Ophthalmology 109 2002 1767 1779
8. R. Allikmets, N. Singh, H. Sun, N.F. Shroyer, A. Hutchinson, A. Chidambaram, B. Gerrard, L. Baird, D. Stauffer, A. Peiffer, A. Rattner, P. Smallwood, Y. Li, K.L. Anderson, R.A. Lewis, J. Nathans, M. Leppert, M. Dean, and J.R. Lupski A photoreceptor cell-specific ATP-binding transporter gene (ABCR) is mutated in recessive Stargardt macular dystrophy Nat. Genet. 15 1997 236 246
9. S.M. Azarian, and G.H. Travis The photoreceptor rim protein is an ABC transporter encoded by the gene for recessive Stargardt's disease (ABCR) FEBS Lett. 409 1997 247 252
10. M. Illing, L.L. Molday, and R.S. Molday The 220-kDa rim protein of retinal rod outer segments is a member of the ABC transporter superfamily J. Biol. Chem. 272 1997 10303 10310
11. C.D. Birnbach, M. Jarvelainen, D.E. Possin, and A.H. Milam Histopathology and immunochemistry of the neurosensory retina in fundus flavimaculatus Ophthalmology 101 1994 1211 1219
12. F.C. Delori, G. Staurenghi, O. Arend, C.K. Dorey, D.G. Goger, and J.J. Weiter In vivo measurements of lipofuscin in Stargardt's disease-fundus flavimaculatus Invest. Ophthalmol. Visual Sci. 36 1995 2327 2331
13. A.V. Cideciyan, T.S. Aleman, M. Swider, S.B. Schwartz, J.D. Steinberg, A.J. Brucker, A.M. Maguire, J. Bennett, E.M. Stone, and S.G. Jacobson Mutations in ABCA4 result in accumulation of lipofuscin before slowing of the retinoid cycle: a reappraisal of the human disease sequence Hum. Mol. Genet. 13 2004 525 534
14. B.S. Winkler, M.E. Boulton, J.D. Gottsch, and P. Sternberg Oxidative damage and age-related macular degeneration Mol. Vision 5 1999 32 42
15. S. Beatty, H.-H. Koh, D. Henson, and M. Boulton The role of oxidative stress in the pathogenesis of age-related macular degeneration Surv. Ophthalmol. 45 2000 115 134
16. M. Boulton, A. Dontsov, J. Jarvis-Evans, M. Ostrovsky, and D. Svistunenko Lipofuscin is a photoinducible free radical generator J. Photochem. Photobiol. B 19 1993 201 204
17. M. Rozanowska, J. Jarvis-Evans, W. Korytowski, M.E. Boulton, J.M. Burke, and T. Sarna Blue light-induced reactivity of retinal age pigment: in vitro generation of oxygen-reactive species J. Biol. Chem. 270 1995 18825 18830
18. K. Reszka, G.E. Eldred, R.H. Wang, C. Chignell, and J. Dillon The photochemistry of human retinal lipofuscin as studied by EPR Photobiol. Photochem. 62 1995 1005 1008
19. E.R. Gaillard, S.J. Atherton, G. Eldred, and J. Dillon Photophysical studies on human retinal lipofuscin Photochem. Photobiol. 61 1995 448 453
20. M. Rozanowska, J. Wessels, M.E. Boulton, J.M. Burke, M.A.J. Rodgers, T.G. Truscott, and T. Sarna Blue light-induced singlet oxygen generation by retinal lipofuscin in non-polar media Free Radic. Biol. Med. 24 1998 1107 1112
21. J. Wassell, S. Davies, W. Bardsley, and M.E. Boulton The photoreactivity of the retinal age pigment lipofuscin J. Biol. Chem. 274 1999 23828 23832
22. S. Davies, M.H. Elliott, E. Floor, T.G. Truscott, M. Zareba, T. Sarna, F.A. Shamsi, and M.E. Boulton Photocytotoxicity of lipofuscin in human retinal pigment epithelial cells Free Radic. Biol. Med. 31 2001 256 265
23. M. Rozanowska, A. Pawlak, B. Rozanowski, C. Skumatz, M. Zareba, M.E. Boulton, J.M. Burke, T. Sarna, and J.D. Simon Age-related changes in the photoreactivity of retinal lipofuscin granules: role of chloroform-insoluble components Invest. Ophthalmol. Visual Sci. 45 2004 1052 1060
24. G.E. Eldred, and M.R. Lasky Retinal age pigments generated by self-assembling lysosomotropic detergents Nature 361 1993 724 726
25. N. Sakai, J. Decatur, and K. Nakanishi Ocular age pigment "A2-E": an unprecedented pyridinium bisretinoid J. Am. Chem. Soc. 118 1996 1559 1560
26. C.A. Parish, M. Hashimoto, K. Nakanishi, J. Dillon, and J. Sparrow Isolation and one-step preparation of A2E and iso-A2E, fluorophores from human retinal pigment epithelium Proc. Natl. Acad. Sci. USA 95 1998 14609 14613
27. J. Liu, Y. Itagaki, S. Ben-Shabat, K. Nakanishi, and J.R. Sparrow The biosynthesis of A2E, a fluorophore of aging retina, involves the formation of the precursor, A2-PE, in the photoreceptor outer segment membrane J. Biol. Chem. 275 2000 29354 29360
28. N.L. Mata, J. Weng, and G.H. Travis Biosynthesis of a major lipofuscin fluorophore in mice and humans with ABCR-mediated retinal and macular degeneration Proc. Natl. Acad. Sci. USA 97 2000 7154 7159
29. F.G. Holz, F. Schutt, J. Kopitz, G.E. Eldred, F.E. Kruse, H.E. Volcker, and M. Cantz Inhibition of lysosomal degradative functions in RPE cells by a retinoid component of lipofuscin Invest. Ophthalmol. Visual Sci. 40 1999 737 743
30. J.R. Sparrow, C.A. Parish, M. Hashimoto, and K. Nakanishi A2E, a lipofuscin fluorophore, in human retinal pigmented epithelial cells in culture Invest. Ophthalmol. Visual Sci. 40 1999 2988 2995
31. F. Schutt, S. Davies, J. Kopitz, F.G. Holz, and M.E. Boulton Photodamage to human RPE cells by A2E, a retinoid component of lipofuscin Invest. Ophthalmol. Visual Sci. 41 2000 2303 2308
32. S.C. Finnemann, L.W. Leung, and E. Rodriguez-Boulan The lipofuscin component A2E selectively inhibits phagolysosomal degradation of photoreceptor phospholipid by the retinal pigment epithelium Proc. Natl. Acad. Sci. USA 99 2002 3842 3847
33. L.E. Lamb, T. Ye, N.M. Haralampus-Grynaviski, T.R. Williams, A. Pawlak, T. Sarna, and J.D. Simon Primary photophysical properties of A2E in solution J. Phys. Chem. B 105 2001 11507 11512
34. A. Cantrell, D.J. McGarvey, J. Roberts, T. Sarna, and T.G. Truscott Photochemical studies of A2-E J. Photochem. Photobiol. B 64 2001 162 165
35. L. Ragauskaite, R.C. Heckathorn, and E.R. Gaillard Environmental effect on the photochemistry of A2E, a component of human retinal lipofuscin Photochem. Photobiol. 74 2001 483 488
36. J.E. Roberts, B.M. Kukielczak, D.-N. Hu, D.S. Miller, P. Bilski, R.H. Sik, A.G. Motten, and C.F. Chignell The role of A2E in prevention or enhancement of light damage in human retinal pigment epithelial cells Photochem. Photobiol. 75 2002 184 190
37. J.R. Kanofsky, P.D. Sima, and C. Richter Singlet-oxygen generation from A2E Photochem. Photobiol. 77 2003 235 242
38. A. Pawlak, M. Wrona, M. Rozanowska, M. Zareba, L.E. Lamb, J.E. Roberts, J.D. Simon, and T. Sarna Comparison of the aerobic photoreactivity of A2E with its precursor retinal Photochem. Photobiol. 77 2003 253 258
39. S. Ben-Shabat, Y. Itagaki, S. Jockusch, J.R. Sparrow, N.J. Turro, and K. Nakanishi Formation of a nonaoxirane from A2E, a lipofuscin fluorophore related to macular degeneration, and evidence of singlet oxygen involvement Angew. Chem. Int. Ed. 41 2002 814 817
40. J. Dillon, Z. Wang, L.B. Avalle, and E.R. Gaillard The photochemical oxidation of A2E results in the formation of a 5,8,5′,8′-bis- furanoid oxide Exp. Eye Res. 79 2004 537 542
41. Z. Wang, J. Dillon, and E.R. Gaillard Melanin protects against A2E photooxidation in RPE cells ARVO annual meeting 2004 752 (abstract)
42. J.R. Sparrow, J. Zhou, and B. Cai DNA is a target of the photodynamic effects elicited in A2E-laden RPE by blue-light illumination Invest. Ophthalmol. Visual Sci. 44 2003 2245 2251
43. J.R. Sparrow, H.R. Vollmer-Snarr, J. Zhou, Y.P. Jang, S. Jockusch, Y. Itagaki, and K. Nakanishi A2E-epoxides damage DNA in retinal pigment epithelial cells: vitamin E and other antioxidants inhibit A2E-epoxide formation J. Biol. Chem. 278 2003 18207 18213
44. R.A. Radu, N.L. Mata, A. Bagla, and G.H. Travis Light exposure stimulates formation of A2E oxiranes in a mouse model of Stargardt's macular degeneration Proc. Natl. Acad. Sci. USA 101 2004 5928 5933
45. D.J. Holder, D. Allan, E.J. Land, and S. Navaratnam Establishment of a pulse radiolysis facility on the SRS linac at Daresbury laboratory Proc. EPAC 2002 2804 2806
46. J. Butler, B.W. Hodgson, B.M. Hoey, M. Brigid, E.J. Land, J.S. Lea, E.J. Lindley, F.A.P. Rushton, and A.J. Swallow Experimental studies of some moderately fast processes initiated by radiation Radiat. Phys. Chem. 34 1989 633 646
47. G.E. Adams, J.W. Boag, B.D. Michael, and J. Currant The pulse radiolysis of thiocyanate ion M. Ebert J.P. Keene A.J. Swallow J.H. Baxendale Pulse radiolysis 1965 Academic Press London 117 129
48. •) with amino acids, pulse radiolysis evidence Life Sci. 23 1978 2617 2620
49. R. Edge, E.J. Land, D.J. McGarvey, L. Mulroy, and T.G. Truscott Relative one-electron reduction potentials of carotenoid radical cations and the interactions of carotenoids with the vitamin E radical cation J. Am. Chem. Soc. 120 1998 4087 4090
50. E.J. Land, and A.J. Swallow One-electron reactions in biochemical systems as studied by pulse radiolysis. I. Nicotinamide-adenine dinucleotide and related compounds Biochim. Biophys. Acta 162 1968 327 337
51. M.P. Hay, S.A. Gamage, M.S. Kovacs, F.B. Pruijn, R.F. Anderson, A.V. Patterson, W.R. Wilson, J.M. Brown, and W.A. Denny Structure-activity relationship of 1,2,4-benzotriazine 1,4-dioxides as hypoxia-selective analogues of tripazamine J. Med. Chem. 46 2003 169 182
52. J.A. Farrington, E.J. Land, and A.J. Swallow The one-electron reduction potentials of NAD Biochim. Biophys. Acta 590 1980 273 276
53. R.V. Bensasson, E.J. Land, and T.G. Truscott Excited states and free radicals in biology and medicine 1993 Oxford Univ. Press Oxford
54. B. Halliwell, and J.M. Gutteridge Free radicals in biology and medicine 1999 Oxford Univ. Press New York
55. • radical J. Am. Chem. Soc. 117 1995 8322 8326
56. J.A. Brent, and B.H. Rumack Role of free radicals in toxic hepatic injury. II. Are free radicals the cause of toxin-induced liver injury? J Toxicol. Clin. Toxicol. 31 1993 173 196
57. S.V. Jovanovic, and M.G. Simic Redox properties of oxy and antioxidant radicals Basic Life Sci. 49 1988 115 122
58. J.T. Landrum, and R.A. Bone Lutein, zeaxanthin, and the macular pigment Arch. Biochem. Biophys. 385 2001 28 40
59. P.S. Bernstein, F. Khachik, L.S. Carvalho, G.J. Muir, D.Y. Zhao, and N.B. Katz Identification and quantitation of carotenoids and their metabolites in the tissues of the human eye Exp. Eye Res. 72 2001 215 223
60. F. Khachik, F.F. de Moura, D.Y. Zhao, C.P. Aebischer, and P.S. Bernstein Transformations of selected carotenoids in plasma, liver, and ocular tissues of humans and in nonprimate animal models Invest. Ophthalmol. Visual Sci. 43 2002 3383 3392
61. T. Sarna Properties and function of the ocular melanin-a photobiophysical view J. Photochem. Photobiol. B 12 1992 215 258
62. M. Boulton Melanin and the retinal pigment epithelium M.F. Marmor T.J. Wolfensberger The retinal pigment epithelium 1998 Oxford Univ. Press Oxford
63. T. Sarna, J.M. Burke, W. Korytowski, M. Rozanowska, C.M. Skumatz, A. Zareba, and M. Zareba Loss of melanin from human RPE with aging: possible role of melanin photooxidation Exp. Eye Res. 76 2003 89 98
64. A.C. Bird, N.M. Bressler, S.B. Bressler, I.H. Chisholm, G. Coscas, M.D. Davis, P.T. de Jong, C.C. Klaver, B.E. Klein, and R. Klein An international classification and grading system for age-related maculopathy and age-related macular degeneration: the International ARM Epidemiological Study Group Surv. Ophthalmol. 39 1995 367 374
65. L.B. Avalle, Z. Wang, J.P. Dillon, and E.R. Gaillard Observation of A2E oxidation products in human retinal lipofuscin Exp. Eye Res. 78 2004 895 898