Ocular age pigment "A2-E": An unprecedented pyridinium bisretinoid

Journal of the American Chemical Society

Volumn 118, Issue 6, 1996, Pages 1559-1560

  Sakai, Naomi ^a   Decatur, John ^a   Nakanishi, Koji ^a   Eldred, Graig E ^b,c  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b University of Missouri   (United States)

^c c/o Debra Schepker   (Ghana)

Author keywords

[No Author keywords available]

Indexed keywords

LIPOFUSCIN; RETINOID;

ADULT; AGED; AGING; ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; EYE; HUMAN; HUMAN TISSUE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY;

EID: 0029985705     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953480g     Document Type: Article

References (25)

1. (a) Feeney-Burns, L.; Hilderbrand, E. S.; Eldridge, S. Invest. Ophthalmol. Visual Sci. 1984, 25, 195-200.
2. (b) Sarna, T. J. Photochem. Photobiol., B 1992, 12, 215-258.
3. (c) Porta, E. A. Arch. Gerontol. Geriatr. 1991, 12, 303-320 and references cited therein.
4. (a) Hyman, L. In Age-Related Macular Degeneration: Principles and Practice, Hampton, G. R., Nelson, P. T., Eds.; Raven Press: New York, 1992; pp 1-35.
5. (b) Tso, M. O. M. Invest. Ophthalmol. Visual Sci. 1989, 30, 2430-2454.
6. Eldred, G. E.; Katz, M. L. Exp. Eye Res. 1988, 47, 71-86.
7. (a) Eldred, G. E.; Lasky, M. R. Nature 1993, 361, 724-726.
8. (b) Eldred, G. E. Nature 1993, 364, 396.
9. 4a
10. 13C NMR data are shown in Figure 1.
11. Birge, R. R.; Murray, L. P.; Zidovetzki, R.; Knapp, H. M. J. Am. Chem. Soc. 1987, 109, 2090-2101.
12. TFA was used for the purification, from which this counterion originated. The counterion of natural A2-E is uncertain.
13. A zwitterionic structure for the pyridinium ethanolamine substructure was described in the following papers. (a) Igarashi, S.; Yotsuyanagi, T. Chem. Lett. 1984, 1871-1874. (b) Rademacher, O.; Ziemens, O.; Scheler, H. Z. Anorg. Allg. Chem. 1984, 519, 165-174.
14. A zwitterionic structure for the pyridinium ethanolamine substructure was described in the following papers. (a) Igarashi, S.; Yotsuyanagi, T. Chem. Lett. 1984, 1871-1874. (b) Rademacher, O.; Ziemens, O.; Scheler, H. Z. Anorg. Allg. Chem. 1984, 519, 165-174.
15. We thank one of the reviewers for drawing our attention to this aspect.
16. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Henderickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
17. Shichi, H. Biochemistry of Vision; Academic Press: New York, 1983; p 46.
18. (a) Kametani, T.; Kato, T.; Fukumoto, K. Tetrahedron 1974, 30, 1043-1046.
19. (b) Maynard, D. F.; Okamura, W. H. J. Org. Chem. 1995, 60, 1763-1771.
20. (c) de Lera, A. R.; Reischl, W.; Okamura, W. H. J. Am. Chem. Soc. 1989, 111, 4051-4063.
21. Sakai, N. Matile, S., Nakanishi, K. Unpublished result.
22. Eldred, G. E.; Kopitz, J.; Monahan, D.; Cantz, M.; Stogsdill, P. L. Submitted for publication in Am. J. Pathol.
23. (a) Gaillard, E. R.; Atherton, S. J.; Eldred, G.; Dillon, J. Photochem. Photobiol. 1995, 61, 448-453.
24. (b) Rózanowska, M.; Jarvis-Evans, J.; Korytowski, W.; Boulton, M. E.; Burke, J. M.; Sarna, T. J. Biol. Chem. 1995, 270, 18825-18830.
25. Girrotti, A. W. Photochem. Photobiol. 1990, 51, 497-509.