Novel lipofuscin bisretinoids prominent in human retina and in a model of recessive stargardt disease

Journal of Biological Chemistry

Volumn 284, Issue 30, 2009, Pages 20155-20166

  Wu, Yalin ^a   Fishkin, Nathan E ^b   Pande, Ajay ^c   Pande, Jayanthi ^c   Sparrow, Janet R ^a,d,e  

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

^b IMMUNOGEN INC   (United States)

^c STATE UNIVERSITY OF NEW YORK   (United States)

^d NewYork Presbyterian Hospital   (United States)

^e NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORBANCE; AGE-RELATED; AGE-RELATED MACULAR DEGENERATION; ATP-BINDING CASSETTE TRANSPORTERS; DIHYDROPYRIDINE; ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRY; ETHANOLAMINE; FLUORESCENT COMPOUNDS; HUMAN RETINA; MACULAR DEGENERATION; OUTER SEGMENTS; PHOSPHATIDYLETHANOLAMINE; PHOTORECEPTOR CELL; REACTION MIXTURE; RETINAL DISEASE; RETINAL PIGMENT EPITHELIAL; STARGARDT DISEASE; VITAMIN A; WILD TYPES;

CELL MEMBRANES; CHROMATOGRAPHIC ANALYSIS; CHROMOPHORES; CONTROLLED DRUG DELIVERY; DENSITY FUNCTIONAL THEORY; DRUG THERAPY; ELECTROSPRAY IONIZATION; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OPHTHALMOLOGY; PATHOLOGY; PHOTOOXIDATION; PYRIDINE; SPECTROSCOPIC ANALYSIS; SPECTROSCOPY;

ALDEHYDES;

A2 DIHYDROPYRIDINE ETHANOLAMINE; A2 DIHYDROPYRIDINE PHOSPHATIDYLETHANOLAMINE; ABC TRANSPORTER; ABC TRANSPORTER 4; BISRETINOID; DIHYDROPYRIDINE; FLUORESCENT DYE; LIPOFUSCIN; PHOSPHATE; PHOSPHATIDYLDIHYDROPYRIDINE BISRETINOID; PHOSPHATIDYLETHANOLAMINE; RETINAL; RETINOID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; ELECTROSPRAY MASS SPECTROMETRY; EPITHELIUM CELL; FLUORESCENCE ANALYSIS; GENE MUTATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HUMAN TISSUE; HYDROLYSIS; INFRARED SPECTROSCOPY; MOUSE; NONHUMAN; NULL ALLELE; PIGMENT EPITHELIUM; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN STRUCTURE; RECESSIVE INHERITANCE; RETINA MACULA DEGENERATION; STARGARDT DISEASE; TANDEM MASS SPECTROMETRY; WILD TYPE;

AGE FACTORS; ANIMALS; ATP-BINDING CASSETTE TRANSPORTERS; CATTLE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; LIPOFUSCIN; MACULAR DEGENERATION; MICE; MICE, INBRED C57BL; MICE, KNOCKOUT; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PIGMENT EPITHELIUM OF EYE; RETINA; RETINALDEHYDE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TANDEM MASS SPECTROMETRY; VITAMIN A;

BOVINAE; MUS;

EID: 67749135744     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M109.021345     Document Type: Article

References (46)

1. Sparrow, J. R. (2007) in Retinal Degenerations: Biology, Diagnostics and Therapeutics (Tombran-Tink, J., and Barnstable, C. J., eds) pp. 213-231, Humana Press, Totowa, NJ
2. Sparrow, J. R. (2007) in Atlas of Autofluorescence Imaging (Holz, F. G., Schmitz-Valckenberg, S., Spaide, R. F., and Bird, A. C., eds) pp. 3-16, Springer, Heidelberg, Germany
3. Sparrow, J. R., Cai, B., Jang, Y. P., Zhou, J., and Nakanishi, K. (2006) Adv. Exp. Med. Biol. 572, 63-68
4. Katz, M. L., Drea, C. M., and Robison, W. G., Jr. (1986) Mech. Ageing Dev. 35, 291-305
5. Katz, M. L., Eldred, G. E., and Robison, W. G., Jr. (1987) Mech. Ageing Dev. 39, 81-90
6. Radu, R. A., Han, Y., Bui, T. V., Nusinowitz, S., Bok, D., Lichter, J., Widder, K., Travis, G. H., and Mata, N. L. (2005) Invest. Ophthalmol. Vis. Sci. 46, 4393-4401
7. Katz, M. L., and Redmond, T. M. (2001) Invest. Ophthalmol. Vis. Sci. 42, 3023-3030
8. Kim, S. R., Fishkin, N., Kong, J., Nakanishi, K., Allikmets, R., and Sparrow, J. R. (2004) Proc. Natl. Acad. Sci. U.S.A. 101, 11668-11672
9. Sparrow, J. R., Kim, S. R., Jang, Y. P., and Zhou, J. (2008) in Eye, Retina, and Visual System of the Mouse (Chalupa, L. M., ed) pp. 539-546, MIT Press, Cambridge, MA
10. Maiti, P., Kong, J., Kim, S. R., Sparrow, J. R., Allikmets, R., and Rando, R. R. (2006) Biochemistry 45, 852-860
11. Sieving, P. A., Chaudhry, P., Kondo, M., Provenzano, M., Wu, D., Carlson, T. J., Bush, R. A., and Thompson, D. A. (2001) Proc. Natl. Acad. Sci. U.S.A. 98, 1835-1840
12. Radu, R. A., Mata, N. L., Nusinowitz, S., Liu, X., Sieving, P. A., and Travis, G. H. (2003) Proc. Natl. Acad. Sci. U.S.A. 100, 4742-4747
13. Maeda, A., Maeda, T., Golczak, M., and Palczewski, K. (2008) J. Biol. Chem. 283, 26684-26693
14. Parish, C. A., Hashimoto, M., Nakanishi, K., Dillon, J., and Sparrow, J. R. (1998) Proc. Natl. Acad. Sci. U.S.A. 95, 14609-14613
15. Liu, J., Itagaki, Y., Ben-Shabat, S., Nakanishi, K., and Sparrow, J. R. (2000) J. Biol. Chem. 275, 29354-29360
16. Ben-Shabat, S., Parish, C. A., Vollmer, H. R., Itagaki, Y., Fishkin, N., Nakanishi, K., and Sparrow, J. R. (2002) J. Biol. Chem. 277, 7183-7190
17. Fishkin, N. E., Sparrow, J. R., Allikmets, R., and Nakanishi, K. (2005) Proc. Natl. Acad. Sci. U.S.A. 102, 7091-7096
18. Kim, S. R., Jang, Y. P., Jockusch, S., Fishkin, N. E., Turro, N. J., and Sparrow, J. R. (2007) Proc. Natl. Acad. Sci. U.S.A. 104, 19273-19278
19. Kim, S. R., He, J., Yanase, E., Jang, Y. P., Berova, N., Sparrow, J. R., and Nakanishi, K. (2007) Biochemistry 46, 10122-10129
20. Eldred, G. E., and Lasky, M. R. (1993) Nature 361, 724-726
21. Sakai, N., Decatur, J., Nakanishi, K., and Eldred, G. E. (1996) J. Am. Chem. Soc. 118, 1559-1560
22. Ren, R. F., Sakai, N., and Nakanishi, K. (1997) J. Am. Chem. Soc. 119, 3619-3620
23. Fishkin, N., Pescitelli, G., Sparrow, J. R., Nakanishi, K., and Berova, N. (2004) Chirality 16, 637-641
24. Sparrow, J. R., Parish, C. A., Hashimoto, M., and Nakanishi, K. (1999) Invest. Ophthalmol. Vis. Sci. 40, 2988-2995
25. Jang, Y. P., Matsuda, H., Itagaki, Y., Nakanishi, K., and Sparrow, J. R. (2005) J. Biol. Chem. 280, 39732-39739
26. Ben-Shabat, S., Itagaki, Y., Jockusch, S., Sparrow, J. R., Turro, N. J., and Nakanishi, K. (2002) Angew. Chem. Int. Ed. 41, 814-817
27. Dillon, J., Wang, Z., Avalle, L. B., and Gaillard, E. R. (2004) Exp. Eye Res. 79, 537-542
28. Mata, N. L., Weng, J., and Travis, G. H. (2000) Proc. Natl. Acad. Sci. U.S.A. 97, 7154-7159
29. Weng, J., Mata, N. L., Azarian, S. M., Tzekov, R. T., Birch, D. G., and Travis, G. H. (1999) Cell 98, 13-23
30. Pang, J. J., Chang, B., Hawes, N. L., Hurd, R. E., Davisson, M. T., Li, J., Noorwez, S. M., Malhotra, R., McDowell, J. H., Kaushal, S., Hauswirth, W. W., Nusinowitz, S., Thompson, D. A., and Heckenlively, J. R. (2005) Mol. Vis. 11, 152-162
31. Schröer, J., Sanner, M., Reymond, J. L., Richard, A., and Lerner, R. A. (1997) J. Org. Chem. 62, 3220-3229
32. Onerus, T. A., Knaus, E., and Giam, C. S. (1978) Can. J. Chem. 56, 1026-1030
33. Bok, D., and Hall, M. O. (1971) J. Cell Biol. 49, 664-682
34. Sparrow, J. R., Kim, S. R., Cuervo, A. M., and Bandhyopadhyayand, U. (2008) Adv. Exp. Med. Biol. 613, 393-398
35. Sun, H., Molday, R. S., and Nathans, J. (1999) J. Biol. Chem. 274, 8269-8281
36. Sun, H., and Nathans, J. (1997) Nat. Genet. 17, 15-16
37. Beharry, S., Zhong, M., and Molday, R. S. (2004) J. Biol. Chem. 279, 53972-53979
38. Allikmets, R., Singh, N., Sun, H., Shroyer, N. F., Hutchinson, A., Chidambaram, A., Gerrard, B., Baird, L., Stauffer, D., Peiffer, A., Rattner, A., Smallwood, P., Li, Y., Anderson, K. L., Lewis, R. A., Nathans, J., Leppert, M., Dean, M., and Lupski, J. R. (1997) Nat. Genet. 15, 236-246
39. Dalvis, D., Zhao, Z., and Castagnoli, N. (1992) J. Org. Chem. 57, 7321-7324
40. Taylor, K. E., and Jones, J. B. (1976) J. Am Chem. Soc. 98, 5689-5694
41. Birnbach, C. D., Järveläinen, M., Possin, D. E., and Milam, A. H. (1994) Ophthalmology 101, 1211-1219
42. Bunt-Milam, A. H., Kalina, R. E., and Pagon, R. A. (1983) Invest. Ophthalmol. Vis. Sci. 24, 458-469
43. Szamier, R. B., and Berson, E. L. (1977) Invest Ophthalmol. Vis. Sci. 16, 947-962
44. Bravaya, K., Bochenkova, A., Granovsky, A., and Nemukhin, A. (2007) J. Am Chem. Soc. 129, 13035-13042
45. Allocca, M., Doria, M., Petrillo, M., Colella, P., Garcia-Hoyos, M., Gibbs, D., Kim, S. R., Maguire, A., Rex, T. S., Di Vicino, U., Cutillo, L., Sparrow, J. R., Williams, D. S., Bennett, J., and Auricchio, A. (2008) J. Clin. Invest. 118, 1955-1964
46. Kong, J., Kim, S. R., Binley, K., Pata, I., Doi, K., Mannik, J., Zernant-Rajang, J., Kan, O., Iqball, S., Naylor, S., Sparrow, J. R., Gouras, P., and Allikmets, R. (2008) Gene Ther. 15, 1311-1320