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Volumn 46, Issue 35, 2007, Pages 10122-10129

Characterization of dihydro-A2PE: An intermediate in the A2E biosynthetic pathway

Author keywords

[No Author keywords available]

Indexed keywords

MACULAR DEGENERATION; PHOTORECEPTORS; STARGARDT DISEASE;

EID: 34548513286     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi7009635     Document Type: Article
Times cited : (28)

References (37)
  • 1
    • 0034754212 scopus 로고    scopus 로고
    • Effect of Rpe65 knockout on accumulation of lipofuscin fluorophores in the retinal pigment epithelium
    • Katz, M. L., and Redmond, T. M. (2001) Effect of Rpe65 knockout on accumulation of lipofuscin fluorophores in the retinal pigment epithelium, Invest. Ophthalmol. Visual Sci. 42, 3023-3030.
    • (2001) Invest. Ophthalmol. Visual Sci , vol.42 , pp. 3023-3030
    • Katz, M.L.1    Redmond, T.M.2
  • 2
    • 4143075923 scopus 로고    scopus 로고
    • The Rpe65 Leu450Met variant is associated with reduced levels of the RPE lipofuscin fluorophores A2E and iso-A2E
    • Kim, S. R., Fishkin, N., Kong, J., Nakanishi, K., Allikmets, R., and Sparrow, J. R. (2004) The Rpe65 Leu450Met variant is associated with reduced levels of the RPE lipofuscin fluorophores A2E and iso-A2E, Proc. Natl. Acad. Sci. U.S.A. 101, 11668-11672.
    • (2004) Proc. Natl. Acad. Sci. U.S.A , vol.101 , pp. 11668-11672
    • Kim, S.R.1    Fishkin, N.2    Kong, J.3    Nakanishi, K.4    Allikmets, R.5    Sparrow, J.R.6
  • 3
    • 31044444376 scopus 로고    scopus 로고
    • Small molecule RPE65 antagonists limit the visual cycle and prevent lipofuscin formation
    • Maiti, P., Kong, J., Kim, S. R., Sparrow, J. R., Allikmets, R., and Rando, R. R. (2006) Small molecule RPE65 antagonists limit the visual cycle and prevent lipofuscin formation, Biochemistry 45, 852-860.
    • (2006) Biochemistry , vol.45 , pp. 852-860
    • Maiti, P.1    Kong, J.2    Kim, S.R.3    Sparrow, J.R.4    Allikmets, R.5    Rando, R.R.6
  • 4
    • 0035852747 scopus 로고    scopus 로고
    • Inhibition of the visual cycle in vivo by 13-cis retinoic acid protects from light damage and provides a mechanism for night blindness in isotretinoin therapy
    • Sieving, P. A., Chaudhry, P., Kondo, M., Provenzano, M., Wu, D., Carlson, T. J., Bush, R. A., and Thompson, D. A. (2001) Inhibition of the visual cycle in vivo by 13-cis retinoic acid protects from light damage and provides a mechanism for night blindness in isotretinoin therapy, Proc. Natl. Acad. Sci. U.S.A. 98, 1835-1840.
    • (2001) Proc. Natl. Acad. Sci. U.S.A , vol.98 , pp. 1835-1840
    • Sieving, P.A.1    Chaudhry, P.2    Kondo, M.3    Provenzano, M.4    Wu, D.5    Carlson, T.J.6    Bush, R.A.7    Thompson, D.A.8
  • 5
    • 0037447253 scopus 로고    scopus 로고
    • Treatment with isotretinoin inhibits lipofuscin and A2E accumulation in a mouse model of recessive Stargardt's macular degeneration
    • Radu, R. A., Mata, N. L., Nusinowitz, S., Liu, X., Sieving, P. A., and Travis, G. H. (2003) Treatment with isotretinoin inhibits lipofuscin and A2E accumulation in a mouse model of recessive Stargardt's macular degeneration, Proc. Natl. Acad. Sci. U.S.A. 100, 4742-4747.
    • (2003) Proc. Natl. Acad. Sci. U.S.A , vol.100 , pp. 4742-4747
    • Radu, R.A.1    Mata, N.L.2    Nusinowitz, S.3    Liu, X.4    Sieving, P.A.5    Travis, G.H.6
  • 6
    • 0022909003 scopus 로고
    • Relationship between dietary retinol and lipofuscin in the retinal pigment epithelium
    • Katz, M. L., Drea, C. M., and Robison, W. G., Jr. (1986) Relationship between dietary retinol and lipofuscin in the retinal pigment epithelium, Mech. Ageing Dev. 35, 291-305.
    • (1986) Mech. Ageing Dev , vol.35 , pp. 291-305
    • Katz, M.L.1    Drea, C.M.2    Robison Jr., W.G.3
  • 7
    • 0023222761 scopus 로고
    • Lipofuscin autofluorescence: Evidence for vitamin A involvement in the retina
    • Katz, M. L., Eldred, G. E., and Robison, W. G., Jr. (1987) Lipofuscin autofluorescence: evidence for vitamin A involvement in the retina, Mech. Ageing Dev. 39, 81-90.
    • (1987) Mech. Ageing Dev , vol.39 , pp. 81-90
    • Katz, M.L.1    Eldred, G.E.2    Robison Jr., W.G.3
  • 8
    • 33644795859 scopus 로고    scopus 로고
    • Reductions in serum vitamin A arrest accumulation of toxic retinal fluorophores: A potential therapy for treatment of lipofuscin-based retinal diseases
    • Radu, R. A., Han, Y., Bui, T. V., Nusinowitz, S., Bok, D., Lichter, J., Widder, K., Travis, G. H., and Mata, N. L. (2005) Reductions in serum vitamin A arrest accumulation of toxic retinal fluorophores: a potential therapy for treatment of lipofuscin-based retinal diseases, Invest. Ophthalmol. Visual Sci. 46, 4393-4401.
    • (2005) Invest. Ophthalmol. Visual Sci , vol.46 , pp. 4393-4401
    • Radu, R.A.1    Han, Y.2    Bui, T.V.3    Nusinowitz, S.4    Bok, D.5    Lichter, J.6    Widder, K.7    Travis, G.H.8    Mata, N.L.9
  • 9
    • 0027410970 scopus 로고
    • Retinal age pigments generated by self-assembling lysosomotropic detergents
    • Eldred, G. E., and Lasky, M. R. (1993) Retinal age pigments generated by self-assembling lysosomotropic detergents, Nature 361, 724-726.
    • (1993) Nature , vol.361 , pp. 724-726
    • Eldred, G.E.1    Lasky, M.R.2
  • 10
    • 0023814969 scopus 로고
    • Fluorophores of the human retinal pigment epithelium: Separation and spectral characterization
    • Eldred, G. E., and Katz, M. L. (1988) Fluorophores of the human retinal pigment epithelium: separation and spectral characterization, Exp. Eye Res. 47, 71-86.
    • (1988) Exp. Eye Res , vol.47 , pp. 71-86
    • Eldred, G.E.1    Katz, M.L.2
  • 11
    • 0029985705 scopus 로고    scopus 로고
    • Ocular age pigment "A2E": An unprecedented pyridinium bisretinoid
    • Sakai, N., Decatur, J., Nakanishi, K., and Eldred, G. E. (1996) Ocular age pigment "A2E": an unprecedented pyridinium bisretinoid, J. Am. Chem. Soc. 118, 1559-1560.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 1559-1560
    • Sakai, N.1    Decatur, J.2    Nakanishi, K.3    Eldred, G.E.4
  • 12
    • 0032438193 scopus 로고    scopus 로고
    • Isolation and one-step preparation of A2E and iso-A2E, fluorophores from human retinal pigment epithelium
    • Parish, C. A., Hashimoto, M., Nakanishi, K., Dillon, J., and Sparrow, J. R. (1998) Isolation and one-step preparation of A2E and iso-A2E, fluorophores from human retinal pigment epithelium, Proc. Natl. Acad. Sci. U.S.A. 95, 14609-14613.
    • (1998) Proc. Natl. Acad. Sci. U.S.A , vol.95 , pp. 14609-14613
    • Parish, C.A.1    Hashimoto, M.2    Nakanishi, K.3    Dillon, J.4    Sparrow, J.R.5
  • 14
    • 0030980348 scopus 로고    scopus 로고
    • Total synthesis of the ocular age pigment A2E: A convergent pathway
    • Ren, R. F., Sakai, N., and Nakanishi, K. (1997) Total synthesis of the ocular age pigment A2E: a convergent pathway, J. Am. Chem. Soc. 119, 3619-3620.
    • (1997) J. Am. Chem. Soc , vol.119 , pp. 3619-3620
    • Ren, R.F.1    Sakai, N.2    Nakanishi, K.3
  • 15
    • 7044247769 scopus 로고    scopus 로고
    • Absolute configurational determination of an all-trans-retinal dimer isolated from photoreceptor outer segments
    • Fishkin, N., Pescitelli, G., Sparrow, J. R., Nakanishi, K., and Berova, N. (2004) Absolute configurational determination of an all-trans-retinal dimer isolated from photoreceptor outer segments, Chirality 16, 637-641.
    • (2004) Chirality , vol.16 , pp. 637-641
    • Fishkin, N.1    Pescitelli, G.2    Sparrow, J.R.3    Nakanishi, K.4    Berova, N.5
  • 16
    • 18844379122 scopus 로고    scopus 로고
    • Isolation and characterization of a retinal pigment epithelial cell fluorophore: An all-trans-retinal dimer conjugate
    • Fishkin, N., Sparrow, J. R., Allikmets, R., and Nakanishi, K. (2005) Isolation and characterization of a retinal pigment epithelial cell fluorophore: an all-trans-retinal dimer conjugate, Proc. Natl. Acad. Sci. U.S.A. 102, 7091-7096.
    • (2005) Proc. Natl. Acad. Sci. U.S.A , vol.102 , pp. 7091-7096
    • Fishkin, N.1    Sparrow, J.R.2    Allikmets, R.3    Nakanishi, K.4
  • 17
    • 0034703010 scopus 로고    scopus 로고
    • The biosynthesis of A2E, a fluorophore of aging retina, involves the formation of the precursor, A2-PE, in the photoreceptor outer segment membrane
    • Liu, J., Itagaki, Y., Ben-Shabat, S., Nakanishi, K., and Sparrow, J. R. (2000) 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, 29354-29360.
    • (2000) J. Biol. Chem , vol.275 , pp. 29354-29360
    • Liu, J.1    Itagaki, Y.2    Ben-Shabat, S.3    Nakanishi, K.4    Sparrow, J.R.5
  • 18
    • 0033538438 scopus 로고    scopus 로고
    • Insights into the function of Rim protein in photoreceptors and etiology of Stargardt's disease from the phenotype in abcr knockout mice
    • Weng, J., Mata, N. L., Azarian, S. M., Tzekov, R. T., Birch, D. G., and Travis, G. H. (1999) Insights into the function of Rim protein in photoreceptors and etiology of Stargardt's disease from the phenotype in abcr knockout mice, Cell 98, 13-23.
    • (1999) Cell , vol.98 , pp. 13-23
    • Weng, J.1    Mata, N.L.2    Azarian, S.M.3    Tzekov, R.T.4    Birch, D.G.5    Travis, G.H.6
  • 19
    • 0000761427 scopus 로고    scopus 로고
    • Retinal stimulates ATP hydrolysis by purified and reconstituted ABCR, the photoreceptor-specific ATP-binding cassette transporter responsible for Stargardt disease
    • Sun, H., Molday, R. S., and Nathans, J. (1999) Retinal stimulates ATP hydrolysis by purified and reconstituted ABCR, the photoreceptor-specific ATP-binding cassette transporter responsible for Stargardt disease, J. Biol. Chem. 274, 8269-8281.
    • (1999) J. Biol. Chem , vol.274 , pp. 8269-8281
    • Sun, H.1    Molday, R.S.2    Nathans, J.3
  • 20
    • 0031230154 scopus 로고    scopus 로고
    • Stargardt's ABCR is localized to the disc membrane of retinal rod outer segments
    • Sun, H., and Nathans, J. (1997) Stargardt's ABCR is localized to the disc membrane of retinal rod outer segments, Nat. Genet. 17, 15-16.
    • (1997) Nat. Genet , vol.17 , pp. 15-16
    • Sun, H.1    Nathans, J.2
  • 22
    • 0003321970 scopus 로고
    • Characterization of an unexpected product from a monoamine oxidase B generated 2,3-dihydropyridinium species
    • Dalvis, D., Zhao, Z., and Castagnoli, N. (1992) Characterization of an unexpected product from a monoamine oxidase B generated 2,3-dihydropyridinium species, J. Org. Chem. 57, 7321-7324.
    • (1992) J. Org. Chem , vol.57 , pp. 7321-7324
    • Dalvis, D.1    Zhao, Z.2    Castagnoli, N.3
  • 24
    • 0000287603 scopus 로고    scopus 로고
    • Molecular excitation energies to high-lying bound states from time-dependent density-functional response theory: Characterization and correction of the time-dependent local density approximation ionization threshold
    • Casida, M. E., Jamorski, C., Casida, K. C., and Salahub, D. R. (1998) Molecular excitation energies to high-lying bound states from time-dependent density-functional response theory: Characterization and correction of the time-dependent local density approximation ionization threshold, J. Chem. Phys 108, 4439-4449.
    • (1998) J. Chem. Phys , vol.108 , pp. 4439-4449
    • Casida, M.E.1    Jamorski, C.2    Casida, K.C.3    Salahub, D.R.4
  • 25
    • 34548510177 scopus 로고    scopus 로고
    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Montgomery, J. A, Jr, Vreven, T, Kudin, K. N, Burant, J. C, Millam, J. M, Iyengar, S. S, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Ortiz, J. V, Cui, Q, Baboul, A. G, Clifford, S, Cioslowski, J, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Martin, R. L, Fox, D. J, Keit
    • Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A., Jr., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., Pople, J. A. (2004) Gaussian 03, revision C.02, Gaussian, Inc., Wallingford, CT.
  • 26
    • 34250817103 scopus 로고
    • A new mixing of Hartree-Fock and local density-functional theories
    • Becke, A. D. (1993) A new mixing of Hartree-Fock and local density-functional theories, J. Chem. Phys. 98, 1372-1377.
    • (1993) J. Chem. Phys , vol.98 , pp. 1372-1377
    • Becke, A.D.1
  • 27
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
    • Lee, C., Yang, W., and Parr, R. G. (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B 37, 785-789.
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 28
    • 0000438332 scopus 로고    scopus 로고
    • A challenge for density functional: Self-interaction error increases for systems with a noninteger number of electrons
    • Zhang, Y., and Yang, W. (1998) A challenge for density functional: self-interaction error increases for systems with a noninteger number of electrons, J. Chem. Phys. 109, 2604-2608.
    • (1998) J. Chem. Phys , vol.109 , pp. 2604-2608
    • Zhang, Y.1    Yang, W.2
  • 29
    • 29144433411 scopus 로고    scopus 로고
    • Absolute configuration of C76 from optical rotatory dispersion
    • Polavarapu, P. L., He, J., Crassous, J., and Ruud, K. (2005) Absolute configuration of C76 from optical rotatory dispersion, ChemPhysChem 6, 2535-2540.
    • (2005) ChemPhysChem , vol.6 , pp. 2535-2540
    • Polavarapu, P.L.1    He, J.2    Crassous, J.3    Ruud, K.4
  • 30
    • 26444433849 scopus 로고    scopus 로고
    • Theoretical investigations of the UV spectra of coumarin derivatives
    • Preat, J., Jacquemin, D., and Perpete, E. A. (2005) Theoretical investigations of the UV spectra of coumarin derivatives, Chem. Phys. Lett. 415, 20-24.
    • (2005) Chem. Phys. Lett , vol.415 , pp. 20-24
    • Preat, J.1    Jacquemin, D.2    Perpete, E.A.3
  • 31
    • 0000800479 scopus 로고    scopus 로고
    • Time-dependent density functional study on the electronic excitation energies of polycyclic aromatic hydrocarbon radical cations of naphthalene, anthracene, pyrene and perylene
    • Hirata, S., Lee, T. J., and Head-Gordon, M. (1999) Time-dependent density functional study on the electronic excitation energies of polycyclic aromatic hydrocarbon radical cations of naphthalene, anthracene, pyrene and perylene, J. Chem. Phys. 111, 8904-8912.
    • (1999) J. Chem. Phys , vol.111 , pp. 8904-8912
    • Hirata, S.1    Lee, T.J.2    Head-Gordon, M.3
  • 32
    • 0038537475 scopus 로고    scopus 로고
    • -: Influence of basis set and geometry
    • -: influence of basis set and geometry, Inorg. Chem. 42, 4046-4056.
    • (2003) Inorg. Chem , vol.42 , pp. 4046-4056
    • Nemykin, V.N.1    Basu, P.2
  • 33
    • 13844271365 scopus 로고    scopus 로고
    • Simulation of UV/visible absorption spectra of (a-diimine)nickel(II) catalysts by time-dependent density functional theory
    • Cavillot, V., and Champagne, B. (2005) Simulation of UV/visible absorption spectra of (a-diimine)nickel(II) catalysts by time-dependent density functional theory, Int. J. Quantum Chem. 101, 840-848.
    • (2005) Int. J. Quantum Chem , vol.101 , pp. 840-848
    • Cavillot, V.1    Champagne, B.2
  • 34
    • 0034944895 scopus 로고    scopus 로고
    • Delayed dark adaptation and lipofuscin accumulation in abcr+/- mice: Implications for involvement of ABCR in age-related macular degeneration
    • Mata, N. L., Tzekov, R. T., Liu, X., Weng, J., Birch, D. G., and Travis, G. H. (2001) Delayed dark adaptation and lipofuscin accumulation in abcr+/- mice: implications for involvement of ABCR in age-related macular degeneration, Invest. Ophthalmol. Visual Sci. 42, 1685-1690.
    • (2001) Invest. Ophthalmol. Visual Sci , vol.42 , pp. 1685-1690
    • Mata, N.L.1    Tzekov, R.T.2    Liu, X.3    Weng, J.4    Birch, D.G.5    Travis, G.H.6
  • 35
    • 0034691089 scopus 로고    scopus 로고
    • Biosynthesis of a major lipofuscin fluorophore in mice and humans with ABCR-mediated retinal and macular degeneration
    • Mata, N. L., Weng, J., and Travis, G. H. (2000) Biosynthesis of a major lipofuscin fluorophore in mice and humans with ABCR-mediated retinal and macular degeneration, Proc. Natl. Acad. Sci. U.S.A. 97, 7154-7159.
    • (2000) Proc. Natl. Acad. Sci. U.S.A , vol.97 , pp. 7154-7159
    • Mata, N.L.1    Weng, J.2    Travis, G.H.3
  • 36
    • 1942533542 scopus 로고    scopus 로고
    • Light exposure stimulates formation of A2E oxiranes in a mouse model of Stargardt's macular degeneration
    • Radu, R. A., Mata, N. L., Bagla, A., and Travis, G. H. (2004) Light exposure stimulates formation of A2E oxiranes in a mouse model of Stargardt's macular degeneration, Proc. Natl. Acad. Sci. U.S.A. 101, 5928-5933.
    • (2004) Proc. Natl. Acad. Sci. U.S.A , vol.101 , pp. 5928-5933
    • Radu, R.A.1    Mata, N.L.2    Bagla, A.3    Travis, G.H.4
  • 37
    • 33745848402 scopus 로고    scopus 로고
    • Characterization of native retinal fluorophores involved in biosynthesis of A2E and lipofuscin-associated retinopathies
    • Bui, T. V., Han, Y., Radu, R. A., Travis, G. H., and Mata, N. L. (2006) Characterization of native retinal fluorophores involved in biosynthesis of A2E and lipofuscin-associated retinopathies, J. Biol. Chem. 281, 18112-18119.
    • (2006) J. Biol. Chem , vol.281 , pp. 18112-18119
    • Bui, T.V.1    Han, Y.2    Radu, R.A.3    Travis, G.H.4    Mata, N.L.5


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