450
Views
22
CrossRef citations to date
0
Altmetric
Original Article

Cross-linking of lens crystallin proteins induced by tryptophan metabolites and metal ions: implications for cataract development

, , , &
Pages 1116-1130 | Received 19 Apr 2016, Accepted 01 Jul 2016, Published online: 27 Jul 2016

References

  • Sliney DH. Estimating the solar ultraviolet radiation exposure to an intraocular lens implant. J Cataract Refract Surg 1987;13:296–301.
  • Zigman S. Environmental near-UV radiation and cataracts. Optom Vis Sci 1995;72:899–901.
  • Dillon J, Atherton SJ. Time resolved spectroscopic studies on the intact human lens. Photochem Photobiol 1990;51:465–468.
  • Goldstein LE, Leopold MC, Huang X, Atwood CS, Saunders AJ, Hartshorn M, et al. 3-Hydroxykynurenine and 3-hydroxyanthranilic acid generate hydrogen peroxide and promote alpha-crystallin cross-linking by metal ion reduction. Biochemistry 2000;39:7266–7275.
  • van Heyningen R. Fluorescent derivatives of 3-hydroxy-L-kynurenine in the lens of man, the baboon and the grey squirrel. Biochem J 1971;123:30–31.
  • van Heyningen R. Fluorescent glucoside in the human lens. Nature 1971;230:393–394.
  • van Heyningen R. The glucoside of 3-hydroxykynurenine and other fluorescent compounds in the human lens. Ciba Found Symp 1973;19:151–168.
  • Wood AM, Truscott RJ. UV filters in human lenses: tryptophan catabolism. Exp Eye Res 1993;56:317–325.
  • Dillon J, Wang RH, Atherton SJ. Photochemical and photophysical studies on human lens constituents. Photochem Photobiol 1990;52:849–854.
  • van Heyningen R. Photo-oxidation of lens proteins by sunlight in the presence of fluorescent derivatives of kynurenine, isolated from the human lens. Exp Eye Res 1973;17:137–147.
  • Vazquez S, Aquilina JA, Jamie JF, Sheil MM, Truscott RJ. Novel protein modification by kynurenine in human lenses. J Biol Chem 2002;277:4867–4873.
  • Bova LM, Sweeney MJH, Jamie JF, Truscott RJW. Major changes in human ocular UV protection with age. Invest Ophthalmol Vis Sci 2001;42:200–205.
  • Hood BD, Garner B, Truscott RJ. Human lens coloration and aging. Evidence for crystallin modification by the major ultraviolet filter, 3-hydroxy-kynurenine O-beta-D-glucosideJ Biol Chem 1999;274:32547–32550.
  • Taylor LM, Andrew Aquilina J, Jamie JF, Truscott RJ. Glutathione and NADH, but not ascorbate, protect lens proteins from modification by UV filters. Exp Eye Res 2002;74:503–511.
  • Korlimbinis A, Truscott RJ. Identification of 3-hydroxykynurenine bound to proteins in the human lens. A possible role in age-related nuclear cataract. Biochemistry 2006;45:1950–1960.
  • Korlimbinis A, Aquilina JA, Truscott RJ. Protein-bound UV filters in normal human lenses: the concentration of bound UV filters equals that of free UV filters in the center of older lenses. Invest Ophthalmol Vis Sci 2007;48:1718–1723.
  • Korlimbinis A, Aquilina JA, Truscott RJ. Protein-bound and free UV filters in cataract lenses. The concentration of UV filters is much lower than in normal lenses. Exp Eye Res 2007;85:219–225.
  • Parker NR, Jamie JF, Davies MJ, Truscott RJW. Protein-bound kynurenine is a photosensitizer of oxidative damage. Free Radic Biol Med 2004;37:1479–1489.
  • Mizdrak J, Hains PG, Truscott RJ, Jamie JF, Davies MJ. Tryptophan-derived ultraviolet filter compounds covalently bound to lens proteins are photosensitizers of oxidative damage. Free Radic Biol Med 2008;44:1108–1119.
  • Garner MH, Spector A. Selective oxidation of cysteine and methionine in normal and senile cataractous lenses. Proc Natl Acad Sci USA 1980;77:1274–1277.
  • Spector A, Wang GM, Wang RR, Li WC, Kleiman NJ. A brief photochemically induced oxidative insult causes irreversible lens damage and cataract. II. Mechanism of action. Exp Eye Res 1995;60:483–493.
  • Finley EL, Busman M, Dillon J, Crouch RK, Schey KL. Identification of photooxidation sites in bovine alpha-crystallin. Photochem Photobiol 1997;66:635–641.
  • Dillon J, Roy D, Spector A, Walker ML, Hibbard LB, Borkman RF. UV laser photodamage to whole lenses. Exp Eye Res 1989;49:959–966.
  • Korlimbinis A, Hains PG, Truscott RJ, Aquilina JA. 3-Hydroxykynurenine oxidizes alpha-crystallin: potential role in cataractogenesis. Biochemistry 2006;45:1852–1860.
  • Davies MJ, Truscott RJW. Photo-oxidation of proteins and its role in cataractogenesis. J Photochem Photobiol B, Biol 2001;63:114–125.
  • Truscott RJ. Age-related nuclear cataract-oxidation is the key. Exp Eye Res 2005;80:709–725.
  • Truscott RJ, Friedrich MG. The etiology of human age-related cataract. Proteins don't last forever. Biochim Biophys Acta 2016;1860:192–198.
  • Garner B, Davies MJ, Truscott RJ. Formation of hydroxyl radicals in the human lens is related to the severity of nuclear cataract. Exp Eye Res 2000;70:81–88.
  • Garner B, Roberg K, Qian M, Eaton JW, Truscott RJ. Distribution of ferritin and redox-active transition metals in normal and cataractous human lenses. Exp Eye Res 2000;71:599–607.
  • Vazquez S, Garner B, Sheil MM, Truscott RJ. Characterisation of the major autoxidation products of 3-hydroxykynurenine under physiological conditions. Free Radic Res 2000;32:11–23.
  • Bindokas VP, Jordan J, Lee CC, Miller RJ. Superoxide production in rat hippocampal neurons: selective imaging with hydroethidine. J Neurosci 1996;16:1324–1336.
  • Zielonka J, Hardy M, Kalyanaraman B. HPLC study of oxidation products of hydroethidine in chemical and biological systems: ramifications in superoxide measurements. Free Radic Biol Med 2009;46:329–338.
  • Zhao H, Joseph J, Fales HM, Sokoloski EA, Levine RL, Vasquez-Vivar J, Kalyanaraman B. Detection and characterization of the product of hydroethidine and intracellular superoxide by HPLC and limitations of fluorescence. Proc Natl Acad Sci USA 2005;102:5727–5732.
  • Davies MJ. Singlet oxygen-mediated damage to proteins and its consequences. Biochem Biophys Res Commun 2003;305:761–770.
  • Pattison DI, Rahmanto AS, Davies MJ. Photo-oxidation of proteins. Photochem Photobiol Sci 2012;11:38–53.
  • Parker NR, Korlimbinis A, Jamie JF, Davies MJ, Truscott RJ. Reversible binding of kynurenine to lens proteins: potential protection by glutathione in young lenses. Invest Ophthalmol Vis Sci 2007;48:3705–3713.
  • Li YT, Jongberg S, Andersen ML, Davies MJ, Lund MN. Quinone-induced protein modifications: Kinetic preference for reaction of 1,2-benzoquinones with thiol groups in proteins. Free Radic Biol Med 2016;97:148–157.
  • Manthey MK, Pyne SG, Truscott RJ. Mechanism of reaction of 3-hydroxyanthranilic acid with molecular oxygen. Biochim Biophys Acta 1990;1034:207–212.
  • Manthey MK, Pyne SG, Truscott RJW. Autoxidation of 3-hydroxyanthranilic acid. J Org Chem 1988;53:1486–1488.
  • Aquilina JA, Carver JA, Truscott RJ. Polypeptide modification and cross-linking by oxidized 3-hydroxykynurenine. Biochemistry 2000;39:16176–16184.
  • Aquilina JA, Carver JA, Truscott RJW. Elucidation of a novel polypeptide cross-link involving 3-hydroxykynurenine. Biochemistry 1999;38:11455–11464.
  • Aquilina JA, Truscott RJ. Cysteine is the initial site of modification of alpha-crystallin by kynurenine. Biochem Biophys Res Commun 2000;276:216–223.
  • Gerken TA. Amino group environments and metal-binding properties of C-13 reductively methylated bovine alpha-lactalbumin. Biochemistry 1984;23:4688–4697.
  • Brunet PCJ. Sclerotins. Endeavour (Eng. Ed.) 1967;26:68–74.
  • Manthey MK. Mechanism and structural elucidation of protein modification by 3-hydroxyanthranilic acid [thesis]. Wollongong, Australia: University of Wollongong; 1990, p. 1–318.
  • Ishii T, Iwahashi H, Sugata R, Kido R. Formation of hydroxanthommatin-derived radical in the oxidation of 3-hydroxykynurenine. Arch Biochem Biophys 1992;294:616–622.
  • Iwahashi H, Ishii T. Detection of the oxidative products of 3-hydroxykynurenine using high-performance liquid chromatography electrochemical detection ultraviolet absorption detection electron spin resonance spectrometry and high-performance liquid chromatography electrochemical detection ultraviolet absorption detection mass spectrometry. J Chromatog A 1997;773:23–31.
  • Christen S, Southwell-Keely PT, Stocker R. Oxidation of 3-hydroxyanthranilic acid to the phenoxazinone cinnabarinic acid by peroxyl radicals and by compound-I of peroxidases or catalase. Biochemistry 1992;31:8090–8097.
  • Ishii T, Iwahashi H, Sugata R, Kido R. Superoxide dismutase enhances the toxicity of 3-hydroxyanthranilic acid to bacteria. Free Radic Res Commun 1991;14:187–194.
  • Truscott RJ, Augusteyn RC. Oxidative changes in human lens proteins during senile nuclear cataract formation. Biochim Biophys Acta 1977;492:43–52.
  • Davies MJ. The oxidative environment and protein damage. Biochim Biophys Acta 2005;1703:93–109.
  • Medinas DB, Gozzo FC, Santos LF, Iglesias AH, Augusto O. A ditryptophan cross-link is responsible for the covalent dimerization of human superoxide dismutase 1 during its bicarbonate-dependent peroxidase activity. Free Radic Biol Med 2010;49:1046–1053.
  • Rzepecki LM, Nagafuchi T, Waite JH. alpha,beta-Dehydro-3,4-dihydroxyphenylalanine derivatives: potential schlerotization intermediates in natural composite materials. Arch Biochem Biophys 1991;285:17–26.
  • Akagawa M, Ishii Y, Ishii T, Shibata T, Yotsu-Yamashita M, Suyama K, Uchida K. Metal-catalyzed oxidation of protein-bound dopamine. Biochemistry 2006;45:15120–15128.
  • McNulty R, Huan W, Mathias RT, Ortwerth BJ, Truscott RJW, Bassnett S. Regulation of tissue oxygen levels in the mammalian lens. J Physiol (Lond.) 2004;559:883–898.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.