Skip to main content
PMC home page
Biochemical Journal logoLink to Biochemical Journal
. 1967 Mar;102(3):853–863.

Possible reactions of 1,2-naphthaquinone in the eye

Jancis R Rees 1, Antoinette Pirie 1
PMCID: PMC1270336  PMID: 16742502

Abstract

1. Reactions of 1,2-naphthaquinone with amino acids, glutathione and proteins of the lens have been studied in connexion with investigations of naphthalene-induced cataract. 2. Cysteine reacts probably through its amino group with 1,2-naphthaquinone to form either purple or brown compounds with characteristic absorption spectra. 3. Glutathione reacts with 1,2-naphthaquinone through its thiol group. 4. Spectroscopic evidence suggests that 1,2-naphthaquinone reacts with the amino group of amino acids. This reaction may take place in the aqueous humour. 5. The proteins of lens react with 1,2-naphthaquinone to form brown compounds. 6. There is loss of protein thiol in this reaction and the products are less easily digestible by pancreatin than normal lens proteins. 7. The compound of α-crystallin and 1,2-naphthaquinone is soluble at neutrality, but the compounds of β-crystallins and of γ-crystallins are largely insoluble. 8. The brown reaction products of glutathione or cysteine with 1,2-naphthaquinone catalyse the oxidation of ascorbic acid in the same way as 1,2-naphthaquinone itself. 9. These results are discussed in relation to naphthalene-induced cataract.

Full text

PDF
854

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Adams D. R. THE NATURE OF THE OCULAR LESIONS PRODUCED EXPERIMENTALLY BY NAPHTHALENE. Br J Ophthalmol. 1930 Feb;14(2):49–60. doi: 10.1136/bjo.14.2.49. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. BJORK I. Studies on gamma-crystallin from calf lens. I. Isolation by gel filtration. Exp Eye Res. 1961 Dec;1:145–154. doi: 10.1016/s0014-4835(61)80020-1. [DOI] [PubMed] [Google Scholar]
  3. BODE F. Eine Vereinfachung und Verbesserung der Methode zur quantitativen Bestimmung von Aminosäuren und Peptiden mittels des Ninhydrin-Kupferkomplexes. Biochem Z. 1955;326(6):433–435. [PubMed] [Google Scholar]
  4. Booth J., Boyland E., Sato T., Sims P. Metabolism of polycyclic compounds. 17. The reaction of 1:2-dihydronaphthalene and 1:2-epoxy-1:2:3:4-tetrahydronaphthalene with glutathione catalysed by tissue preparations. Biochem J. 1960 Oct;77(1):182–186. doi: 10.1042/bj0770182. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. CALAM D. H. Some new compounds in the lens. Exp Eye Res. 1962 Jun;1:436–442. doi: 10.1016/s0014-4835(62)80035-9. [DOI] [PubMed] [Google Scholar]
  6. GRASSMANN W., HANNIG K., PLOCKL M. Eine Methode zur quantitativen Bestimmung der Aminosäurezusammensetzung von Eiweisshydrolysaten durch Kombination von Elektrophorese und Chromatographie. Hoppe Seylers Z Physiol Chem. 1955;299(5-6):258–276. [PubMed] [Google Scholar]
  7. KINSEY V. E. AMINO ACID TRANSPORT IN THE LENS. Invest Ophthalmol. 1965 Aug;4:691–699. [PubMed] [Google Scholar]
  8. KNIGHT R. H., YOUNG L. Biochemical studies of toxic agents. 11. The occurrence of premercapturic acids. Biochem J. 1958 Sep;70(1):111–119. doi: 10.1042/bj0700111. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Markham R. A steam distillation apparatus suitable for micro-Kjeldahl analysis. Biochem J. 1942 Dec;36(10-12):790–791. doi: 10.1042/bj0360790. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. PIRIE A. GLUTATHIONE PEROXIDASE IN LENS AND A SOURCE OF HYDROGEN PEROXIDE IN AQUEOUS HUMOUR. Biochem J. 1965 Jul;96:244–253. doi: 10.1042/bj0960244. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Testa M., Armand G., Balazs E. A. Separation of the soluble proteins of bovine lenses on polacrylamide gels. Exp Eye Res. 1965 Dec;4(4):327–339. doi: 10.1016/s0014-4835(65)80048-3. [DOI] [PubMed] [Google Scholar]
  12. Van Heyningen R., Pirie A. The metabolism of naphthalene and its toxic effect on the eye. Biochem J. 1967 Mar;102(3):842–852. doi: 10.1042/bj1020842. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. WALEY S. G., VAN HEYNINGEN R. Neutral proteinases in the lens. Biochem J. 1962 May;83:274–283. doi: 10.1042/bj0830274. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. WIGGINS L. F., WILLIAMS J. H. Use of n-butanol-formic acid-water mixture in the paper chromatography of amino-acids and sugars. Nature. 1952 Aug 16;170(4320):279–280. doi: 10.1038/170279a0. [DOI] [PubMed] [Google Scholar]
  15. Waley S. G. Structural studies of alpha-crystallin. Biochem J. 1965 Sep;96(3):722–728. doi: 10.1042/bj0960722. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES