Literature DB >> 16742502

Possible reactions of 1,2-naphthaquinone in the eye.

J R Rees1, A Pirie.   

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 alpha-crystallin and 1,2-naphthaquinone is soluble at neutrality, but the compounds of beta-crystallins and of gamma-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.

Entities:  

Year:  1967        PMID: 16742502      PMCID: PMC1270336     

Source DB:  PubMed          Journal:  Biochem J        ISSN: 0264-6021            Impact factor:   3.857


  15 in total

1.  AMINO ACID TRANSPORT IN THE LENS.

Authors:  V E KINSEY
Journal:  Invest Ophthalmol       Date:  1965-08

2.  Neutral proteinases in the lens.

Authors:  S G WALEY; R VAN HEYNINGEN
Journal:  Biochem J       Date:  1962-05       Impact factor: 3.857

3.  Studies on gamma-crystallin from calf lens. I. Isolation by gel filtration.

Authors:  I BJORK
Journal:  Exp Eye Res       Date:  1961-12       Impact factor: 3.467

4.  Biochemical studies of toxic agents. 11. The occurrence of premercapturic acids.

Authors:  R H KNIGHT; L YOUNG
Journal:  Biochem J       Date:  1958-09       Impact factor: 3.857

5.  [Simplification and improvement in the method for the quantitative determination of amino acids and peptides by means of ninhydrin-copper complexes].

Authors:  F BODE
Journal:  Biochem Z       Date:  1955

6.  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.

Authors:  J Booth; E Boyland; T Sato; P Sims
Journal:  Biochem J       Date:  1960-10       Impact factor: 3.857

7.  THE NATURE OF THE OCULAR LESIONS PRODUCED EXPERIMENTALLY BY NAPHTHALENE.

Authors:  D R Adams
Journal:  Br J Ophthalmol       Date:  1930-02       Impact factor: 4.638

8.  Separation of the soluble proteins of bovine lenses on polacrylamide gels.

Authors:  M Testa; G Armand; E A Balazs
Journal:  Exp Eye Res       Date:  1965-12       Impact factor: 3.467

9.  The metabolism of naphthalene and its toxic effect on the eye.

Authors:  R Van Heyningen; A Pirie
Journal:  Biochem J       Date:  1967-03       Impact factor: 3.857

10.  GLUTATHIONE PEROXIDASE IN LENS AND A SOURCE OF HYDROGEN PEROXIDE IN AQUEOUS HUMOUR.

Authors:  A PIRIE
Journal:  Biochem J       Date:  1965-07       Impact factor: 3.857

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  10 in total

1.  Distribution and characterization of dihydrodiol dehydrogenases in mammalian ocular tissues.

Authors:  A Hara; T Nakayama; T Harada; T Kanazu; M Shinoda; Y Deyashiki; H Sawada
Journal:  Biochem J       Date:  1991-04-01       Impact factor: 3.857

2.  Inhibition of dimeric dihydrodiol dehydrogenases of rabbit and pig lens by ascorbic acid.

Authors:  A Hara; M Shinoda; T Kanazu; T Nakayama; Y Deyashiki; H Sawada
Journal:  Biochem J       Date:  1991-04-01       Impact factor: 3.857

3.  The metabolism of naphthalene and its toxic effect on the eye.

Authors:  R Van Heyningen; A Pirie
Journal:  Biochem J       Date:  1967-03       Impact factor: 3.857

4.  Identification of quinoide redox mediators that are formed during the degradation of naphthalene-2-sulfonate by Sphingomonas xenophaga BN6.

Authors:  Andreas Keck; Jörg Rau; Thorsten Reemtsma; Ralf Mattes; Andreas Stolz; Joachim Klein
Journal:  Appl Environ Microbiol       Date:  2002-09       Impact factor: 4.792

5.  o-Quinones formed in plant extracts. Their reactions with amino acids and peptides.

Authors:  W S Pierpoint
Journal:  Biochem J       Date:  1969-05       Impact factor: 3.857

6.  Isolation from pig lens of two proteins with dihydrodiol dehydrogenase and aldehyde reductase activities.

Authors:  A Hara; T Harada; M Nakagawa; K Matsuura; T Nakayama; H Sawada
Journal:  Biochem J       Date:  1989-12-01       Impact factor: 3.857

7.  Cataract produced by tyrosinase and tyrosine systems in rabbitens in vitro.

Authors:  S K Srivastava; E Beutler
Journal:  Biochem J       Date:  1969-05       Impact factor: 3.857

8.  Reaction of tyrosine oxidation products with proteins of the lens.

Authors:  A Pirie
Journal:  Biochem J       Date:  1968-09       Impact factor: 3.857

Review 9.  Genetic differences in drug metabolism associated with ocular toxicity.

Authors:  H Shichi; D W Nebert
Journal:  Environ Health Perspect       Date:  1982-04       Impact factor: 9.031

10.  Selective toxicity of 1-naphthol to human colorectal tumour tissue.

Authors:  G D Wilson; M d'Arcy Doherty; G M Cohen
Journal:  Br J Cancer       Date:  1985-06       Impact factor: 7.640

  10 in total

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