Pyrrole Oxidation and Protein Cross-Linking as Necessary Steps in the Development of γ-Diketone Neuropathy

Chemical Research in Toxicology

Volumn 1, Issue 3, 1988, Pages 179-185

  Clair, M B Genter ^a   Amarnath, V ^a   Moody, M Anthony ^a   Anthony, Douglas C ^a   Anderson, C William ^b   Graham, Doyle G ^a  

^a DUKE UNIVERSITY MEDICAL CENTER   (United States)

^b HAMPDEN SYDNEY COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIKETONE; ACETONYLACETONE; HEXANE; PYRROLE;

3,4 DIMETHYL 2,5 HEXANEDIONE; ANIMAL EXPERIMENT; MALE; NEUROPATHY; NEUROTOXICITY; NONHUMAN; PROTEIN CROSS LINKING; RAT;

ANIMAL; CROSS-LINKING REAGENTS; HEMOGLOBINS; HEXANONES; KINETICS; MALE; NEUROTOXINS; PYRROLES; RATS; RATS, INBRED STRAINS; SPECTRIN; SPINAL CORD; SPINAL NERVE ROOTS; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0023887103     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx00003a009     Document Type: Article

References (45)

1. Yamamura, Y. (1969) “n-Hexane polyneuropathy”. Folia Psychiat. Neurol. Jpn. 23, 45–47.
2. Herskowitz, A., Ishii, N., and Schaumburg, H. (1971) “n-Hexane neuropathy”. N. Engl. J. Med. 285, 82–85.
3. Goto, I., Matsumura, M. Inoue, N., Murai, Y., Shida, K., Santa, T., and Kuroiwa, Y. (1974) “Toxic polyneuropathy due to glue sniffing”. J. Neurol. Neurosurg. Psychiatry 37, 848–853.
4. Korobkin, R., Asbury, A. K., Summer, A. J., Nielsen, S. L. (1975) “Glue-sniffing neuropathy”. Arch. Neurol. 32, 158–162.
5. Billmaier, D., Yee, H. T., Allen, N., Craft, B., Williams, N., Epstein, S., and Fontaine, R. (1974) “Peripheral neuropathy in a coated fabrics plant”. J. Occup. Med. 16, 665–671.
6. Krasavage, W. J., O'Donoghue, J. L., DiVincenzo, G. D., and Tehaar, C. J. (1980) “The relative neurotoxicity of methyl n-butyl ketone, n-hexane and their metabolites”. Toxicol. Appl. Pharmacol 562, 443–444.
7. Sabri, M. I., Ederle, K., Holdsworth, C. H., and Spencer, P. S. (1979 a) “Studies on the biochemical basis of distal axonopathies II Specific inhibition of fructose-6-phosphate kinase by 2,5-hexanedione and methyl n-butyl ketone”. Neurotoxicology 1, 285–297.
8. Sabri, M. I., Moore, C. L. and Spencer, P. S. (1979 b) “Studies on the biochemical basis of distal axonopathies I Inhibition of glycolysis by neurotoxic hexacarbon compounds”. J. Neurochem. 32, 683–689.
9. Spencer, P. S., Sabri, M I and Moore, C. L. (1979) “Does a defect of energy metabolism in the nerve fiber underlie axonal degeneration in polyneuropathies?” Ann. Neurol. 5, 683–689.
10. DeCaprio, A. P., Olajos, E. J., and Weber, P. (1982) “Covalent binding of a neurotoxic n-hexane metabolite: conversion of primary amines to substituted pyrrole adducts by 2,5-hexanedione”. Toxicol. Appl. Pharmacol. 65, 440–450.
11. DeCaprio, A. P., Strominger, N. L., and Weber, P. (1983) “Neurotoxicity and protein binding of 2,5-hexanedione in the hen”. Toxicol. Appl. Pharmacol. 68, 297–307.
12. Graham, D. G., Anthony, D. C., Boekelheide, K., Maschmann, N. A., Richards, R. G., Wolfram, J. W., and Shaw, B. R. (1982 b) “Studies of the molecular pathogenesis of hexane neuropathy II Evidence that pyrrole derivatization of lysyl residues leads to protein crosslinking”. Toxicol. Appl. Pharmacol. 64, 415–422.
13. Anthony, D. C., Boekelheide, K., Anderson, C. W., and Graham, D. G. (1983 a) “The effect of 3,4-dimethyl substitution on the neurotoxicity of 2,5-hexanedione II Dimethyl substitution accelerates pyrrole formation and protein crosslinking”. Toxicol. Appl. Pharmacol. 71, 372–382.
14. Anthony, D. C., Boekelheide, K., and Graham, D. G. (1983 b) “The effect of 3,4-dimethyl substitution on the neurotoxicity of 2,5-hexanedione I Accelerated clinical neuropathy is accompanied by more proximal axonal swellings”. Toxicol. Appl. Pharmacol 71, 362–371.
15. Anthony, D. C., Giangaspero, F., and Graham, D. G. (1983 c) “The spatio-temporal pattern of the axonopathy associated with the neurotoxicity of 3,4-dimethyl-2,5-hexanedione in the rat”. J. Neuropathol. Exp. Neurol. 42, 548–560.
16. Szakal-Quin, G., Graham, D. G., Millington, D. S., Maltby, D. A. and McPhail, A. T. (1986) “Stereoisomer effects on the Paal-Knorr synthesis of pyrroles”. J. Org. Chem. 51, 621–624.
17. Genter, M. B., Szakal-Quin, G., Anderson, C. W., Anthony, D. C. and Graham, D. G. (1987) “Evidence that pyrrole formation is a pathogenetic step in γ-diketone neuropathy”. Toxicol. Appl. Pharmacol. 87, 351–362.
18. Sayre, L. M., Shearson, C. M., Wongmongkolrit, T., Medori, R., and Gambetti, P. (1986) “Structural basis of γ-diketone neurotoxicity: non-neurotoxicity of 3,3-dimethyl-2,5-hexanedione, a γ-diketone incapable of pyrrole formation”. Toxicol. Appl. Pharmacol. 84, 36–44.
19. Carden, M. J., Lee, V.M.-Y., and Schlaepfer, W. W. (1986) “2,5-Hexanedione neuropathy is associated with the covalent crosslinking of neurofilament proteins”. Neurochem. Pathol. 5, 25–35.
20. Lapadula, D. M., Irwin, R., Suwita, E., and Abou-Donia, M. B. (1986) “Cross-linking of neurofilament proteins of rat spinal cord in vivo after administration of 2,5-hexanedione”. J. Neurochem. 46, 1843–1850.
21. Graham, D. G., Anthony, D. C., and Boekelheide, K. (1982 a) “In vitro and in vivo studies of the molecular pathogenesis of n-hexane neuropathy”. Neurobehav. Toxicol. Teratol. 4, 629–634.
22. Graham, D. G., Szakal-Quin, G., Priest, J. W., and Anthony, D. C. (1984) “In vitro evidence that covalent crosslinking of neurofilaments occurs in γ-diketone neuropathy”. Proc. Natl. Acad. Sci. U.S.A. 81, 4979–4982.
23. Graham, D. G., Szakal-Quin, G., Milam, L., Gottfried, M. R., and Anthony, D. C. (1986) “Pathogenetic studies of the neurofilamentous neuropathies”. In The Cytoskeleton (Clarkson, T. W., Sagar, P. R., and Syversen, T. L. M., Eds.) pp 167–174. Plenum, New York.
24. Rosenberg, C. K., Anthony, D. C., Szakal-Quin, G., Genter, M. B. and Graham, D. G. (1987) “Hyperbaric oxygen accelerates the neurotoxicity of 2,5-hexanedione”. Toxicol. Appl. Pharmacol. 87, 374–379.
25. DeCaprio, A. P. and O'Neill, E. A. (1985) “Alterations in rat axonal cytoskeletal proteins induced by in vitro and in vivo 2,5-hexanedione exposure”. Toxicol. Appl. Pharmacol. 78, 235–247.
26. DeCaprio, A. P. (1985 Molecular mechanisms of diketone neurotoxicity Chem.-Biol. Interactions 54, 257–270
27. Sayre, L. M., Autilio-Gambetti, L., and Gambetti, P. (1985) “Pathogenesis of experimental giant neurofilamentous axonopathies: a unified hypothesis based on chemical modification of neurofilaments”. Brain Res. Rev. 10, 69–83.
28. Boya, M., Marquet, J., Moreno-Manas, M., and Prior, M. (1979) “Metal complexes in organic synthesis. III. Preparation of 3-al-kylpentane-2,4-diones by alkylation of nickel bis-pentane-2,4-dionate with alkyl halides”. An. Quim. 75, 920–926.
29. Fairbanks, G., Steck, T. L., and Wallach, D. F. H. (1971) “Electrophoretic analysis of the major polypeptides of the human erythrocyte membrane”. Biochemistry 10, 2606–2617.
30. Hanahan, D. J., and Ekholm, J. E. (1974) “The preparation of red cell ghosts (membranes)”. In Methods in Enzymology (Colowick, S. R., and Kaplan, N. O., Eds.) Vol. 31, pp 168–172, Academic, New York.
31. Garrick, L., Sharma, V. S., McDonald, M. J., and Ranney, H. M. (1975) “Rat haemoglobin heterogeneity. Two structurally distinct a-chains and functional behavior of selected components”. Biochem. J. 149, 245–258.
32. f-measurement, and optimized procedure”. Anal. Biochem. 78, 459–482.
33. Boekelheide, K. (1987) “2,5-Hexanedione alters microtubule assembly II Enhanced polymerization of crosslinked tubulin”. Toxicol. Appl. Pharmacol. 88, 383–396.
34. Bradford, M. M. (1976) “A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein binding”. Anal. Biochem. 72, 248–254.
35. Hunkapiller, M. W., Lujan, E., Ostrander, F. and Hood, L. E. (1983) “Isolation of microgram quantities of proteins from polyacrylamide gels for amino acid sequence analysis”. In Methods in Enzymology (Hirs, C. H. W., and Timasheff, S. N., Eds.) Vol. 91, pp 227–236, Academic, New York.
36. Rosenberg, C. K., Genter, M. B., Szakal-Quin, G., Anthony, D. C., and Graham, D. G. (1987 b) “d,l versus meso 3,4-dimethyl-2,5-hexanedione: a morphometric study of the proximodistal and temporal distribution of axonal swellings in the anterior root of the rat”. Toxicol. Appl. Pharmacol. 87, 363–373.
37. Berthold, C.-H. (1978) “Morphology of normal peripheral axons”. In Physiology and Pathobiology of Axons (Waxman, S. G., Ed.) pp 3–63, Raven, New York.
38. Hoffman, P. N., Cleveland, D. W., Griffin, J. W., Landes, P. W., Cowan, N. J., and Price, D. L. (1986) “Neurofilament gene expression: a major determinant of axonal caliber”. Proc. Natl. Acad. Sci. U.S.A. 84, 3472–3476.
39. Carpenter, S., Karpati, G., Andermann, F., and Gold, R. (1974) “Giant axonal neuropathy. A clinically and morphologically distinct neurological disease”. Arch. Neurol. 31, 312–316.
40. Gottfried, M. R., Graham, D. G., Morgan, M., Casey, H. W., and Bus, J. S. (1985) “The morphology of carbon disulfide neurotoxicity”. NeuroToxicology 6, 89–96.
41. Rowland, L. P. (1984) “Motor neuron disease and amyotrophic lateral sclerosis”. Trends Neurosci. 7, 110–112.
42. Graham, D. G., and Abou-Donia, M. B. (1980) “Studies of the molecular pathogenesis of hexane neuropathy I Evaluation of the inhibition of glyceraldehyde-3-phosphate dehydrogenase by 2,5-hexanedione”. J. Toxicol. Environ. Health 6, 621–631.
43. Spencer, P. S., and Schaumburg, H. H. (1977) “Ultrastructural studies of the dying back process. III. The evolution of experimental peripheral axonal degeneration”. J. Neuropathol. Exp. Neurol. 36, 276–299.
44. Jones, R. A., and Bean, G. P. (1977) “The chemistry of pyrroles”. In Organic Chemistry (Blomquist, A. T., and Wasserman, H. H., Eds.) Vol. 34, pp 209–247, Academic, New York.
45. Jones, R. A. (1984) “Pyrroles and their benzo derivatives: (ii) reactivity”. In Comprehensive Heterocyclic Chemistry (Katritzky, A. R., and Rees, C. W., Eds.) Vol. 4, pp 201–315, Pergamon, Oxford.