165
Views
14
CrossRef citations to date
0
Altmetric
Original Articles

Comparative Covalent Protein Binding of 2,5-Hexanedione and 3-Acetyl-2,5-Hexanedione in the Rat

, &
Pages 861-869 | Received 04 Dec 2008, Accepted 12 Feb 2009, Published online: 22 Jul 2009

REFERENCES

  • Abou-Donia, M. B., 1978. Role of acid phosphatase in delayed neurotoxicity induced by leptophos in hens, Biochem. Pharmacol. 27 (1978), pp. 2055–2058.
  • Alexander, R. S., and Butler, A. R., 1976. Electrophilic substitution in pyrroles. Part 1. Reaction with 4-dimethylaminobenzaldehyde (Ehrlich's reagent) in acid solution, J. Chem. Soc. Perkin Trans. II (1976), pp. 696–701.
  • Amarnath, V., Valentine, W. M., Amarnath, K., Eng, M. A., and Graham, D. G., 1994. The mechanism of nucleophilic substitution of alkylpyrroles in the presence of oxygen, Chem. Res. Toxicol. 7 (1994), pp. 56–61.
  • Anthony, D. C., Boekelheide, K., Anderson, C. W., and Graham, D. G., 1983. 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 (1983), pp. 372–382.
  • Boya, M., Marquet, J., Moreno-Mañas, M., and Prior, M., 1979. Metal complexes in organic synthesis. III. Preparation of 3-alkylpentane-2,4-diones by alkylation of nickel bis-pentane-2,4-dionato with alkyl halides, Anal. Quim. 75 (1979), pp. 920–926.
  • Chiu, F.-C., and Norton, W. T., 1982. Bulk preparation of CNS cytoskeleton and the separation of individual neurofilament by gel filtration: Dye-binding characteristics and amino acid compositions, J. Neurochem. 39 (1982), pp. 1252–1260.
  • DeCaprio, A. P., 1986. Mechanisms of in vitro pyrrole adduct autoxidation in 2,5-hexanedione-treated protein, Mol. Pharmacol. 30 (1986), pp. 452–458.
  • DeCaprio, A. P., 2000. "n-Hexane, metabolites, and derivatives". In: Spencer, P. S., Schaumburg, H. H., and Ludolph, A. C., eds. Experimental and Clinical Neurotoxicology. New York: Oxford University Press; 2000. pp. 633–648.
  • DeCaprio, A. P., Briggs, R. G., Jackowski, S. J., and Kim, J. C. S., 1988. Comparative neurotoxicity and pyrrole-forming potential of 2,5-hexanedione and perdeuterio-2,5-hexanedione in the rat, Toxicol. Appl. Pharmacol. 92 (1988), pp. 75–85, .
  • DeCaprio, A. P., and Fowke, J. H., 1992. Limited and selective adduction of carboxyl-terminal lysines in the high molecular weight neurofilament proteins by 2,5-hexanedione in vitro, Brain Res. 586 (1992), pp. 219–228.
  • DeCaprio, A. P., Jackowski, S. J., and Regan, K. A., 1987. Mechanism of formation and quantitation of imines, pyrroles, and stable nonpyrrole adducts in 2,5-hexanedione-treated protein, Mol. Pharmacol. 32 (1987), pp. 542–548.
  • DeCaprio, A. P., Kinney, E. A., and Fowke, J. H., 1997. Regioselective binding of 2,5-hexanedione to high-molecular-weight rat neurofilament proteins in vitro, Toxicol. Appl. Pharmacol. 145 (1997), pp. 211–217.
  • 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 (1985), pp. 235–247.
  • 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 derivatives by 2,5-hexanedione, Toxicol. Appl. Pharmacol. 65 (1982), pp. 440–450.
  • Derelanko, M. J., 1987. Determination of erythrocyte life span in F-344, Wistar, and Sprague-Dawley rats using a modification of the [3H]diisopropylfluorophosphate ([3H]DFP) method, Toxicol. Sci. 9 (1987), pp. 271–276.
  • deSousa, B. N, and Horrocks, L. P., 1979. Development of rat spinal cord. I. Weight and length with a method for rapid removal, Dev. Neurosci. 2 (1979), pp. 115–121.
  • Fedtke, N., and Bolt, H. M., 1987. 4,5-Dihydroxy-2-hexanone: A new metabolite of n-hexane and of 2,5-hexanedione in rat urine, Biomed. Environ. Mass Spectrom. 14 (1987), pp. 563–572.
  • Fletcher, H., 1966. 1,3,4,7-Substituted isoindoles and isoindolenines, Tetrahedron 22 (1966), pp. 2481–2486.
  • Gardini, G. P., 1973. The oxidation of monocyclic pyrroles, Adv. Heterocyclic Chem. 15 (1973), pp. 67–98.
  • Genter St.Clair, M. B., Amarnath, V., Moody, M. A., Anthony, D. C., Anderson, C. W., and Graham, D. G., 1988. Pyrrole oxidation and protein cross-linking as necessary steps in the development of γ-diketone neuropathy, Chem. Res. Toxicol. 1 (1988), pp. 179–185.
  • Genter, M. B., Szakál-Quin, G., Anderson, W., Anthony, D. C., and Graham, D. G., 1986. Evidence that pyrrole formation is a pathogenetic step in γ-diketone neuropathy, Toxicol. Appl. Pharmacol. 87 (1986), pp. 351–362.
  • Graham, D. G., Anthony, D. C., Boekelheide, K., Maschmann, N. A., Richards, R. G., Wolfram, J. W., and Shaw, B. R., 1982. Studies of the molecular pathogenesis of hexane neuropathy. II. Evidence that pyrrole derivatization of lysyl residues leads to protein crosslinking, Toxicol. Appl. Pharmacol. 64 (1982), pp. 415–422.
  • Graham, D. G., Genter St.Clair, M. B., Amarnath, V., and Anthony, D. C., 1991. Molecular mechanisms of γ-diketone neuropathy, Adv. Exp. Med. Biol. 283 (1991), pp. 427–431.
  • Helfand, B. T., Chang, L., and Goldman, R. D., 2003. The dynamic and motile properties of intermediate filaments, Ann. Rev. Cell Dev. Biol. 19 (2003), pp. 445–467.
  • Krasavage, W. J., O'Donoghue, J. L., DiVincenzo, G. D., and Terhaar, C. J., 1980. The relative neurotoxicity of methyl-n-butyl ketone, n-hexane and their metabolites, Toxicol. Appl. Pharmacol. 52 (1980), pp. 433–441.
  • Lehning, E. J., Jortner, B. S., Fox, J. H., Arezzo, J. C., Kitano, T.-A., and LoPachin, R. M., 2000. γ-Diketone peripheral neuropathy I. Quantitative morphometric analyses of axonal atrophy and swelling, Toxicol. Appl. Pharmacol. 165 (2000), pp. 127–140.
  • LoPachin, R. M., and DeCaprio, A. P., 2004. γ-Diketone neuropathy: Axon atrophy and the role of cytoskeletal protein adduction, Toxicol. Appl. Pharmacol. 199 (2004), pp. 20–34.
  • LoPachin, R. M., and DeCaprio, A. P., 2005. Protein adduct formation as a molecular mechanism in neurotoxicity, Toxicol. Sci. 86 (2005), pp. 214–225.
  • LoPachin, R. M., He, D., and Reid, M. L., 2005. 2,5-Hexanedione-induced changes in the neurofilament subunit pools of rat peripheral nerve, NeuroToxicology 26 (2005), pp. 229–240.
  • LoPachin, R. M., He, D., Reid, M. L., and Opanashuk, L. A., 2004. 2,5-Hexanedione-induced changes in the monomeric neurofilament protein content of rat spinal cord fractions, Toxicol. Appl. Pharmacol. 198 (2004), pp. 61–73.
  • LoPachin, R. M., Jortner, B. S., Reid, M. L., and Das, S., 2003. γ-Diketone central neuropathy: Quantitative morphometric analysis of axons in rat spinal cord white matter regions and nerve roots, Toxicol. Appl. Pharmacol. 193 (2003), pp. 29–46.
  • LoPachin, R. M., Ross, J. F., Reid, M. L., Das, S., Mansukhani, S., and Lehning, E. J., 2002. Neurological evaluation of toxic axonopathies in rats: Acrylamide and 2,5-hexanedione, NeuroToxicology 23 (2002), pp. 95–110.
  • Monaco, S., Wongmongkolrit, T., Shearson, C. M., Patton, A., Schaetzle, B., Autilio-Gambetti, L., Gambetti, P., and Sayre, L. M., 1990. Giant axonopathy characterized by intermediate location of axonal enlargements and acceleration of neurofilament transport, Brain Res. 519 (1990), pp. 73–81.
  • Pyle, S. J., Amarnath, V., Graham, D. G., and Anthony, D. C., 1992. The role of pyrrole formation in the alteration of neurofilament transport induced during exposure to 2,5-hexanedione, J. Neuropathol. Exp. Neurol. 51 (1992), pp. 451–458.
  • Rosenberg, C. K., Genter, M. B., Szakal-Quin, G., Anthony, D. C., and Graham, D. G., 1986. dl- Versus meso-3,4-Dimethyl-2,5-hexanedione: A morphometric study of the proximo-distal distribution of axonal swellings in the anterior root of the rat, Toxicol. Appl. Pharmacol. 87 (1986), pp. 363–373.
  • Shea, T. B., Jung, C., Yabe, J., Ma, D., and Fischer, I., 1998. "Extensive phosphorylation and axonal transport of triton-soluble neurofilament subunits". In: Herrmann, H. D., and Harris, R. A., eds. Sub-cellular Biochemistry. Vol. 31. New York: Plenum Press; 1998. pp. 527–561, Intermediate Filaments.
  • Spencer, P. S., Bischoff, M. C., and Schaumburg, H. H., 1978. On the specific molecular configuration of neurotoxic aliphatic hexacarbon compounds causing central-peripheral distal axonopathy, Toxicol. App. Pharmacol. 44 (1978), pp. 17–28.
  • Spencer, P. S., Schaumburg, H. H., Sabri, M. I., and Veronesi, B., 1980. The enlarging view of hexacarbon neurotoxicity, CRC Crit. Rev. Toxicol. 7 (1980), pp. 279–356.
  • Stone, J. D., Peterson, A. P., Eyer, J., Oblak, T. G., and Sickles, D. W., 1999. Axonal neurofilaments are nonessential elements of toxicant-induced reductions in fast axonal transport: Video-enhanced differential interference microscopy in peripheral nervous system axons, Toxicol. Appl. Pharmacol. 161 (1999), pp. 50–58.
  • Stone, J. D., Peterson, A. P., Eyer, J., Oblak, T. G., and Sickles, D. W., 2001. Neurofilaments are nonessential to the pathogenesis of toxicant-induced axonal degeneration, J. Neurosci. 21 (2001), pp. 2278–2287.
  • Stone, J. D., Peterson, A. P., Eyer, J., and Sickles, D. W., 2000. Neurofilaments are non-essential elements of toxicant-induced reductions in fast axonal transport: Pulse labeling in CNS neurons, NeuroToxicology 21 (2000), pp. 447–457.
  • Wang, Q. S., Hou, L. Y., Zhang, C. L., Song, F. Y., and Xie, K. Q., 2008. Changes of cytoskeletal proteins in nerve tissues and serum of rats treated with 2,5-hexanedione, Toxicology 244 (2008), pp. 166–178.
  • Xu, G. Z., Singh, M. P., Gopal, D., and Sayre, L. M., 2001. Novel 2,5-hexanedione analogues. Substituent-induced control of the protein cross-linking potential and oxidation susceptibility of the resulting primary amine-derived pyrroles, Chem. Res. Toxicol. 14 (2001), pp. 264–274.
  • Yu, R. C., Hattis, D., Landaw, E. M., and Froines, J. R., 2002. Toxicokinetic interaction of 2,5-hexanedione and methyl ethyl ketone, Arch. Toxicol. 75 (2002), pp. 643–652.
  • Zhu, M., Spink, D. C., Yan, B., Bank, S., and DeCaprio, A. P., 1994. Formation and structure of crosslinking and monomeric pyrrole autoxidation products in 2,5-hexanedione-treated amino acids, peptides, and protein, Chem. Res. Toxicol. 7 (1994), pp. 551–558.
  • Zhu, M., Spink, D. C., Yan, B., Bank, S., and DeCaprio, A. P., 1995. Inhibition of 2,5-hexanedione-induced covalent protein crosslinking by biological thiols: Chemical mechanisms and toxicological implications, Chem. Res. Toxicol. 8 (1995), pp. 764–771.

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.