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Volumn 95, Issue 1, 2007, Pages 136-146

Structure-toxicity analysis of Type-2 Alkenes: In vitro neurotoxicity

Author keywords

Acrolein; Acrylamide; Adduct formation; Distal axonopathy; Neurodegeneration; Synapse

Indexed keywords

ACROLEIN; ACRYLAMIDE; ALDEHYDE DERIVATIVE; ALKENE; HYDRALAZINE; KETONE DERIVATIVE; NETHYLMALEIMIDE; NETHYLMALEIMIDE SENSITIVE FACTOR; NEUROTRANSMITTER; SYNAPTOBREVIN; SYNAPTOPHYSIN; SYNAPTOSOMAL ASSOCIATED PROTEIN 25; THIOL GROUP;

EID: 33845606362     PISSN: 10966080     EISSN: 10960929     Source Type: Journal    
DOI: 10.1093/toxsci/kfl127     Document Type: Article
Times cited : (72)

References (44)
  • 1
    • 8444241129 scopus 로고    scopus 로고
    • Proteomic analysis of acrylamideprotein adduct formation in rat brain synaptosomes
    • Barber, D. S., and LoPachin, R. M. (2004). Proteomic analysis of acrylamideprotein adduct formation in rat brain synaptosomes. Toxicol. Appl. Pharmacol. 201, 120-136.
    • (2004) Toxicol. Appl. Pharmacol. , vol.201 , pp. 120-136
    • Barber, D.S.1    LoPachin, R.M.2
  • 3
    • 0027302114 scopus 로고
    • Synergistic neurotoxic effects of styrene oxide and acrylamide: Glutathione-independent necrosis of cerebellar granule cells
    • Beiswanger, C. M., Mandella, R. D., Graessle, T. R., Reuhl, K. R., and Lowndes, H. E. (1993). Synergistic neurotoxic effects of styrene oxide and acrylamide: Glutathione-independent necrosis of cerebellar granule cells. Toxicol. Appl. Pharmacol. 118, 233-244.
    • (1993) Toxicol. Appl. Pharmacol. , vol.118 , pp. 233-244
    • Beiswanger, C.M.1    Mandella, R.D.2    Graessle, T.R.3    Reuhl, K.R.4    Lowndes, H.E.5
  • 4
    • 0041386256 scopus 로고    scopus 로고
    • Modulation of benzo[a]pyrene-induced p53 activity by acrolein
    • Biswal, S., Maxwell, T., Rangasamy, T., and Kehrer, J. P. (2003). Modulation of benzo[a]pyrene-induced p53 activity by acrolein. Carcinogenesis 24, 1401-1406.
    • (2003) Carcinogenesis , vol.24 , pp. 1401-1406
    • Biswal, S.1    Maxwell, T.2    Rangasamy, T.3    Kehrer, J.P.4
  • 5
    • 0034121606 scopus 로고    scopus 로고
    • Probing acrylamide alkylation sites in cysteine-free proteins by matrix-assisted laser desorption/ionisation time-of-flight
    • Bordini, E., Hamdan, M., and Righette, P. G. (2000). Probing acrylamide alkylation sites in cysteine-free proteins by matrix-assisted laser desorption/ionisation time-of-flight. Rapid Commun. Mass Spectrom. 14, 840-848.
    • (2000) Rapid Commun. Mass Spectrom. , vol.14 , pp. 840-848
    • Bordini, E.1    Hamdan, M.2    Righette, P.G.3
  • 6
    • 0029903973 scopus 로고    scopus 로고
    • The metabolism and pharmacokinetics of acrylamide: Implications for mechanisms of toxicity and human risk estimation
    • Calleman, C. J. (1996). The metabolism and pharmacokinetics of acrylamide: Implications for mechanisms of toxicity and human risk estimation. Drug Metab. Rev. 28, 527-590.
    • (1996) Drug Metab. Rev. , vol.28 , pp. 527-590
    • Calleman, C.J.1
  • 7
    • 0345276572 scopus 로고    scopus 로고
    • Synaptic slaughter in Alzheimer's disease
    • Coleman, P. D., and Yao, P. J. (2003). Synaptic slaughter in Alzheimer's disease. Neurobiol. Aging 24, 1023-1027.
    • (2003) Neurobiol. Aging , vol.24 , pp. 1023-1027
    • Coleman, P.D.1    Yao, P.J.2
  • 8
    • 0021610533 scopus 로고
    • Effects of modifying structure on electrophilic reactions with biological nucleophiles
    • Coles, B. (1984-1985). Effects of modifying structure on electrophilic reactions with biological nucleophiles. Drug Metab. Rev. 15, 1307-1334.
    • (1984) Drug Metab. Rev. , vol.15 , pp. 1307-1334
    • Coles, B.1
  • 9
    • 0021720049 scopus 로고
    • Interaction of acrylamide with glutathione in rat erythrocytes
    • Dixit, R., Das, M., Seth, P. K., and Mukhtar, H. (1984). Interaction of acrylamide with glutathione in rat erythrocytes. Toxicol. Lett. 23, 291-298.
    • (1984) Toxicol. Lett. , vol.23 , pp. 291-298
    • Dixit, R.1    Das, M.2    Seth, P.K.3    Mukhtar, H.4
  • 10
    • 0025814980 scopus 로고
    • Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes
    • Esterbauer, H., Schaur, R. J., and Zollner, H. (1991). Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radic. Biol. Med. 11, 81-128.
    • (1991) Free Radic. Biol. Med. , vol.11 , pp. 81-128
    • Esterbauer, H.1    Schaur, R.J.2    Zollner, H.3
  • 12
    • 0027477312 scopus 로고
    • Mass spectrometric and Edman sequencing of lipocortin I isolated by two-dimensional SDS/PAGE of human melanoma lysates
    • Hall, S. C., Smith, D. M., Masiarz, R. R., Soo, V. W., Tran, H. M., Epstein, L. B., and Burlinggame, A. L. (1993). Mass spectrometric and Edman sequencing of lipocortin I isolated by two-dimensional SDS/PAGE of human melanoma lysates. Proc. Natl. Acad. Sci. U.S.A. 90, 1927-1931.
    • (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 1927-1931
    • Hall, S.C.1    Smith, D.M.2    Masiarz, R.R.3    Soo, V.W.4    Tran, H.M.5    Epstein, L.B.6    Burlinggame, A.L.7
  • 13
    • 0014838710 scopus 로고
    • Biochemical studies on acrylamide, a neurotoxic agent
    • Hashimoto, K., and Aldridge, W. N. (1970). Biochemical studies on acrylamide, a neurotoxic agent. Biochem. Pharmacol. 19, 2591-2604.
    • (1970) Biochem. Pharmacol. , vol.19 , pp. 2591-2604
    • Hashimoto, K.1    Aldridge, W.N.2
  • 14
    • 0028819983 scopus 로고
    • Modifications of neurofilament proteins by possible metabolites of allyl chloride in vitro
    • He, Y., Nagano, M., Yamamoto, H., Miyamoto, E., and Futatsuka, M. (1995). Modifications of neurofilament proteins by possible metabolites of allyl chloride in vitro. Drug Chem. Toxicol. 18, 315-331.
    • (1995) Drug Chem. Toxicol. , vol.18 , pp. 315-331
    • He, Y.1    Nagano, M.2    Yamamoto, H.3    Miyamoto, E.4    Futatsuka, M.5
  • 15
    • 0026643209 scopus 로고
    • Role of covalent and noncovalent interactions in cell toxicity: Effects on proteins
    • Hinson, J. A., and Roberts, D. W. (1992). Role of covalent and noncovalent interactions in cell toxicity: Effects on proteins. Annu. Rev. Pharmacol. Toxicol. 32, 471-510.
    • (1992) Annu. Rev. Pharmacol. Toxicol. , vol.32 , pp. 471-510
    • Hinson, J.A.1    Roberts, D.W.2
  • 16
    • 0023129279 scopus 로고
    • The role of acrolein in allyl alcohol-induced lipid peroxidation and liver cell damage in mice
    • Jaeschke, H., Kleinwaechter, C., and Wendel, A. (1987). The role of acrolein in allyl alcohol-induced lipid peroxidation and liver cell damage in mice. Biochem. Pharmacol. 36, 51-57.
    • (1987) Biochem. Pharmacol. , vol.36 , pp. 51-57
    • Jaeschke, H.1    Kleinwaechter, C.2    Wendel, A.3
  • 17
    • 4243084363 scopus 로고    scopus 로고
    • Strong protein adduct trapping accompanies abolition of acrolein-mediated hepatotoxicity by hydralazine in mice
    • Kaminskas, L. M., Pyke, S. M., and Burcham, P. C. (2004). Strong protein adduct trapping accompanies abolition of acrolein-mediated hepatotoxicity by hydralazine in mice. J. Pharmacol. Exp. Toxicol. 310, 1003-1010.
    • (2004) J. Pharmacol. Exp. Toxicol. , vol.310 , pp. 1003-1010
    • Kaminskas, L.M.1    Pyke, S.M.2    Burcham, P.C.3
  • 18
    • 32944454634 scopus 로고    scopus 로고
    • Differences in lysine adduction by acrolein and methyl vinyl ketone: Implications for cytotoxicity in cultured hepatocytes
    • Kaminskas, L. M., Pyke, S. M., and Burcham, P. C. (2005). Differences in lysine adduction by acrolein and methyl vinyl ketone: Implications for cytotoxicity in cultured hepatocytes. Chem. Res. Toxicol. 18, 1627-1633.
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 1627-1633
    • Kaminskas, L.M.1    Pyke, S.M.2    Burcham, P.C.3
  • 19
    • 0033864802 scopus 로고    scopus 로고
    • The molecular effects of acrolein
    • Kehrer, J. P., and Biswal, S. S. (2000). The molecular effects of acrolein. Toxicol. Sci. 57, 6-15.
    • (2000) Toxicol. Sci. , vol.57 , pp. 6-15
    • Kehrer, J.P.1    Biswal, S.S.2
  • 20
    • 26444489281 scopus 로고
    • Conjugated alkenes
    • In Chapter 19, Worth Publishers, New York
    • Kemp, D. S., and Vellaccio, F. (1980). Conjugated alkenes. In Organic Chemistry, Chapter 19, pp. 650-684. Worth Publishers, New York.
    • (1980) Organic Chemistry , pp. 650-684
    • Kemp, D.S.1    Vellaccio, F.2
  • 21
    • 0022474482 scopus 로고
    • The role mitochondrial glutathione and cellular protein sulfhydryls in formaldehyde toxicity in glutathione-depleted rat hepatocytes
    • Ku, R. H., and Billings, R. E. (1986). The role mitochondrial glutathione and cellular protein sulfhydryls in formaldehyde toxicity in glutathione-depleted rat hepatocytes. Arch. Biochem. Biophys. 247, 183-189.
    • (1986) Arch. Biochem. Biophys. , vol.247 , pp. 183-189
    • Ku, R.H.1    Billings, R.E.2
  • 22
    • 0037458649 scopus 로고    scopus 로고
    • -deoxyguanosine adducts of acrolein, crotonaldehyde and trans-4-hydryoxynonenal cross-fink to peptides via Schiff base linkage
    • -deoxyguanosine adducts of acrolein, crotonaldehyde and trans-4-hydryoxynonenal cross-fink to peptides via Schiff base linkage. J. Biol. Chem. 278, 5970-5976.
    • (2003) J. Biol. Chem. , vol.278 , pp. 5970-5976
    • Kurtz, A.J.1    Lloyd, R.S.2
  • 23
    • 0020323179 scopus 로고
    • The sensitivities of creatine and adenylate kinases to the neurotoxins acrylamide and methyl n-butyl ketone
    • Lapin, E. P., Weissbarth, S., Maker, H. S., and Lehrer, G. M. (1982). The sensitivities of creatine and adenylate kinases to the neurotoxins acrylamide and methyl n-butyl ketone. Environ. Res. 28, 21-31.
    • (1982) Environ. Res. , vol.28 , pp. 21-31
    • Lapin, E.P.1    Weissbarth, S.2    Maker, H.S.3    Lehrer, G.M.4
  • 24
    • 0037271780 scopus 로고    scopus 로고
    • Acrylamide neuropathy. III. Spatiotemporal characteristics of nerve cell damage in rat forebrain
    • Lehning, E. J., Balaban, C. D., Ross, J. F., and LoPachin, R. M. (2003). Acrylamide neuropathy. III. Spatiotemporal characteristics of nerve cell damage in rat forebrain. Neurotoxicology 24, 125-136.
    • (2003) Neurotoxicology , vol.24 , pp. 125-136
    • Lehning, E.J.1    Balaban, C.D.2    Ross, J.F.3    LoPachin, R.M.4
  • 26
    • 33751429238 scopus 로고    scopus 로고
    • Synaptic cysteine sulfhydryl groups as targets of electrophilic neurotoxicants
    • (in press)
    • LoPachin, R. M., and Barber, D. S. (2006). Synaptic cysteine sulfhydryl groups as targets of electrophilic neurotoxicants. Toxicol. Sci. (in press).
    • (2006) Toxicol. Sci.
    • LoPachin, R.M.1    Barber, D.S.2
  • 27
    • 29544443571 scopus 로고    scopus 로고
    • Acrylamide inhibits dopamine uptake in rat striatal synaptic vesicles
    • LoPachin, R. M., Barber, D. S., He, D., and Das, S. (2006). Acrylamide inhibits dopamine uptake in rat striatal synaptic vesicles. Toxicol. Sci. 89, 224-234.
    • (2006) Toxicol. Sci. , vol.89 , pp. 224-234
    • LoPachin, R.M.1    Barber, D.S.2    He, D.3    Das, S.4
  • 28
    • 26444512720 scopus 로고    scopus 로고
    • Protein adduct formation as a molecular mechanism in neurotoxicity
    • LoPachin, R. M., and DeCaprio, A. P. (2005). Protein adduct formation as a molecular mechanism in neurotoxicity. Toxicol. Sci. 86, 214-225.
    • (2005) Toxicol. Sci. , vol.86 , pp. 214-225
    • LoPachin, R.M.1    DeCaprio, A.P.2
  • 29
    • 2942739141 scopus 로고    scopus 로고
    • 2,5-Hexanedione-induced changes in the monomeric neurofilament protein content of rat spinal cord fractions
    • LoPachin, R. M., He, D., Reid, M. L., and Opanashuk, L. A. (2004a). 2,5-Hexanedione-induced changes in the monomeric neurofilament protein content of rat spinal cord fractions. Toxicol. Appl. Pharmacol. 198, 61-73.
    • (2004) Toxicol. Appl. Pharmacol. , vol.198 , pp. 61-73
    • LoPachin, R.M.1    He, D.2    Reid, M.L.3    Opanashuk, L.A.4
  • 30
    • 0036562871 scopus 로고    scopus 로고
    • Nerve terminals as the primary site of acrylamide action: A hypothesis
    • LoPachin, R. M., Ross, J. F., and Lehning, E. J. (2002). Nerve terminals as the primary site of acrylamide action: A hypothesis. Neurotoxicology 23, 43-60.
    • (2002) Neurotoxicology , vol.23 , pp. 43-60
    • LoPachin, R.M.1    Ross, J.F.2    Lehning, E.J.3
  • 31
    • 1442263139 scopus 로고    scopus 로고
    • In vivo and in vitro effects of acrylamide on synaptosomal neurotransmitter uptake and release
    • LoPachin, R. M., Schwarcz, A. I., Gaughan, C. L., Mansukhani, S., and Das, S. (2004b). In vivo and in vitro effects of acrylamide on synaptosomal neurotransmitter uptake and release. Neurotoxicology 25, 349-363.
    • (2004) Neurotoxicology , vol.25 , pp. 349-363
    • LoPachin, R.M.1    Schwarcz, A.I.2    Gaughan, C.L.3    Mansukhani, S.4    Das, S.5
  • 32
    • 12744277558 scopus 로고    scopus 로고
    • Acrolein induces oxidative stress in brain mitochondria
    • Luo, J., and Shi, R. (2005). Acrolein induces oxidative stress in brain mitochondria. Neurochem. Int. 46, 243-252.
    • (2005) Neurochem. Int. , vol.46 , pp. 243-252
    • Luo, J.1    Shi, R.2
  • 33
    • 0028920624 scopus 로고
    • In vitro acrylamide exposure alters growth cone morphology
    • Martenson, C. H., Sheetz, M. P., and Graham, D. G. (1995). In vitro acrylamide exposure alters growth cone morphology. Toxicol. Appl. Pharmacol. 131, 119-129.
    • (1995) Toxicol. Appl. Pharmacol. , vol.131 , pp. 119-129
    • Martenson, C.H.1    Sheetz, M.P.2    Graham, D.G.3
  • 35
    • 0025869692 scopus 로고
    • Neurotoxicity of allyl chloride in rats. Dose-effect relationship following long-term exposure
    • Nagano, M., Hitoshi, T., and Futatsuka, M. (1991). Neurotoxicity of allyl chloride in rats. Dose-effect relationship following long-term exposure. Jpn. J. Ind. Health 33, 73-81.
    • (1991) Jpn. J. Ind. Health , vol.33 , pp. 73-81
    • Nagano, M.1    Hitoshi, T.2    Futatsuka, M.3
  • 37
    • 0027442066 scopus 로고
    • Acrolein-induced injury to cultured pulmonary artery endothelial cells
    • Patel, J. M., and Block, E. R. (1993). Acrolein-induced injury to cultured pulmonary artery endothelial cells. Toxicol. Appl. Pharmacol. 122, 46-53.
    • (1993) Toxicol. Appl. Pharmacol. , vol.122 , pp. 46-53
    • Patel, J.M.1    Block, E.R.2
  • 38
    • 33947332005 scopus 로고
    • Application of the principle of hard and soft acids and bases to organic chemistry
    • Pearson, R. G., and Songstad, J. (1967). Application of the principle of hard and soft acids and bases to organic chemistry. J. Am. Chem. Soc. 89, 1827-1836.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 1827-1836
    • Pearson, R.G.1    Songstad, J.2
  • 39
    • 0034988283 scopus 로고    scopus 로고
    • Glutathione elevation and its protective role in acrolein-induced protein damage in synaptosomal membranes: Relevance to brain lipid perioxidation in neurodegenerative disease
    • Pocernich, C. B., Cardin, A. L., Racine, C. L., Lauderback, C. M., and Butterfield, D. A. (2001). Glutathione elevation and its protective role in acrolein-induced protein damage in synaptosomal membranes: Relevance to brain lipid perioxidation in neurodegenerative disease. Neurochem. Int. 39, 141-149.
    • (2001) Neurochem. Int. , vol.39 , pp. 141-149
    • Pocernich, C.B.1    Cardin, A.L.2    Racine, C.L.3    Lauderback, C.M.4    Butterfield, D.A.5
  • 40
    • 0025317268 scopus 로고
    • Glutathione: Toxicological implications
    • Reed, D. J. (1990). Glutathione: Toxicological implications. Annu. Rev. Pharmacol. Toxicol. 30, 603-631.
    • (1990) Annu. Rev. Pharmacol. Toxicol. , vol.30 , pp. 603-631
    • Reed, D.J.1
  • 42
    • 0026543799 scopus 로고
    • Selective modulation of glutathione in mouse brain regions and its effect on acrylamide-induced neurotoxicity
    • Shivakumar, B. R., and Ravindranath, V. (1992). Selective modulation of glutathione in mouse brain regions and its effect on acrylamide-induced neurotoxicity. Biochem. Pharmacol. 43, 263-269.
    • (1992) Biochem. Pharmacol. , vol.43 , pp. 263-269
    • Shivakumar, B.R.1    Ravindranath, V.2
  • 43
    • 0033452913 scopus 로고    scopus 로고
    • Current status of acrolein as a lipid peroxidation product
    • Uchida, K. (1999). Current status of acrolein as a lipid peroxidation product. Trends Cardiovasc. Med. 9, 109-113.
    • (1999) Trends Cardiovasc. Med. , vol.9 , pp. 109-113
    • Uchida, K.1
  • 44
    • 0024456697 scopus 로고
    • Biological interactions of α,β-unsaturated aldehydes
    • Witz, G. (1989). Biological interactions of α,β-unsaturated aldehydes. Free Radic. Biol. Med. 7, 333-349.
    • (1989) Free Radic. Biol. Med. , vol.7 , pp. 333-349
    • Witz, G.1


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