Abstract
Catecholamine derived aldehydes are the products of monoamine oxidase (MAO) action on catecholamines (CA). There are three major CA in human tissues: norepinephrine (NE), epinephrine (Epi), and dopamine (DA). All three are central neurotransmitters and, in addition, NE and Epi are hormones secreted by the adrenal medulla. MAO has two isoforms: A and B. NE and Epi are the preferred substrates for MAO A (Rivett et al., 1982). DA is metabolized by both MAO A and B (Rivett et al., 1982). The MAO A product of either NE or Epi is 3,4-dihydroxyphenylglycolaldehyde (DOPEGAL). The MAO product of DA is 3,4-dihydroxyphenylacetaldehyde (DOP-AL). Researchers initially considered these aldehydes, synthesized on the outer mitochondrial membrane, merely ephemeral intermediates in CA metabolism. However, the synthesis of sufficient quantities of chemically pure CA aldehydes has led to an understanding of their role in mitochondrially mediated apoptotic neuron death.
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Anglade, P., Vyas, S., Javoy-Agid, J., Herrero, M.T., Michel, P.P., Marquez, J., Mouatt-Prigent, A., Ruberg, M., Hirsch, E.C., Agid, Y., 1997, Apoptosis and autophagy in nigral neurons of patients with Parkinson’s disease,Histol. Histopathol. 12: 25.
Blashko, H., 1952, Amine oxidase and amine metabolism,Pharmacol. Rev. 4: 415.
Blashko H., Burn, J.H., 1951, Oxidation of adrenaline and noradrenaline by amine oxidase,J. Physiol. 112: 37p.
Bondareff, W., Mountjoy, CD., Roth, M., 1982, Loss of neurons of the adrenergic projection to cerebral cortex (nucleus locus ceruleus) in senile dementia,Neurology 32: 164.
Burke W.J., Chung, H.D., Marshall, G.L., Gillespie, K.N., Joh, T.H., 1990a, Evidence for decreased transport of PNMT protein in advanced Alzheimer’s disease,J. Am. Geriatr. Soc. 38: 1275.
Burke, W.J., Chung, H.D., Li, S.W., 1999d, Quantitation of 3,4-dihydroxyphenyl-acetaldehyde and 3,4-dihydroxyphenylglycolaldehyde, the monoamine oxidase metabolites of dopamine and noradrenaline, in human tissues by microcolumn high-performance liquid chromatography,Anal. Biochem. 273: 111.
Burke, W.J., Coronado, P.G., Schmitt, C.A., Gillespie, K.M., Chung, H.D., 1994b, Blood pressure regulation in Alzheimer’s disease,J. Autonom. Nerv. Syst. 38: 65.
Burke, W.J., Li, S.W., Schmitt, C.A., Xia, P., Chung, H.D., Gillespie, K.N., 1999c, Accumulation of 3,4-dihydroxyphenylglycolaldehyde, the neurotoxic monamine oxidase A metabolite of norepinephrine in locus ceruleus cell bodies in Alzheimer’s disease: mechanism of neuron death,Brain Res. 816: 633.
Burke, W.J., Park, D.H., Chung, H.D., Marshall, G.L., Haring, J.H., Joh, T.H., 1990b, Evidence for decreased transport of tryptophan hydroxylase in Alzheimer’s disease,Brain Res. 537: 83.
Burke, W.J., Galvin, N.J., Chung, H.D., Stoff, A.D., Gillespie, K.N., Cataldo, A.M., Nixon, R.A., 1994a Degenerative changes in epinephrine tonic vasomotor neurons in Alzheimer’s disease,Brain Res. 661: 35.
Burke, W.J., Kristal, B.S., Yu, B.P., Li, S.W., Lin, T.S., 1998b, Norepinephrine transmitter metabolite generates free radicals and activates mitochondrial permeability transition: a mechanism for DOPEGAL-induced apoptosis,Brain Res. 787: 328.
Burke, W.J., Li, S.W., Zahm, D.S., Kristal, B.S., 1999a, Neurotoxicity of DOPAL, the MAO metabolite of dopamine: implications for Parkinson’s disease,Neurology 52: A 345.
Burke, W.J., Li, S.W., Anwar, M., Glickstein, S.B., Ruggiero, D.A., 1999b, The aldehyde metabolite of catecholamine neurotransmitters induces apoptosis in adrenergic neurons in the rostral ventral lateral medulla, submitted.
Burke, W.J., Mattammal, M.B., Marshall G.L., Chung, H.D., 1989, Detection of 3,4-dihydroxy-phenylglycolaldehyde in human brain by high-performance liquid chromatographay,Anal. Biochem. 180: 79.
Burke, W.J., Schmitt, C.A., Gillespie, K.N., Li, S.W., 1996, Norepinephrine transmitter metabolite is a selective cell death messenger in differentiated rat pheochromocytoma cells,Brain Res. 722: 232.
Burke, W.J., Schmitt, C.A., Miller, C, Chung, H.D., Johnson, E.M., Ruggiero, D.A., Reis D.J., 1997a, 3,4-Dihydroxyphenylglycolaldehyde, a toxic product of catecholamine neurons, is increased in locus ceruleus neurons in Alzheimer’s disease,Neurology 48: A 103.
Burke, W.J., Schmitt, C.A., Miller C, Li, S.W., 1997b, Norepinephrine transmitter metabolite induces apoptosis in differentiated rat pheochromocytoma cells,Brain Res. 760: 290.
Burke, W.J., Schmitt, C.A., Li, S.W., Lin, T.S., Lampe, P., Johnson, E.M., 1998a, Norepinephrine MAO metabolite but not NE forms free radicals, induces mitochondrial permeability transition and kills NE neurons: a mechanism for NE neuron death in AD,Neurology 50: A 429.
Busciglio, J., Lorenzo, A., Yeh, J., Yankner, B.A., 1995, B-Amyloid fibrils induce tau phosphorylation and loss of microtubule binding,Neuron 14: 879.
Colzi, A., Musolino, A., Juliano, A., Fornai, F., Bonuccelli, U., Corsini, G.U., 1996, Identification and determination of 3,4-dihydroxyphenylacetaldehyde, the dopamine metabolite in in vivo dialysate form rat striatum,J. Neurochem. 66: 1510.
Davis, V.E., Cashaw, J.L., McLaughlin, B.R., Hamlin, T.A., 1974, Alteration of norepinephrine metabolism by barbiturates,Biochem. Pharmac. 23: 1877.
Davis, V.E., Walsh, M.J., Yamanaka, Y., 1970, Augmentation of alkaloid formation from dopamine by alcohol and acetaldehyde in vitro,J. Pharmac and Exptl. Physiol. 174: 401.
Duncan, R.J.S., 1975, The preparation of some biochemically important aldehydes,Can. J. Biochem. 53: 920.
Duncan, R.J.S., Sourkes, T.L., 1974, Some enzymic aspects of the production of oxidized or reduced metabolites of catecholamines and 5-hydroxytryptamine by brain tissues,J. Neurochem. 22: 663.
Fellman, J.H., 1958, The rearrangement of epinephrine,Nature 182: 311.
Filloux, F., Townsend, J.J., 1993, Pre- and post-synaptic neurotoxic effects of dopamine demonstrated by intrastriatal injection,Exp. Neurol. 119: 79.
Goate, A., Chartier-Harlin, M.C., Mullan, M., 1991, Segregation of a missense mutation in the amyloid precursor protein gene with familial Alzheimer’s disease,Nature 349: 704.
Heintz, N., Zoghbi, H., 1997, α-Synuclein - a link between Parkinson and Alzheimer diseases,Nature Genetics 16: 325.
Hong, M., Zhukareva, V., Vogelsberg-Ragaglia, V., Wszolek, Z., Reed, L., Miller, B.I., Geschwind, D.H., Bird, T.D., McKeel, D., Goate, A., Morris, J.C., Wilhelmsen, K.C., Schellenberg,G.D., Trojanowski, J.Q., Lee, V.M.Y., 1998, Mutation-specific functional impairments in distinct tau isoforms of hereditary FTDP-17,Science 282: 1914.
Iqbal, K., Zaidi, T., Wen, G.Y., Grundke–Iqbal, I., Merz, P.A., Shaikh, S.S., Alafuzoff, I., Winblad, B., Wisniewski, H.M., 1986, Defective brain microtubule assembly in Alzheimer’s disease,Lancet 421.
Kitada, T., Asakawa, S., Hattori, N., Matsumine, H., Yamamura, Y., Minoshima, S., Yokoshi,M., Mizuno, Y., Shimizu, N., 1998, Mutations in parkin gene cause autosomal recessive juvenile parkinsonism,Nature 392: 605.
Kluck, R.M., Bossy-Wetzel, E., Green, D.R., Newmyer, D.D., 1997, The release of cytochromec from mitochondria: a primary site for bcl-2 regulation of apoptosis,Science 275: 1132.
Kothakota, S., Azuma, T., Reinhard, C, Klipper, A., Tang, J., Chu, K., McGarry, T.J.,Kirschner, M.W., Koths, K., Kwiatkowski, D.J., Williams, L.T., 1997, Capsase-3-generated fragment of gelsolin: effector of morphological change in apoptosis,Science 278: 294.
Kristal, B.S., Brown, A.M., Jain, J.X., Ulluci, P.X., Li, S.W., Burke, W.J., 1999, 3,4-Dihydroxy-phenylacetaldehyde: endogenous neurotoxin in Parkinson’s disease, submitted.
Kristal, B.S., Park, B.K., Yu, B.P., 1996, 4-Hydroxyhexenal is a potent inducer of the mitochondrial permeaiblity transition,J. Biol. Chem. 271: 6033.
Lassman, H., Bancher, C, Breitschopf, H., Wegiel, J., Bobinski, M., Jellinger, K., Wisniewski,H., 1995, Cell death in Alzheimer’s disease evaluated by DNA fragmentation in situ,Acta Neuropathol. 89: 35.
Lee, V.M., Balin, B.J., Otur, S.L., Trojanowski, J.D., 1991, A68: a major subunit of paired helical filaments and derivative forms of acetylcholine esterase in Alzheimer’s disease,Science 251: 675.
Leeper, L., Weissbach H., Udenfriend, S., 1958, Studies on the metabolism of norepinephrine,epinephrine and their O-methyl analogs by partially purified enzyme preparations,Arch.Biochem. Biophys. 77: 417.
Li, S.W., Elliott, W.H., Burke, W.J., 1994, Synthesis of a biochemically important aldehyde,3,4-dihydroxyphenylglycolaldehyde,Bioorg. Chem. 22: 337.
Li, S.W., Spaziano, V.T., Burke, W.J., 1998, Synthesis of a biochemically important aldehyde3,4-dihydroxyphenylacetaldehyde,Bioorg. Chem. 26: 45.
Mattammal, M.B., Chung, H.D., Strong, R., 1993, Confirmation of a dopamine metabolite in parkinsonian brain tissue by gas chromatography-mass spectrometry,J. Chromatog. 614:205.
Orrenius, S., Nicotera, P., 1994, The calcium ion and cell death,J. Neural Transm. (Suppl.) 43:1.
Renson, J., Weissbach, H., Udenfriend, S., 1964, Studies on the biological activities of the aldehydes derived from norepinephrine, serotonin, tryptamine and histamine,J. Pharmac and Exptl. Therap. 143: 326.
Rivett, A.J., Eddy, B.J., Roth, J.A., 1982, Contribution of sulfate conjugation, deamination, and O-methylation to metabolism of dopamine and norepinephrine in human brain,J.Neurochem. 39: 1009.
Robbins, J.H., 1966, Preparation and properties of p-hydroxyphenylacetaldehyde and 3-me-thoxy-4-hydroxyphenylacetaldehyde,Arch. Biochem. Biophys. 114: 576.
Scarlett, J.L., Murphy, M.P., 1997, Release of apoptogenic proteins from the mitochondrialintermembrane space during mitochondria permeability transition,FEBS Lett. 418: 282.
Stoyanovsky, D.A., Cederbaum, A.I., 1998, ESR and HPLC-EC of ethanol oxidation to 1-hydroxyethylradical:rapid reduction and quantificaiton of PDBN and PBN nitroxides,Free Radical Biol. Med. 25: 536.
Strittmatter, W.J., Weisgraber, K.H., Goedert, M., Saunders, A.M., Huang, D., Corder, E.H.,Dong, L.M., Jakes, R., Alberts, M.J., Gilbert, J.R., Han, S.H., Hulette, C, Einstein,G., Schmechl, D.E., Pericak-Vance, M.A., Roses, A.D., 1994, Hypothesis: microtubuleinstability and paired helical filament formation in the Alzheimer disease brain are related to apolipoprotein E genotype,Exp. Neurol. 125: 163.
Tabakoff, B., Anderson, R., Alivisatos, S.G.A., 1973, Enzymatic reaction of biogenic aldehydes in brain,Mol. Pharmacol. 9: 428.
Tank, A.W., Weiner H., 1979, Ethanol-induced alteration of dopamine metabolism in rat liver,Biochem. Pharmacol. 28: 3139.
Tottmar, O., 1986, Assay of brain aldehyde dehydrogenase using high-performance liquid chromatography with electrochemical detection,Anal. Biochem. 158: 6.
Wallace, D.C., 1999, Mitochondrial diseases in man and mouse,Science 283: 1482.
Younkin, S.G., Goodridge, B., Katz, J., Lockett, G., Nafziger, D., Usiak, M.F., Younkin, L.H., 1988, Molecular forms of acetylcholine esterase in Alzheimer’s disease,Fed. Proc. 45: 2982.
Zoratti, M., Szabo, I., 1995, The mitochondrial permeaiblity transition,Biochem. Biophys. Acta 1241: 139.
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Burke, W.J. et al. (2000). Catecholamine-Derived Aldehyde Neurotoxins. In: Storch, A., Collins, M.A. (eds) Neurotoxic Factors in Parkinson’s Disease and Related Disorders. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-1269-1_18
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