Human aldehyde dehydrogenases: Potential pathological, pharmacological, and toxicological impact

Journal of Biochemical and Molecular Toxicology

Volumn 17, Issue 1, 2003, Pages 7-23

  Sládek, Norman E ^a  

^a UNIVERSITY OF MINNESOTA MEDICAL SCHOOL   (United States)

Author keywords

Aldehyde dehydrogenases; In born errors of metabolism; Xenobiotic metabolism

Indexed keywords

ACID; ALDEHYDE; ALDEHYDE DEHYDROGENASE; PYRIDINE NUCLEOTIDE; XENOBIOTIC AGENT;

BIOTRANSFORMATION; CATALYSIS; CELLULAR DISTRIBUTION; CHROMOSOMAL LOCALIZATION; DETOXIFICATION; ENVIRONMENTAL FACTOR; ENZYME ACTIVITY; ENZYME SPECIFICITY; ENZYME STRUCTURE; GENETIC ORGANIZATION; HOMEOSTASIS; HUMAN; NOMENCLATURE; NONHUMAN; OXIDATION; PHENOTYPE; PHYSICAL CHEMISTRY; PHYSICAL DEVELOPMENT; RAT; REVIEW; SEQUENCE ANALYSIS; STRUCTURE ANALYSIS; TISSUE DISTRIBUTION;

ALDEHYDE DEHYDROGENASE; ANIMALS; HUMANS; MUTATION; PROTEIN SUBUNITS; SIGNAL TRANSDUCTION; SUBCELLULAR FRACTIONS; SUBSTRATE SPECIFICITY; TISSUE DISTRIBUTION;

EID: 0037259979     PISSN: 10956670     EISSN: None     Source Type: Journal    
DOI: 10.1002/jbt.10057     Document Type: Review

References (207)

1. Williams RT. Comparative patterns of drug metabolism. Fed Proc 1967;26:1029-1039.
2. Vasiliou V, Bairoch A, Tipton KF, Nebert DW. Eukaryotic aldehyde dehydrogenase (ALDH) genes: Human polymorphisms, and recommended nomenclature based on divergent evolution and chromosomal mapping. Pharmacogenetics 1999;9:421-434.
3. Sophos NA, Pappa A, Ziegler TL, Vasiliou V. Aldehyde dehydrogenase gene superfamily: The 2000 update. Chem Biol Interact 2001;130-132:323-337.
4. Nebert DW. Suggestions for the nomenclature of human alleles: Relevance to exogenetics, pharmacogenetics and molecular epidemiology. Pharmacogenetics 2000; 10:279-290.
5. Hsu LC, Yoshida A, Mohandas T. Chromosomal assignment of the genes for human aldehyde dehydrogenase-1 and aldehyde dehydrogenase-2. Am J Hum Genet 1986;38:641-648.
6. Raghunathan L, Hsu LC, Klisak I, Sparkes RS, Yoshida A, Mohandas T. Regional localization of the human genes for aldehyde dehydrogenase-1 and aldehyde dehydrogenase-2. Genomics 1988;2:267-269.
7. Hsu LC, Chang W-C, Yoshida A. Genomic structure of the human cytosolic aldehyde dehydrogenase gene. Genomics 1989;5:857-865.
8. Hsu LC, Chang W-C, Yoshida A. Mouse type-2 retinaldehyde dehydrogenase (RALDH2): Genomic organization, tissue-dependent expression, chromosome assignment and comparison to other types. Biochem Biophys Acta 2000;1492:289-293.
9. Ono Y, Fukuhara N, Yoshie O. TAL1 and LIM-only proteins synergistically induce retinaldehyde dehydrogenase 2 expression in T-cell acute lymphoblastic leukemia by acting as cofactors for GATA3. Mol Cell Biol 1998;18:6939-6950.
10. Hsu LC, Chang W-C, Hiraoka L, Hsieh C-L. Molecular cloning, genomic organization, and chromosomal localization of an additional human aldehyde dehydrogenase gene, ALDH6. Genomics 1994;24:333-341.
11. Hsu LC, Chang W-C. Cloning and characterization of a new functional human aldehyde dehydrogenase gene. J Biol Chem 1991;266:12257-12265.
12. Hiraoka LR, Hsu L, Hsieh C-L. Assignment of ALDH3 to human chromosome 17p11.2 and ALDH5 to human chromosome 9p13. Genomics 1995;25:323-325.
13. Hong M, Lee Y, Kim JW, Lim J-S, Chang SY, Lee KS, Paik S-G, Choe IS. Isolation and characterization of cDNA clone for human liver 10-formyltetrahydrofolate dehydrogenase. Biochem Mol Biol Int 1999;47:407-415.
14. Hsu LC, Bendel RE, Yoshida A. Genomic structure of the human mitochondrial aldehyde dehydrogenase gene. Genomics 1988;2:57-65.
15. Craig IW, McBride OW. Report of the committee on the genetic constitution of chromosome 12. Cytogenet Cell Genet 1991;58:555-579.
16. Santisteban I, Povey S, West LF, Parrington JM, Hopkinson DA. Chromosome assignment, biochemical and immunological studies on a human aldehyde dehydrogenase, ALDH3. Ann Hum Genet 1985;49:87-100.
17. Hsu LC, Chang W-C, Shibuya A, Yoshida A. Human stomach aldehyde dehydrogenase cDNA and genomic cloning, primary structure, and expression in Escherichia coli. J Biol Chem 1992;267:3030-3037.
18. 3. Adv Exp Med Biol 1993;328:141-152.
19. Hsu LC, Chang W-C, Chang C, Tsukamoto N, Yoshida A. The human aldehyde dehydrogenase 3 gene (ALDH3): Identification of a new exon and diverse mRNA isoforms, and functional analysis of the promoter. Gene Expr 1996;6:87-99.
20. De Laurenzi V, Rogers GR, Hamrock DJ, Marekov LN, Steinert PM, Compton JG, Markova N, Rizzo WB. Sjögren-Larsson syndrome is caused by mutations in the fatty aldehyde dehydrogenase gene. Nat Genet 1996;12:52-57.
21. Rogers GR, Markova NG, De Laurenzi V, Rizzo WB, Compton JG. Genomic organization and expression of the human fatty aldehyde dehydrogenase gene (FALDH). Genomics 1997;39:127-135.
22. Chang C, Yoshida A. Human fatty aldehyde dehydrogenase gene (ALDH10): Organization and tissue-dependent expression. Genomics 1997;40:80-85.
23. Rizzo WB, Lin Z, Carney G. Fatty aldehyde dehydrogenase: Genomic structure, expression and mutation analysis in Sjögren-Larsson syndrome. Chem Biol Interact 2001;130-132:297-307.
24. Hsu LC, Chang W-C, Yoshida A. Cloning of a cDNA encoding human ALDH7, a new member of the aldehyde dehydrogenase family. Gene 1994;151:285-289.
25. Hsu LC, Chang W-C, Lin SW, Yoshida A. Cloning and characterization of genes encoding four additional human aldehyde dehydrogenase isozymes. Adv Exp Med Biol 1995;372:159-168.
26. Hsu LC, Chang W-C, Yoshida A. Human aldehyde dehydrogenase genes, ALDH7 and ALDH8: Genomic organization and gene structure comparison. Gene 1997;189:89-94.
27. Hsu LC, Chang W-C. Sequencing and expression of the human ALDH8 encoding a new member of the aldehyde dehydrogenase family. Gene 1996;174:319-322.
28. Vasiliou V, Pappa A, Petersen DR. Role of aldehyde dehydrogenases in endogenous and xenobiotic metabolism. Chem Biol Interact 2000;129:1-19.
29. 1-pyrroline-5-carboxylate dehydrogenase. J Biol Chem 1996;271:9795-9800.
30. +-dependent succinic semialdehyde dehydrogenase from rat and human. cDNA isolation, evolutionary homology, and tissue expression. J Biol Chem 1995;270:461-467.
31. Trettel F, Malaspina P, Jodice C, Novelletto A, Slaughter CA, Caudle DL, Hinson DD, Chambliss KL, Gibson KM. Human succinic semialdehyde dehydrogenase. Molecular cloning and chromosomal localization. Adv Exp Biol Med 1997;414:253-260.
32. Chambliss KL, Hinson DD, Trettel F, Malaspina P, Novelletto A, Jakobs C, Gibson KM. Two exon-skipping mutations as the molecular basis of succinic semialdehyde dehydrogenase deficiency (4-hydroxybutyric aciduria). Am J Hum Genet 1998;63:399-408.
33. Kedishvili NY, Popov KM, Rougraff PM, Zhao Y, Crabb DW, Harris RA. CoA-dependent methylmalonate-semialdehyde dehydrogenase, a unique member of the aldehyde dehydrogenase superfamily. cDNA cloning, evolutionary relationships, and tissue distribution. J Biol Chem 1992;267:19724-19729.
34. Chambliss KL, Gray RGF, Rylance G, Pollitt RJ, Gibson KM. Molecular characterization of methylmalonate semialdehyde dehydrogenase deficiency. J Inherit Metab Dis 2000;23:497-504.
35. Lee P, Kuhl W, Gelbart T, Kamimura T, West C, Beutler E. Homology between a human protein and a protein of the green garden pea. Genomics 1994;21:371-378.
36. Skvorak AB, Robertson NG, Yin Y, Weremowicz S, Her H, Bieber FR, Beisel KW, Lynch ED, Beier DR, Morton CC. An ancient conserved gene expressed in the human inner ear: Identification, expression analysis, and chromosomal mapping of human and mouse antiquitin (ATQ1). Genomics 1997;46:191-199.
37. Lynch M, Cameron TL, Knight M, Kwok TY, Thomas P, Forrest SM, Skvorak Giersch AB, Briggs RJS, Pyman BC. Structural and mutational analysis of antiquitin as a candidate gene for Menière Disease. Am J Med Genet 2002;110:397-399.
38. Lin M, Napoli JL. cDNA cloning and expression of a human aldehyde dehydrogenase (ALDH) active with 9-cis-retinal and identification of a rat ortholog, ALDH12. J Biol Chem 2000;275:40106-40112.
39. Lin SW, Chen JC, Hsu LC, Hsieh C-L, Yoshida A. Human γ-aminobutyraldehyde dehydrogenase (ALDH9): cDNA sequence, genomic organization, polymorphism, chromosomal localization, and tissue expression. Genomics 1996;34:376-380.
40. 1-pyrroline-5-carboxylate synthetase (P5CS) cDNA: A bifunctional enzyme catalyzing the first 2 steps in proline biosynthesis. Comptes Rendus Acad Sci Paris 1996;319:171-178.
41. 1-pyrroline-5-carboxylate synthase. Alternative splice donor utilization generates isoforms with different sensitivity to ornithine inhibition. J Biol Chem 1999;274:6754-6762.
42. Pietruszko R. Aldehyde dehydrogenase isozymes. In: Rattazzi MC, Scandalios JG, Whitt GS, editors. Isozymes: Current Topics in Biological and Medical Research. Vol 8: Cellular Localization, Metabolism, and Physiology. New York: Alan R Liss; 1983. pp 195-217.
43. Agarwal DP, Goedde HW. Human aldehyde dehydrogenase isozymes and alcohol sensitivity. In: Rattazzi MC, Scandalios JG, Whitt GS, editors. Isozymes: Current Topics in Biological and Medical Research. Vol 16: Agriculture, Physiology, and Medicine. New York: Alan R Liss; 1987. pp 21-48.
44. Sládek NE, Manthey CL, Maki PA, Zhang Z, Landkamer GJ. Xenobiotic oxidation catalyzed by aldehyde dehydrogenases. Drug Metab Rev 1989;20:697-720.
45. Goedde HW, Agarwal DP. Pharmacogenetics of aldehyde dehydrogenase (ALDH). Pharmacol Ther 1990;45:345-371.
46. Lindahl R. Aldehyde dehydrogenases and their role in carcinogenesis. Crit Rev Biochem Mol Biol 1992;27:283-335.
47. Yoshida A, Rzhetsky A, Hsu LC, Chang C. Human aldehyde dehydrogenase gene family. Eur J Biochem 1998;251:549-557.
48. Sládek NE. Aldehyde dehydrogenase-mediated relative insensitivity to the oxazaphosphorines. Curr Pharm Des 1999;5:607-625.
49. Vasiliou V, Pappa A. Polymorphisms of human aldehyde dehydrogenases. Pharmacology 2000;61:192-198.
50. Greenfield NJ, Pietruszko R. Two aldehyde dehydrogenases from human liver. Isolation via affinity chromatography and characterization of the isozymes. Biochim Biophys Acta 1977;483:35-45.
51. Harada S, Agarwal DP, Goedde HW. Electrophoretic and biochemical studies of human aldehyde dehydrogenase isozymes in various tissues. Life Sci 1980;26:1773-1780.
52. Hempel J, von Bahr-Lindström H, Jörnvall H. Aldehyde dehydrogenase from human liver. Primary structure of the cytoplasmic isoenzyme. Eur J Biochem 1984;141:21-35.
53. Dockham PA, Lee M-O, Sládek NE. Identification of human liver aldehyde dehydrogenases that catalyze the oxidation of aldophosphamide and retinaldehyde. Biochem Pharmacol 1992;43:2453-2469.
54. Klyosov AA, Rashkovetsky LG, Tahir MK, Keung W-M. Possible role of liver cytosolic and mitochondrial aldehyde dehydrogenases in acetaldehyde metabolism. Biochemistry 1996;35:4445-4456.
55. Rexer BN, Zheng WL, Ong DE. Retinoic acid biosynthesis by normal human breast epithelium is via aldehyde dehydrogenase 6, absent in MCF-7 cells. Cancer Res 2001;61:7065-7070.
56. Stewart MJ, Malek K, Xiao Q, Dipple KM, Crabb DW. The novel aldehyde dehydrogenase gene, ALDH5, encodes an active aldehyde dehydrogenase enzyme. Biochem Biophys Res Commun 1995;211:144-151.
57. Krupenko SA, Wagner C, Cook RJ. Cysteine 707 is involved in the dehydrogenase active site of rat 10-formyltetrahydrofolate dehydrogenase. J Biol Chem 1995;270:519-522.
58. Hempel J, Kaiser R, Jörnvall H. Mitochondrial aldehyde dehydrogenase from human liver. Primary structure, differences in relation to the cytosolic enzyme, and functional correlations. Eur J Biochem 1985;153:13-28.
59. Duley JA, Harris O, Holmes RS. Analysis of human alcohol- and aldehyde-metabolizing isozymes by electrophoresis and isoelectric focusing. Alcohol Clin Exp Res 1985;9:263-271.
60. Sreerama L, Sládek NE. Identification and characterization of a novel class 3 aldehyde dehydrogenase overexpressed in a human breast adenocarcinoma cell line exhibiting oxazaphosphorine-specific acquired resistance. Biochem Pharmacol 1993;45:2487-2505.
61. Kelson TL, Secor McVoy JR, Rizzo WB. Human liver fatty aldehyde dehydrogenase: Microsomal localization, purification, and biochemical characterization. Biochim, Biophys Acta 1997;1335:99-110.
62. Tsukamoto N, Chang C, Yoshida A. Mutations associated with Sjögren-Larsson syndrome. Ann Hum Genet 1997;61:235-242.
63. Forte-McRobbie CM, Pietruszko R. Aldehyde dehydrogenase content and composition of human liver. Alcohol 1985;2:375-381.
64. m" aldehyde dehydrogenase and its identification as glutamic γ-semialdehyde dehydrogenase. J Biol Chem 1986;261:2154-2163.
65. Farrés J, Julià P, Parés X. Aldehyde oxidation in human placenta. Purification and properties of 1-pyrroline-5-carboxylate dehydrogenase. Biochem J 1988;256:461-467.
66. m" aldehyde dehydrogenase isozymes in human tissues: Constitutive and tumor-associated forms. Prog Clin Biol Res 1989;290:119-131.
67. +-dependent succinic semialdehyde dehydrogenase. Arch Biochem Biophys 1988;266:386-396.
68. Tang W-K, Cheng CHK, Fong W-P. First purification of the antiquitin protein and demonstration of its enzymatic activity. FEBS Lett 2002;516:183-186.
69. m for γ-aminobutyraldehyde. J Biol Chem 1989;264:4715-4721.
70. Ambroziak W, Pietruszko R. Metabolic role of aldehyde dehydrogenase. Adv Exp Med Biol 1993;328:5-15.
71. Inoue K, Nishimukai H, Yamasawa K. Purification and partial characterization of aldehyde dehydrogenase from human erythrocytes. Biochim Biophys Acta 1979;569:117-123.
72. Agarwal DP, Cohn P, Goedde HW, Hempel J. Aldehyde dehydrogenases from human erythrocytes: Structural relationship to the liver cytosolic isozyme. Enzyme 1989;42:47-52.
73. Stewart MJ, Malek K, Crabb DW. Distribution of messenger RNAs for aldehyde dehydrogenase 1, aldehyde dehydrogenase 2, and aldehyde dehydrogenase 5 in human tissues. J Invest Med 1996;44:42-46.
74. Sreerama L, Sládek NE. Cellular levels of class 1 and class 3 aldehyde dehydrogenases and certain other drug metabolizing enzymes in human breast malignancies. Clin Cancer Res 1997;3:1901-1914.
75. Dockham PA, Sreerama L, Sládek NE. Relative contribution of human erythrocyte aldehyde dehydrogenase to the systemic detoxification of the oxazaphosphorines. Drug Metab Dispos 1997;25:1436-1441.
76. Wang X, Penzes P, Napoli JL. Cloning of a cDNA encoding an aldehyde dehydrogenase and its expression in Escherichia coli. Recognition of retinal as substrate. J Biol Chem 1996;271:16288-16293.
77. Johlin FC, Swain E, Smith C, Tephly TR. Studies on the mechanism of methanol poisoning: Purification and comparison of rat and human liver 10-formyltetrahydrofolate dehydrogenase. Mol Pharmacol 1989;35:745-750.
78. Holmes RS. Alcohol dehydrogenases and aldehyde dehydrogenases of anterior eye tissues from humans and other mammals. In: Kuriyama K, Takada A, Ishii H, editors. Biomedical and Social Aspects of Alcohol and Alcoholism. Amsterdam: Elsevier; 1988. pp 51-57.
79. Gondhowiardjo TD, van Haeringen NJ, Hoekzema R, Pels L, Kijlstra A. Detection of aldehyde dehydrogenase activity in human corneal extracts. Curr Eye Res 1991;10:1001-1007.
80. Yin S-J, Chou F-J, Chao S-F, Tsai S-F, Liao C-S, Wang S-L, Wu C-W, Lee S-C. Alcohol and aldehyde dehydrogenases in human esophagus: Comparison with stomach activities. Alcohol Clin Exp Res 1993;17:376-381.
81. Sreerama L, Sládek NE. Over-expression of glutathione S-transferases, DT-diaphorase and an apparently tumor-specific cytosolic class-3 aldehyde dehydrogenase by Warthin tumours and mucoepidermoid carcinomas of the human parotid gland. Arch Oral Biol 1996;41:597-605.
82. Cheung C, Smith CK, Hoog J-O, Hotchkiss SAM. Expression and localization of human alcohol and aldehyde dehydrogenase enzymes in skin. Biochem Biophys Res Commun 1999;261:100-107.
83. Koivula T. Subcellular distribution and characterization of human liver aldehyde dehydrogenase fractions. Life Sci 1975;16:1563-1570.
84. Masaki R, Yamamoto A, Tashiro Y. Microsomal aldehyde dehydrogenase is localized to the endoplasmic reticulum via its carboxyl-terminal 35 amino acids. J Cell Biol 1994;126:1407-1420.
85. Chambliss KL, Zhang Y-A, Rossier E, Vollmer B, Gibson KM. Enzymatic and immunologic identification of succinic semialdehyde dehydrogenase in rat and human neural and nonneural tissues. J Neurochem 1995;65:851-855.
86. Ambroziak W, Kurys G, Pietruszko R. Aldehyde dehydrogenase (EC 1.2.1.3): Comparison of subcellular localization of the third isozyme that dehydrogenates γ-aminobutyraldehyde in rat, guinea pig and human liver. Comp Biochem Physiol 1991;100B:321-327.
87. Kikonyogo A, Pietruszko R. Aldehyde dehydrogenase from adult human brain that dehydrogenates γ-aminobutyraldehyde: Purification, characterization, cloning and distribution. Biochem J 1996;316:317-324.
88. Izaguirre G, Kikonyogo A, Pietruszko R. Tissue distribution of human aldehyde dehydrogenase E3 (ALDH9): Comparison of enzyme activity with E3 protein and mRNA distribution. Comp Biochem Physiol 1997;118B: 59-64.
89. Sládek NE, Dockham PA, Lee M-O. Human and mouse hepatic aldehyde dehydrogenases important in the biotransformation of cyclophosphamide and the retinoids. Adv Exp Med Biol 1990;284:97-104.
90. Ambroziak W, Pietruszko R. Human aldehyde dehydrogenase. Activity with aldehyde metabolites of monoamines, diamines, and polyamines. J Biol Chem 1991;266:13011-13018.
91. Yoshida A, Hsu LC, Yanagawa Y. Biological role of human cytosolic aldehyde dehydrogenase 1: Hormonal response, retinal oxidation and implication in testicular feminization. Adv Exp Med Biol 1993;328:37-44.
92. Rashkovetsky LG, Maret W, Klyosov AA. Human liver aldehyde dehydrogenases: New method of purification of the major mitochondrial and cytosolic enzymes and re-evaluation of their kinetic properties. Biochim Biophys Acta 1994;1205:301-307.
93. Klyosov AA. Kinetics and specificity of human liver aldehyde dehydrogenases toward aliphatic, aromatic, and fused polycyclic aldehydes. Biochemistry 1996;35:4457-4467.
94. Rekha GK, Sládek NE. Inhibition of human class 3 aldehyde dehydrogenase, and sensitization of tumor cells that express significant amounts of this enzyme to oxazaphosphorines, by the naturally occurring compound gossypol. Adv Exp Med Biol 1997;414:133-146.
95. Bhat PV, Samaha H. Kinetic properties of the human liver cytosolic aldehyde dehydrogenase for retinal isomers. Biochem Pharmacol 1999;57:195-197.
96. Ambroziak W, Izaguirre G, Pietruszko R. Metabolism of retinaldehyde and other aldehydes in soluble extracts of human liver and kidney. J Biol Chem 1999;274:33366-33373.
97. Cook RJ, Lloyd RS, Wagner C. Isolation and characterization of cDNA clones for rat liver 10-formyltetrahydrofolate dehydrogenase. J Biol Chem 1991;266:4965-4973.
98. Krupenko SA, Wagner C, Cook RJ. Expression, purification, and properties of the aldehyde dehydrogenase homologous carboxyl-terminal domain of rat 10-formyltetrahydrofolate dehydrogenase. J Biol Chem 1997;272:10266-10272.
99. Sharpe AL, Carter DE. Substrate specificity of rat liver aldehyde dehydrogenase with chloroacetaldehydes. J Biochem Toxicol 1993;8:155-160.
100. Farrés J, Wang X, Takahashi K, Cunningham SJ, Wang TT, Weiner H. Effects of changing glutamate 487 to lysine in rat and human liver mitochondrial aldehyde dehydrogenase. A model to study human (Oriental type) class 2 aldehyde dehydrogenase. J Biol Chem 1994;269:13854-13860.
101. Blair AH, Bodley FH. Human liver aldehyde dehydrogenase: Partial purification and properties. Can J Biochem 1969;47:265-272.
102. Yin S-J, Liao C-S, Wang S-L, Chen Y-J, Wu C-W. Kinetic evidence for human liver and stomach aldehyde dehydrogenase-3 representing a unique class of isozymes. Biochem Genet 1989;27:321-331.
103. m aldehyde dehydrogenase isoenzymes from human gastric mucosa. Biochem Int 1990;22:199-204.
104. m" aldehyde dehydrogenase. Adv Exp Med Biol 1990;284:43-52.
105. Sreerama L, Sládek NE. Identification of the class-3 aldehyde dehydrogenases present in human MCF-7/0 breast adenocarcinoma cells and normal human breast tissue. Biochem Pharmacol 1994;48:617-620.
106. Townsend AJ, Leone-Kabler S, Haynes RL, Wu Y, Szweda L, Bunting KD. Selective protection by stably transfected human ALDH3A1 (but not human ALDH1A1) against toxicity of aliphatic aldehydes in V79 cells. Chem Biol Interact 2001;130-132:261-273.
107. Goodwin GW, Rougraff PM, Davis EJ, Harris RA. Purification and characterization of methylmalonate-semialdehyde dehydrogenase from rat liver. Identity to malonate-semialdehyde dehydrogenase. J Biol Chem 1989;264:14965-14971.
108. Chern M-K, Pietruszko R. Human aldehyde dehydrogenase E3 isozyme is a betaine aldehyde dehydrogenase. Biochem Biophys Res Commun 1995;213:561-568.
109. Vaz FM, Fouchier SW, Ofman R, Sommer M, Wanders RJA. Molecular and biochemical characterization of rat γ-trimethylaminobutyraldehyde dehydrogenase and evidence for the involvement of human aldehyde dehydrogenase 9 in carnitine biosynthesis. J Biol Chem 2000;275:7390-7394.
110. Hayzer DJ, Leisinger T. Proline biosynthesis in Escherichia coli. Stoichiometry and end-product identification of the reaction catalyzed by glutamate semialdehyde dehydrogenase. Biochem J 1981;197:269-274.
111. Niederreither K, Subbarayan V, Dollé P, Chambon P. Embryonic retinoic acid synthesis is essential for early mouse post-implantation development. Nat Genet 1999;21:444-448.
112. Mic FA, Haselbeck RJ, Cuenca AE, Duester G. Novel retinoic acid generating activities in the neural tube and heart identified by conditional rescue of Raldh2 null mutant mice. Development 2002;129:2271-2282.
113. Giometti CS, Tollaksen SL, Grahn D. Altered protein expression detected in the F1 offspring of male mice exposed to fission neutrons. Mutat Res 1994;320:75-85.
114. Champion KM, Cook RJ, Tollaksen SL, Giometti CS. Identification of a heritable deficiency of the folate-dependent enzyme 10-formyltetrahydrofolate dehydrogenase in mice. Proc Natl Acad Sci USA 1994;91:11338-11342.
115. Cook RJ. Disruption of histidine catabolism in NEUT2 mice. Arch Biochem Biophys 2001;392:226-232.
116. Cook RJ, Champion KM, Giometti CS. Methanol toxicity and formate oxidation in NEUT2 mice. Arch Biochem Biophys 2001;393:192-198.
117. Impraim C, Wang G, Yoshida A. Structural mutation in a major human aldehyde dehydrogenase gene results in loss of enzyme activity. Am J Hum Genet 1982;34:837-841.
118. Ikawa M, Impraim CC, Wang G, Yoshida A. Isolation and characterization of aldehyde dehydrogenase isozymes from usual and atypical human livers. J Biol Chem 1983;258:6282-6287.
119. 2 locus. Am J Hum Genet 1983;35:1107-1116.
120. Yoshida A, Huang I-Y, Ikawa M. Molecular abnormality of an inactive aldehyde dehydrogenase variant commonly found in Orientals. Proc Natl Acad Sci USA 1984;81:258-261.
121. Yoshida A, Ikawa M, Hsu LC, Tani K. Molecular abnormality and cDNA cloning of human aldehyde dehydrogenases. Alcohol 1985;2:103-106.
122. 2 allele is dominant. J Clin Invest 1989;83:314-316.
123. m aldehyde dehydrogenase in a Japanese population. Hum Genet 1994;94:217-223.
124. Yokoyama A, Muramatsu T, Ohmori T, Higuchi S, Hayashida M, Ishii H. Esophageal cancer and aldehyde dehydrogenase-2 genotypes in Japanese males. Cancer Epidemiol Biomark Prev 1996;5:99-102.
125. Yokoyama A, Muramatsu T, Ohmori T, Makuuchi H, Higuchi S, Matsushita S, Yoshino K, Maruyama K, Nakano M, Ishii H. Multiple primary esophageal and concurrent upper aerodigestive tract cancer and the aldehyde dehydrogenase-2 genotype of Japanese alcoholics. Cancer 1996;77:1986-1990.
126. Yokoyama A, Ohmori T, Muramatsu T, Higuchi S, Yokoyama T, Matsushita S, Matsumoto M, Maruyama K, Hayashida M, Ishii H. Cancer screening of upper aerodigestive tract in Japanese alcoholics with reference to drinking and smoking habits and aldehyde deydrogenase-2 genotype. Int J Cancer 1996;68:313-316.
127. Yokoyama A, Ohmori T, Muramatsu T, Yokoyama T, Okuyama K, Makuuchi H, Takahashi H, Higuchi S, Hayashida M, Maruyama K, Ishii H. Short-term follow-up after endoscopic mucosectomy of early esophageal cancer and aldehyde dehydrogenase-2 genotype in Japanese alcoholics. Cancer Epidemiol Biomark Prev 1998;7:473-476.
128. Murata M, Tagawa M, Watanabe S, Kimura H, Takeshita T, Morimoto K. Genotype difference of aldehyde dehydrogenase 2 gene in alcohol drinkers influences the incidence of Japanese colorectal cancer patients. Jpn J Cancer Res 1999;90:711-719.
129. Yokoyama A, Muramatsu T, Omori T, Matsushita S, Yoshimizu H, Higuchi S, Yokoyama T, Maruyama K, Ishii H. Alcohol and aldehyde gene polymorphisms influence susceptibility to esophageal cancer in Japanese alcoholics. Alcohol Clin Exp Res 1999;23:1705-1710.
130. Akiyama Y, Yano M, Fujiwara Y, Doki Y, Inoue M, Shiozaki H, Fujii T, Yoshino K, Monden M. Aldehyde dehydrogenase 2 gene polymorphism in patients with upper aerodigestive tract cancer. Proc Am Assoc Cancer Res 2000;41:598.
131. Chao YC, Wang LS, Hsieh TY, Chu CW, Chang FY, Chu HC. Chinese alcoholic patients with esophageal cancer are genetically different from alcoholics with acute pancreatitis and liver cirrhosis. Am J Gastroenter 2000;95:2958-2964.
132. Muto M, Hitomi Y, Ohtsu A, Ebihara S, Yoshida S, Esumi H. Association of aldehyde dehydrogenase 2 polymorphism with multiple oesophageal dysplasia in head and neck cancer patients. Gut 2000;47:256-261.
133. Kamino K, Nagasaka K, Imagawa M, Yamamoto H, Yoneda H, Ueki A, Kitamura S, Namekata K, Miki T, Ohta S. Deficiency in mitochondrial aldehyde dehydrogenase increases the risk for late-onset Alzheimer's disease in the Japanese population. Biochem Biophys Res Commun 2000;273:192-196.
134. Wang M, McIntee EJ, Cheng G, Shi Y, Villalta PW, Hecht SS. Identification of DNA adducts of acetaldehyde. Chem Res Toxicol 2000;13:1149-1157.
135. Matsuo K, Hamajima N, Shinoda M, Hatooka S, Inoue M, Takezaki T, Tajima K. Gene-environment interaction between an aldehyde dehydrogenase-2 (ALDH2) polymorphism and alcohol consumption for the risk of esophageal cancer. Carcinogenesis 2001;22:913-916.
136. Yokoyama A, Muramatsu T, Omori T, Yokoyama T, Matsushita S, Higuchi S, Maruyama K, Ishii H. Alcohol and aldehyde dehydrogenase polymorphisms and oropharyngolaryngeal, esophageal and stomach cancers in Japanese alcoholics. Carcinogenesis 2001;22:433-439.
137. Seitz HK, Matsuzaki S, Yokoyama A, Homann N, Vakevainen S, Wang XD. Alcohol and cancer. Alcohol Clin Exp Res 2001;25(Suppl 1):137S-143S.
138. Yokoyama A, Watanabe H, Fukuda H, Haneda T, Kato H, Yokoyama T, Muramatsu T, Igaki H, Tachimori Y. Multiple cancers associated with esophageal and oropharyngolaryngeal squamous cell carcinoma and the Aldehyde Dehydrogenase-2 genotype in male Japanese drinkers. Cancer Epidemiol Biomark Prev 2002;11:895-900.
139. Downes JE, Swann PG, Holmes RS. Differential corneal sensitivity to ultraviolet light among inbred strains of mice. Correlation of ultraviolet B sensitivity with aldehyde dehydrogenase deficiency. Cornea 1994;13:67-72.
140. Downes JE, Swann PG, Holmes RS. A genetic basis for corneal sensitivity to ultraviolet light among recombinant SWXJ inbred strains of mice. Curr Eye Res 1997;16:539-546.
141. Shiao T, Tran P, Siegel D, Lee J, Vasiliou V. Four amino acid changes are associated with the Aldh3a1 locus polymorphism in mice which may be responsible for corneal sensitivity to ultraviolet light. Pharmacogenetics 1999;9:145-153.
142. Pappa A, Sophos NA, Vasiliou V. Corneal and stomach expression of aldehyde dehydrogenases: From fish to mammals. Chem Biol Interact 2001;130-132:181-191.
143. + oxidoreductase in cultured fibroblasts. J Clin Invest 1991;88:1643-1648.
144. De Laurenzi V, Rogers GR, Tarcsa E, Carney G, Marekov L, Bale SJ, Compton JG, Markova N, Steinert PM, Rizzo WB. Sjögren-Larsson syndrome is caused by a common mutation in northern European and Swedish patients. J Invest Dermatol 1997;109:79-83.
145. Rizzo WB, Carney G, De Laurenzi V. A common deletion mutation in European patients with Sjögren-Larsson syndrome. Biochem Mol Med 1997;62:178-181.
146. Sillén A, Jagell S, Wadelius C. A missense mutation in the FALDH gene identified in Sjögren-Larsson syndrome patients originating from the northern part of Sweden. Hum Genet 1997;100:201-203.
147. Sillén A, Anton-Lamprecht I, Braun-Quentin C, Kraus CS, Sayli BS, Ayuso C, Jagell S, Küster W, Wadelius C. Spectrum of mutations and sequence variants in the FALDH gene in patients with Sjögren-Larsson syndrome. Hum Mutat 1998;12:377-384.
148. Rizzo WB, Carney G, Lin Z. The molecular basis of Sjögren-Larsson syndrome: Mutation analysis of the fatty aldehyde dehydrogenase gene. Am J Hum Genet 1999;65:1547-1560.
149. 1-pyrroline 5-carboxylate dehydrogenase gene cause type II hyperprolinemia. Hum Mol Genet 1998;7:1411-1415.
150. Gibson KM, Hoffmann GF, Hodson AK, Bottiglieri T, Jakobs C. 4-Hydroxybutyric acid and the clinical phenotype of succinic semialdehyde dehydrogenase deficiency, an inborn error of GABA metabolism. Neuropediatrics 1998;29:14-22.
151. Hogema BM, Akaboshi S, Taylor M, Salomons GS, Jakobs C, Schutgens RB, Wilcken B, Worthington S, Maropoulos G, Grompe M, Gibson KM. Prenatal diagnosis of succinic semialdehyde dehydrogenase deficiency: Increased accuracy employing DNA, enzyme, and metabolite analyses. Mol Genet Metab 2001;72:218-222.
152. 1-pyrroline-5-carboxylate synthase. Hum Mol Genet 2000;9:2853-2858.
153. Tuschl T, Borkhardt A. Small interfering RNAs: A revolutionary tool for the analysis of gene function and gene therapy. Mol Interv 2002;2:158-167.
154. Tephly TR. The toxicity of methanol. Life Sci 1991; 48:1031-1041.
155. Sidhu RS, Blair AH. Human liver aldehyde dehydrogenase. Esterase activity. J Biol Chem 1975;250:7894-7898.
156. Mukerjee N, Pietruszko R. Human mitochondrial aldehyde dehydrogenase substrate specificity: Comparison of esterase with dehydrogenase reaction. Arch Biochem Biophys 1992;299:23-29.
157. Devaraj VR, Sreerama L, Lee MJC, Nagasawa HT, Sládek NE. Yeast aldehyde dehydrogenase sensitivity to inhibition by chlorpropamide analogues as an indicator of human aldehyde dehydrogenase sensitivity to these agents. Adv Exp Med Biol 1996;414;155-169.
158. Pereira F, Rosenmann E, Nylen E, Kaufman M, Pinsky L, Wrogemann K. The 56 kDa androgen binding protein is an aldehyde dehydrogenase. Biochem Biophys Res Commun 1991;175:831-838.
159. Schnier JB, Kaur G, Kaiser A, Stinson SF, Sausville EA, Gardner J, Nishi K, Bradbury EM, Senderowicz AM. Identification of cytosolic aldehyde dehydrogenase 1 from non-small cell lung carcinomas as a flavopiridol-binding protein. FEBS Lett 1999;454:100-104.
160. Zhou J, Weiner H. Binding of thyroxine analogs to human liver aldehyde dehydrogenases. Eur J Biochem 1997;245:123-128.
161. r 54,000 is an aldehyde dehydrogenase and is down-regulated in mouse liver tumors and in tumor cell lines. Mol Pharmacol 1994;46:896-900.
162. Landin JS, Cohen SD, Khairallah EA. Identification of a 54-kDa mitochondrial acetaminophen-binding protein as aldehyde dehydrogenase. Toxicol Appl Pharmacol 1996;141:299-307.
163. De Luca LM. Retinoids and their receptors in differentiation, embryogenesis, and neoplasia. FASEB J 1991;5:2924-2933.
164. Hofmann C, Eichele G. Retinoids in development. In: Sporn MB, Roberts AB, Goodman DS, editors. The Retinoids: Biology, Chemistry, and Medicine, 2nd edition. New York: Raven Press; 1994. pp 387-441.
165. Gudas LJ, Sporn MB, Roberts AB. Cellular biology and biochemistry of the retinoids. In: Sporn MB, Roberts AB, Goodman DS, editors. The Retinoids: Biology, Chemistry, and Medicine, 2nd edition. New York: Raven Press; 1994. pp 443-520.
166. Duester G. Families of retinoid dehydrogenases regulating vitamin A function. Production of visual pigment and retinoic acid. Eur J Biochem 2000;267:4315-4324.
167. Eckey R, Agarwal DP, Saha N, Goedde HW. Detection and partial characterization of a variant form of cytosolic aldehyde dehydrogenase isozyme. Hum Genet 1986;72:95-97.
168. Yoshida A, Davé V, Ward RJ, Peters TJ. Cytosolic aldehyde dehydrogenase (ALDH1) variants found in alcohol flushers. Ann Hum Genet 1989;53:1-7.
169. Ueshima Y, Matsuda Y, Tsutsumi M, Takada A. Role of the aldehyde dehydrogenase-1 isozyme in the metabolism of acetaldehyde. Alcohol Alcohol 1993;28:15-19.
170. Okamura S, Ng CC, Koyama K, Takei Y, Arakawa H, Monden M, Nakamura Y. Identification of seven genes regulated by wild-type p53 in a colon cancer cell line carrying a well-controlled wild-type p53 expression system. Oncology Res 1999;11:281-285.
171. Mira-Y-Lopez R, Zheng WL, Kuppumbatti YS, Rexer B, Jing Y, Ong DE. Retinol conversion to retinoic acid is impaired in breast cancer cell lines relative to normal cells. J Cell Physiol 2000;185:302-309.
172. Sládek NE. Metabolism and pharmacokinetic behavior of cyclophosphamide and related oxazaphosphorines. In: Powis G, editor. Anticancer Drugs: Reactive Metabolism and Drug Interactions. United Kingdom: Pergamon Press; 1994. pp 79-156.
173. Sreerama L, Sládek NE. Primary breast tumor levels of suspected molecular determinants of cellular sensitivity to cyclophosphamide, ifosfamide, and certain other anticancer agents as predictors of paired metastatic tumor levels of these determinants. Rational individualization of cancer chemotherapeutic regimens. Cancer Chemother Pharmacol 2001;47:255-262.
174. Sládek NE, Kollander R, Sreerama L, Kiang DT. Cellular levels of aldehyde dehydrogenases (ALDH1A1 and ALDH3A1) as predictors of therapeutic responses to cyclophosphamide-based chemotherapy of breast cancer: A retrospective study. Rational individualization of oxazaphosphorine-based cancer chemotherapeutic regimens. Cancer Chemother Pharmacol 2002;49:309-321.
175. Sreerama L, Sládek NE. Overexpression or polycyclic aromatic hydrocarbon-mediated induction of an apparently novel class 3 aldehyde dehydrogenase in human breast adenocarcinoma cells and its relationship to oxazaphosphorine-specific acquired resistance. Adv Exp Med Biol 1993;328:99-113.
176. Sreerama L, Sládek NE. Identification of a methylcholanthrene-induced aldehyde dehydrogenase in a human breast adenocarcinoma cell line exhibiting oxazaphosphorine-specific acquired resistance. Cancer Res 1994;54:2176-2185.
177. Sreerama L, Rekha GK, Sládek NE. Phenolic antioxidant-induced overexpression of class-3 aldehyde dehydrogenase and oxazaphosphorine-specific resistance. Biochem Pharmacol 1995;49:669-675.
178. 1 gene. Proc Natl Acad Sci USA 1996;93:14960-14965.
179. Wasserman WW, Fahl WE. Functional antioxidant responsive elements. Proc Natl Acad Sci USA 1997;94: 5361-5366.
180. Itoh K, Chiba T, Takahashi S, Ishii T, Igarashi K, Katoh Y, Oyake T, Hayashi N, Satoh K, Hatayama I, Yamamoto M, Nabeshima Y-I. An Nrf2/small Maf heterodimer mediates the induction of phase II detoxifying enzyme genes through antioxidant response elements. Biochem Biophys Res Commun 1997;236:313-322.
181. Venugopal R, Jaiswal AK. Nrf2 and Nrf1 in association with Jun proteins regulate antioxidant response element-mediated expression and coordinated induction of genes encoding detoxifying enzymes. Oncogene 1998;17:3145-3156.
182. Itoh K, Wakabayashi N, Katoh Y, Ishii T, Igarashi K, Engel JD, Yamamoto M. Keap1 represses nuclear activation of antioxidant responsive elements by Nrf2 through binding to the amino-terminal Neh2 domain. Genes Dev 1999;13:76-86.
183. Burczynski ME, Lin H-K, Penning TM. Isoform-specific induction of a human aldo-keto reductase by polycyclic aromatic hydrocarbons (PAHs), electrophiles, and oxidative stress: Implications for the alternative pathway of PAH activation catalyzed by human dihydrodiol dehydrogenase. Cancer Res 1999;59:607-614.
184. Jaiswal AK. Nrf1 and Nrf2 regulate ARE-mediated expression and coordinated induction of a battery of genes encoding proteins that protect cells against oxidative stress. In: Hashimoto I, Tsuchida S, Shinkawa H, Yagihashi S, Suda T, Uitto J, editors. Molecular Medicine: Novel Findings of Gene Diagnosis, Regulation of Gene Expression, and Gene Therapy. Amsterdam: Elsevier; 1999. International Congress Series, Vol. 1172, pp 103-112.
185. Münzel PA, Schmohl S, Heel H, Kälberer K, Bock-Hennig BS, Bock KW. Induction of human UDP glucuronosyltranferases (UGT1A6, UGT1A9, and UGT2B7) by t-butylhydroquinone and 2,3,7,8-tetrachlorodibenzo-p-dioxin in Caco-2 cells. Drug Metab Dispos 1999;27:569-573.
186. Primiano T, Sutter TR, Kensler TW. Antioxidant-inducible genes. Adv Pharmacol 1997;38:293-328.
187. Itoh K, Ishii T, Wakabayashi N, Yamamoto M. Regulatory mechanisms of cellular response to oxidative stress. Free Radic Res 1999;31:319-324.
188. 10 (CYP1A1) gene. Int J Biochem 1989;21:243-252.
189. 1 (DT-diaphorase) expression in normal and tumor tissues. Cancer Metastasis Rev 1993;12:103-117.
190. Nebert DW. Drug-metabolizing enzymes in ligand-modulated transcription. Biochem Pharmacol 1994;47:25-37.
191. Sládek NE, Sreerama L, Rekha GK. Constitutive and overexpressed human cytosolic class-3 aldehyde dehydrogenases in normal and neoplastic cells/secretions. Adv Exp Med Biol 1995;372:103-114.
192. Lai ZW, Pineau T, Esser C. Identification of dioxin-responsive elements (DREs) in the 5′ regions of putative dioxin-inducible genes. Chem Biol Interact 1996;100:97-112.
193. Nebert DW, Roe AL, Dieter MZ, Solis WA, Yang Y, Dalton TP. Role of the aromatic hydrocarbon receptor and [Ah] gene battery in the oxidative stress response, cell cycle control, and apoptosis. Biochem Pharmacol 2000;59:65-85.
194. 1-aldehyde reductase. Biochem J 1998;332:21-34.
195. Shrenk D. Impact of dioxin-type induction of drug-metabolizing enzymes on the metabolism of endo- and xenobiotics. Biochem Pharmacol 1998;55:1155-1162.
196. Sládek NE. Transient induction of increased aldehyde dehydrogenase 3A1 levels in cultured human breast (adeno)carcinoma cell lines via 5′-upstream xenobiotic, and electrophile responsive elements is, respectively, estrogen receptor-dependent and -independent. Chem Biol Interact (in press).
197. Rekha GK, Sládek NE. Multienzyme-mediated stable and transient multidrug resistance and collateral sensitivity induced by xenobiotics. Cancer Chemother Pharmacol 1997;40:215-224.
198. Chan K, Kan YW. Nrf2 is essential for protection against acute pulmonary injury in mice. Proc Natl Acad Sci USA 1999;96:12731-12736.
199. Ross D, Kepa JK, Winski SL, Beall HD, Anwar A, Siegel D. NAD(P)H:quinone oxidoreductase 1 (NQO1): Chemoprotection, bioactivation, gene regulation and genetic polymorphisms. Chem Biol Interact 2000;129:77-97.
200. Sreerama L, Hedge MW, Sládek NE. Identification of a class 3 aldehyde dehydrogenase in human saliva and increased levels of this enzyme, glutathione S-transferases, and DT-diaphorase in the saliva of subjects who continually ingest large quantities of coffee or broccoli. Clin Cancer Res 1995;1:1153-1163.
201. Verhoeven DTH, Goldbohm RA, van Poppel G, Verhagen H, van den Brandt PA. Epidemiological studies on brassica vegetables and cancer risk. Cancer Epidemiol Biomark Prev 1996;5:733-748.
202. Giovannucci E. Meta-analysis of coffee consumption and risk of colorectal cancer. Am J Epidemiol 1998;147:1043-1052.
203. Vasiliou V, Kozak CA, Lindahl R, Nebert DW. Mouse microsomal class 3 aldehyde dehydrogenase: AHD3 cDNA sequence, inducibility by dioxin and clofibrate, and genetic mapping. DNA Cell Biol 1996;15:235-245.
204. International Agency for Research on Cancer. Allyl compounds, aldehydes, epoxides and peroxides. In: IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Lyons, France: IARC; 1985. Vol 36, pp 101-132.
205. International Agency for Research on Cancer. Re-evaluation of some organic chemicals, hydrazine and hydrogen peroxide. In: IARC Monographs of the Evaluation on the Carcinogenic Risk of Chemicals to Humans, Lyons, France: IARC; 1999. Vol. 71, pp 319-335.
206. Watanabe T. Mechanism of ethanol-induced bronchoconstriction in Japanese asthmatic patients. Arerugi 1991;40:1210-1217.
207. Chen Z, Zhang J, Stamler JS. Identification of the enzymatic mechanism of nitroglycerin bioactivation. Proc Natl Acad Sci USA 2002;99:8306-8311.