| Name | alcohol dehydrogenase (protein family or complex) |
|---|---|
| Synonyms | ADH; alcohol dehydrogenase; alcohol dehydrogenases |
| Name | acrolein |
|---|---|
| CAS | 2-propenal |
| PubMed | Abstract | RScore(About this table) | |
|---|---|---|---|
| 14751302 | Lapierre C, Pilate G, Pollet B, Mila I, Leple JC, Jouanin L, Kim H, Ralph J: Signatures of cinnamyl alcohol dehydrogenase deficiency in poplar lignins. Phytochemistry. 2004 Feb;65(3):313-21. |
2(0,0,0,2) | Details |
| 2741179 | Benn MH, McDiarmid RE, Majak W: In-vitro biotransformation of 3-nitropropanol (miserotoxin aglycone) by horse liver alcohol dehydrogenase. Toxicol Lett. 1989 May;47(2):165-72. At neutral pH, NPAL spontaneously decomposed to and acrolein but in the presence of ADH, NPAL was partially oxidized to 3-nitropropionic acid (NPA). |
2(0,0,0,2) | Details |
| 12184789 | Fontaine FR, Dunlop RA, Petersen DR, Burcham PC: Oxidative bioactivation of crotyl to the toxic endogenous crotonaldehyde: association of protein carbonylation with toxicity in mouse hepatocytes. Chem Res Toxicol. 2002 Aug;15(8):1051-8. This is analogous to the way allyl is converted in vivo to its toxic oxidation product, acrolein. In kinetic studies, we found that crotyl was readily oxidized by equine liver alcohol dehydrogenase, with electrospray-mass spectrometry confirming that CA was the main product formed. |
2(0,0,0,2) | Details |
| 11394713 | Karas M, Chakrabarti SK: Influence of on allyl -induced hepatotoxicity in rats. J Environ Pathol Toxicol Oncol. 2001;20(2):141-54. Pretreatment of rats with phenobarbital further significantly enhanced the formation of 2,4-dinitrophenylhydrazine (DNP)-reactive metabolite (s) (measured as DNP-acrolein adduct equivalents) in rat liver induced by AA (30.7 mg/kg) plus CF (150 mg/kg) within 1 hour following such treatment. Treatment of rats with 4-methylpyrazole (4-MP) (0.5 mmol/kg, i.p.) (an inhibitor liver alcohol dehydrogenase) for 30 minutes, followed by similar cotreatment with AA and CF, completely prevented the elevation of plasma levels of ALT and histological damage induced by cotreatment with CF and AA 24 hours following their administration. |
1(0,0,0,1) | Details |
| 11042091 | Smith CK, Moore CA, Elahi EN, Smart AT, Hotchkiss SA: Human skin absorption and metabolism of the contact allergens, and cinnamic Toxicol Appl Pharmacol. 2000 Nov 1;168(3):189-99. It has been hypothesized that cinnamic is a "prohapten" that requires metabolic activation, presumably by oxidoreductase enzymes such as alcohol dehydrogenase (ADH) or cytochrome P450 2E1 (CYP2E1), to the protein-reactive (a hapten). |
1(0,0,0,1) | Details |
| 11486835 | Smith CK, Cheung C, Elahi EN, Hotchkiss SA: High-performance liquid chromatography method for the quantification of non-radiolabelled cinnamic compounds in analytes derived from human skin absorption and metabolism experiments. J Chromatogr B Biomed Sci Appl. 2001 Jul 15;758(2):249-64. Skin absorption and metabolism experiments were performed in the absence and presence of the alcohol dehydrogenase inhibitor, pyrazole. |
1(0,0,0,1) | Details |
| 9972923 | Lee JY, Chung SM, Lee MY, Chung JH: co-exposure increases lethality of allyl in male Sprague-Dawley rats. J Toxicol Environ Health A. 1999 Jan 22;56(2):121-30. These data suggest a possible role for a metabolite of allyl acrolein, in the increased lethality of allyl and coexposure in rats. Since allyl and are both metabolized by alcohol dehydrogenase (ADH) and aldehyde dehydrogenase (ALDH), could affect allyl- induced toxicity under in vivo coexposure conditions. |
1(0,0,0,1) | Details |
| 2596853 | Silva JM, O'Brien PJ: Allyl - and acrolein-induced toxicity in isolated rat hepatocytes. . Arch Biochem Biophys. 1989 Dec;275(2):551-8. Incubation of isolated hepatocytes with allyl results in GSH depletion and subsequent cytotoxicity which is prevented by pyrazole, an inhibitor of alcohol dehydrogenase. |
1(0,0,0,1) | Details |
| 19420690 | Zucca P, Littarru M, Rescigno A, Sanjust E: Cofactor recycling for selective enzymatic biotransformation of to cinnamyl Biosci Biotechnol Biochem. 2009 May;73(5):1224-6. Epub 2009 May 7. Yeast alcohol dehydrogenase was used in a substrate-coupled process with cofactor recycling. |
1(0,0,0,1) | Details |
| 2886987 | Penttila KE, Makinen J, Lindros KO: Allyl liver injury: suppression by and relation to transient depletion. Pharmacol Toxicol. 1987 May;60(5):340-4. Oxidation of AIOH to acrolein was accompanied by an equally rapid, but only transient depletion of hepatic reduced glutathione (GSH). Inhibition of alcohol dehydrogenase by 4-methyl pyrazole completely counteracted these effects. |
1(0,0,0,1) | Details |
| 2714629 | Pelmont J, Tournesac C, Mliki A, Barrelle M, Beguin C: A new bacterial alcohol dehydrogenase active on degraded lignin and several low molecular weight aromatic compounds. FEMS Microbiol Lett. 1989 Jan 1;48(1):109-13. |
1(0,0,0,1) | Details |
| 1471152 | Horvath JJ, Witmer CM, Witz G: Nephrotoxicity of the 1:1 acrolein- adduct in the rat. Toxicol Appl Pharmacol. 1992 Dec;117(2):200-7. |
0(0,0,0,0) | Details |
| 12482448 | Fournand D, Cathala B, Lapierre C: Initial steps of the peroxidase-catalyzed polymerization of coniferyl and/or sinapyl capillary zone electrophoresis study of pH effect. Phytochemistry. 2003 Jan;62(2):139-46. The major dimer observed was the beta,beta'-di-sinapyl a red-brown exhibiting compound which might partly participate in the red coloration usually observed in cinnamyl alcohol dehydrogenase-deficient angiosperms. |
1(0,0,0,1) | Details |
| 12615359 | Cheung C, Hotchkiss SA, Pease CK: Cinnamic compound metabolism in human skin and the role metabolism may play in determining relative sensitisation potency. J Dermatol Sci. 2003 Feb;31(1):9-19. It is postulated that can be detoxified by aldehyde dehydrogenase (ALDH) to and/or by alcohol dehydrogenase (ADH) to cinnamic |
1(0,0,0,1) | Details |
| 16347373 | Osman YA, Ingram LO: Zymomonas mobilis Mutants with an Increased Rate of Production. . Appl Environ Microbiol. 1987 Jul;53(7):1425-1432. Alcohol dehydrogenase isozymes were altered in both new strains and no longer catalyzed the oxidation of allyl into the toxic product acrolein. |
0(0,0,0,0) | Details |
| 8905240 | Atzori L, Congiu L: Effect of on allyl hepatotoxicity. Drug Metabol Drug Interact. 1996;13(2):87-98. In vitro, but not in vivo, inhibited the activity of alcohol dehydrogenase (ADH), the key enzyme in the conversion of AA into the toxic metabolite acrolein. |
0(0,0,0,0) | Details |
| 2565200 | Kershaw WC, Barsotti DA, Leonard TB, Dent JG, Lage GL: Methoxyflurane enhances allyl hepatotoxicity in rats. Drug Metab Dispos. 1989 Mar-Apr;17(2):117-22. The possibility that methoxyflurane increases alcohol dehydrogenase-dependent oxidation of allyl to acrolein, the proposed toxic metabolite, was evaluated by measuring the rate of acrolein formation in the presence of allyl and liver cytosol. |
94(1,1,3,4) | Details |
| 3377801 | Haenen GR, Vermeulen NP, Tai Tin Tsoi JN, Ragetli HM, Timmerman H, Blast A: Activation of the microsomal glutathione-S-transferase and reduction of the dependent protection against lipid peroxidation by acrolein. Biochem Pharmacol. 1988 May 15;37(10):1933-8. Administration of 375 mg pyrazole/kg, an inhibitor of the alcohol dehydrogenase, thus reducing the acrolein formation, prevented the in vivo stimulation of GSH-tr by allyl |
87(1,1,2,2) | Details |
| 10092940 | Trivic S, Leskovac V: Novel substrates of yeast alcohol dehydrogenase--4. Biochem Mol Biol Int. 1999 Jan;47(1):1-8. In addition, it was found that acrolein is a potent inhibitor of yeast alcohol dehydrogenase. |
83(1,1,1,3) | Details |
| 11835630 | Burcham PC, Fontaine F: Extensive protein carbonylation precedes acrolein-mediated cell death in mouse hepatocytes. J Biochem Mol Toxicol. 2001;15(6):309-16. Allyl hepatotoxicity is mediated by an alcohol dehydrogenase-derived biotranformation product, acrolein. |
82(1,1,1,2) | Details |
| 2489200 | Atzori L, Dore M, Congiu L: Aspects of allyl toxicity. Drug Metabol Drug Interact. 1989;7(4):295-319. AA is inactive per se and its toxic expression is modulated by its alcohol dehydrogenase (ADH) oxidation to form acrolein, which is responsible for the hepatotoxic action. |
81(1,1,1,1) | Details |
| 8937432 | Glascott PA Jr, Gilfor E, Serroni A, Farber JL: Independent antioxidant action of vitamins E and C in cultured rat hepatocytes intoxicated with allyl Biochem Pharmacol. 1996 Oct 25;52(8):1245-52. Alcohol dehydrogenase rapidly metabolizes allyl to the potent electrophile acrolein. |
81(1,1,1,1) | Details |
| 10905545 | Burcham PC, Kerr PG, Fontaine F: The antihypertensive hydralazine is an efficient scavenger of acrolein. . Redox Rep. 2000;5(1):47-9. Hydralazine also protected isolated mouse hepatocytes against cell killing by allyl which undergoes in situ alcohol dehydrogenase-catalysed conversion to acrolein. |
81(1,1,1,1) | Details |
| 2930914 | Ohno Y, Ormstad K, Ross D, Orrenius S: Mechanism of allyl toxicity and protective effects of low-molecular-weight thiols studied with isolated rat hepatocytes. Toxicol Appl Pharmacol. 1985 Apr;78(2):169-79. The toxicity was prevented by inhibitors of alcohol dehydrogenase and augmented by the aldehyde dehydrogenase inhibitor disulfiram, suggesting that the toxic metabolite was the reactive acrolein. |
62(0,2,2,2) | Details |
| 7943667 | Mapoles JE, Iwahashi M, Lucas D, Zimmerman BT, Simon FR: exposure causes growth inhibition in a Chinese hamster ovary cell line that expresses alcohol dehydrogenase. Alcohol Clin Exp Res. 1994 Jun;18(3):632-9. Cells expressing alcohol dehydrogenase were identified by screening with allyl which is metabolized by alcohol dehydrogenase to the toxic acrolein. |
37(0,1,1,7) | Details |
| 2933316 | Belinsky SA, Bradford BU, Forman DT, Glassman EB, Felder MR, Thurman RG: Hepatotoxicity due to allyl in deermice depends on alcohol dehydrogenase. Hepatology. 1985 Nov-Dec;5(6):1179-82. Thus, these data demonstrate that metabolism of allyl to acrolein by alcohol dehydrogenase is obligatory for the hepatotoxicity of allyl |
34(0,1,1,4) | Details |
| 3421708 | Miccadei S, Nakae D, Kyle ME, Gilfor D, Farber JL: Oxidative cell injury in the killing of cultured hepatocytes by allyl Arch Biochem Biophys. 1988 Sep;265(2):302-10. The killing of cultured hepatocytes by allyl depended on the metabolism of this hepatotoxin by alcohol dehydrogenase to the reactive electrophile, acrolein. |
32(0,1,1,2) | Details |
| 3156001 | Ohno Y, Jones TW, Ormstad K: Allyl toxicity in isolated renal epithelial cells: protective effects of low molecular weight thiols. Chem Biol Interact. 1985 Jan;52(3):289-99. The sensitivity of female rat renal cells appears to relate to the higher activity of alcohol dehydrogenase found in the female rat kidney, which metabolizes allyl to the highly reactive acrolein. |
32(0,1,1,2) | Details |
| 9169072 | Sneed RA, Grimes SD, Schultze AE, Brown AP, Ganey PE: Bacterial endotoxin enhances the hepatotoxicity of allyl . Toxicol Appl Pharmacol. 1997 May;144(1):77-87. On the other hand, pretreatment with 4-methylpyrazole, an inhibitor of alcohol dehydrogenase, abolished the hepatotoxicity of allyl in LPS-treated rats, indicating that production of acrolein was needed for LPS enhancement of the toxicity of allyl |
31(0,1,1,1) | Details |
| 2795457 | Mitchell DY, Petersen DR: Metabolism of the -acrolein adduct, S-(2-aldehydo-ethyl) by rat liver and aldehyde dehydrogenase. J Pharmacol Exp Ther. 1989 Oct;251(1):193-8. The oxidative and reductive metabolism of the acrolein- adduct, S-(2,aldehydo-ethyl) by rat liver aldehyde dehydrogenase (ALDH) and alcohol dehydrogenase (ADH) was characterized. |
31(0,1,1,1) | Details |
| 16930132 | Hao Q, Maret W: Aldehydes release zinc from proteins. FEBS J. 2006 Sep;273(18):4300-10. Epub 2006 Aug 23. Stoichiometric amounts of acrolein release zinc from zinc-thiolate coordination sites in proteins such as metallothionein and alcohol dehydrogenase. |
6(0,0,1,1) | Details |
| 15829607 | Bomati EK, Noel JP: Structural and kinetic basis for substrate selectivity in Populus tremuloides sinapyl alcohol dehydrogenase. Plant Cell. 2005 May;17(5):1598-611. Epub 2005 Apr 13. |
4(0,0,0,4) | Details |
| 17123572 | Pacaud-Mercier K, Blaghen M, Lee KM, Tritsch D, Biellmann JF: Electron transfer from bound to horse liver alcohol dehydrogenase (NAD+ dependent dehydrogenase): visualisation of the activity in the enzyme crystals and adsorption of formazan derivatives by these crystals. Bioorg Chem. 2007 Feb;35(1):59-67. Epub 2006 Nov 22. |
3(0,0,0,3) | Details |
| 11449052 | Li L, Cheng XF, Leshkevich J, Umezawa T, Harding SA, Chiang VL: The last step of syringyl monolignol biosynthesis in angiosperms is regulated by a novel gene encoding sinapyl alcohol dehydrogenase. Plant Cell. 2001 Jul;13(7):1567-86. |
3(0,0,0,3) | Details |
| 9377488 | Logemann E, Reinold S, Somssich IE, Hahlbrock K: A novel type of pathogen defense-related cinnamyl alcohol dehydrogenase. . Biol Chem. 1997 Aug;378(8):909-13. |
3(0,0,0,3) | Details |
| 3801056 | Jaeschke H, Kleinwaechter C, Wendel A: The role of acrolein in allyl -induced lipid peroxidation and liver cell damage in mice. Biochem Pharmacol. 1987 Jan 1;36(1):51-7. About 80% of the cytosolic alcohol dehydrogenase activity and about 50% of the microsomal P450-content were destroyed. |
2(0,0,0,2) | Details |