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Chemical Compound Review

propanal     propanal

Synonyms: Propional, Propaldehyde, Propanaldehyde, Propionaldehyd, Propylaldehyde, ...
 
 
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Disease relevance of propanal

 

High impact information on propanal

  • Messenger RNA levels correlated well with hALDH-1 protein levels and enzyme activities (1.5-13.6 milliunits/mg with propionaldehyde/NAD+ substrate, compared to < 1 milliunit/mg in controls) in individual clonal transfectant lines, and slot blot analysis confirmed the presence of the transfected cDNA [4].
  • The dehydrogenase activity of the mitochondrial isozyme (E2) of human liver aldehyde dehydrogenase was stimulated about 2-fold by the presence of low concentrations (about 120-140 microM) of Mg2+ in the assay at pH 7.0 using propionaldehyde as substrate [5].
  • To investigate the role of this enzyme in GTN tolerance, cumulative GTN concentration-response curves were obtained for both GTN-tolerant and -nontolerant rat aortic rings treated with the ALDH inhibitor cyanamide or the ALDH substrate propionaldehyde [6].
  • This work describes a novel approach for the analysis of selected aldehydes (formaldehyde, acetaldehyde, propionaldehyde, and acrolein) and acetone in environmental samples using micellar electrokinetic chromatography (MEKC) [7].
  • Conversely, purified rabbit 2E1 exhibited K(m) and V(max) values for depropylation of 52 microM and 13.4 nmol propionaldehyde/min/nmol P450, respectively [8].
 

Chemical compound and disease context of propanal

 

Biological context of propanal

 

Anatomical context of propanal

 

Associations of propanal with other chemical compounds

 

Gene context of propanal

  • The ALDH III isozymes accounted for more than 80% of the total ALDH activities in gastric mucosa and exhibited Km values in the millimolar range for propionaldehyde at pH 9 [26].
  • Consistent with this hypothesis, the inhibitory effects of acetaldehyde and propionaldehyde on the growth of this polA mutant were demonstrated [27].
  • The kcat value for the oxidation of propionaldehyde by sheep liver cytosolic aldehyde dehydrogenase increased 3-fold, from 0.16 s-1 at pH 7.6 to 0.49 s-1 at pH 5.2, in parallel with the increase in the rate of displacement of NADH from binary enzyme.NADH complexes [12].
  • Reduction of glutathionyl propanal [gammaGlu-Cys(propanal)-Gly] was more efficient than that of Gly-Cys(propanal)-Gly and gamma-aminobutyric acid-Cys(propanal)-Gly suggesting a possible interaction between alpha-carboxyl of the conjugate and AR [28].
  • However, subsequent analysis of hALDH2 activity toward propionaldehyde revealed that both 4ONE and the oxidation product, 4ONEA, were potent, irreversible inhibitors of the enzyme [29].
 

Analytical, diagnostic and therapeutic context of propanal

  • Microgram per m(3) (sub-ppb) levels of the aliphatic aldehydes, propanal, 1-butanal, 1-heptanal, and 1-hexanal, in ambient air were successfully determined by HPLC separation with fluorometric detection [30].
  • Forearm cutaneous blood flow was monitored continuously by laser Doppler velocimetry in 12 normal human subjects before and after a 5-min topical challenge with 5 M propionaldehyde [31].

References

  1. Structural rationalization for the lack of stereospecificity in coenzyme B12-dependent diol dehydratase. Shibata, N., Nakanishi, Y., Fukuoka, M., Yamanishi, M., Yasuoka, N., Toraya, T. J. Biol. Chem. (2003) [Pubmed]
  2. Aldehyde dehydrogenase activities in hepatocyte nodules and hepatocellular carcinomas from Wistar rats. Ritter, E., Eriksson, L.C. Carcinogenesis (1985) [Pubmed]
  3. PduP is a coenzyme-a-acylating propionaldehyde dehydrogenase associated with the polyhedral bodies involved in B12-dependent 1,2-propanediol degradation by Salmonella enterica serovar Typhimurium LT2. Leal, N.A., Havemann, G.D., Bobik, T.A. Arch. Microbiol. (2003) [Pubmed]
  4. De novo expression of transfected human class 1 aldehyde dehydrogenase (ALDH) causes resistance to oxazaphosphorine anti-cancer alkylating agents in hamster V79 cell lines. Elevated class 1 ALDH activity is closely correlated with reduction in DNA interstrand cross-linking and lethality. Bunting, K.D., Townsend, A.J. J. Biol. Chem. (1996) [Pubmed]
  5. Interaction of Mg2+ with human liver aldehyde dehydrogenase. I. Species difference in the mitochondrial isozyme. Vallari, R.C., Pietruszko, R. J. Biol. Chem. (1984) [Pubmed]
  6. Role of mitochondrial aldehyde dehydrogenase in nitrate tolerance. DiFabio, J., Ji, Y., Vasiliou, V., Thatcher, G.R., Bennett, B.M. Mol. Pharmacol. (2003) [Pubmed]
  7. Determination of low-aliphatic aldehydes indoors by micellar electrokinetic chromatography using sample dissolution manipulation for signal enhancement. Pereira, E.A., Cardoso, A.A., Tavares, M.F. Electrophoresis (2003) [Pubmed]
  8. Identification of the human liver microsomal cytochrome P450s involved in the metabolism of N-nitrosodi-n-propylamine. Teiber, J.F., Hollenberg, P.F. Carcinogenesis (2000) [Pubmed]
  9. Aldehyde metabolism in the human lens. Jedziniak, J., Rokita, J. Exp. Eye Res. (1983) [Pubmed]
  10. Purification and properties of methanol dehydrogenase from Methylocystis sp. GB 25. Grosse, S., Wendlandt, K.D., Kleber, H.P. J. Basic Microbiol. (1997) [Pubmed]
  11. Synergistic effect of chlorpromazine and alkanals on the human red blood cells. Makita, Y., Vercesi, A.E., Haun, M., Durán, N. An. Acad. Bras. Cienc. (1981) [Pubmed]
  12. Steady-state and pre-steady-state kinetics of propionaldehyde oxidation by sheep liver cytosolic aldehyde dehydrogenase at pH 5.2. Evidence that the release of NADH remains rate-limiting in the enzyme mechanism at acid pH values. Hill, J.P., Blackwell, L.F., Buckley, P.D., Motion, R.L. Biochemistry (1991) [Pubmed]
  13. Genetic characterization of the pdu operon: use of 1,2-propanediol in Salmonella typhimurium. Walter, D., Ailion, M., Roth, J. J. Bacteriol. (1997) [Pubmed]
  14. Prodrugs as drug delivery systems XXV: Hydrolysis of oxazolidines--a potential new prodrug type. Johansen, M., Bundgaard, H. Journal of pharmaceutical sciences. (1983) [Pubmed]
  15. Purification and properties of aldose reductase and aldehyde reductase II from human erythrocyte. Das, B., Srivastava, S.K. Arch. Biochem. Biophys. (1985) [Pubmed]
  16. Oxidation of N-butyl-N-(3-formylpropyl)nitrosamine to N-butyl-N-(3-carboxypropyl)nitrosamine in rat liver and inhibition by disulfiram. Irving, C.C. Carcinogenesis (1988) [Pubmed]
  17. Identification of 4-(N,N-dipropylamino)benzaldehyde as a potent, reversible inhibitor of mouse and human class I aldehyde dehydrogenase. Russo, J., Chung, S., Contreras, K., Lian, B., Lorenz, J., Stevens, D., Trousdell, W. Biochem. Pharmacol. (1995) [Pubmed]
  18. Comparative subcellular distribution of aldehyde dehydrogenase in rat, mouse and rabbit liver. Lindahl, R., Evces, S. Biochem. Pharmacol. (1984) [Pubmed]
  19. Biotransformations of R-(+)-pulegone and menthofuran in vitro: chemical basis for toxicity. Madyastha, K.M., Raj, C.P. Biochem. Biophys. Res. Commun. (1990) [Pubmed]
  20. Human brain: aldehyde dehydrogenase activity and isozyme distribution in different areas. Pietruszko, R., Meier, J., Major, L.F., Saini, N., Manz, H., Hawley, R.J. Alcohol (1984) [Pubmed]
  21. Kinetic properties of highly purified preparations of sheep liver cytoplasmic aldehyde dehydrogenase. Hart, G.J., Dickinson, F.M. Biochem. J. (1982) [Pubmed]
  22. Effect of pyrophosphate ions and alkaline pH on the kinetics of propionaldehyde oxidation by sheep liver cytosolic aldehyde dehydrogenase. Hill, J.P., Buckley, P.D., Blackwell, L.F., Motion, R.L. Biochem. J. (1991) [Pubmed]
  23. The binding of NADH to cytoplasmic aldehyde dehydrogenase after modification with p-nitrophenyl dimethylcarbamate. Kitson, T.M. Biochem. J. (1989) [Pubmed]
  24. Drug metabolism in isolated proximal tubule cells: aldehyde dehydrogenase. Hjelle, J.T., Petersen, D.R., Hjelle, J.J. J. Pharmacol. Exp. Ther. (1983) [Pubmed]
  25. Organ-specific expressions and chromosomal locations of two mitochondrial aldehyde dehydrogenase genes from rice (Oryza sativa L.), ALDH2a and ALDH2b. Tsuji, H., Tsutsumi, N., Sasaki, T., Hirai, A., Nakazono, M. Gene (2003) [Pubmed]
  26. Human stomach alcohol and aldehyde dehydrogenases (ALDH): a genetic model proposed for ALDH III isozymes. Yin, S.J., Cheng, T.C., Chang, C.P., Chen, Y.J., Chao, Y.C., Tang, H.S., Chang, T.M., Wu, C.W. Biochem. Genet. (1988) [Pubmed]
  27. DNA polymerase I function is required for the utilization of ethanolamine, 1,2-propanediol, and propionate by Salmonella typhimurium LT2. Rondon, M.R., Horswill, A.R., Escalante-Semerena, J.C. J. Bacteriol. (1995) [Pubmed]
  28. Selective recognition of glutathiolated aldehydes by aldose reductase. Ramana, K.V., Dixit, B.L., Srivastava, S., Balendiran, G.K., Srivastava, S.K., Bhatnagar, A. Biochemistry (2000) [Pubmed]
  29. Inhibition of human mitochondrial aldehyde dehydrogenase by 4-hydroxynon-2-enal and 4-oxonon-2-enal. Doorn, J.A., Hurley, T.D., Petersen, D.R. Chem. Res. Toxicol. (2006) [Pubmed]
  30. Polymer-mediated extraction of the fluorescent compounds derived by Hantzsch reaction with dimedone for the sensitive determination of aliphatic aldehydes in air. Saitoh, T., Suzuki, S., Hiraide, M. Journal of chromatography. A (2006) [Pubmed]
  31. Periodic cutaneous blood flow during aldehyde-provoked hyperemia. Wilkin, J.K. Microvasc. Res. (1988) [Pubmed]
 
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