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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

ACROLEIN     prop-2-enal

Synonyms: Aerolein, Akrolein, Aqualin, Acraldehyde, Acrylaldehyde, ...
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Disease relevance of acrylaldehyde

  • Finally, for M161V, an InhA mutation that correlates with resistance to the common biocide triclosan in Mycobacterium smegmatis, binding to form the initial EI complex is significantly weakened, explaining why this mutant inactivates more slowly than WT InhA when incubated with INH, NADH, and KatG [1].
  • The biocide triclosan selects Stenotrophomonas maltophilia mutants that overproduce the SmeDEF multidrug efflux pump [2].
  • Autolysis contributed to ADBAC and DDAC lethality, although high biocide concentrations may have inhibited autolytic enzyme activity [3].
  • Groups of guinea pigs received 9 induction doses of the biocide, 3 times a week, at concentrations ranging from 25-2000 ppm a.i. These guinea pigs were challenged with the biocide at concentrations ranging from 20-2000 ppm a.i., and the application sites were scored for erythema 24 and 48 h after the challenge [4].
  • Electrical enhancement of biocide efficacy against Pseudomonas aeruginosa biofilms [5].

Psychiatry related information on acrylaldehyde


High impact information on acrylaldehyde


Chemical compound and disease context of acrylaldehyde

  • OBJECTIVES: Polyquaternium-1 (PQ-1) is a biocide used commercially in a contact lens disinfecting solution, 'Opti-Free Express (Alcon) Multi-Purpose Disinfecting Solution'. The genetic basis for resistance of Serratia marcescens to PQ-1 was investigated using a random transposon-based mutagenesis approach [11].
  • The industrial biocide chloracetamide-N-metholol (CAM) has been shown to be non-mutagenic to 6 strains of Salmonella using both the plate-incorporation and a pre-incubation test protocol [12].
  • An optimized procedure of covalent glucose oxidase, urease, Bacillus subtilis alpha-amylase and Bacillus licheniformis alpha-amylase immobilization on paramagnetic, non-porous, polyacrolein beads is presented [13].
  • Sensitization either to this biocide and/or formaldehyde allergy was considered to have been likely to have made a contribution to the workers' dermatitis [14].
  • CONCLUSIONS: Successful treatment of a chronic Lecythophora hoffmannii fungal mastoiditis involved a combination of radical surgical removal of all apparent infected tissue along with local treatments with polyhexamethylene biguanide, a common swimming pool biocide agent under the brand name Baquacil (Avecia, Manchester, United Kingdom) [15].

Biological context of acrylaldehyde

  • Effective disinfection requires applied biocide concentration that increases quadratically or exponentially with biofilm thickness [16].
  • Similar treatments with the lipid peroxidation products acrolein (ACR) and 4-oxononenal (4-ONE) resulted in 60 and 100% inhibition, respectively, suggesting inactivation of the chaperone via Cys modification [17].
  • Decontamination treatments of burning and biocide application, alone and in combination with tillage, were evaluated for their ability to reduce populations of bacteria applied to the leaves of plants in field plots [18].
  • This study demonstrates that Legionella spp. are present in tropical air-conditioning cooling systems and that, without continuous biocide treatment, they may reach densities that present a health risk [19].
  • Acquired resistance arises through mutation or via the acquisition of plasmids or transposons; efflux of biocide is a major mechanism, although plasmid-mediated inactivation has also been shown to occur [20].

Anatomical context of acrylaldehyde


Associations of acrylaldehyde with other chemical compounds

  • It is significant that the phosphonium biocide containing double decyl groups exhibited the broadest spectrum of activity against microorganisms tested and showed the greatest bacteriostatic activity against MRSA (MIC = 0.78 micrograms/ml) [26].
  • Triclosan is a biocide currently used in a plethora of consumer and medical products that has recently been loaded into a ureteral stent [27].
  • Alpha,beta-unsaturated aldehydes such as acrolein (ACR) and crotonaldehyde (CRO) have been shown previously in our laboratory to inhibit the production of superoxide anion radical (O2-) by stimulated phagocytic cells in vitro in a dose-related manner [21].
  • Biofilms, homoserine lactones and biocide susceptibility [28].
  • The dispersion-deficient phenotype of the bdlA mutant was confirmed by treatment with the biocide H(2)O(2) and by microscopic observations [29].

Gene context of acrylaldehyde

  • The layered plastic film stained for carbonyls and for amyloid (cross-beta structures) suggesting a polyacrolein-albumin colloidal mixture [6].
  • We also show that the toxic actions of this biocide are zinc dependent and require the activation of p44/42 extracellular signal-regulated kinase (ERK) via a 12-lipoxygenase-mediated pathway [30].
  • Abeta (1-42) induces membrane lipid peroxidation, and 4-hydroxynonenal (HNE) and 2-propenal (acrolein) are the two reactive products of lipid peroxidation, which structurally modify proteins by covalent interaction and inhibit enzyme function [31].
  • In addition, in PMN and PAM preincubated with 5-40 microM ACR, there was a dose-related inhibition in the rate of O2- production with no effect on the lag time as measured by cytochrome c reduction [21].
  • An increase of biocide incorporation in the PS/DVB beads was accompanied by a corresponding enhancement of its concentration in liquid mixtures [32].

Analytical, diagnostic and therapeutic context of acrylaldehyde


  1. The isoniazid-NAD adduct is a slow, tight-binding inhibitor of InhA, the Mycobacterium tuberculosis enoyl reductase: adduct affinity and drug resistance. Rawat, R., Whitty, A., Tonge, P.J. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  2. The biocide triclosan selects Stenotrophomonas maltophilia mutants that overproduce the SmeDEF multidrug efflux pump. Sanchez, P., Moreno, E., Martinez, J.L. Antimicrob. Agents Chemother. (2005) [Pubmed]
  3. Action of Disinfectant Quaternary Ammonium Compounds against Staphylococcus aureus. Ioannou, C.J., Hanlon, G.W., Denyer, S.P. Antimicrob. Agents Chemother. (2007) [Pubmed]
  4. Kathon biocide: manifestation of delayed contact dermatitis in guinea pigs is dependent on the concentration for induction and challenge. Chan, P.K., Baldwin, R.C., Parsons, R.D., Moss, J.N., Stiratelli, R., Smith, J.M., Hayes, A.W. J. Invest. Dermatol. (1983) [Pubmed]
  5. Electrical enhancement of biocide efficacy against Pseudomonas aeruginosa biofilms. Blenkinsopp, S.A., Khoury, A.E., Costerton, J.W. Appl. Environ. Microbiol. (1992) [Pubmed]
  6. Albumin-bound polyacrolein: implications for Alzheimer's disease. Seidler, N.W., Yeargans, G.S. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
  7. The involvement of cell-to-cell signals in the development of a bacterial biofilm. Davies, D.G., Parsek, M.R., Pearson, J.P., Iglewski, B.H., Costerton, J.W., Greenberg, E.P. Science (1998) [Pubmed]
  8. Health impacts of environmental mycobacteria. Primm, T.P., Lucero, C.A., Falkinham, J.O. Clin. Microbiol. Rev. (2004) [Pubmed]
  9. Mechanisms of biofilm resistance to antimicrobial agents. Mah, T.F., O'Toole, G.A. Trends Microbiol. (2001) [Pubmed]
  10. High-dose chemotherapy-induced platelet defect: inhibition of platelet signal transduction pathways. Karolak, L., Chandra, A., Khan, W., Marks, B., Petros, W.P., Peters, W.P., Greenberg, C.S., Hannun, Y.A. Mol. Pharmacol. (1993) [Pubmed]
  11. Identification of genes involved in the susceptibility of Serratia marcescens to polyquaternium-1. Codling, C.E., Jones, B.V., Mahenthiralingam, E., Russell, A.D., Maillard, J.Y. J. Antimicrob. Chemother. (2004) [Pubmed]
  12. Chloracetamide-N-metholol: an example of an in vitro and in vivo clastogen which is non-mutagenic to Salmonella. Ashby, J., Richardson, C.R., Lefevre, P.A., Callander, R.D., Styles, J.A. Mutat. Res. (1985) [Pubmed]
  13. Covalent enzyme immobilization on paramagnetic polyacrolein beads. Varlan, A.R., Sansen, W., Van Loey, A., Hendrickx, M. Biosensors & bioelectronics. (1996) [Pubmed]
  14. Occupational allergic contact dermatitis from N,N-methylene-bis-5-methyl-oxazolidine in coolant oils. Madan, V., Beck, M.H. Contact Derm. (2006) [Pubmed]
  15. Novel use of a swimming pool biocide in the treatment of a rare fungal mastoiditis. Chang, C.Y., Schell, W.A., Perfect, J.R., Hulka, G.F. Laryngoscope (2005) [Pubmed]
  16. Adaptive responses to antimicrobial agents in biofilms. Szomolay, B., Klapper, I., Dockery, J., Stewart, P.S. Environ. Microbiol. (2005) [Pubmed]
  17. Cysteine modification by lipid peroxidation products inhibits protein disulfide isomerase. Carbone, D.L., Doorn, J.A., Kiebler, Z., Petersen, D.R. Chem. Res. Toxicol. (2005) [Pubmed]
  18. Efficacy of burning, tillage, and biocides in controlling bacteria released at field sites and effects on indigenous bacteria and fungi. Donegan, K., Fieland, V., Fowles, N., Ganio, L., Seidler, R. Appl. Environ. Microbiol. (1992) [Pubmed]
  19. Legionella spp. in Puerto Rico cooling towers. Negrón-Alvíra, A., Pérez-Suarez, I., Hazen, T.C. Appl. Environ. Microbiol. (1988) [Pubmed]
  20. Mechanisms of bacterial insusceptibility to biocides. Russell, A.D. American journal of infection control. (2001) [Pubmed]
  21. Inhibition by reactive aldehydes of superoxide anion radical production from stimulated polymorphonuclear leukocytes and pulmonary alveolar macrophages. Effects on cellular sulfhydryl groups and NADPH oxidase activity. Witz, G., Lawrie, N.J., Amoruso, M.A., Goldstein, B.D. Biochem. Pharmacol. (1987) [Pubmed]
  22. Methylisothiazolinone, a neurotoxic biocide, disrupts the association of SRC family tyrosine kinases with focal adhesion kinase in developing cortical neurons. He, K., Huang, J., Lagenaur, C.F., Aizenman, E. J. Pharmacol. Exp. Ther. (2006) [Pubmed]
  23. Chlorhexidine-induced ultrastructural alterations in oral biofilm. Vitkov, L., Hermann, A., Krautgartner, W.D., Herrmann, M., Fuchs, K., Klappacher, M., Hannig, M. Microsc. Res. Tech. (2005) [Pubmed]
  24. Adaptation of Pseudomonas aeruginosa ATCC 15442 to didecyldimethylammonium bromide induces changes in membrane fatty acid composition and in resistance of cells. Méchin, L., Dubois-Brissonnet, F., Heyd, B., Leveau, J.Y. J. Appl. Microbiol. (1999) [Pubmed]
  25. Deoxyribonucleic acid (DNA) damage induced by bleomycin-Fe(II) in vitro: formation of 8-hydroxyguanine residues in DNA. Kohda, K., Kasai, H., Ogawa, T., Suzuki, T., Kawazoe, Y. Chem. Pharm. Bull. (1989) [Pubmed]
  26. Synthesis and antimicrobial activity of dimethyl- and trimethyl-substituted phosphonium salts with alkyl chains of various lengths. Kanazawa, A., Ikeda, T., Endo, T. Antimicrob. Agents Chemother. (1994) [Pubmed]
  27. Triclosan loaded ureteral stents decrease proteus mirabilis 296 infection in a rabbit urinary tract infection model. Cadieux, P.A., Chew, B.H., Knudsen, B.E., Dejong, K., Rowe, E., Reid, G., Denstedt, J.D. J. Urol. (2006) [Pubmed]
  28. Biofilms, homoserine lactones and biocide susceptibility. MacLehose, H.G., Gilbert, P., Allison, D.G. J. Antimicrob. Chemother. (2004) [Pubmed]
  29. BdlA, a Chemotaxis Regulator Essential for Biofilm Dispersion in Pseudomonas aeruginosa. Morgan, R., Kohn, S., Hwang, S.H., Hassett, D.J., Sauer, K. J. Bacteriol. (2006) [Pubmed]
  30. In vitro neurotoxicity of methylisothiazolinone, a commonly used industrial and household biocide, proceeds via a zinc and extracellular signal-regulated kinase mitogen-activated protein kinase-dependent pathway. Du, S., McLaughlin, B., Pal, S., Aizenman, E. J. Neurosci. (2002) [Pubmed]
  31. Protection against amyloid beta-peptide (1-42)-induced loss of phospholipid asymmetry in synaptosomal membranes by tricyclodecan-9-xanthogenate (D609) and ferulic acid ethyl ester: implications for Alzheimer's disease. Mohmmad Abdul, H., Butterfield, D.A. Biochim. Biophys. Acta (2005) [Pubmed]
  32. Incorporation of low molecular weight biocides into polystyrene-divinyl benzene beads with controlled release characteristics. Iconomopoulou, S.M., Andreopoulou, A.K., Soto, A., Kallitsis, J.K., Voyiatzis, G.A. Journal of controlled release : official journal of the Controlled Release Society. (2005) [Pubmed]
  33. Molecular basis for resistance to silver cations in Salmonella. Gupta, A., Matsui, K., Lo, J.F., Silver, S. Nat. Med. (1999) [Pubmed]
  34. Polyacrolein microspheres as a new tool in cell biology. Margel, S., Beitler, U., Ofarim, M. J. Cell. Sci. (1982) [Pubmed]
  35. Detection of viable Legionella pneumophila in water by polymerase chain reaction and gene probe methods. Bej, A.K., Mahbubani, M.H., Atlas, R.M. Appl. Environ. Microbiol. (1991) [Pubmed]
  36. Therapy of digoxin intoxication in dogs by specific hemoperfusion through agarose polyacrolein microsphere beads-antidigoxin antibodies. Marcus, L., Margel, S., Savin, H., Offarim, M., Ravid, M. Am. Heart J. (1985) [Pubmed]
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