Disease relevance of MOLI001868

• Equipped with a benzaldehyde dehydrogenase (XylC from Pseudomonas putida), the lacZ-based host responded to the oxidation of benzaldehyde and 2-hydroxybenzaldehyde to the corresponding benzoic acids by forming blue colonies, whereas XylC- cells did not [1].
• The microsomal metabolism of the rat esophageal carcinogen N-nitrosomethylbenzylamine (NMBZA) at the methylene carbon atom to yield benzaldehyde was studied in various organs of a number of species to determine the role of metabolic activation in the carcinogenicity or toxicity of the nitrosamine [2].
• Differential enhancement of cytotoxicity by combination of the carcinostatic agent benzaldehyde and hyperthermia in simian virus 40-transformed and normal cell lines [3].
• Purification and characterization of benzaldehyde dehydrogenase I from Acinetobacter calcoaceticus [4].
• Enhanced benzaldehyde tolerance in Zymomonas mobilis biofilms and the potential of biofilm applications in fine-chemical production [5].

Psychiatry related information on MOLI001868

• In a behavioral study, blood levels of 0.12 ng/ml Benzaldehyde produced a 44% reduction in motor activity in mice [6].

High impact information on MOLI001868

• Primary and secondary protium-to-tritium (H/T) and deuterium-to-tritium (D/T) kinetic isotope effects for the catalytic oxidation of benzyl alcohol to benzaldehyde by yeast alcohol dehydrogenase (YADH) at 25 degrees Celsius have been determined [7].
• In addition, MALD-MS was used to follow a chemical reaction inside intact FaDu cells: the formation of a hydrazone (II-51) from benzaldehyde and an acylhydrazide, 5-[tris(4-dimethylaminophenyl)phosphonio]pentanoyl hydrazide (II-25) [8].
• An olfactory gene olfE, which affects response to benzaldehyde in larvae and adults of Drosophila melanogaster, has been mapped between two breakpoints on the X chromosome [9].
• An additional five neoplasms had barely detectable levels of benzaldehyde and NADP+ ALDH activity [10].
• Like the tumor-associated aldehyde dehydrogenase, bladder NADP+-ALDH is cytosolic and preferentially oxidizes benzaldehyde-like aromatic aldehydes [11].

Chemical compound and disease context of MOLI001868

• Anaerobic toluene oxidation to benzyl alcohol and benzaldehyde in a denitrifying Pseudomonas strain [12].
• Experiments performed with Lactobacillus plantarum demonstrated that Mn(II), present at high levels in this strain, is involved in benzaldehyde formation by catalyzing the conversion of phenylpyruvic acid [13].
• An inducible phenylserine aldolase (L-threo-3-phenylserine benzaldehyde-lyase, EC 4.1.2.26), which catalyzes the cleavage of L-3-phenylserine to yield benzaldehyde and glycine, was purified to homogeneity from a crude extract of Pseudomonas putida 24-1 isolated from soil [14].
• Although pretreatment with disulfiram led to benzaldehyde levels which were 368% of control values, toxicity was unchanged [15].
• We report the kinetic behavior of the enzyme aldehyde oxidoreductase (AOR) from the sulfate reducing bacterium Desulfovibrio gigas (Dg) encapsulated in reverse micelles of sodium bis-(2-ethylhexyl) sulfosuccinate in isooctane using benzaldehyde, octaldehyde, and decylaldehyde as substrates [16].

Biological context of MOLI001868

• The effect of the benzaldehyde derivative 4,6-benzylidene-D-glucose (BG) on cell-cycle kinetics, protein synthesis, and cell survival of human NHIK 3025 cells has been investigated [17].
• The concentration of BG and the hydrolysis product benzaldehyde were determined in cell culture medium by high-performance liquid chromatography [17].
• 4,6-Benzylidene-D-glucose, a benzaldehyde derivative that inhibits protein synthesis but not mitosis of NHIK 3025 cells [17].
• BG exerted an effect on protein synthesis similar to that of benzaldehyde, but did not affect metaphase [17].
• The very poor activity of AKR11C1 on standard, small substrates such as benzaldehyde or DL-glyeraldehyde is consistent with the observed, very open active site lacking a binding pocket for these substrates [18].

Anatomical context of MOLI001868

• The rate of benzaldehyde formation by forestomach microsomes was not detectable in tissue from rats on either diet [19].
• The effects of benzaldehyde, which has been found in figs as a carcinostatic element, were studied on the uptake of nucleosides, 2-deoxy-D-glucose, and amino acids into simian virus 40-transformed rat fibroblast cells (SV40-transformed cells) and into the parent normal cells (normal cells) [20].
• UGT1A10 compared with UGT1A7, -1A8, and -1A3 generally exhibited high activity toward acidic nonsteroidal anti-inflammatory drugs and natural benzaldehyde derivatives, while UGT1A3 metabolized most efficiently aromatic transcinnamic acids known to be generated from flavonoid glycosides by microflora in the lower gastrointestinal tract [21].
• ALDH-3, judged to be so because it is a polymorphic enzyme (pI values ca. 6.0) present in the cytosol that is heat labile, is insensitive to inhibition by disulfiram (25 microM), much prefers benzaldehyde to acetaldehyde as a substrate and, at concentrations of 4 mM, prefers NADP to NAD as a cofactor [22].
• PBN also decreased hepatocyte GSH content, probably as the result of its metabolism to benzaldehyde [23].

Associations of MOLI001868 with other chemical compounds

• AO activity was visualized using formazan- or horseradish peroxidase-mediated staining coupled to the AO-catalyzed oxidation of benzaldehyde [24].
• If whole cells are used, the biomass may be grown and allowed to synthesize endogenous pyruvate, or the cells may be used as a catalyst only, with both pyruvate and benzaldehyde being added [25].
• In black cherry (Prunus serotina Ehrh.) seed homogenates, (R)-amygdalin is degraded to HCN, benzaldehyde, and glucose by the sequential action of amygdalin hydrolase (AH), prunasin hydrolase (PH), and mandelonitrile lyase [26].
• Variation of transition-state structure as a function of the nucleotide in reactions catalyzed by dehydrogenases. 1. Liver alcohol dehydrogenase with benzyl alcohol and yeast aldehyde dehydrogenase with benzaldehyde [27].
• The mechanism of oxidation of benzaldehyde to benzoic acid catalyzed by horse liver alcohol dehydrogenase (HLADH) has been investigated using the HLADH structure at 2.1 A resolution with NAD+ and pentafluorobenzyl alcohol in the active site [Ramaswamy et al. (1994) Biochemistry 33,5230-5237] [28].

Gene context of MOLI001868

• This confirms the interpretation of the N-terminal sequence comparisons and also indicates that benzaldehyde dehydrogenase I from Acinetobacter may be related to the other two benzaldehyde dehydrogenases [29].
• Behavioral assays show that a threefold decrease in DSC1 mRNA is accompanied by a threefold shift in the dose response for avoidance of the repellent odorant, benzaldehyde, toward higher odorant concentrations [30].
• One isozyme, designated ALDH3, which is very active against benzaldehyde, was found to show variable expression in hybrids made between rat hepatoma cells and human fibroblasts or fetal liver [31].
• More potent inhibition of human CYP2A6 than mouse CYP2A5 enzyme activities by derivatives of phenylethylamine and benzaldehyde [32].
• Furthermore, the AOH1 protein has benzaldehyde oxidizing activity with electrophoretic characteristics identical to those of a previously identified aldehyde oxidase isoenzyme (Holmes, R. S. (1979) Biochem. Genet. 17, 517-528) [33].

Analytical, diagnostic and therapeutic context of MOLI001868

• The effect of the carcinostatic drug benzaldehyde (BA) on hyperthermia-induced cytotoxicity was studied in various types of cultured mammalian cell lines by colony formation assay [3].
• Methods examined to reduce toxicity include modification of benzaldehyde dosing regimes, immobilization of biomass or purified enzymes, modification of benzaldehyde solubility and the use of two-phase reaction systems [25].
• Benzaldehyde dehydrogenase I was purified from Acinetobacter calcoaceticus by DEAE-Sephacel, phenyl-Sepharose and f.p.l.c. gel-filtration chromatography [4].
• Electrophoretically mediated microanalysis (EMMA) combined with micellar electrokinetic capillary chromatography (MEKC) was used to perform an on-capillary enzymatic reaction and to separate the generated benzaldehyde from the other reaction products [34].
• Natural glycosides containing allopyranose from the passion fruit plant and circular dichroism of benzaldehyde cyanohydrin glycosides [35].

References