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The Journal of Urology Jul 1992The active metabolite of cyclophosphamide, acrolein, which is capable of damaging the transitional epithelium of the bladder, was evaluated in both in vivo and in vitro...
The active metabolite of cyclophosphamide, acrolein, which is capable of damaging the transitional epithelium of the bladder, was evaluated in both in vivo and in vitro models to determine if its damaging effect could be reduced by the presence of a sulfated polysaccharide pentosampolysulfate. It was discovered that in all models pentosanpolysulfate was capable of reducing transitional cell injury due to acrolein.
Topics: Acrolein; Animals; Cells, Cultured; Female; Pentosan Sulfuric Polyester; Rats; Rats, Inbred Strains; Urinary Bladder Diseases
PubMed: 1377288
DOI: 10.1016/s0022-5347(17)36545-x -
Food Chemistry Sep 2021Lipid peroxidation-derived reactive carbonyl species (RCS) such as acrolein and 4-hydroxynonenal pose health risks. We characterized the RCS-scavenging reactions of tea...
Lipid peroxidation-derived reactive carbonyl species (RCS) such as acrolein and 4-hydroxynonenal pose health risks. We characterized the RCS-scavenging reactions of tea catechins in an aqueous solution and in baked cake. Acrolein's reaction with each of the major tea catechins (epicatechin, epigallocatechin, epicatechin gallate, and epigallocatechin gallate) resulted in the formation of mono-, di-, and tri-acrolein conjugates of each catechin as revealed by our LC-linear ion trap MS analysis. The formation of the acrolein-conjugates of the four catechins was confirmed in the reaction of acrolein with green tea powder (matcha) extract. The addition of matcha tea powder to cake dough significantly suppressed the accumulation of RCS during cake baking. The mono-acrolein conjugates of the four major catechins were detected in the baked cake. The RCS-scavenging capability of tea catechins offers a new functionality of matcha tea powder, and its heat stability demonstrates the usefulness of matcha as a food additive.
Topics: Acrolein; Aldehydes; Catechin; Chromatography, High Pressure Liquid; Cooking; Free Radical Scavengers; Hot Temperature; Mass Spectrometry; Plant Extracts; Powders; Tea
PubMed: 33773455
DOI: 10.1016/j.foodchem.2021.129403 -
Environmental Science & Technology Aug 2012Aldehyde emissions were measured from two heavy-duty trucks, namely 2000 and 2008 model year vehicles meeting different EPA emission standards. The tests were conducted...
Aldehyde emissions were measured from two heavy-duty trucks, namely 2000 and 2008 model year vehicles meeting different EPA emission standards. The tests were conducted on a chassis dynamometer and emissions were collected from a constant volume dilution tunnel. For the 2000 model year vehicle, four different fuels were tested, namely California ultralow sulfur diesel (CARB ULSD), soy biodiesel, animal biodiesel, and renewable diesel. All of the fuels were tested with simulated city and high speed cruise drive cycles. For the 2008 vehicle, only soy biodiesel and CARB ULSD fuels were tested. The research objective was to compare aldehyde emission rates between (1) the test fuels, (2) the drive cycles, and (3) the engine technologies. The results showed that soy biodiesel had the highest acrolein emission rates while the renewable diesel showed the lowest. The drive cycle also affected emission rates with the cruise drive cycle having lower emissions than the urban drive cycle. Lastly, the newer vehicle with the diesel particulate filter had greatly reduced carbonyl emissions compared to the other vehicles, thus demonstrating that the engine technology had a greater influence on emission rates than the fuels.
Topics: Acrolein; Aldehydes; Biofuels; Motor Vehicles; Quality Control
PubMed: 22746209
DOI: 10.1021/es301659u -
Mini Reviews in Medicinal Chemistry 2017Cinnamaldehyde analogues are a class of chemical substances originated from derivatization of cinnamaldehyde, and are structurally characterized by the presence of... (Review)
Review
Cinnamaldehyde analogues are a class of chemical substances originated from derivatization of cinnamaldehyde, and are structurally characterized by the presence of cinnamoyl moiety. Due to the presence of highly reactive α,α-unsaturated carbonyl pharmacophore (Michael acceptor) in their structures, these molecules are apt to react with some enzymes and/or receptors as electrophiles, and consequently produce diverse therapeutically relevant pharmacological functions. Naturally occurring molecules, trans-cinnamaldehyde (CA), 2-benzoyloxycinnam-aldehyde (2-BCA), and 2- hydroxycinnamaldehyde (2-HCA) are representatives of this group, and have attracted lots of interest for their bioactivities, especially the anti-cancer and anti-inflammatory properties. Owing to the potential of CA, 2-BCA, and 2-HCA as therapeutic agents, researches on chemical syntheses and modifications have been carried out to gain chemical entities with potent bioactivity and favorable druggability. This review summarizes the progress on phytochemical and pharmacological aspects of natural cinnamaldehyde analogues, illustrate the representative of synthetic molecules with potent bioactivity, and discuss their potential as therapeutic agents.
Topics: Acrolein; Anti-Infective Agents; Anti-Inflammatory Agents, Non-Steroidal; Antineoplastic Agents; Humans; Hypoglycemic Agents; Molecular Structure; Neoplasms; Neuroprotective Agents
PubMed: 26791737
DOI: 10.2174/1389557516666160121120744 -
Brazilian Journal of Medical and... Nov 2006Acrolein is a urinary metabolite of cyclophosphamide and ifosfamide, which has been reported to be the causative agent of hemorrhagic cystitis induced by these...
Acrolein is a urinary metabolite of cyclophosphamide and ifosfamide, which has been reported to be the causative agent of hemorrhagic cystitis induced by these compounds. A direct cytotoxic effect of acrolein, however, has not yet been demonstrated. In the present study, the effects of intravesical injection of acrolein and mesna, the classical acrolein chemical inhibitor, were evaluated. Male Swiss mice weighing 25 to 35 g (N = 6 per group) received saline or acrolein (25, 75, 225 microg) intravesically 3, 6, 12, and 24 h before sacrifice for evaluation of bladder wet weight, macroscopic and histopathological changes by Gray's criteria, and 3 and 24 h for assessment of increase in vascular permeability. In other animals, mesna was administered intravesically (2 mg) or systemically (80 mg/kg) 1 h before acrolein. Intravesical administration of acrolein induced a dose- and time-dependent increase in vascular permeability and bladder wet weight (within 3 h: 2.2- and 21-fold increases in bladder wet weight and Evans blue dye exuded, respectively, at doses of 75 microg/bladder), as confirmed by Gray's criteria. Pretreatment with mesna (2-mercaptoethanesulfonic acid), which interacts with acrolein resulting in an inactive compound, inhibited all changes induced by acrolein. Our results are the first demonstration that intravesical administration of acrolein induces hemorrhagic cystitis. This model of acrolein-induced hemorrhagic cystitis in mice may be an important tool for the evaluation of the mechanism by which acrolein induces bladder lesion, as well as for investigation of new uroprotective drugs.
Topics: Acrolein; Animals; Cystitis; Disease Models, Animal; Dose-Response Relationship, Drug; Edema; Hemorrhage; Male; Mesna; Mice; Protective Agents; Urinary Bladder
PubMed: 17146560
DOI: 10.1590/s0100-879x2006001100011 -
Food Chemistry Nov 2021In physiological and thermally-processed conditions, alanine and serine efficiently eliminate acrolein to generate two main adducts,...
In physiological and thermally-processed conditions, alanine and serine efficiently eliminate acrolein to generate two main adducts, 2-(5-formyl-3,6-dihydropyridin-1(2H)-yl) propanoic acid and 2-(5-formyl-3,6-dihydropyridin-1(2H)-yl)-3-hydroxypropanoic acid, with amounts of 81.6 ± 4.24 μg/kg and 23.72 ± 0.40 μg/kg in fried potato crisps, respectively. Adduct formation markedly decreased the cytotoxicity of acrolein against Caco-2, GES-1 and HUVEC cells. The cell viability of them remained approximately100% after incubation with 200 µmolL adducts, while the IC values for acrolein in the three cells were 66, 54, and 16 µmolL respectively. The adducts express the protective effects by tremendous reduction of cell apoptosis, reactive oxygen species (ROS) production, and DNA damage.
Topics: Acrolein; Alanine; Apoptosis; Caco-2 Cells; Cell Survival; DNA Damage; Food-Processing Industry; Humans; Inactivation, Metabolic; Reactive Oxygen Species; Serine; Solanum tuberosum
PubMed: 34062460
DOI: 10.1016/j.foodchem.2021.130164 -
Environmental Science & Technology Apr 2006Acrolein is a highly toxic alpha,beta-unsaturated aldehyde that is widely used as a biocide, a cross-linking agent, and an intermediate in the chemical industry, among...
Acrolein is a highly toxic alpha,beta-unsaturated aldehyde that is widely used as a biocide, a cross-linking agent, and an intermediate in the chemical industry, among other applications. In this study we investigated the reductive transformation of acrolein by elemental iron and evaluated the feasibility of using iron to detoxify acrolein. At acidic and neutral pH, acrolein was transformed by iron through reduction of the C=C double bond to propionaldehyde. The reduction appeared to involve the chemisorption of acrolein to the iron surface followed by reduction of adsorbed acrolein. Both the adsorption and reduction rate constants decreased with increasing pH. Between pH 7.0 and 7.4, the acrolein adsorption rate constant decreased precipitously, resulting in a sharp decline in its removal rate. At higher pH, acrolein disappeared rapidly in control without iron, presumably due to reversible, base-catalyzed hydration. At equilibrium, approximately 93% of acrolein was hydrated, corresponding to an equilibrium constant of 13. Acrolein at 25 mg/L completely inhibited aerobic respiration; in contrast, its reduction product propionaldehyde was biodegradable. This suggests that elemental iron may be used to pretreat acrolein-containing wastes prior to aerobic biodegradation. To our knowledge, this is the first report of reduction and detoxification of an alpha,beta-unsaturated aldehyde by elemental iron.
Topics: Acrolein; Adsorption; Aldehydes; Bacteria, Aerobic; Biodegradation, Environmental; Hydrogen-Ion Concentration; Iron; Kinetics; Oxidation-Reduction; Oxygen; Waste Disposal, Fluid; Water Pollutants, Chemical; Water Purification
PubMed: 16683621
DOI: 10.1021/es052246f -
Toxicology and Industrial Health Sep 1987Acrolein and two of its more stable derivatives, the oxime and the diethylacetal, and the related allyl alcohol were given in drinking water to groups of 20 male and 20...
Acrolein and two of its more stable derivatives, the oxime and the diethylacetal, and the related allyl alcohol were given in drinking water to groups of 20 male and 20 female F344 rats at doses close to the maximum that could be tolerated by the animals, for most of their lifetime. Acetaldoxime served as a control for the hydroxylamine derivative of acrolein. Most of the tumors were common in untreated rats of this strain. Only adenomas of the adrenal cortex in females were more numerous than in untreated controls. Acrolein itself was too toxic to hamsters to conduct a carcinogenesis study. Acrolein oxime, acrolein diethylacetal and allyl alcohol were all quite toxic to hamsters, but 2 mg per week by gavage was tolerated by groups of 20 male Syrian hamsters. There was a small number of tumors of the pancreatic ducts and of the forestomach in the treated hamsters, but the incidence was not statistically significant.
Topics: 1-Propanol; Acrolein; Adenoma; Adrenal Cortex Neoplasms; Aldehydes; Animals; Carcinogens; Cricetinae; Female; Male; Mesocricetus; Mutagenicity Tests; Propanols; Rats; Rats, Inbred F344; Sex Factors
PubMed: 3686537
DOI: 10.1177/074823378700300306 -
Toxicology Nov 2004Acrolein is a widespread environmental pollutant that reacts rapidly with nucleophiles, especially cellular thiols. In addition to glutathione (GSH), thioredoxin (Trx)...
Acrolein is a widespread environmental pollutant that reacts rapidly with nucleophiles, especially cellular thiols. In addition to glutathione (GSH), thioredoxin (Trx) and thioredoxin reductase (TR) contain thiol groups and may react with electrophiles. In the present study, A549 cells treated with 5-25 microM acrolein for 30 min lost cellular Trx activity in a dose-dependent fashion. Over 90% of Trx activity was lost at concentrations of 25 microM or greater. In contrast, Trx protein content, as assessed by western blotting, was not altered immediately after the 30 min acrolein treatment. Both Trx activity and protein levels increased 4h after the acrolein treatment. However, Trx activity remained below control levels at 24h. A similar dose-response relationship was seen with TR in A549 cells exposed to acrolein. There was, however, a rapid recovery of TR activity such that it attained normal levels by 4h after doses < or = 75 microM acrolein. Diethyl maleate (DEM), a common but not highly specific, agent used to deplete GSH, also inactivated Trx. A 2 h exposure of A549 cells to 1 mM DEM depleted cellular GSH by ~50% and diminished Trx activity by over 67%. Lower DEM doses (0.125 mM and 0.25 mM) for 1h had no significant effect on GSH but significantly decreased Trx activity 12 and 23%, respectively. Similar to immediately after acrolein exposure, DEM did not affect Trx protein levels. A Trx-1-GFP fusion protein was transfected into A549 cells. While the fusion protein was expressed, the Trx component was inactive by the insulin reducing assay. In summary, Trx and TR are inactivated by acrolein. In addition, the GSH depleting agent DEM inactivates Trx somewhat more effectively than it depletes GSH. The Trx-1-GFP fusion protein, while readily expressed, appears to have little or no activity, perhaps because the small size of Trx-1 (12 kDa) is affected by the larger GFP.
Topics: Acrolein; Binding Sites; Cell Line, Tumor; Dose-Response Relationship, Drug; Glutathione; Humans; Maleates; Thioredoxins
PubMed: 15388247
DOI: 10.1016/j.tox.2004.06.056 -
Mutation Research May 1994In order to investigate the role of metabolism in acrolein genotoxicity in D. melanogaster, the action of several metabolism modifiers, namely phenobarbital, an inducer...
In order to investigate the role of metabolism in acrolein genotoxicity in D. melanogaster, the action of several metabolism modifiers, namely phenobarbital, an inducer of xenobiotic metabolism, phenylimidazole and iproniazid, inhibitors of oxidative activities of cytochrome P450, and diethyl maleate, a glutathione-depleting agent, have been assayed using the sex-linked recessive lethal (SLRL) test, with two different administration routes (feeding and injection). The results support the hypothesis that acrolein is not only a direct mutagen but is also transformed, by oxidative activities of cytochrome P450 after glutathione conjugation, into an active metabolite, possibly glycidaldehyde. Moreover, acrolein is deactivated by an enzymatic activity induced by phenobarbital.
Topics: Acrolein; Animals; Biotransformation; Cytochrome P-450 Enzyme Inhibitors; Drosophila melanogaster; Female; Glutathione; Imidazoles; Iproniazid; Male; Maleates; Mutagenicity Tests; Mutation; Phenobarbital
PubMed: 7513061
DOI: 10.1016/0165-1218(94)90035-3