Polycyclic Hydrocarbons, Aromatic
HPLC/fluorescence determination of anti-BPDE-DNA adducts in mononuclear white blood cells from PAH-exposed humans. (1/632)
The aim of this study was to compare (+/-)-r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene (anti-BPDE)-DNA adduct levels in groups of humans subjected to various levels of polycyclic aromatic hydrocarbon (PAH) (benzo[a]pyrene) exposure. An HPLC/fluorescence method was applied to detect specifically anti-BPDE-DNA adducts in mononuclear white blood cells [lymphocyte plus monocyte fraction (LMF)] from humans exposed to PAHs. A total of 130 subjects comprised the sample population: 26 psoriatic patients (3 days after clinical coal tar treatment of the skin), 15 coke oven workers, 19 chimney sweeps, 36 aluminium anode plant workers and 34 non-occupationally PAH-exposed subjects (controls). PAH exposure was assessed in each group by means of the urinary excretion of 1-pyrenol (mean group levels: 1.2, 0.7, 0.3, 65.0 and 0.1 micromol/mol creatinine in coke oven workers, chimney sweeps, aluminium plant anode workers, psoriatic patients and non-occupationally PAH-exposed subjects, respectively). HPLC/fluorescence analysis of BPDE-DNA adducts showed that the percentage of subjects with adduct levels exceeding the 95 percentile control subject value (8.9 adducts/10(8) nucleotides) was significantly high in coke oven workers (46.7%) and chimney sweeps (21.0%) (chi2 test, P < 0.01 and P < 0.05, respectively) but not in aluminium plant workers (11.1%) and psoriatic patients (0%). The increase in BPDE-DNA adduct levels in LMF (Ln values) was significantly related to chronic inhalatory and high PAH exposure (linear multiple regression analysis, F = 6.37, P < 0.01; t = 4.2, P < 0.001). Skin acute (or short-term) and high PAH exposure, charcoal-grilled meat consumption and smoking habit did not seem to influence BPDE-DNA adduct formation in LMF. (+info)Structure-activity relationship of schisandrins in enhancing liver mitochondrial glutathione status in CCl4-poisoned mice. (2/632)
AIM: To explore whether the methylenedioxy group and cyclooctadiene ring of the dibenzocyclooctadiene skeleton of schisandrins (Sch) play a role in the liver mitochondrial glutathione status enhancing activity. METHOD: The effects of three dibenzocyclooctadiene derivatives, Sch A, Sch B, Sch C, and a synthetic intermediate of Sch C, (dimethyl biphenyl dicarboxylate, DBD) on carbon tetrachloride (CCl4)-hepatotoxicity and liver mitochondrial glutathione status were examined in mice. RESULTS: Pretreating mice with intragastric Sch B, Sch C, or DBD 1.mmol.kg-1.d-1 for 3 d protected against CCl4-hepatotoxicity. The hepatoprotection afforded by Sch B or Sch C pretreatment was associated with increases in liver mitochondrial reduced glutathione (mtGSH) level and glutathione reductase (mtGRD) activity, an indication of enhanced mitochondrial glutathione status. In contrast, the hepatoprotective action of DBD was not accompanied by any detectable changes in mtGSH level and mtGRD activity. CONCLUSION: Both the methylenedioxy group and the cyclooctadiene ring of the dibenzocyclooctadiene molecule are important structural determinants in the enhancement of liver mitochondrial glutathione status. (+info)Dose-dependent preferential binding of polycyclic aromatic hydrocarbons to reiterated DNA of murine skin cells in culture. (3/632)
The distribution of active metabolites of polycyclic aromatic hydrocarbons bound to reiterated or unique regions of murine DNA has been studied by a DNA-DNA renaturation technique. Murine skin cells were exposed to different doses of radioactive polycyclic aromatic hydrocarbons for 24 hr; then the hydrocarbon-labeled DNA was isolated, fragmented, and denatured. Renaturation kinetics and thermal stabilities of DNA-DNA duplexes were studied. At high carcinogen doses, polycyclic aromatic hydrocarbon adducts seem to be distributed equally among the DNA of all reiteration frequencies. At low carcinogen doses, however, a dose-dependent preferential binding to reiterated DNA sequences occurs. An inverse linear relationship appears to exist between the enrichment of hydrocarbon adducts in reiterated DNA sequences and the logarithm of the amount of total hydrocarbon bound to DNA. (+info)Cancer initiation by polycyclic aromatic hydrocarbons results from formation of stable DNA adducts rather than apurinic sites. (4/632)
Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous environmental pollutants with high carcinogenic potencies that have been linked to the etiology of human cancers through their presence in cigarette smoke and environmental mixtures. They are metabolically activated in cells by cytochrome P450 enzymes and/or peroxidases to reactive intermediates that damage DNA. One pathway of activation forms dihydrodiol epoxides that covalently bind to exocyclic amino groups of purines in DNA to form stable adducts. Another pathway involves formation of radical cations that bind to the N7 or C8 of purines to form unstable adducts that depurinate to leave apurinic (AP) sites in DNA. In the present study the proportions of stable DNA adducts and AP sites formed by the carcinogenic PAHs dibenzo[a,l]-pyrene (DB[a,l]P), 7,12-dimethylbenz[a]anthracene (DMBA), and benzo[a]pyrene (B[a]P) have been investigated in a target tissue for carcinogenesis, mouse epidermis. After topical application of the PAHs on the skin of female SENCAR mice epidermal DNA was isolated and the formation of stable DNA adducts was measured by (33)P-postlabeling and HPLC analysis. AP sites in DNA were measured with an aldehyde reactive probe in a slot-blot assay. At both 4 and 24 h after exposure, DB[a,l]P formed significantly higher amounts of stable DNA adducts than DMBA, and B[a]P exhibited the lowest level of binding. In contrast, the number of AP sites present in mice treated with these PAHs was in the order: DMBA > B[a]P >> DB[a,l]P. The level of AP sites was significantly lower than the level of stable adducts for each PAH. The most potent carcinogen, DB[a,l]P, induced the highest level of stable adducts and the lowest level of AP sites in epidermal DNA. These results indicate that stable DNA adducts rather than AP sites are responsible for tumor initiation by carcinogenic PAHs. (+info)Environmental pollution and human exposure to polycyclic aromatic hydrocarbons in the east Baltic region. (5/632)
Environmental contamination by polycyclic aromatic hydrocarbons (PAH) and human exposure were surveyed in the east Baltic region. Polluted and heavily industrialized areas are upper Silesia in Poland, northern Bohemia in the Czech Republic, and the northeast part of Estonia. In Estonia the pollution is in a defined geographic area, where lung cancer incidence is higher than elsewhere. In Silesia, exposure of some 5 million people appears to be elevated; DNA (deoxyribonucleic acid) adduct levels in white blood cells are increased in groups of residents with apparently only environmental exposure. By extrapolation, some 150 annual lung cancer cases could be predicted due to PAH in Silesia. Air levels of benzo[a]pyrene were increased in northern Bohemia, and domestic heating and power plants using brown coal appeared to be major contributors to particulate air pollution in winter. Further studies are needed to assess health risks of PAH exposure in central and eastern Europe. (+info)Alternative pathways of polycyclic aromatic hydrocarbons activation: the formation of polar DNA adducts. (6/632)
Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous environmental pollutants, and some are potent carcinogens in rodents. Carcinogenic PAHs are activated in the cells to metabolites that react with DNA to form covalent adducts. For most PAHs the reactive, electrophilic species which bind to DNA, are bay-region diol-epoxides. Application of 32P-postlabeling to PAH-DNA adducts analysis revealed that for some PAHs the adduct profiles generated in model systems are more complex and include adducts which are more polar than those formed by classic bay-region diol-epoxides. This minireview summaries the information gained on typical representatives of polar PAH-DNA adducts. Formation of triol-epoxide-DNA adducts was proposed for chrysene and a non-alterant PAH, benzo[b]fluoranthene (B[b]F). 5-OH-B[b]F, the precursor of B[b]F triol-epoxide, was found to be a potent tumor initiator in mouse skin. For planar PAHs such as dibenzanthracenes the possibility of bis-diol epoxide-DNA adducts formation was suggested. The most comprehensive data were obtained for dibenz[a,j]anthracene (DB[a,j]A). This hydrocarbon when applied to SENCAR mouse skin forms up to 23 species of adducts, most of which are polar. Among these polar adducts seven were identified as derived from DB[aj]A-3,4-10,11-bis-diol. Analysis of tumor-initiating activity showed, however, that this proximate metabolite was inactive in this respect. In contrast, an excellent correlation was observed between levels of less polar DNA adducts (i.e. those derived from bay-region diolepoxides) and skin tumor initiating activity of DB[a,j]A. Thus, while triol-epoxides seems to be involved in tumor initiating activity of the parent compound, non alterant B[b]F, the significance of bis-diol epoxide-DNA adducts, at least those derived from DB[aj]A, is minor. (+info)Mutability of different genetic loci in mammalian cells by metabolically activated carcinogenic polycyclic hydrocarbons. (7/632)
The relationship between carcinogenesis and mutagenesis in mammalian cells has been determined with 10 polycyclic hydrocarbons with different degrees of carcinogenicity. Mutagenesis was determined in Chinese hamster cells with genetic markers that affect the surface membrane, nucleic-acid synthesis, and protein synthesis. The mutations were characterized by resistance to ouabain, 8-azaguanine, and temperature. Mutagenesis by the carcinogens required metabolic activation and this was provided by the presence of lethally irradiated metabolizing cells. The degree of carcinogenicity was related to the degree of mutagenicity for all three genetic markers. The most potent carcinogen, 7,12-dimethylbenz[a]anthracene, gave the highest mutagenicity and mutagenicity was obtained with 0.01 mug/ml. Treatment of the cells with aminophylline, which increases polycyclic hydrocarbon metabolism, increased mutagenesis by the carcinogens. It is suggested that such an experimental system with these and other mammalian cells should be useful as a sensitive assay for hazardous environmental chemicals. (+info)Effect of plant matrix and fluid ethanol concentration on supercritical fluid extraction efficiency of schisandrin derivatives. (8/632)
An investigation of the effect of plant matrix on the supercritical fluid extraction efficiency of five schisandrin derivatives is reported, exhibiting a great difference with respect to extraction efficiency depending on the matrix. Pure supercritical CO2 at 60 degrees C and 34.0 MPa cannot fully recover schisandrin derivatives from the leaves as much as from the other matrices. Only 36.9% of these compounds are extracted from leaves of Schisandra chinensis by supercritical CO2 in comparison with organic solvent extraction. However, more than 80% of schisandrin derivatives are obtained from both stem and fruit parts. Ethanol addition also shows a different effect depending on plant matrix; that is, CO2 modified with 10% ethanol could enhance the yield of schisandrin derivatives from leaves by four times when compared with that of pure CO2, but it has little effect on both stems and fruits. (+info)Medical definitions typically focus on the relevance of a term to medicine or healthcare, so here's a medical perspective on polycyclic compounds:
Polycyclic compounds are organic substances that contain two or more chemical rings in their structure. While not all polycyclic compounds are relevant to medicine, some can have significant medical implications. For instance, polycyclic aromatic hydrocarbons (PAHs) are a type of polycyclic compound that can be found in tobacco smoke and certain types of air pollution. PAHs have been linked to an increased risk of cancer, particularly lung cancer, due to their ability to damage DNA.
Another example is the class of drugs called steroids, which include hormones like cortisol and sex hormones like testosterone and estrogen. These compounds are polycyclic because they contain several interconnected rings in their structure. Steroid medications are used to treat a variety of medical conditions, including inflammation, asthma, and Addison's disease.
In summary, while not all polycyclic compounds are relevant to medicine, some can have important medical implications, either as harmful environmental pollutants or as useful therapeutic agents.
Polycyclic aromatic hydrocarbons (PAHs) are a group of organic compounds characterized by the presence of two or more fused benzene rings. They are called "polycyclic" because they contain multiple cyclic structures, and "aromatic" because these structures contain alternating double bonds that give them distinctive chemical properties and a characteristic smell.
PAHs can be produced from both natural and anthropogenic sources. Natural sources include wildfires, volcanic eruptions, and the decomposition of organic matter. Anthropogenic sources include the incomplete combustion of fossil fuels, such as coal, oil, and gasoline, as well as tobacco smoke, grilled foods, and certain industrial processes.
PAHs are known to be environmental pollutants and can have harmful effects on human health. They have been linked to an increased risk of cancer, particularly lung, skin, and bladder cancers, as well as reproductive and developmental toxicity. PAHs can also cause skin irritation, respiratory problems, and damage to the immune system.
PAHs are found in a variety of environmental media, including air, water, soil, and food. They can accumulate in the food chain, particularly in fatty tissues, and have been detected in a wide range of foods, including meat, fish, dairy products, and vegetables. Exposure to PAHs can occur through inhalation, ingestion, or skin contact.
It is important to limit exposure to PAHs by avoiding tobacco smoke, reducing consumption of grilled and smoked foods, using ventilation when cooking, and following safety guidelines when working with industrial processes that produce PAHs.
I'm sorry for any confusion, but "Pyrenes" is not a medical term. It is a term used in chemistry and materials science, referring to a type of aromatic hydrocarbon molecule that consists of two benzene rings fused together. If you have a different term or concept in mind, please provide it so I can give you an accurate definition or information.
Polycyclic compound
Polycyclic aromatic hydrocarbon
Frémy's salt
Fluoranthene
Tandoor bread
Bicalicene
Benzo(c)fluorene
Phenalene
Frederick George Mann
Aromatic compound
Sasanka Chandra Bhattacharyya
Organic mineral
Gambierol
Favorskii rearrangement
Hydrocarbon
Ring expansion and contraction
Mutagenesis
Alkene
Air pollution
Sphingomonas formosensis
Polyring forming processes
Boraacenes
Cyclobuxine
Polyquinane
Chlorinated polycyclic aromatic hydrocarbon
Mallory reaction
Iptycene
Diesel exhaust
Danheiser benzannulation
Tetracyclopropylmethane
PAHs8
- In industrial sites historically contaminated by coal-tar (abandoned coking and manufactured-gas plants), other families of organic pollutants than the 16 PAHs (polycyclic aromatic hydrocarbons) classified by the US-EPA can occur and induce potential risk for groundwater resources. (univ-lorraine.fr)
- In addition, a variety of substances such as fuel, water, antifreeze, dust, and various combustion products such as polycyclic aromatic hydrocarbons (PAHs), metals, and metallic oxides accumulate in the oil. (cdc.gov)
- When power stations burn coal, a class of compounds called Polycyclic Aromatic Hydrocarbons, or PAHs, form part of the resulting air pollution. (eurekalert.org)
- Researchers have found that PAHs toxins degrade in sunlight into 'children' compounds and by-products. (eurekalert.org)
- Some 'children' compounds can be more toxic than the 'parent' PAHs. (eurekalert.org)
- Polycyclic aromatic hydrocarbons (PAHs) are chemicals that are released into the environment during activities of the petroleum industry. (researchgate.net)
- Benzo(a)pyrene (BaP) is a compound in a group of chemicals called polycyclic aromatic hydrocarbons (PAHs). (chej.org)
- Polycyclic aromatic hydrocarbons (PAHs) are lipophilic compounds formed during the incomplete burning of coal, tobacco or other organic substances. (cdc.gov)
Including polycyclic aromatic hyd1
- In general, the term polycyclic includes polycyclic aromatic compounds, including polycyclic aromatic hydrocarbons, as well as heterocyclic aromatic compounds with multiple rings (where heteroaromatic compounds are aromatic compounds that contain sulfur, nitrogen, oxygen, or another non-carbon atoms in their rings in addition to carbon). (wikipedia.org)
PACs4
- Polar PACs (polycyclic aromatic compounds), especially oxygenated PACs (O-PACs), are present in the initial pollution and can also be generated over time. (univ-lorraine.fr)
- A new study in the Proceeding of the National Academy of Sciences (PNAS) shows that the Alberta's oil sands are likely releasing more PACs (polycyclic aromatic compounds) into nearby Athabasca River and its tributaries than the industry-funded and government-supported Regional Aquatics Monitoring Program (RAMP) has reported. (mongabay.com)
- Harnessing In Silico, In Vitro, and In Vivo Data to Understand the Toxicity Landscape of Polycyclic Aromatic Compounds (PACs). (nih.gov)
- The main compounds found in oil and petroleum products called polycyclic aromatic compounds, or PACs, can harm birds in the marine environment . (phys.org)
Charged polycyclic aromatic1
- Potential-driven molecular tiling of a charged polycyclic aromatic compound. (mpg.de)
Hydrocarbons12
- The degradation of polycyclic aromatic hydrocarbons by different algae seems to be related to the molecular structures of the compound and physiological metabolism of the algae. (omicsonline.org)
- The by-products of all this rampant combustion are smelly compounds called polycyclic aromatic hydrocarbons. (popsci.com)
- Not surprisingly, polycyclic aromatic hydrocarbons can be found in coal, oil and even food. (popsci.com)
- Airborne pollutants include particles, volatile organic compounds (VOCs), and polycyclic aromatic hydrocarbons," reports explain. (newstarget.com)
- 2018. Occurrence, distribution and composition of aliphatic and polycyclic aromatic hydrocarbons in sediment cores from the Lower Fox River, Wisconsin, US. (nih.gov)
- 2018. Utilizing ion mobility spectrometry and mass spectrometry for the analysis of polycyclic aromatic hydrocarbons, polychlorinated biphenyls, polybrominated diphenyl ethers and their metabolites. (nih.gov)
- Metalworking fluids are oil-water emulsions that contain paraffins, pine oils, polycyclic aromatic hydrocarbons, and heavy metals ( 10 , 11 ). (cdc.gov)
- The contaminants include coal tar, polycyclic aromatic hydrocarbons, volatile organic compounds, and petroleum hydrocarbons. (canadianunderwriter.ca)
- Phenolic compounds, polycyclic aromatic hydrocarbons and drugs have also been reported in e-cigarette refill solutions, cartridges and aerosols. (bmj.com)
- 2] In addition, production of asphalt releases hazardous chemicals such as polycyclic aromatic hydrocarbons, hydrogen sulfide, lead, and copper into the environment exposing fenceline communities to a wide array of chemicals that can impact their health. (healthybuilding.net)
- But the soil on the site was contaminated with polychlorinated biphenyls, metals, oil, volatile organic compounds, and polycyclic aromatic hydrocarbons. (cdc.gov)
- The last two chapters on polynuclear aromatic hydrocarbons and heterocyclic compounds, though not exactly the part of the curriculum of chemistry of natural products, but are essential to understand the chemistry of natural products. (researchandmarkets.com)
Aromatic compound2
- Polycyclic aromatic compound Polycyclic aromatic hydrocarbon William Reusch. (wikipedia.org)
- A modern depiction of a molecule of benzene, the prototypical aromatic compound. (newworldencyclopedia.org)
Volatile1
- Results The levels of nicotine, tobacco-specific nitrosamines (TSNAs), aldehydes, metals, volatile organic compounds (VOCs), flavours, solvent carriers and tobacco alkaloids in e-cigarette refill solutions, cartridges, aerosols and environmental emissions vary considerably. (bmj.com)
Structurally similar compounds2
- Compound groups are useful because in some cases, lists will instead identify a group of structurally similar compounds (such as lead compounds) as all having the same hazard. (pharosproject.net)
- s) and other structurally similar compounds. (gov.scot)
Lead compounds1
- Natural products have been an important source of drugs and novel lead compounds in drug discovery. (uwc.ac.za)
Heterocyclic Compounds1
- Special care has been taken to elaborate IUPAC nomenclature of certain chemical classes like steroids, eicosanoids, polycyclic aromatic compounds and heterocyclic compounds. (researchandmarkets.com)
Phenolic1
- EI-Sheekh MM, Ghareib MM, EL-Souod GW A (2011) IBiodegradation of Phenolic and Polycyclic Aromatic Compounds by Some Algae and Cyanobacteria. (omicsonline.org)
Steroids2
- They come in sizes of three atoms and upward, and in combinations of linkages that include tethering (such as in biaryls), fusing (edge-to-edge, such as in anthracene and steroids), links via a single atom (such as in spiro compounds), bridged compounds, and longifolene. (wikipedia.org)
- Life also prefers working with particular types of polycyclic carbon compounds such as "sterols" (these include cholesterol and steroids) and "hopanoids" that stabilize cell membranes. (bakersfieldcollege.edu)
Aliphatic1
- But terpenes and benzenoid substances do have a chemical characteristic in common, namely higher unsaturation indexes than many aliphatic compounds , and Hofmann may not have been making a distinction between the two categories. (newworldencyclopedia.org)
Benzene1
- Many of the earliest-known examples of aromatic compounds, such as benzene and toluene , have distinctive pleasant smells. (newworldencyclopedia.org)
Molecule1
- Neither structure is an adequate representation of the actual compound, and the double-headed arrow indicates that the molecule is best represented by a hybrid (average) of these two structures. (newworldencyclopedia.org)
Nitrogen2
- An example of a polycyclic compound based on a nitrogen cage is hexanitrohexaazaisowurtzitane. (wikipedia.org)
- Polycyclic nitrogen compounds. (edu.ng)
Pollutants1
- Persistent organic pollutants (POPs) are a class of harmful compounds that are resistant to natural biological. (researchgate.net)
Chemical4
- Organic chemists have developed a rich set of reactions for the construction of chemical compounds. (uni-erlangen.de)
- The first known use of the word "aromatic" as a chemical term-namely, to apply to compounds that contain the phenyl radical-occurs in an article by August Wilhelm Hofmann in 1855. (newworldencyclopedia.org)
- Besides it provides a valuable snapshot of the chemical structure-activity relationship of compounds, highlighting the presence or absence of some specific atoms and chemical units in the structure of compounds can greatly influence their biological activities. (frontiersin.org)
- Compound groups are groups of chemicals that share structural or chemical features. (pharosproject.net)
Atoms1
- In the field of organic chemistry, a polycyclic compound is an organic compound featuring several closed rings of atoms, primarily carbon. (wikipedia.org)
Organic chemistry1
- In organic chemistry , a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon . (wikipedia.org)
Molecular2
- This compound group is defined by the SMILES string 'C(=O)(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O'. For more information on SMILES, see https://en.wikipedia.org/wiki/Simplified_molecular-input_line-entry_system . (pharosproject.net)
- For more information on SMILES, see https://en.wikipedia.org/wiki/Simplified_molecular-input_line-entry_system . (pharosproject.net)
Heavy metals1
- and other organometallic compounds that contain heavy metals. (cdc.gov)
Substances1
- It was also shown, that planar polycyclic ring system is essential structure peculiarity for such substances high activity. (doaj.org)
Review2
- This review is a holistic picture on actinobacter-derived cytotoxic compounds against CRC that provides a good perspective for drug development and design in near future. (frontiersin.org)
- To the best of our knowledge, this is the first comprehensive review on natural actinobacterial compounds affecting different types of CRC. (frontiersin.org)
Development1
- Citation: Oil sands development contributes polycyclic aromatic compounds to the Athabasca River and its tributaries. (mongabay.com)
Work1
- The purpose of this work was design planar polycyclic compounds as inhibitors of kinases, involved in the pro-inflammatory cascade. (doaj.org)
Group1
- This compound group has not yet been assigned a structural definition. (pharosproject.net)
Drug1
- These compounds can be used as potential hits for the further anti-inflammatory drug design. (doaj.org)
Structure1
- Bioisosteric modification of this compound leads to indeno[1,2,3-de]phthalazin-3(2H)-one (3), which also contains =N-NH- fragment in its structure. (doaj.org)