Benz(a)Anthracenes: Four fused benzyl rings with three linear and one angular, that can be viewed as a benzyl-phenanthrenes. Compare with NAPHTHACENES which are four linear rings.Anthracenes: A group of compounds with three aromatic rings joined in linear arrangement.9,10-Dimethyl-1,2-benzanthracene: 7,12-Dimethylbenzanthracene. Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.Carcinogens: Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.Papilloma: A circumscribed benign epithelial tumor projecting from the surrounding surface; more precisely, a benign epithelial neoplasm consisting of villous or arborescent outgrowths of fibrovascular stroma covered by neoplastic cells. (Stedman, 25th ed)Mammary Neoplasms, Experimental: Experimentally induced mammary neoplasms in animals to provide a model for studying human BREAST NEOPLASMS.Polycyclic Compounds: Compounds consisting of two or more fused ring structures.Cocarcinogenesis: The combination of two or more different factors in the production of cancer.Skin Neoplasms: Tumors or cancer of the SKIN.Mice, Inbred SENCAR: Mice selectively bred for hypersusceptibility to two-stage chemical skin carcinogenesis. They are also hypersusceptible to UV radiation tumorigenesis with single high-dose, but not chronic low-dose, exposures. SENCAR (SENsitive to CARcinogenesis) mice are used in research as an animal model for tumor production.Polycyclic Hydrocarbons, Aromatic: A major group of unsaturated cyclic hydrocarbons containing two or more rings. The vast number of compounds of this important group, derived chiefly from petroleum and coal tar, are rather highly reactive and chemically versatile. The name is due to the strong and not unpleasant odor characteristic of most substances of this nature. (From Hawley's Condensed Chemical Dictionary, 12th ed, p96)Benzopyrenes: A class of chemicals that contain an anthracene ring with a naphthalene ring attached to it.Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.Mucorales: An order of zygomycetous fungi, usually saprophytic, causing damage to food in storage, but which may cause respiratory infection or MUCORMYCOSIS in persons suffering from other debilitating diseases.PhenanthrenesBiotransformation: The chemical alteration of an exogenous substance by or in a biological system. The alteration may inactivate the compound or it may result in the production of an active metabolite of an inactive parent compound. The alterations may be divided into METABOLIC DETOXICATION, PHASE I and METABOLIC DETOXICATION, PHASE II.Cheek: The part of the face that is below the eye and to the side of the nose and mouth.Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.Chrysenes: 1,2-Benzphenanthrenes. POLYCYCLIC COMPOUNDS obtained from coal tar.Ethers, Cyclic: Compounds of the general formula R-O-R arranged in a ring or crown formation.Anticarcinogenic Agents: Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.Neoplasms, Experimental: Experimentally induced new abnormal growth of TISSUES in animals to provide models for studying human neoplasms.Mammary Glands, Animal: MAMMARY GLANDS in the non-human MAMMALS.Mutagens: Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.Epoxy Compounds: Organic compounds that include a cyclic ether with three ring atoms in their structure. They are commonly used as precursors for POLYMERS such as EPOXY RESINS.Biodegradation, Environmental: Elimination of ENVIRONMENTAL POLLUTANTS; PESTICIDES and other waste using living organisms, usually involving intervention of environmental or sanitation engineers.Mesocricetus: A genus of the family Muridae having three species. The present domesticated strains were developed from individuals brought from Syria. They are widely used in biomedical research.Epoxide Hydrolases: Enzymes that catalyze reversibly the formation of an epoxide or arene oxide from a glycol or aromatic diol, respectively.Cyclohexenes: Six-carbon alicyclic hydrocarbons which contain one or more double bonds in the ring. The cyclohexadienes are not aromatic, in contrast to BENZOQUINONES which are sometimes called 2,5-cyclohexadiene-1,4-diones.DNA Adducts: The products of chemical reactions that result in the addition of extraneous chemical groups to DNA.Mutagenicity Tests: Tests of chemical substances and physical agents for mutagenic potential. They include microbial, insect, mammalian cell, and whole animal tests.Skin: The outer covering of the body that protects it from the environment. It is composed of the DERMIS and the EPIDERMIS.Croton Oil: Viscous, nauseating oil obtained from the shrub Croton tiglium (Euphorbaceae). It is a vesicant and skin irritant used as pharmacologic standard for skin inflammation and allergy and causes skin cancer. It was formerly used as an emetic and cathartic with frequent mortality.Soil Pollutants: Substances which pollute the soil. Use for soil pollutants in general or for which there is no specific heading.Microsomes, Liver: Closed vesicles of fragmented endoplasmic reticulum created when liver cells or tissue are disrupted by homogenization. They may be smooth or rough.Chromatography, Thin Layer: Chromatography on thin layers of adsorbents rather than in columns. The adsorbent can be alumina, silica gel, silicates, charcoals, or cellulose. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)Chromatography, High Pressure Liquid: Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed.Cell Transformation, Neoplastic: Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.Moringa oleifera: A plant species of the family Moringaceae, order Capparales, subclass Dilleniidae. It is a source of niaziminin and hypotensive thiocarbamate glycosides.Tracheal NeoplasmsSpectrophotometry, Ultraviolet: Determination of the spectra of ultraviolet absorption by specific molecules in gases or liquids, for example Cl2, SO2, NO2, CS2, ozone, mercury vapor, and various unsaturated compounds. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)Aryl Hydrocarbon Hydroxylases: A large group of cytochrome P-450 (heme-thiolate) monooxygenases that complex with NAD(P)H-FLAVIN OXIDOREDUCTASE in numerous mixed-function oxidations of aromatic compounds. They catalyze hydroxylation of a broad spectrum of substrates and are important in the metabolism of steroids, drugs, and toxins such as PHENOBARBITAL, carcinogens, and insecticides.Epidermis: The external, nonvascular layer of the skin. It is made up, from within outward, of five layers of EPITHELIUM: (1) basal layer (stratum basale epidermidis); (2) spinous layer (stratum spinosum epidermidis); (3) granular layer (stratum granulosum epidermidis); (4) clear layer (stratum lucidum epidermidis); and (5) horny layer (stratum corneum epidermidis).Methylophilus: A genus of straight or slightly curved gram-negative rods occurring singly or in pairs and isolated from sludge, mud, and river and pond water. (From Bergey's Manual of Determinative Bacteriology, 9th ed)Rats, Inbred Strains: Genetically identical individuals developed from brother and sister matings which have been carried out for twenty or more generations or by parent x offspring matings carried out with certain restrictions. This also includes animals with a long history of closed colony breeding.Bromine: A halogen with the atomic symbol Br, atomic number 36, and atomic weight 79.904. It is a volatile reddish-brown liquid that gives off suffocating vapors, is corrosive to the skin, and may cause severe gastroenteritis if ingested.Pyrenes: A group of condensed ring hydrocarbons.Stereoisomerism: The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)HydrocarbonsAnthraquinones: Compounds based on ANTHRACENES which contain two KETONES in any position. Substitutions can be in any position except on the ketone groups.Creosote: A greasy substance with a smoky odor and burned taste created by high temperature treatment of BEECH and other WOOD; COAL TAR; or resin of the CREOSOTE BUSH. It contains CRESOLS and POLYCYCLIC AROMATIC HYDROCARBONS which are CARCINOGENS. It has been widely used as wood preservative and in PESTICIDES and had former use medicinally in DISINFECTANTS; LAXATIVES; and DERMATOLOGIC AGENTS.Mouth Neoplasms: Tumors or cancer of the MOUTH.Cricetinae: A subfamily in the family MURIDAE, comprising the hamsters. Four of the more common genera are Cricetus, CRICETULUS; MESOCRICETUS; and PHODOPUS.Adenofibroma: A benign neoplasm composed of glandular and fibrous tissues, with a relatively large proportion of glands. (Stedman, 25th ed)Enzyme Induction: An increase in the rate of synthesis of an enzyme due to the presence of an inducer which acts to derepress the gene responsible for enzyme synthesis.Chlorodiphenyl (54% Chlorine)Aroclors: Industrial chemicals which have become widespread environmental pollutants. Each aroclor is a mixture of chlorinated biphenyls (1200 series) or chlorinated terphenyls (5400 series) or a combination of both (4400 series).Structure-Activity Relationship: The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups.Vinyl CompoundsDNA: A deoxyribonucleotide polymer that is the primary genetic material of all cells. Eukaryotic and prokaryotic organisms normally contain DNA in a double-stranded state, yet several important biological processes transiently involve single-stranded regions. DNA, which consists of a polysugar-phosphate backbone possessing projections of purines (adenine and guanine) and pyrimidines (thymine and cytosine), forms a double helix that is held together by hydrogen bonds between these purines and pyrimidines (adenine to thymine and guanine to cytosine).

Pathologic changes induced in respiratory tract mucosa by polycyclic hydrocarbons of differing carcinogenic activity. (1/915)

Seven aromatic polycyclic hydrocarbons (PCHs) were investigated for their toxic effects on respiratory mucosa: benzo(e)pyrene (BeP), pyrene, anthracene, benz(a)anthracene(BaA), dibenz(a,c)anthracene(DBacA), benzo (a)pyrene (BaP), and dimethylbenz(a)anthracene (DMBA). The compounds were chosen because they comprise a spectrum of PCHs ranging from noncarcinogens, to initiators, to weak and strong carcinogens. All of them except DMBA are environmentally relevant chemicals. The chemicals were tested over an 8-week period. Heterotopic tracheal transplants were continously exposed and the histopathologic effects induced by the various PCHs were periodically assessed semiquantitatively. All PCHs exhibited varying degrees of toxicity for respiratory epithelium and submucosa. BeP clearly showed the least toxicity followed by pyrene and anthracene. BaA and DBacA caused marked epithelial and submucosal changes. In addition to epithelial hyperplasia, undifferentiated epithelium and squamous metaplasia developed. Marked mononuclear infiltration occurred in the subepithelial connective tissue. With BaP the epithelial and submucosal changes were similar but were much stronger. DMBA was the most toxic substance, causing epithelial necrosis followed by generalized keratinizing squamous metaplasia; the subepithelial changes consisted of an early acellular exudate and, later (at 8 weeks), marked condensation and hyalinization of the lamina propria. The toxic response pattern of the tracheal mucosa to carcinogenic agents was characterized by the chronicity of epithelial and connective tissue damage, as opposed to the short-lived hyperplastic and inflammatory response elicited by the noncarcinogens and weak initiators.  (+info)

Formation of bound residues during microbial degradation of [14C]anthracene in soil. (2/915)

Carbon partitioning and residue formation during microbial degradation of polycyclic aromatic hydrocarbons (PAH) in soil and soil-compost mixtures were examined by using [14C]anthracenes labeled at different positions. In native soil 43.8% of [9-14C]anthracene was mineralized by the autochthonous microflora and 45.4% was transformed into bound residues within 176 days. Addition of compost increased the metabolism (67.2% of the anthracene was mineralized) and decreased the residue formation (20. 7% of the anthracene was transformed). Thus, the higher organic carbon content after compost was added did not increase the level of residue formation. [14C]anthracene labeled at position 1,2,3,4,4a,5a was metabolized more rapidly and resulted in formation of higher levels of residues (28.5%) by the soil-compost mixture than [14C]anthracene radiolabeled at position C-9 (20.7%). Two phases of residue formation were observed in the experiments. In the first phase the original compound was sequestered in the soil, as indicated by its limited extractability. In the second phase metabolites were incorporated into humic substances after microbial degradation of the PAH (biogenic residue formation). PAH metabolites undergo oxidative coupling to phenolic compounds to form nonhydrolyzable humic substance-like macromolecules. We found indications that monomeric educts are coupled by C-C- or either bonds. Hydrolyzable ester bonds or sorption of the parent compounds plays a minor role in residue formation. Moreover, experiments performed with 14CO2 revealed that residues may arise from CO2 in the soil in amounts typical for anthracene biodegradation. The extent of residue formation depends on the metabolic capacity of the soil microflora and the characteristics of the soil. The position of the 14C label is another important factor which controls mineralization and residue formation from metabolized compounds.  (+info)

Diverse oxygenations catalyzed by carbazole 1,9a-dioxygenase from Pseudomonas sp. Strain CA10. (3/915)

Carbazole 1,9a-dioxygenase (CARDO) from Pseudomonas sp. strain CA10 is a multicomponent enzyme that catalyzes the angular dioxygenation of carbazole, dibenzofuran, and dibenzo-p-dioxin. It was revealed by gas chromatography-mass spectrometry and 1H and 13C nuclear magnetic resonance analyses that xanthene and phenoxathiin were converted to 2,2',3-trihydroxydiphenylmethane and 2,2',3-trihydroxydiphenyl sulfide, respectively. Thus, for xanthene and phenoxathiin, angular dioxygenation by CARDO occurred at the angular position adjacent to the oxygen atom to yield hetero ring-cleaved compounds. In addition to the angular dioxygenation, CARDO catalyzed the cis dihydroxylation of polycyclic aromatic hydrocarbons and biphenyl. Naphthalene and biphenyl were converted by CARDO to cis-1, 2-dihydroxy-1,2-dihydronaphthalene and cis-2,3-dihydroxy-2, 3-dihydrobiphenyl, respectively. On the other hand, CARDO also catalyzed the monooxygenation of sulfur heteroatoms in dibenzothiophene and of the benzylic methylenic group in fluorene to yield dibenzothiophene-5-oxide and 9-hydroxyfluorene, respectively. These results indicate that CARDO has a broad substrate range and can catalyze diverse oxygenation: angular dioxygenation, cis dihydroxylation, and monooxygenation. The diverse oxygenation catalyzed by CARDO for several aromatic compounds might reflect the differences in the binding of the substrates to the reaction center of CARDO.  (+info)

Comparative tumorigenicity of the cyclopenta-fused polycyclic aromatic hydrocarbons aceanthrylene, dihydroaceanthrylene and acephenanthrylene in preweanling CD-1 and BLU:Ha mouse bioassays. (4/915)

Cyclopenta-fused polycyclic aromatic hydrocarbons are ubiquitous environmental pollutants and potential human health biohazards. In this study, the tumorigenicity of three single cyclopenta-fused polycyclic aromatic hydrocarbons, aceanthrylene, dihydroaceanthrylene and acephenanthrylene, was examined in preweanling CD-1 and BLU:Ha mouse bioassays at total doses of 175, 437.5 and 875 micrograms/mouse. No death or significant toxicity was observed with the treatment protocol in the tested animals. In CD-1 mice, a significant increase in lung tumor incidence (18-26%, P < 0. 025-0.01) for these three compounds was recorded in animals treated with 875 micrograms as compared with the control animals (3%). Significant numbers of liver tumors (25-41%, P < 0.01-0.001) were induced in all aceanthrylene treatment groups and in animals treated with 875 micrograms acephenanthrylene (35%) at the termination at 9 months. Most liver tumors were induced in male animals. The ED50 values were estimated as 8.5, 10.6 and 12.8 micromol and the TM1.0 were 15.1, 20.4 and 23.1 micromol for aceanthrylene, acephenanthrylene and dihydroaceanthrylene, respectively. In BLU:Ha mice, there was a significant dose-dependent increase in lung tumor incidence, from 4% for the control group to 33% (P < 0.001) for the animals treated with 875 micrograms aceanthrylene and to 24% (P < 0.02) for the animals treated with 437.5 micrograms acephenanthrylene. The ED50 values were 6.0 and 4.4 micromol and the TM1.0 were 9.8 and 6.8 micromol for aceanthrylene and acephenanthrylene, respectively. No significant difference in lung tumor incidence between male and female mice was found. Based on these data and comparisons of tumorigenic potency with other polycyclic aromatic hydrocarbons previously tested in these newborn mouse bioassays, aceanthrylene and acephenanthrylene were classified as weak tumorigens.  (+info)

Myeloma cells selected for resistance to CD95-mediated apoptosis are not cross-resistant to cytotoxic drugs: evidence for independent mechanisms of caspase activation. (5/915)

We have previously shown that selection for resistance to the anthracenes, doxorubicin or mitoxantrone, results in coselection for resistance to CD95-mediated apoptosis (Landowski et al: Blood 89:1854, 1997). In the present study, we were interested in determining if the converse is also true; that is, does selection for CD95 resistance coselect for resistance to chemotherapeutic drugs. To address this question, we used two isogenic models of CD95-resistant versus CD95-sensitive cell lines: 8226/S myeloma cells selected for resistance to CD95-mediated apoptosis; and K562 cells expressing ectopic CD95. Repeated exposure of the CD95-sensitive human myeloma cell line, 8226/S, to agonistic anti-CD95 antibody resulted in a cell line devoid of CD95 receptor surface expression and completely resistant to CD95-mediated apoptosis. Multiple clonal populations derived from the CD95-resistant cell line showed no difference in sensitivity to doxorubicin, mitoxantrone, Ara-C, or etoposide, demonstrating that cross-resistance between Fas-mediated apoptosis and drug-induced apoptosis occurs only when cytotoxic drugs are used as the selecting agent. Using the inverse approach, we transfected the CD95-negative cell line, K562, with a CD95 expression vector. Clones expressing variable levels of cell-surface CD95 were isolated by limiting dilution, and analyzed for sensitivity to CD95-mediated apoptosis and response to chemotherapeutic drugs. We show that CD95 surface expression confers sensitivity to CD95-mediated apoptosis; however, it does not alter response to chemotherapeutic drugs. Similarly, doxorubicin-induced activation of caspases 3 and 8 was identical in the CD95-sensitive and CD95-resistant cell lines in both isogenic cell systems. In addition, prior treatment with the CD95 receptor-blocking antibody, ZB4, inhibited CD95-activated apoptosis in 8226/S cells, but had no effect on doxorubicin cytotoxicity. These results show that CD95 and chemotherapeutic drugs use common apoptotic effectors, but the point of convergence in these two pathways is downstream of CD95 receptor/ligand interaction.  (+info)

Development of a new bioluminescent mutagenicity assay based on the Ames test. (6/915)

A newly developed rapid mutagenicity assay based on the adenosine triphosphate (ATP)-bioluminescence technique and the Ames test is described. Salmonella typhimurium strains TA98 and TA100 were exposed in an appropriate liquid medium to the direct mutagens 4-nitroquinoline-N-oxide and methyl methanesulphonate, respectively, and to the indirect mutagen 2-aminoanthracene. Both auxotrophic and prototrophic growth were monitored throughout the incubation period as variations in the intracellular ATP levels by means of the luciferin-luciferase assay. After 9-12 h of incubation a dose-response increase in the levels of ATP was readily detected. In order to demonstrate that this increase was due to the growth of revertant bacteria, aliquots from each culture were plated on minimal agar plates. A very good correlation between the changes in ATP levels and the appearance of revertant colonies on the plates was found. Given the rapidity of this method as compared with conventional mutagenicity assays, it has potential for industrial and environmental applications. Other potential applications are also discussed.  (+info)

Polycyclic aromatic hydrocarbon metabolism by white rot fungi and oxidation by Coriolopsis gallica UAMH 8260 laccase. (7/915)

We studied the metabolism of polycyclic aromatic hydrocarbons (PAHs) by using white rot fungi previously identified as organisms that metabolize polychlorinated biphenyls. Bran flakes medium, which has been shown to support production of high levels of laccase and manganese peroxidase, was used as the growth medium. Ten fungi grown for 5 days in this medium in the presence of anthracene, pyrene, or phenanthrene, each at a concentration of 5 microg/ml could metabolize these PAHs. We studied the oxidation of 10 PAHs by using laccase purified from Coriolopsis gallica. The reaction mixtures contained 20 microM PAH, 15% acetonitrile in 60 mM phosphate buffer (pH 6), 1 mM 2,2'-azinobis-(3-ethylbenzthiazoline-6-sulfonate) (ABTS), and 5 U of laccase. Laccase exhibited 91% of its maximum activity in the absence of acetonitrile. The following seven PAHs were oxidized by laccase: benzo[a]pyrene, 9-methylanthracene, 2-methylanthracene, anthracene, biphenylene, acenaphthene, and phenanthrene. There was no clear relationship between the ionization potential of the substrate and the first-order rate constant (k) for substrate loss in vitro in the presence of ABTS. The effects of mediating substrates were examined further by using anthracene as the substrate. Hydroxybenzotriazole (HBT) (1 mM) supported approximately one-half the anthracene oxidation rate (k = 2.4 h(-1)) that ABTS (1 mM) supported (k = 5.2 h(-1)), but 1 mM HBT plus 1 mM ABTS increased the oxidation rate ninefold compared with the oxidation rate in the presence of ABTS, to 45 h(-1). Laccase purified from Pleurotus ostreatus had an activity similar to that of C. gallica laccase with HBT alone, with ABTS alone, and with 1 mM HBT plus 1 mM ABTS. Mass spectra of products obtained from oxidation of anthracene and acenaphthene revealed that the dione derivatives of these compounds were present.  (+info)

Nepalolide A inhibits the expression of inducible nitric oxide synthase by modulating the degradation of IkappaB-alpha and IkappaB-beta in C6 glioma cells and rat primary astrocytes. (8/915)

1 The effects of nepalolide A on the expression of inducible nitric oxide synthase (iNOS) caused by incubation with lipopolysaccharide/interferon-gamma (LPS/IFN-gamma) or tumour necrosis factor-alpha/interleukin-1beta/IFN-gamma (TNF-alpha/IL-1beta/IFN-gamma, mixed cytokines) in C6 glioma cells and primary astrocytes of rat were investigated. The mechanisms by which nepalolide A confers its effect on iNOS expression were also elucidated. 2 Treatment with LPS/IFN-gamma and mixed cytokines for 24 h elicited the induction of iNOS activity as determined by nitrite accumulation in the culture medium and assay of enzyme activity. Nepalolide A at 10 microM abrogated the LPS/IFN-gamma- and mixed cytokines-mediated induction of iNOS by more than 90% in C6 glioma cells, and by 80% for mixed cytokines-induced induction of iNOS in primary astrocytes. The effect of nepalolide A (2-10 microM) was concentration-dependent. 3 The inhibition of iNOS induction by nepalolide A was attributed to decreases in the content of iNOS protein and the level of iNOS mRNA, as measured by immunoblotting and reverse transcriptase-polymerase chain reaction. 4 Electrophoretic mobility shift assay was used to evaluate the effect of nepalolide A on the activation of nuclear factor-kappaB (NF-kappaB). Results showed that nepalolide A diminished the LPS/IFN-gamma-mediated association of NF-kappaB with consensus oligonucleotide in a concentration-dependent manner. The activation of NF-kappaB by mixed cytokines was modulated both in the extent of activation and in its time-course by nepalolide A. 5 The ability of nepalolide A to inhibit NF-kappaB activation was further confirmed by studies on the degradation of the inhibitor of NF-kappaB, IkappaB, as measured by immunoblotting. 6 The present study demonstrates that the attenuation of NF-kappaB activation by nepalolide A was mediated by blockade of the degradation of IkappaB, leading to suppression of the expression of iNOS.  (+info)

  • Identification and quantitation of the depurination and stable DNA adducts of 7,12-dimethylbenz[a]anthracene (DMBA) formed by cytochrome P450 in rat liver microsomes previously established one-electron oxidation as the predominant mechanism of activation of DMBA to bind to DNA. (nih.gov)
  • The depurination adducts, which constitute 99% of all the adducts detected, are DMBA bound at the 12-methyl group to the N-7 of adenine or guanine, namely, 7-methylbenz[a]anthracene (MBA)-12-CH2-N7Ade and 7-MBA-12-CH2-N7Gua. (nih.gov)
  • The present study evaluated the chemopreventive potential of (6)-paradol, a pungent phenolic constituent of ginger, on 7,12-dimethylbenz(a)anthracene (DMBA)-induced hamster buccal pouch carcinogenesis. (nih.gov)
  • Because NF-κB suppression has been linked with chemoprevention, this prompted us to investigate the chemopreventive potential of resveratrol by testing it against mammary carcinogenesis induced by 7,12-dimethylbenz( a )anthracene (DMBA) in female Sprague Dawley rats. (aacrjournals.org)
  • We explored the basis of the combinatorial chemopreventive effect of Butyric acid (BA), Nicotinamide (NA) and Calcium Glucarate (CAG) on mouse skin exposed to 7, 12-dimethylbenz (a) anthracene (DMBA). (biomedsearch.com)
  • Treatment with 2.56 micrograms (10 nmol) 7,12-dimethylbenz[a] anthracene (DMBA) resulted in maximal MN induction in cells removed from skin 12-24 hr after topical administration (79-88 MN/1,000 cells compared with 10-16 MN/1,000 cells in acetone-treated controls). (biomedsearch.com)
  • 7,12-DMBA was almost two orders of magnitude more active as a tumor -initiator than 7- and 12-methylbenz[a] anthracene . (curehunter.com)
  • Immunohistochemistry and autoradiography were used to identify sites of the cytochrome P450 enzymes (P450) 1A1 and 1B1 expression and activation of 7,12-dimethylbenz(a)anthracene (DMBA), in the brain of rodents pretreated with the aryl hydrocarbon receptor (AhR) agonists beta-naphthoflavone (BNF), 3,3',4,4',5-pentachlorobiphenyl or vehicle. (diva-portal.org)
  • Aim of the present study was to evaluate the anti-tumor effect of orally administered rosmarinic acid in 7,12-dimethylbenz(a)anthracene (DMBA) induced skin carcinogenesis in Swiss albino mice. (niscair.res.in)
  • Our aim of this study was to examine the chemopreventive potential of fish oil on 7, 12-Dimethylbenz (a) Anthracene (DMBA)-initiated and croton oil-promoted skin papillomagenesis model in mice. (alliedacademies.org)
  • 7,12-Dimethylbenz[a]anthracene (DMBA) depletes ovarian follicles and induces DNA damage in extra-ovarian tissues, thus, we investigated ovarian DMBA-induced DNA damage. (ovid.com)
  • Mammary tumours were induced in female Sprague-Dawley rats by feeding orally with dimethylbenz [a]anthracene (DMBA) (60 mg/kg). (biomedcentral.com)
  • In February 2014, NASA announced a greatly upgraded database for tracking polycyclic aromatic hydrocarbons (PAHs), including benz[a]anthracene, in the universe. (wikipedia.org)
  • Benz(a)anthracene is a constituent of tobacco smoke. (wikipedia.org)
  • Tetracene, also known as benz[b]anthracene Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). (wikipedia.org)
  • Mouse skin tumor-initiating activity of 5-, 7-, and 12-methyl- and fluorine-substituted benz[a]anthracenes. (curehunter.com)
  • Methyl substitution at the 7- and 7,12-positions of benz[a]anthracene was significantly more effective in the enhancement of tumorigenic activity than fluorine substitution at these positions. (curehunter.com)
  • In cultured human bronchial mucosa, activity of aryl hydrocarbon hydroxylase was inducible by both benz[a]anthracene and BP. (au.dk)
  • Prior exposure of the bronchial expiants to benz[a]anthracene altered the qualitative features of the metabolite profile of BP as analyzed by highpressure liquid chromatography. (au.dk)
  • Dibenz[ a,h ]anthracene has been shown to be carcinogenic to experimental animals. (inchem.org)
  • Dibenz[ a,h ]anthracene is embryotoxic to rats when given at high doses. (inchem.org)
  • Dibenz[ a,h ]anthracene was positive in differential survival assays using DNA-repair-proficient/-deficient strains of bacteria and was mutagenic to Salmonella typhimurium in the presence of an exogenous metabolic system. (inchem.org)
  • In cultured mammalian cells, dibenz[ a,h ]anthracene was mutagenic and induced unscheduled DNA synthesis in the presence of an exogenous metabolic system. (inchem.org)
  • There is sufficient evidence that dibenz[ a,h ]anthracene is active in short-term tests. (inchem.org)
  • Dibenz[ a,h ]anthracene is present as a minor component of the total content of polynuclear aromatic compounds in the environment. (inchem.org)
  • Human exposure to dibenz[ a,h ]anthracene occurs primarily through the smoking of tobacco, inhalation of polluted air and by ingestion of food and water contaminated with combustion products. (inchem.org)
  • There is sufficient evidence that dibenz[ a,h ]anthracene is carcinogenic to experimental animals. (inchem.org)
  • Dibenz( a , h )anthracene has produced tumours by different routes of administration in mice, rats, guinea pigs, frogs, pigeons and chickens. (inchem.org)
  • Dibenz( a , h )anthracene induced local sarcomas and increased the incidence of lung adenomas following a single s.c. injection in newborn mice at dose levels which were ineffective with 3-methylcholanthrene. (inchem.org)
  • No case reports or epidemiological studies on the significance of dibenz( a , h )anthracene exposure to man are available. (inchem.org)
  • However, coal-tar and other materials which are known to be carcinogenic to man may contain dibenz( a , h )anthracene. (inchem.org)
  • This experiment involved a reaction between anthracene and maleic anhydride via a Diels Alder reaction to yield 9, 10-dihydroanthracene-9,10-α, β-succinic anhydride. (bartleby.com)
  • The purpose of this experiment is to form 9,10-dihydroanthracene-9,10-α,β-succinic anhydride by way of a Diels Alder reaction between anthracene and maleic anhydride, as shown in the reaction below. (vernier.com)
  • The structure of newly formed fullerene/anthracene cluster cations and the bonding energy for these reaction pathways are investigated with quantum chemistry calculations. (arxiv.org)
  • The synthesis involved a Diels-Alder reaction of anthracene and dimethyl fumarate to afford 3 followed by reduction, oxidation and esterification reactions to provide methyl ester anthracene adduct 8, which further converted to the the allylic alcohol (12). (edu.au)
  • Then, Ring-Closing Metathesis (RCM) reaction afforded the cyclopentenol anthracene adduct, which after oxidation provided the spirocyclopente-dione anthracene adduct in good yields. (edu.au)
  • The nature of reaction conditions influenced the extent of anthracene degradation. (bibsys.no)
  • 1.1,8,9-Tris (phenylseleno) anthracene (1) has been tried to prepare in the reaction of 1,8-bis (phenylseleno) anthracene (2) with various organometallic reagents. (nii.ac.jp)
  • Zuschriften Expanded Porphyrins Anthracene-Bridged Z-Shaped Hexaphyrin(1.1.1.1.1.1.1) Dimer from the Regioselective Diels-Alder Reaction of a Hexaphyrin with Bis-o-xylylene Equivalents Hiroshi Hata, Hiroshi Shinokubo,* and Atsuhiro Osuka* Expanded porphyrins which are porphyrin analogues with more than five pyrrolic subunits have recently attracted much attention because of their interesting structural and functional features and unique metal-coordination properties. (docme.ru)
  • Hydrous pyrolysis is explored as a technique for the treatment of industrial water containing PAH, using anthracene as a model compound. (bibsys.no)
  • 6. The anthracene-based compound as claimed in claim 1, wherein: n is an integer of 1 to 3, and a moiety represented by (L) n is selected from Formulae 3-1 to 3-9, below: ##STR00114## ##STR00115## in Formulae 3-1 to 3-9 above, ** is a binding site to an anthracene core, and * is a binding site to Ar. (patentsencyclopedia.com)
  • Whey Protein Hydrolysate but not Whole Whey Protein Protects Against 7,12-Dimethylbenz(a)anthracene-Induced Mammary Tumors in Rats. (nih.gov)
  • Experiments were done to study the effect of 7,12-dimethylbenz(a)anthracene on the incorporation of thymidine-methyl- 3 H (thymidine- 3 H) into mammary gland DNA of female and male rats in vitro and in vivo and on DNA polymerase activity of mammary gland tissue. (aacrjournals.org)
  • At age 50 days, F 1 (experiment A) or F 2 (experiment B) female offspring (≥19 rats/group) were p.o. gavaged with 80 mg/kg 7,12-dimethylbenz( a )anthracene, and mammary glands were evaluated when 100% of the casein-fed group developed at least one palpatable tumor. (aacrjournals.org)
  • The K-region trans-5,6-dihydrodiols formed in the metabolism of 12-methylbenz[a]anthracene (12-MBA) by liver microsomal preparations from untreated, phenobarbital-treated and 3-methylcholanthrene-treated male Sprague-Dawley rats were found by chiral stationary-phase h.p.l.c. (c.s.p.-h.p.l.c.) analyses to contain (5S,6S)/(5R,6R) enantiomer ratios of 93:7, 88:12 and 97:3 respectively. (biochemj.org)
  • The administration of 2.5 mg retinyl acetate daily in the diet to female Sprague-Dawley rats beginning 7 days after the intragastric instillation of either 2.5, 5, or 15 mg 7,12-dimethylbenz(a)anthracene (CMBA) resulted in a reduction in the incidence of benign mammary tumors of 37, 30, and 31%, respectively. (semanticscholar.org)
  • Combinatorial chemopreventive effect of butyric acid, nicotinamide and calcium glucarate against the 7,12-dimethylbenz(a)anthracene induced mouse skin tumorigenesis attained by enhancing the induction of intrinsic apoptotic events. (biomedsearch.com)
  • By encapsulating AIE molecule 9,10-divinyl anthracene (DSA) with poly(styrene-co-maleic anhydride) and poly(isobutylene-alt-maleic anhydride) (PSMA and PIMA), novel bright AIE organic dots were obtained. (ingentaconnect.com)
  • Their magnitudes were close to values predicted for an ellipsoid of shape and size equivalent to an anthracene molecule, and exhibited predictable variation with external conditions-increasing with temperature and decreasing with solventviscosity. (ku.edu)
  • ANTHRACENE OIL (CAS 65996-91-0) Market Research Report 2018 aims at providing comprehensive data on anthracene oil market globally and regionally (Europe, Asia, North America, Latin America etc. (marketpublishers.com)
  • Globally North America dominated the market for anthracene in 2015 due higher consumption and high R&D activities in the region related to anthracene and its applications. (industryarc.com)
  • This is report has been further segmented into major regions, which includes detailed analysis of each region such as North America, Europe, Asia-Pacific (APAC) and Rest of the World (RoW) covering all the major country level markets for anthracene in each of the region. (industryarc.com)
  • Based on experimental data, anthracene shows acute toxicity within the range of its water solubility (~40 - 70 µg/L). Aquatic toxicity is most pronounced in fish, daphnia and algae in the presence of UV-A light. (europa.eu)
  • Anthracene-polyamine conjugates inhibit the in vitro proliferation of the intraerythrocytic human malaria parasite, Plasmodium falciparum, with IC50 values in the nM-μM range. (up.ac.za)
  • Substitution of fluorine or methyl at the 5-position of 7-methylbenz[a] anthracene and substitution of fluorine at the 5-position of 12-methylbenz[a] anthracene dramatically reduced their tumorigenic activity. (curehunter.com)
  • In this work, we study the formation and photo-dissociation processes of astronomically relevant fullerene/anthracene (C14H10) cluster cations in the gas phase. (arxiv.org)
  • C14H10)nC and [(C14H10)nC), fullerene (C56 and C58)/anthracene (i.e. (arxiv.org)
  • C14H10)nC and [(C14H10)nC) and fullerene (C66 and C68)/anthracene (i.e. (arxiv.org)
  • Published values range between 30 and 75 µg/L (25 °C). The measured water solubility of 47 µg/L is adopted as most representative (see also EU 2008, Risk Assessment for Anthracene). (europa.eu)
  • The products formed are more reactive (less stable) as compared to anthracene the starting material and will therefore be less persistent in the environment. (bibsys.no)
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