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Query: CAS:781-43-1 (9,10-dimethylanthracene)
 112 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

Fluorescence spectra of DNA isolated from hamster embryo cells incubated with 7,12-dimethylbenz(a)anthracene, or DNA modified in a microsomal system by reaction with this carcinogen or its 7-hydroxymethyl derivative, were compared to various model compounds. The spectra indicate that the DMBA derivative bound to DNA, in all 3 cases, has a 9,10-dimethylanthracene-like chromophore. They also provide the first evidence of the similarity in structure of the DNA-bound products between 7,12-dimethylbenz(a)anthracene and its 7-hydroxymethyl derivative. Our results are consistent with an activation mechanism that involves saturation of the 1,2,3,4-ring positions.
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PMID:Cell and microsome mediated binding of 7,12-dimethylbenz(a)anthracene to DNA studied by fluorescence spectroscopy. 41 2

We evaluated the influence of near-ultraviolet light (UVA) on the cytotoxicity and genotoxicity of 7 polycyclic aromatic hydrocarbons (PAH) in larvae of the amphibian Pleurodeles waltl. Benz[a]anthracene (BA), 7,12-benz[a]anthraquinone (BAQ) and anthracene (Ac) proved to be lethal at low doses (some ppb), and the following order of genotoxicity was observed: BA approximately BAQ > DMBA > DMA (9,10-dimethylanthracene). Ac, AQ (9,10-anthraquinone) and DBA (dibenz[a,h]anthracene) were not found to be clastogenic. In the larvae reared in normal conditions (subdued natural daylight/darkness alternation) or in continuous darkness, the BA derivatives were shown to be more genotoxic than BA itself: DMBA > BAQ > BA; BA (> or = 187.5 ppb) slightly increased the level of micronuclei in circulating erythrocytes, while DMBA was strongly clastogenic, in line with their reported carcinogenicity. In other experiments, rearing media alone (i.e., water containing BA, BAQ or DMBA) were UVA-irradiated for 24 h, and then tested on larvae in the dark ('IR-UV/dark' conditions). Photodegradation of BA (50 and 100 ppb) gave rise to clastogenic products. By contrast, DMBA (12.5, 25 or 50 ppb) was destroyed by UVA, and we suggested that any potentially mutagenic photoproducts formed were not in sufficient amounts to yield a positive response in the newt micronucleus test.
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PMID:Influence of lighting conditions on toxicity and genotoxicity of various PAH in the newt in vivo. 127 14

The metabolism of two polycyclic aromatic hydrocarbons i.e. anthracene and 9,10-dimethylanthracene by Micrococcus sp., Pseudomonas sp. and Bacillus macerans was examined. The above compounds were used as a sole carbon source for their growth. Using the reversed-phase thin layer chromatography techniques a number of anthracene and 9,10-dimethylanthracene metabolites were isolated and their structures identified spectroscopically. These included anthracene and 9,10-dimethylanthracene cis-dihydrodiols, hydroxy-methyl-derivatives and various phenolic compounds. Bacteria metabolise hydrocarbons using the dioxygenase enzyme system, which differs from the mammalian cytochrome P-450 monoxygenase. Hence in addition rat liver microsomal metabolism of the above hydrocarbons was investigated using the same separation techniques.
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PMID:The metabolism of anthracene and 9,10-dimethylanthracene by bacteria isolated from waters. 172 22

Typical 11 ultraviolet (UV) absorbers in cosmetic products were separated and determined by high performance liquid chromatography. The recommended conditions for the analysis were as follows: column, 4.6 mm i.d. x 250 mm, Capcell Pak C18 SG (5 microns); detector, UV spectrophotometer (280 nm); column temperature, 40 degrees C; mobile phase, H2O-CH3OH (15:85 v/v) containing 3 mM stearyltrimethyl ammonium chloride; flow rate, 1.0 ml/min. In the case of the products containing 2-ethylhexyl p-methoxycinnamate (OMC) and/or 4-tert-butyl-4'-methoxydibenzoylmethane (BMD), it was necessary to use H2O-1,4-dioxane (34:66 v/v) containing 6 mM stearyltrimethyl ammonium chloride as the mobile phase in order to separate OMC and BMD. Anthracene and 9,10-dimethylanthracene were used as an internal standard for the H2O-CH3OH mobile phase and the H2O-1,4-dioxane mobile phase, respectively. Calibration curves were linear within a range of 50-150 micrograms/ml for the 11 UV absorbers. Recoveries and reproducibilities of the method were satisfactory. By using this method, typical UV absorbers in several commercial cosmetic products such as lip creams, sun oils, lotions and emulsions were able to be rapidly determined without any interference.
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PMID:[High performance liquid chromatographic analysis of typical ultraviolet absorbers in cosmetic products]. 176 56

It was found that the DNA-damaging agents N-methyl-N'-nitro-N-nitrosoguanidine (MNNG), methyl-methanesulphonate (MMS) and 4-nitroquinoline-N-oxide (4NQO) could stimulate ADP-ribosyl transferase (ADPRT) activity and reduce the cellular NAD content in a dose-dependent way. The reduction of NAD after DNA damage could be partially or completely prevented by ADPRT inhibitors, 3-aminobenzamide or nicotinamide, which showed no influence on reduction of NAD induced by metabolic blocking agents. Therefore, a simple and specific method to detect DNA-damaging mutagens by measuring ADPRT-mediated decrease of cellular NAD content was explored. Using beta-naphthoflavone, a mixed function oxygenase inducer, together with induced or uninduced human amnion FL cells, it was found that aflatoxin B1, benzo(a)pyrene, 2-acetylaminofluorene, 9,10-dimethylanthracene and ethylcarbamate could induce the ADPRT-mediated decrease of cellular NAD content, while 4-acetylaminofluorene, anthracene, isopropyl-N-(3-chlorophenyl)-carbamate, beta-propiolactone, gamma-butyrolactone, cyclophosphamide and safrol could not. The results indicate that this is a cheap and specific method to detect DNA damage caused by chemical carcinogens/mutagens with a specificity approaching that of the unscheduled DNA synthesis assay.
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PMID:ADPRT-mediated decrease of cellular NAD content and the detection of chemically induced DNA damage--development of a new short-term screening test for mutagens. 211 65

This paper reports the results of a study on the genotoxic activities of 12 mutagens and clastogens of widely differing mode of action in somatic cells in vivo, i.e., in the eye primordia of Drosophila larvae. After emergence, adult flies were monitored for aberrantly colored sectors in the compound eyes of the following genotypes: UZ males and females (zeste) carrying a genetically unstable transposable element, SZ males and females (zeste) carrying a partial duplication of the w+ locus plus a transposon insert, white-coral/white (wco/w) females, w+/w females and w+ males. The UZ and SZ marker sets make it possible to monitor shifts from zeste to red (scored as mosaic red spots, RS) and for loss of the white locus (light spots, LS). wco/w+ females were scored for mosaic twin spots (TS) and LS, w+ genotypes for just LS. The genotoxins analyzed were methyl methanesulfonate (MMS), dimethyl sulfate (DMS) and ethylnitrosourea (ENU) (alkylating), adriamycin (AM) and daunomycin (DM) (intercalating), Trenimon, Thio-TEPA and cisplatin (DDP) (cross-linking), bleomycin (strand-breaking), 7,12-dimethylbenz[a]anthracene (DMBA) and 9,10-dimethylanthracene (DA) (bulky monoadducts) and cytosine arabinofuranoside (inhibition of DNA synthesis). The relative mutabilities with frequencies of mosaic light spots (LS) in w+/w female as the standard (relative mutability = 1) vs. genotypes UZ (RS in male) vs. SZ (RS in male) vs. w+ (LS in male) were 1:0.6:0.2:0.3 for MMS, 1:0.09:0.05:0.7 for DDP, and 1:1.6:0.2:1.0 for ENU, ENU showed exceptional behavior in that it was the only compound for which mutational response, measured by the induction of red spots, was highest with the UZ marker set. Occurrence of large light spots (LS) in male but not in female genotypes was negatively correlated with efficiency of agents for chromosomal damage, suggesting that in the hemizygous condition, as in males, selection of damaged cells and mitotic delay may have played a significant role. In general, the results indicate that there is no association between the ability of an agent to act as a clastogen and the recovery of aberrant (red spots) sectors in either the UZ or the SZ strain, and of single light spots (LS) in w+, UZ and SZ males. The possibility is considered that the process causing the genetic instability in the UZ strain is under genetic control, and that strong point mutagens such as ENU through efficient gene mutation induction can interfere with it.
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PMID:Somatic cell mutagenesis in Drosophila: recovery of genetic damage in relation to the types of DNA lesions induced in mutationally unstable and stable X-chromosomes. 246 99

With the intention of assessing the general performance, sensitivity and the underlying mechanisms of somatic cell mutagenicity assays in Drosophila, a study was undertaken to compare the effectiveness of 5 procarcinogens and 4 direct-acting agents in the white/white-coral eye mosaic assay (SMART) with their activity in early (premeiotic) male and female germ-cell stages, after exposure of Drosophila larvae. The outcome indicated a lack of agreement in the results from recessive lethal assays (SLRL) in comparison with the somatic mutation and recombination test (SMART). The procarcinogens 2-naphthylamine (NA), 3-methylcholanthrene (MC), 9,10-dimethylanthracene (DA) and 7,12-dimethylbenz[a]anthracene (DMBA), and the direct-acting mutagens bleomycin (BM), methyl methanesulfonate (MMS) and ethyl methanesulfonate (EMS), were quite efficient in producing somatic recombination and mutations in white/white-coral larvae, as opposed to only weak effects in early germ-cell stages. 2-Acetylaminofluorene (2AAF) showed marginal effects in both germ cells and somatic tissue after exposure of female larvae, but was inactive in testis. The discrepancy in mutational response between somatic cells and premeiotic germ cells is most impressive for MMS and BM. There is sufficient evidence for attributing a good sized proportion of the encountered variation to efficient error-free DNA repair of premutational damage and to segregational elimination during meiosis of deleterious mutations: (1) The efficient point mutagen ENU was the but one agent producing high levels of viable genetic alterations in early germ cells and in somatic cells. A similar behaviour was previously described for diethylnitrosamine, which ethylates DNA in the same fashion as ENU. (2) In early germ-cell stages of mei-9L1 male larvae, MMS induced multiple mutations (putative clusters) at a low dose differing by a factor 20-40 from those needed to produce an equivalent response in repair-competent strains. This is consistent with the concept of an active excision repair in premeiotic cells. (3) In the case of EMS, next to DNA repair, germinal selection seems to restrict the realization of EMS-induced genetic damage in premeiotic cells. (4) Bleomycin-induced chromosome aberrations caused high mortality rates in males (hemizygous for an X-chromosome) but not in females. MMS and BM, agents known to show preference for chromosome aberration induction, produced 3-6-fold higher rates of somatic mutational events (SME) in female genotypes as compared with the other sex.(ABSTRACT TRUNCATED AT 400 WORDS)
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PMID:Somatic cell mutagenicity in Drosophila melanogaster in comparison with genetic damage in early germ-cell stages. 311 19

Anthracene undergoes biomethylation in rat liver cytosol preparations in vitro and in rat subcutaneous tissue, in vivo. The in vitro reaction is dependent on cytosol preparations fortified by the addition of S-adenosyl-L-methionine. The products of the reaction are the meso-anthracenic or L-region derivatives 9-methylanthracene and 9,10-dimethylanthracene. The latter compound may be the simplest polynuclear aromatic hydrocarbon carcinogen known. These reactive methylated metabolites are readily oxidized in cytosol preparations and in subcutaneous tissue, in vivo, to hydroxymethyl and formyl derivatives. Oxidation takes place mainly on the methyl groups since ring oxidized products were not detected.
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PMID:Bioalkylation and biooxidation of anthracene, in vitro and in vivo. 335 64

Stereoselective metabolism of 9-methylanthracene (9-M-A), 9-hydroxymethylanthracene (9-OHM-A) and 9,10-dimethylanthracene (9,10-DM-A) by liver microsomes from untreated rats, and from rats pretreated with either 3-methylcholanthrene or phenobarbital was studied. The metabolites were separated by h.p.l.c. and characterized by analysis of the u.v.-visible, mass and n.m.r. spectral data and compared to published spectral data. The identified trans-dihydrodiol metabolites were 9-M-A trans-1,2- and 3,4-dihydrodiols, 9-OHM-A trans-1,2- and 3,4-dihydrodiols, and 9,10-DM-A trans-1,2-dihydrodiol. The absolute configuration and optical (enantiomeric) purity of the trans-dihydrodiol metabolites were determined. In order to assist in determining the absolute configuration of these trans-dihydrodiols, metabolism of 9-bromoanthracene by liver microsomes of rats pretreated with 3-methylcholanthrene was performed and its trans-1,2- and 3,4-dihydrodiol metabolites were determined to both possess an R,R absolute configuration. Absolute configurations of the trans-dihydrodiol metabolites of 9-methylanthracene, 9-hydroxymethylanthracene and 9,10-dimethylanthracene were then determined by comparison of their CD spectra with those of anthracene 1R,2R-dihydrodiol or 9-bromoanthracene 1R,2R-dihydrodiol. The optical purities of the trans-dihydrodiol metabolites were determined by analysis of the chiral stationary phase h.p.l.c. profiles of the dihydrodiols or their corresponding tetrahydrodiol derivatives. The results indicated that the R,R enantiomers were the predominant products and that liver microsomes of rats pretreated with 3-methylcholanthrene exhibited much higher stereoselectivity than the liver microsomes of untreated rats or rats pretreated with phenobarbital in the formation of trans-dihydrodiols from anthracene, 9-methylanthracene, 9-hydroxymethylanthracene and 9,10-dimethylanthracene. The methyl and hydroxymethyl substituents slightly decreased the stereoselectivity of the trans-dihydrodiol formation.
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PMID:Stereoselective metabolism of 9-methyl-, 9-hydroxymethyl- and 9,10-dimethylanthracenes: absolute configurations and optical purities of trans-dihydrodiol metabolites. 371 9

Specific methylated derivatives of anthracene are mutagenic in S. typhimurium and have tumor-initiating activity on mouse skin. In this study, the mutagenic activities of 1-, 2-, and 9-methylanthracene, 2,9- and 9,10-dimethylanthracene, 2,9,-10-trimethylanthracene, 2,3,9,10-tetramethylanthracene, and the photo-oxide of 9,10-dimethylanthracene were determined in S. typhimurium TA98 and TA100. The relative tumor-initiating activities of these compounds were also evaluated. These bioassays indicate that increased mutagenic potency and tumor-initiating activity are associated with the presence of a methyl substituent at both the 9- and 10- position of anthracene. Metabolism studies suggest that the biological activity of specific methylated anthracenes may be related to the formation of a simple epoxide adjacent to a peri-methyl substituent.
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PMID:Tumor-initiating activity, mutagenicity, and metabolism of methylated anthracenes. 389


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