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Chemical Compound Review

anthracene     anthracene

Synonyms:
 
 
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Disease relevance of anthracene

 

Psychiatry related information on anthracene

 

High impact information on anthracene

  • Variable-temperature (1)H NMR spectroscopy of the intramolecular host-guest complexes has revealed that the site residency time of the anthracene guests is 1.6 x 10(-5) sec at 20 degrees C and 1.3 sec at -90 degrees C in acetone solution [8].
  • We have deleted the murine GstP gene cluster and established the effects on skin tumorigenesis induced by the polycyclic aromatic hydrocarbon 7, 12-dimethylbenz anthracene and the tumor promoting agent 12-O-tetradecanoylphorbol-13-acetate [9].
  • Following v-Ha-ras transfection of nonmetastatic dimethylbenz(( a ))anthracene-induced rat mammary cancer (RMC1) cells, occasional transfectants were isolated that acquired high metastatic ability [10].
  • To address these problems, the metabolism of anthracene (AC) and its in vitro oxidation product, 9,10-anthraquinone (AQ), was examined by chromatographic and isotope dilution techniques in Phanerochaete chrysosporium [11].
  • Aromatase inhibitor, 4-hydroxyandrostene-3,17-dione (4-OHA), is a highly effective treatment in rats with 7,12-dimethylbenz(a) anthracene-induced hormone-dependent mammary tumors [12].
 

Chemical compound and disease context of anthracene

 

Biological context of anthracene

 

Anatomical context of anthracene

 

Associations of anthracene with other chemical compounds

  • Differential stereoselectivity of cytochromes P-450b and P-450c in the formation of naphthalene and anthracene 1,2-oxides. The role of epoxide hydrolase in determining the enantiomer composition of the 1,2-dihydrodiols formed [27].
  • A theoretical study of anthracene and phenanthrene derivatives acting as A-T specific intercalators [28].
  • While the UV-vis and fluorescence spectra of 2a (Phi(F) = 0.87) show the characteristic vibronic structure of anthracene, the UV-vis spectra of ruby-red aceanthrylene 2b and greenish-black cyclopent[hi]aceanthrylene 2c extend well into the visible range [29].
  • Aqueous solvolyses of acyl derivatives of hydrates (water adducts) of anthracene and benzofuran yield carbocations which undergo competitive deprotonation to form the aromatic molecules and nucleophilic reaction with water to give the aromatic hydrates [30].
  • For anthracene, the immediate result of electron transfer, that is formation of an anthracene radical cation and reduced polyoxometalate, was observed by ESR spectroscopy [31].
 

Gene context of anthracene

  • We tested the epigenetic toxicity of PAHs containing bay-like regions by comparing the effects of methylated vs. chlorinated isomers of anthracene on the temporal activation of mitogen-activated protein kinase (MAPK) and the regulation of GJIC [32].
  • Gel mobility shift assays revealed that Chr, BkF and BaP inhibited the binding of AR in nuclear extracts to oligonucleotide probes containing the AR-responsive element (ARE), whereas Ant and Pyr had no effect [33].
  • We found that only immunotoxic PAHs activated the Fyn and ZAP-70 PTKs at 10 min, but total PTK activity was still increased by nonimmunotoxic PAHs, BeP, or anthracene after 10 min of exposure [34].
  • Chr, BkF and BaP acted as AhR agonists in LNCaP cells, while Ant and Pyr did not [33].
  • All papillomas and carcinomas induced with 7, 12-dimethylbenz[a]anthracene and 12-O-tetradecanoylphorbol 13-acetate contained the 7,12-dimethylbenz[a] anthracene-specific mutation in the ras gene (A to T transversion at the 61st codon) [35].
 

Analytical, diagnostic and therapeutic context of anthracene

  • Scanning tunneling microscopy of prochiral anthracene derivatives on graphite: chain length effects on monolayer morphology [36].
  • Photochemical ligation of DNA conjugates through anthracene cyclodimer formation and its fidelity to the template sequences [37].
  • BAC cell cultures incubated with Su-10603, a specific 17 alpha-hydroxylase inhibitor, exhibited similar changes in the pattern of steroidogenesis, as did benz[a]anthracene-treated cells, suggesting that benz[a] anthracene also inhibits steroidogenesis as an inhibitor of 17 alpha-hydroxylase [38].
  • On irradiation of intact bacteria at 360 nm, anthracene-labeled lipids form stable photodimers which can be extracted and separated by thin-layer chromatography [3].
  • 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 [39].

References

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  2. Inverse relation between estrogen receptors and cyclic adenosine 3':5'-monophosphate-binding proteins in hormone-dependent mammary tumor regression due to dibutyryl cyclic adenosine 3':5'-monophosphate treatment or ovariectomy. Bodwin, J.S., Clair, T., Cho-Chung, Y.S. Cancer Res. (1978) [Pubmed]
  3. Transverse and lateral distribution of phospholipids and glycolipids in the membrane of the bacterium Micrococcus luteus. de Bony, J., Lopez, A., Gilleron, M., Welby, M., Lanéelle, G., Rousseau, B., Beaucourt, J.P., Tocanne, J.F. Biochemistry (1989) [Pubmed]
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  11. Ring fission of anthracene by a eukaryote. Hammel, K.E., Green, B., Gai, W.Z. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  12. Effects of aromatase inhibitor 4-hydroxyandrostenedione and other compounds in the 7, 12-dimethylbenz(a)anthracene-induced breast carcinoma model. Brodie, A.M., Garrett, W.M., Hendrickson, J.R., Tsai-Morris, C.H. Cancer Res. (1982) [Pubmed]
  13. Degradation of phenanthrene and anthracene by cell suspensions of Mycobacterium sp. strain PYR-1. Moody, J.D., Freeman, J.P., Doerge, D.R., Cerniglia, C.E. Appl. Environ. Microbiol. (2001) [Pubmed]
  14. Impact of inoculation protocols, salinity, and pH on the degradation of polycyclic aromatic hydrocarbons (PAHs) and survival of PAH-degrading bacteria introduced into soil. Kästner, M., Breuer-Jammali, M., Mahro, B. Appl. Environ. Microbiol. (1998) [Pubmed]
  15. Enantioselective intramolecular aromatic [4 + 4] photocycloaddition in crystalline state: parameters for reactivity. Kohmoto, S., Ono, Y., Masu, H., Yamaguchi, K., Kishikawa, K., Yamamoto, M. Org. Lett. (2001) [Pubmed]
  16. Phase II study of bisantrene in relapsed/refractory acute non lymphoid leukemias (ANLL). Tosi, P., Visani, G., Colombini, R., Verlicchi, F., Benfenati, D., Cenacchi, A., Russo, D., Zuffa, E., Papadopulu, P., Tura, S. Haematologica (1989) [Pubmed]
  17. Degradation of anthracene by Mycobacterium sp. strain LB501T proceeds via a novel pathway, through o-phthalic acid. van Herwijnen, R., Springael, D., Slot, P., Govers, H.A., Parsons, J.R. Appl. Environ. Microbiol. (2003) [Pubmed]
  18. Interfacial nonradiative energy transfer in responsive core-shell hydrogel nanoparticles. Gan, D., Lyon, L.A. J. Am. Chem. Soc. (2001) [Pubmed]
  19. Diels-Alder ribozyme catalysis: a computational approach. Zhang, X., Bruice, T.C. J. Am. Chem. Soc. (2007) [Pubmed]
  20. Distribution of DNA damage in chromatin and its relation to repair in human cells treated with 7-bromomethylbenz(a) anthracene. Oleson, F.B., Mitchell, B.L., Dipple, A., Lieberman, M.W. Nucleic Acids Res. (1979) [Pubmed]
  21. Breast cancer resistance protein and P-glycoprotein in 149 adult acute myeloid leukemias. Benderra, Z., Faussat, A.M., Sayada, L., Perrot, J.Y., Chaoui, D., Marie, J.P., Legrand, O. Clin. Cancer Res. (2004) [Pubmed]
  22. Metabolic activation of 3-methylcholanthrene in mouse skin: fluorescence spectral evidence indicates the involvement of diol-epoxides formed in the 7,8,9,10-ring. Cooper, C.S., Vigny, P., Kindts, M., Grover, P.L., Sims, P. Carcinogenesis (1980) [Pubmed]
  23. Estriol prevention of mammary carcinoma induced by 7,12-dimethylbenzanthracene and procarbazine. Lemon, H.M. Cancer Res. (1975) [Pubmed]
  24. Diesel exhaust particle extracts and associated polycyclic aromatic hydrocarbons inhibit Cox-2-dependent prostaglandin synthesis in murine macrophages and fibroblasts. Rudra-Ganguly, N., Reddy, S.T., Korge, P., Herschman, H.R. J. Biol. Chem. (2002) [Pubmed]
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  26. Regioselectivity and stereoselectivity in the metabolism of trans-1,2-dihydroxy-1,2-dihydrobenz[a]anthracene by rat liver microsomes. Vyas, K.P., van Bladeren, P.J., Thakker, D.R., Yagi, H., Sayer, J.M., Levin, W., Jerina, D.M. Mol. Pharmacol. (1983) [Pubmed]
  27. Differential stereoselectivity of cytochromes P-450b and P-450c in the formation of naphthalene and anthracene 1,2-oxides. The role of epoxide hydrolase in determining the enantiomer composition of the 1,2-dihydrodiols formed. van Bladeren, P.J., Sayer, J.M., Ryan, D.E., Thomas, P.E., Levin, W., Jerina, D.M. J. Biol. Chem. (1985) [Pubmed]
  28. A theoretical study of anthracene and phenanthrene derivatives acting as A-T specific intercalators. Chen, K.X., Gresh, N., Pullman, B. Nucleic Acids Res. (1986) [Pubmed]
  29. One step Pd(0)-catalyzed synthesis, X-ray analysis, and photophysical properties of cyclopent[hi]aceanthrylene: fullerene-like properties in a nonalternant cyclopentafused aromatic hydrocarbon. Dang, H., Levitus, M., Garcia-Garibay, M.A. J. Am. Chem. Soc. (2002) [Pubmed]
  30. Protonated benzofuran, anthracene, naphthalene, benzene, ethene, and ethyne: measurements and estimates of pK(a) and pK(R). McCormack, A.C., McDonnell, C.M., More O'Ferrall, R.A., O'Donoghue, A.C., Rao, S.N. J. Am. Chem. Soc. (2002) [Pubmed]
  31. Electron and oxygen transfer in polyoxometalate, H(5)PV(2)Mo(10)O(40), catalyzed oxidation of aromatic and alkyl aromatic compounds: evidence for aerobic Mars-van Krevelen-type reactions in the liquid homogeneous phase. Khenkin, A.M., Weiner, L., Wang, Y., Neumann, R. J. Am. Chem. Soc. (2001) [Pubmed]
  32. Polycyclic aromatic hydrocarbons with bay-like regions inhibited gap junctional intercellular communication and stimulated MAPK activity. Rummel, A.M., Trosko, J.E., Wilson, M.R., Upham, B.L. Toxicol. Sci. (1999) [Pubmed]
  33. A role of aryl hydrocarbon receptor in the antiandrogenic effects of polycyclic aromatic hydrocarbons in LNCaP human prostate carcinoma cells. Kizu, R., Okamura, K., Toriba, A., Kakishima, H., Mizokami, A., Burnstein, K.L., Hayakawa, K. Arch. Toxicol. (2003) [Pubmed]
  34. Protein tyrosine kinase activation by polycyclic aromatic hydrocarbons in human HPB-ALL T cells. Davila, D.R., Lane, J.L., Lauer, F.T., Burchiel, S.W. J. Toxicol. Environ. Health Part A (1999) [Pubmed]
  35. Induction of skin papillomas, carcinomas, and sarcomas in mice in which the connexin 43 gene is heterologously deleted. Yamakage, K., Omori, Y., Zaidan-Dagli, M.L., Cros, M.P., Yamasaki, H. J. Invest. Dermatol. (2000) [Pubmed]
  36. Scanning tunneling microscopy of prochiral anthracene derivatives on graphite: chain length effects on monolayer morphology. Wei, Y., Kannappan, K., Flynn, G.W., Zimmt, M.B. J. Am. Chem. Soc. (2004) [Pubmed]
  37. Photochemical ligation of DNA conjugates through anthracene cyclodimer formation and its fidelity to the template sequences. Ihara, T., Fujii, T., Mukae, M., Kitamura, Y., Jyo, A. J. Am. Chem. Soc. (2004) [Pubmed]
  38. The interrelationship of polycyclic hydrocarbon metabolism and steroidogenesis in primary cultures of bovine adrenal cortical cells. Dibartolomeis, M.J., Jefcoate, C.R. Mol. Pharmacol. (1984) [Pubmed]
  39. Tumor-initiating activity, mutagenicity, and metabolism of methylated anthracenes. La Voie, E.J., Coleman, D.T., Rice, J.E., Geddie, N.G., Hoffmann, D. Carcinogenesis (1985) [Pubmed]
 
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