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Chemical Compound Review

CHRYSENE     chrysene

Synonyms: Chrysen, CCRIS 161, CHEMBL85685, NSC-6175, ACMC-1CS8C, ...
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Disease relevance of chrysene

  • The ability of prostaglandin synthetase (PGS) to cooxidize benzo(a)pyrene, benzo(a)anthracene, chrysene, and several of their dihydrodiol derivatives to mutagenic products was tested with Salmonella typhimurium strains TA98 and TA100 [1].
  • In this study, the enzymes involved in polycyclic aromatic hydrocarbon (PAH) degradation in the chrysene-degrading organism Sphingomonas sp. strain CHY-1 were investigated [2].
  • As part of a systematic analysis of mechanisms of PAH developmental toxicity in zebrafish, we show here that three tetracyclic PAHs (pyrene, chrysene, and benz[a]anthracene) activate the AHR pathway tissue-specifically to induce distinct patterns of CYP1A expression [3].
  • Singlet oxygen was generated at room temperature in the solutions via photosensitization of sodium chrysene sulfonate; this sulfonated polycyclic hydrocarbon was synthesized to provide a water soluble chromophore inert to usual dye-ascorbate photobleaching [4].
  • At a concentration of 6.8 microM, F23Q also substantially inhibited the mineralization of benz[a]anthracene, benzo[a]pyrene (BaP), and chrysene by strain R1 as well as BaP mineralization by Pseudomonas saccharophila P15 [5].

High impact information on chrysene

  • Comparison of the uptake rate of chrysene from the unperturbed crystal state, sonicated crystals, and the silica-adsorbed state demonstrated that the last condition results in the most rapid transport of chrysene into model membranes [6].
  • METHODS: Here we have mapped the distribution of adducts induced by diol epoxides of additional PAHs: chrysene (CDE), 5-methylchrysene (5-MCDE), 6-methylchrysene (6-MCDE), benzo[c]phenanthrene (B[c]PDE), and benzo[g]chrysene (B[g]CDE) within exons 5, 7, and 8 of the p53 gene in human bronchial epithelial cells [7].
  • Specificity analysis of the antibodies demonstrated that serological cross-reactions between the benzo[a]pyrene and the chrysene diol-epoxide adducts were present [8].
  • Hydrolysis with trypsin and pronase gave products with the characteristic UV spectrum of substituted chrysene [9].
  • All autoradiograms of DNA from fish from the contaminated sites exhibited a diagonal radioactive zone where DNA adducts of chrysene, benzo(a)pyrene, and dibenz(a,h)anthracene, formed in vitro using English sole hepatic microsomes, were shown to chromatograph [10].

Chemical compound and disease context of chrysene


Biological context of chrysene

  • Evidence for bay region activation of chrysene 1,2-dihydrodiol to an ultimate carcinogen [16].
  • Metabolic activation of chrysene in mouse skin appears to involve r-1,t-2-dihydroxy-t-3,4-oxy-1,2,3,4-tetrahydrochrysene (anti-chrysene-1,2-diol 3,4-oxide) and 9-hydroxy-r-1,t-2-dihydroxy-t-3,4-oxy-1,2,3,4-tetrahydrochrysene (anti-9-OH-chrysene-1,2-diol 3,4-oxide) [17].
  • Adducts derived from the covalent binding of two positional monomethyl-substituted isomers of a bay region chrysene diol epoxide to supercoiled pIBI30 DNA (2926 base pairs/genome) were prepared, and their characteristics were investigated by a combination of gel electrophoresis and flow linear dichroism techniques [18].
  • The kinetics of chrysene loss are first order in chrysene [19].
  • The early ozonation mixture, 1.75 mol O3/mol Chr, exhibited greater inhibition to GJIC than chrysene and irreversible damage to cells leading to cell death [20].

Anatomical context of chrysene


Associations of chrysene with other chemical compounds


Gene context of chrysene

  • None of the 14 PAHs bound the hrER, but five of the PAHs (anthracene, B[a]A, chrysene, B[b]F, and B[a]P) induced ER-reporter activity [31].
  • 6-Nitrochrysene induced CYP1 mRNAs to the same extent or more potently than chrysene [32].
  • Treatment of the Caco-2 cells with B[a]P, chrysene, B[k]F, or DB[a,l]P induced mRNA expression of CYP1A1 and CYP1B1 specifically as measured by RT-PCR [33].
  • Mono- and Diglucuronide formation from benzo[a]pyrene and chrysene diphenols by AHH-1 cell-expressed UDP-glucuronosyltransferase UGT1A7 [34].
  • V79 cell-expressed rat UGT1A6 also catalyzed these reactions, except for chrysene diphenol diglucronide formation (Bock et al., Mol Pharmacol 42: 613-618, 1992) [34].

Analytical, diagnostic and therapeutic context of chrysene

  • The presence of serum antibodies to the diol-epoxide DNA adducts of representative polycyclic aromatic hydrocarbons (PAH), chrysene, benz[a]anthracene and benzo[a]pyrene, was determined by ELISA using serum samples obtained from normal healthy individuals [8].
  • The enantiomers of chrysene 1,2-epoxide and 3,4-epoxide were also resolved by chiral stationary phase HPLC [35].
  • Results from these bioassays indicate that methylene-bridged bay-region derivatives of chrysene and benz[a]anthracene contribute to the overall genotoxicity of environmentally occurring PAHs [36].
  • The separation of monohydroxylated derivatives (phenols) of benzo[a]pyrene, benz[a]anthracene, and chrysene was studied by reversed-phase high-performance liquid chromatography using a monomeric Zorbax ODS column and a polymeric Vydac C18 column [37].
  • Induction of TG resistance was also observed in P3 cells cocultivated in a cell-mediated assay with human breast carcinoma cells, which are capable of polycyclic aromatic hydrocarbon (PAH) metabolism, after treatment with the carcinogenic PAHs: B[a]P, chrysene, 7,12-dimethylbenz[a]anthracene (DMBA), and 3-methylcholanthrene (MCA) [38].


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  12. Methylene-bridged bay region chrysene and phenanthrene derivatives and their keto-analogs: mutagenicity in Salmonella typhimurium and tumor-initiating activity on mouse skin. Rice, J.E., Makowski, G.S., Hosted, T.J., Lavoie, E.J. Cancer Lett. (1985) [Pubmed]
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  14. Microbiological evaluation of toxicity of three polycyclic aromatic hydrocarbons and their decomposition products formed by advanced oxidation processes. Jamroz, T., Ledakowicz, S., Miller, J.S., Sencio, B. Environ. Toxicol. (2003) [Pubmed]
  15. Electronic considerations in the mutagenesis of some 4,5-bridged chrysenes. Lee-Ruff, E., Raj, A.S., Kruk, H., Katz, M. Environmental mutagenesis. (1987) [Pubmed]
  16. Evidence for bay region activation of chrysene 1,2-dihydrodiol to an ultimate carcinogen. Levin, W., Wood, A.W., Chang, R.L., Yagi, H., Mah, H.D., Jerina, D.M., Conney, A.H. Cancer Res. (1978) [Pubmed]
  17. Metabolism of the bay-region diol-epoxide of chrysene to a triol-epoxide and the enzyme-catalysed conjugation of these epoxides with glutathione. Hodgson, R.M., Seidel, A., Bochnitschek, W., Glatt, H.R., Oesch, F., Grover, P.L. Carcinogenesis (1986) [Pubmed]
  18. Unwinding and hydrodynamic flow linear dichroism characteristics of supercoiled DNA covalently modified with two isomeric methylchrysene diol epoxides of different biological activities. Balasta, L., Xu, R., Geacintov, N.E., Swenberg, C.E., Amin, S., Hecht, S.S. Chem. Res. Toxicol. (1993) [Pubmed]
  19. Effect of salinity on the photolysis of chrysene adsorbed to a smectite clay. Kong, L., Ferry, J.L. Environ. Sci. Technol. (2003) [Pubmed]
  20. Ozonation of chrysene: evaluation of byproduct mixtures and identification of toxic constituent. Luster-Teasley, S.L., Yao, J.J., Herner, H.H., Trosko, J.E., Masten, S.J. Environ. Sci. Technol. (2002) [Pubmed]
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  22. Morphological transformation in three mammalian cell systems following treatment with 6-nitrochrysene and 6-nitrobenzo[a]pyrene. Sala, M., Lasne, C., Lu, Y.P., Chouroulinkov, I. Carcinogenesis (1987) [Pubmed]
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