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Chemical Compound Review

Ravatite     phenanthrene

Synonyms: Phenantrin, Phenanthren, Phenanthrin, PHENANTHRENE, Phenanthracene, ...
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Disease relevance of phenanthrene


Psychiatry related information on phenanthrene


High impact information on phenanthrene

  • The structure reveals that the phenanthrene ring system is stacked with the base pair immediately 3' to the modified guanine, thereby occluding the normal binding site for the correct incoming nucleoside triphosphate [7].
  • Treatment of primary mixed fibroblasts and epithelial cell cultures with methylcholanthrene, but not phenanthrene, led to development of actively growing fibroblastic cultures with many heteroploid cells [8].
  • Subsurface microorganisms detected at a former manufactured gas plant site contaminated with coal tars mineralized significant amounts of naphthalene (8-43%) and phenanthrene (3-31%) in sediment-water microcosms incubated for 4 weeks under aerobic conditions [9].
  • These results indicate that the position of a nitrogen heteroatom in phenanthrene (the analogous carbocyclic aromatic hydrocarbon) not only has a marked effect on the mutagenic activities of the diol epoxide derivatives, but also can alter the metabolic activation pathways of the parent hydrocarbon [10].
  • A structurally related noncarcinogenic polycyclic aromatic hydrocarbon, phenanthrene, had no effect on [3H]spiperone binding or PRL release [11].

Chemical compound and disease context of phenanthrene


Biological context of phenanthrene


Anatomical context of phenanthrene

  • The comparative hydration of styrene 7,8-oxide, octene 1,2-oxide, naphthalene 1,2-oxide, phenanthrene 9,10-oxide, benzo[a]anthracene 5,6-oxide, 3-methylcholanthrene 11,12-oxide, dibenzo[a,h]anthracene 5,6-oxide, and benzo[a, 7,8-, 9,10-, and 11,12-oxides to their respective dihydrodiols was investigated in microsomes from nine human autopsy livers [21].
  • The MAbs obtained from four of the 16 hybridomas exhibited strong inhibitory activity to CYP2A6-catalysed phenanthrene metabolism [22].
  • This study has evaluated the effect of boldine (B), and two phenanthrene alkaloids semisynthesized by us, secoboldine (SB) and boldine methine (BM), on Ang-II-induced neutrophil recruitment [23].
  • The results indicate that there are differences in both the regio- and stereoselective metabolism of anthracene and phenanthrene between the fungus C. elegans and rat liver microsomes [24].
  • We conducted an experiment in two-compartment devices to show the selection of bacterial communities by root exudates and phenanthrene as a function of distance to roots [25].

Associations of phenanthrene with other chemical compounds

  • However, phenanthrene quinone was a potent inhibitor (approximate K(i) = 6.3 +/- 1 microm) [26].
  • Along the reaction pathway, desolvation of the thiolate sulfur of glutathione is observed, in agreement with solvent isotope experiments, as well as increased solvation of the epoxide oxygen of phenanthrene 9,10-oxide, illustrating an important stabilizing role for active site solvent molecules [27].
  • We developed a liquid chromatography-tandem mass spectrometry method for the determination of phenolic metabolites of naphthalene, fluorene, phenanthrene, and pyrene in human urine [28].
  • In this work, stir bar sorptive extraction and liquid desorption was combined with MEKC and diode-array detection (SBSE-LD-MEKC-DAD) for the determination of polynuclear aromatic hydrocarbons (PAHs) in aqueous medium, using biphenyl, fluorene, anthracene, phenanthrene, fluoranthene and pyrene as model compounds [29].
  • There were three exceptions, namely benzo[e]pyrene, phenanthrene and perylene (each possessing a bay region), which were not mutagenic [30].

Gene context of phenanthrene


Analytical, diagnostic and therapeutic context of phenanthrene


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  10. Mutagenicity and tumorigenicity of dihydrodiols, diol epoxides, and other derivatives of benzo(f)quinoline and benzo(h)quinoline. Kumar, S., Sikka, H.C., Dubey, S.K., Czech, A., Geddie, N., Wang, C.X., LaVoie, E.J. Cancer Res. (1989) [Pubmed]
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  12. Identification of pyrene-induced proteins in Mycobacterium sp. strain 6PY1: evidence for two ring-hydroxylating dioxygenases. Krivobok, S., Kuony, S., Meyer, C., Louwagie, M., Willison, J.C., Jouanneau, Y. J. Bacteriol. (2003) [Pubmed]
  13. Isolation and characterization of Pseudoalteromonas strains with divergent polycyclic aromatic hydrocarbon catabolic properties. Hedlund, B.P., Staley, J.T. Environ. Microbiol. (2006) [Pubmed]
  14. 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]
  15. Degradation of phenanthrene, fluorene, fluoranthene, and pyrene by a Mycobacterium sp. Boldrin, B., Tiehm, A., Fritzsche, C. Appl. Environ. Microbiol. (1993) [Pubmed]
  16. Molecular cloning, nucleotide sequence, and expression of genes encoding a polycyclic aromatic ring dioxygenase from Mycobacterium sp. strain PYR-1. Khan, A.A., Wang, R.F., Cao, W.W., Doerge, D.R., Wennerstrom, D., Cerniglia, C.E. Appl. Environ. Microbiol. (2001) [Pubmed]
  17. Molecular mechanics explanation for the stereochemical and shape selectivity of B-DNA for "bay-region" carcinogens. Von Szentpaly, L., Shamovsky, I.L. Mol. Pharmacol. (1995) [Pubmed]
  18. Effect of humic fractions and clay on biodegradation of phenanthrene by a Pseudomonas fluorescens strain isolated from soil. Ortega-Calvo, J.J., Saiz-Jimenez, C. Appl. Environ. Microbiol. (1998) [Pubmed]
  19. Quantifying the biodegradation of phenanthrene by Pseudomonas stutzeri P16 in the presence of a nonionic surfactant. Grimberg, S.J., Stringfellow, W.T., Aitken, M.D. Appl. Environ. Microbiol. (1996) [Pubmed]
  20. Cloning and characterization of a chromosomal gene cluster, pah, that encodes the upper pathway for phenanthrene and naphthalene utilization by Pseudomonas putida OUS82. Kiyohara, H., Torigoe, S., Kaida, N., Asaki, T., Iida, T., Hayashi, H., Takizawa, N. J. Bacteriol. (1994) [Pubmed]
  21. Hydration of arene and alkene oxides by epoxide hydrase in human liver microsomes. Kapitulnik, J., Levin, W., Morecki, R., Dansette, P.M., Jerina, D.M., Conney, A.H. Clin. Pharmacol. Ther. (1977) [Pubmed]
  22. An inhibitory monoclonal antibody to human cytochrome P450 2A6 defines its role in the metabolism of coumarin, 7-ethoxycoumarin and 4-nitroanisole in human liver. Sai, Y., Yang, T.J., Krausz, K.W., Gonzalez, F.J., Gelboin, H.V. Pharmacogenetics (1999) [Pubmed]
  23. Effect of boldine, secoboldine, and boldine methine on angiotensin II-induced neutrophil recruitment in vivo. Estellés, R., Milian, L., Nabah, Y.N., Mateo, T., Cerdá-Nicolás, M., Losada, M., Ivorra, M.D., Issekutz, A.C., Cortijo, J., Morcillo, E.J., Blázquez, M.A., Sanz, M.J. J. Leukoc. Biol. (2005) [Pubmed]
  24. Stereoselective metabolism of anthracene and phenanthrene by the fungus Cunninghamella elegans. Cerniglia, C.E., Yang, S.K. Appl. Environ. Microbiol. (1984) [Pubmed]
  25. Spatial distribution of bacterial communities and phenanthrene degradation in the rhizosphere of Lolium perenne L. Corgié, S.C., Beguiristain, T., Leyval, C. Appl. Environ. Microbiol. (2004) [Pubmed]
  26. Interactions of quinones with thioredoxin reductase: a challenge to the antioxidant role of the mammalian selenoprotein. Cenas, N., Nivinskas, H., Anusevicius, Z., Sarlauskas, J., Lederer, F., Arnér, E.S. J. Biol. Chem. (2004) [Pubmed]
  27. Quantum mechanical/molecular mechanical free energy simulations of the glutathione S-transferase (M1-1) reaction with phenanthrene 9,10-oxide. Ridder, L., Rietjens, I.M., Vervoort, J., Mulholland, A.J. J. Am. Chem. Soc. (2002) [Pubmed]
  28. Determination of phenolic metabolites of polycyclic aromatic hydrocarbons in human urine as their pentafluorobenzyl ether derivatives using liquid chromatography-tandem mass spectrometry. Jacob, P., Wilson, M., Benowitz, N.L. Anal. Chem. (2007) [Pubmed]
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