Summary: 1,2-Benzphenanthrenes. POLYCYCLIC COMPOUNDS obtained from coal tar.

Top Publications

  1. Machala M, Svihálková Sindlerová L, Pencikova K, Krcmar P, Topinka J, Milcova A, et al. Effects of methylated chrysenes on AhR-dependent and -independent toxic events in rat liver epithelial cells. Toxicology. 2008;247:93-101 pubmed publisher
    Methylated chrysenes (MeChry) are important cigarette smoke constituents and 5-MeChry has been listed as possibly carcinogenic to humans...
  2. Peden Adams M, Liu J, Knutson S, Dancik J, Bryant K, Bodine A, et al. Alterations in immune function and CYP450 activity in adult male deer mice (Peromyscus maniculatus) following exposure to benzo[a]pyrene, pyrene, or chrysene. J Toxicol Environ Health A. 2007;70:1783-91 pubmed
    ..These results indicate that immune function endpoints appear to be more sensitive to these PAHs than measured hepatic CYP450 activity...
  3. Beckmann P, Buser C, Mallory C, Mallory F, Mosher J. Methyl reorientation in solid 3-ethylchrysene and 3-isopropylchrysene. Solid State Nucl Magn Reson. 1998;12:251-6 pubmed
    ..The barriers of 11-12 kJ mol-1 are typical for methyl groups in 'isolated' ethyl and isopropyl groups. ..
  4. Mahadevan B, Luch A, Atkin J, Nguyen T, Sharma A, Amin S, et al. Investigation of the genotoxicity of dibenzo[c,p]chrysene in human carcinoma MCF-7 cells in culture. Chem Biol Interact. 2006;164:181-91 pubmed
  5. Sun Y, Herzog C, Krzeminski J, Amin S, Perdew G, El Bayoumy K. Effects of the environmental mammary carcinogen 6-nitrochrysene on p53 and p21(Cip1) protein expression and cell cycle regulation in MCF-7 and MCF-10A cells. Chem Biol Interact. 2007;170:31-9 pubmed
    ..g. DNA repair machinery) after exposure to 6-NC and this may, in part, account for its remarkable carcinogenicity in the mammary tissue. ..
  6. Yao L, Pan L, Guo R, Miao J. Expression profiles of different glutathione S-transferase isoforms in scallop Chlamys farreri exposed to benzo[a]pyrene and chrysene in combination and alone. Ecotoxicol Environ Saf. 2017;142:480-488 pubmed publisher
    ..In summary, this study investigated the classification of GSTs and provided information about the expression profiles of different class GSTs after PAHs exposure. ..
  7. Yun C, Shimada T, Guengerich F. Purification and characterization of human liver microsomal cytochrome P-450 2A6. Mol Pharmacol. 1991;40:679-85 pubmed
    ..These results emphasize the need to characterize individual P-450 enzymes in order to understand their functions in the context of more complex systems. ..
  8. Minhas J, Vasiluk L, Pinto L, Gobas F, Moore M. Mobilization of chrysene from soil in a model digestive system. Environ Toxicol Chem. 2006;25:1729-37 pubmed
  9. Ping L, Luo Y, Zhang H, Li Q, Wu L. Distribution of polycyclic aromatic hydrocarbons in thirty typical soil profiles in the Yangtze River Delta region, east China. Environ Pollut. 2007;147:358-65 pubmed
    ..Phenanthrene was found in soils below a depth of 100 cm in half of the sampling sites, but the detectable ratio of benzo(a)pyrene decreased sharply from 100% in topsoil to 0 in the 4th horizon. ..

More Information


  1. Kocyigit O, Kursunlu A, Guler E. Complexation properties and synthesis of a novel Schiff base with triphenylene nucleus. J Hazard Mater. 2010;183:334-40 pubmed publisher
    ..The structures of these new compounds (ligand and complexes) were characterized with FT-IR, magnetic susceptibility measurement, thermal methods (TGA), (1)H NMR and elemental analyses. ..
  2. Tang X, Zhu X, Liu S, Wang S, Ni X. Isoflavones suppress cyclic adenosine 3',5'-monophosphate regulatory element-mediated transcription in osteoblastic cell line. J Nutr Biochem. 2011;22:865-73 pubmed publisher
    ..6,11,12-tetradro-2,8-chrysenediol. Our results indicate that isoflavones genistein and daidzein might modulate bone remodeling through ERs by regulating target gene expression through the CRE motifs. ..
  3. Yamada K, Hakura A, Kato T, Mizutani T, Saeki K. Nitrogen-substitution effects on the mutagenicity and cytochrome P450 isoform-selectivity of chrysene analogs. Mutat Res. 2005;586:87-95 pubmed
  4. Diamante G, do Amaral E Silva Müller G, Menjivar Cervantes N, Xu E, Volz D, Dias Bainy A, et al. Developmental toxicity of hydroxylated chrysene metabolites in zebrafish embryos. Aquat Toxicol. 2017;189:77-86 pubmed publisher
    ..Our findings also demonstrate the regio-selective toxicity of hydroxy-PAHs in the effects on eye and circulatory development and raise the need to identify mechanisms and ecological risks of oxy-PAHs to fish populations. ..
  5. Agarwal R, Coffing S, Baird W, Harvey R, Dipple A. Metabolic activation of 4H-cyclopenta[def]chrysene in human mammary carcinoma MCF-7 cell cultures. Chem Res Toxicol. 1999;12:437-41 pubmed
    ..Thus, the human cells used in these studies can activate C[def]C to carcinogenic metabolites. ..
  6. Dhasmana A, Jamal Q, Gupta R, Siddiqui M, Kesari K, Wadhwa G, et al. Titanium dioxide nanoparticles provide protection against polycyclic aromatic hydrocarbon BaP and chrysene-induced perturbation of DNA repair machinery: A computational biology approach. Biotechnol Appl Biochem. 2016;63:497-513 pubmed publisher
    ..TiO2 NPs thereby prevent the entry of PAHs into the cell via AHR and hence protect cells against the deleterious effects induced by PAHs. ..
  7. Opitz S, Hölscher D, Oldham N, Bartram S, Schneider B. Phenylphenalenone-related compounds: chemotaxonomic markers of the haemodoraceae from Xiphidium caeruleum. J Nat Prod. 2002;65:1122-30 pubmed
    ..The natural product distribution of other genera of the Haemodoraceae is used as the basis to elaborate biogeographic characteristics of this plant family. ..
  8. Chabre Y, Roy R. Multivalent glycoconjugate syntheses and applications using aromatic scaffolds. Chem Soc Rev. 2013;42:4657-708 pubmed publisher
  9. Boyiri T, Leszczynska J, Desai D, Amin S, Nixon D, El Bayoumy K. Metabolism and DNA binding of the environmental pollutant 6-nitrochrysene in primary culture of human breast cells and in cultured MCF-10A, MCF-7 and MDA-MB-435s cell lines. Int J Cancer. 2002;100:395-400 pubmed
    ..This is the first report to demonstrate the ability of human breast cells, MCF-10A, and breast cancer cell lines to activate 6-NC to metabolites that can damage DNA. ..
  10. KAAS G, Zhong C, Eason D, Ross D, Vachhani R, Ming G, et al. TET1 controls CNS 5-methylcytosine hydroxylation, active DNA demethylation, gene transcription, and memory formation. Neuron. 2013;79:1086-93 pubmed publisher
    ..In summary, we show that neuronal Tet1 regulates DNA methylation levels and that its expression, independent of its catalytic activity, regulates the expression of CNS activity-dependent genes and memory formation. ..
  11. Shultz C, Palackal N, Mangal D, Harvey R, Blair I, Penning T. Fjord-region benzo[g]chrysene-11,12-dihydrodiol and benzo[c]phenanthrene-3,4-dihydrodiol as substrates for rat liver dihydrodiol dehydrogenase (AKR1C9): structural basis for stereochemical preference. Chem Res Toxicol. 2008;21:668-77 pubmed publisher
    ..The similarity between rates of trans-dihydrodiol oxidation by the rat and human liver specific AKRs (AKR1C9 and AKR1C4) implicate these enzymes in hepatocarcinogenesis in rats observed with the fjord-region PAH. ..
  12. Wang R, Xia X, Meng L. [Effect of particulate size and composition on the biodegradation of PAHS in nature waters]. Huan Jing Ke Xue. 2006;27:855-61 pubmed
    ..Therefore, the biodegradation rates of PAHs in water system with middle size particulates were higher than that with small size particulates. ..
  13. Zhong Y, Gauthier D, Shi Y, McLaughlin M, Chung J, Dagneau P, et al. Synthesis of antifungal glucan synthase inhibitors from enfumafungin. J Org Chem. 2012;77:3297-310 pubmed publisher
    ..Multi-hundred gram quantities of the target drug candidates 1 and 2 were prepared, in 12 linear steps with 25% isolated yield and 13 linear steps with 22% isolated yield, respectively. ..
  14. Bhalla V, Singh H, Kumar M, Prasad S. Triazole-modified triphenylene derivative: self-assembly and sensing applications. Langmuir. 2011;27:15275-81 pubmed publisher
    ..Further, strong emission of derivative 3 in its nonaggregated form makes it a promising fluorescence sensory material for nitroaromatic compounds. ..
  15. Shihadeh A, Saleh R. Polycyclic aromatic hydrocarbons, carbon monoxide, "tar", and nicotine in the mainstream smoke aerosol of the narghile water pipe. Food Chem Toxicol. 2005;43:655-61 pubmed
    ..The results indicate that narghile smoke likely contains an abundance of several of the chemicals thought to be causal factors in the elevated incidence of cancer, cardiovascular disease and addiction in cigarette smokers. ..
  16. Srinivasan G, Villanueva Garibay J, Muller K, Oelkrug D, Milian Medina B, Beljonne D, et al. Dynamics of guest molecules in PHTP inclusion compounds as probed by solid-state NMR and fluorescence spectroscopy. Phys Chem Chem Phys. 2009;11:4996-5009 pubmed publisher
  17. Vaca Chavez F, Sebastião P, Miyake Y, Monobe H, Shimizu Y. Dynamics of discotic fluoroalkylated triphenylene molecules studied by proton NMR relaxometry. J Phys Chem B. 2012;116:2339-46 pubmed publisher
    ..The effect of fluorination of the pheripheral chain enhances the columnar mesophase's stability. ..
  18. Villalona Calero M, Petit T, Kuhn J, Cobb P, Kraynak M, Eckhardt S, et al. A phase I and pharmacological study of protracted infusions of crisnatol mesylate in patients with solid malignancies. Clin Cancer Res. 1999;5:3369-78 pubmed
    ..However, the mechanisms for the apparently increased thrombogenicity observed in this trial are unclear and require further elucidation. ..
  19. Yang J, Yin M. [Effect of 5 polycyclic aromatic hydrocarbons on estrogen receptor binding in rats]. Wei Sheng Yan Jiu. 2002;31:154-6 pubmed
    ..05). The results from this study indicate that penzo(a)pyrene, 7,12-dimethyl benz(a) anthracene and pentacene have significant estrogenic activity. ..
  20. Sharma H, Jain V, Khan Z. Identification of polycyclic aromatic hydrocarbons (PAHs) in suspended particulate matter by synchronous fluorescence spectroscopic technique. Spectrochim Acta A Mol Biomol Spectrosc. 2007;68:43-9 pubmed
    ..This is in agreement with our earlier work for determination of these PAHs using gas chromatography (GC). The seasonal variation of the PAHs was found to be maximum in winter and minimum during the monsoon. ..
  21. Falahatpisheh M, Donnelly K, Ramos K. Antagonistic interactions among nephrotoxic polycyclic aromatic hydrocarbons. J Toxicol Environ Health A. 2001;62:543-60 pubmed
    ..Based on these data, it is concluded that PAHs exhibit chemical- and cell-specific nephrotoxicity, but that toxicological outcomes are influenced by the presence of multiple hydrocarbons in complex mixtures. ..
  22. Shappell N, Carlino MacDonald U, Amin S, Kumar S, Sikka H. Comparative metabolism of chrysene and 5-methylchrysene by rat and rainbow trout liver microsomes. Toxicol Sci. 2003;72:260-6 pubmed
    ..In contrast the reverse is true in the case of 5-MeCHR, indicating that a non-benzo ring methyl substituent alters the regioselectivity of the enzymes involved in the oxidative metabolism of PAHs. ..
  23. Zhang Y, Hwang H, Ekunwe S. Comparing cytotoxicity and genotoxicity in HaCaT cells caused by 6-aminochrysene and 5,6-chrysenequinone under ultraviolet A irradiation. Environ Toxicol Chem. 2006;25:1920-5 pubmed
    ..Our study indicated that 5,6-CQ, the major photoproduct of 6AC, was less photocytotoxic than the parent compound and was not photogenotoxic to HaCaT cells under the experimental conditions. ..
  24. Husain M, Tandon H, Varadwaj P. Singlet and doublet states UV-vis spectrum and electronic properties of 3-methylchrysene and 4-methylchrysene in glass matrix. Spectrochim Acta A Mol Biomol Spectrosc. 2008;69:693-700 pubmed
    ..50 and 473.85 nm closely match with the available diffuse intersteallar bands (DIBs) at 417.55 and 472.64 nm, respectively. Also the observed 474.85 nm band of 4-methylchrysene cation matches the DIB at 476.00 nm. ..
  25. Jinno K. Study on retention in liquid chromatography. Se Pu. 2002;20:21-9 pubmed
    ..On the occasion of being awarded by The Society for Chromatographic Sciences the author would like to summarize his contributions to this topic which asks us "What Is Chromatographic Retention?" ..
  26. Stephens P, Devlin F, Pan J. The determination of the absolute configurations of chiral molecules using vibrational circular dichroism (VCD) spectroscopy. Chirality. 2008;20:643-63 pubmed
    ..The power of VCD spectroscopy in determining ACs, even for large organic molecules and for substantially conformationally-flexible organic molecules is clearly documented. ..
  27. Lim D, Ikeda A, Vu K, Yamaguchi K, Tyner T, Hasson A. Method development for the measurement of quinone levels in urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2011;879:3592-8 pubmed publisher
    ..Samples were also collected and analyzed periodically from human subjects over the course of six months. Eight quinones were detected in the samples, with levels varying from below the detection limit up to 3 ?mol dm(-3). ..
  28. Hilton C, Crowfoot J, Rempala P, King B. 18,18'-Dihexyl[9,9']biphenanthro[9,10-b]triphenylene: construction and consequences of a profoundly hindered aryl-aryl single bond. J Am Chem Soc. 2008;130:13392-9 pubmed publisher
    ..Calculations demonstrate that rotation does not involve a simple torsion of the equilibrium structure, but rather a complex movement with a barrier of 49 kcal/mol from a slipped-parallel, C(2h) intermediate. ..
  29. Morelis S, van den Heuvel H, Van Noort P. Competition between phenanthrene, chrysene, and 2,5-dichlorobiphenyl for high-energy adsorption sites in a sediment. Chemosphere. 2007;68:2028-32 pubmed
    ..Phenanthrene, chrysene, and 2,5-dichlorobiphenyl seem to share about 30% of the accessible high-energy adsorption sites in the sediment employed. ..
  30. Alam M, Motoyanagi J, Yamamoto Y, Fukushima T, Kim J, Kato K, et al. "Bicontinuous cubic" liquid crystalline materials from discotic molecules: a special effect of paraffinic side chains with ionic liquid pendants. J Am Chem Soc. 2009;131:17722-3 pubmed publisher
    ..5 A. Consistently, upon laser flash photolysis, it showed a transient microwave conductivity comparable to that of a Col(h) LC reference. ..
  31. Fromherz P, Hübener G, Kuhn B, Hinner M. ANNINE-6plus, a voltage-sensitive dye with good solubility, strong membrane binding and high sensitivity. Eur Biophys J. 2008;37:509-14 pubmed
    ..ANNINE-6plus will be particularly useful for sensitive optical recording of neuronal excitation when organic solvents and surfactants must be avoided as with intracellular or extracellular staining of brain tissue. ..
  32. Dvinskikh S, Zimmermann H, Maliniak A, Sandström D. Separated local field spectroscopy of columnar and nematic liquid crystals. J Magn Reson. 2003;163:46-55 pubmed
    ..The PDLF sequence provides in most cases the best dipolar resolution. This is especially obvious for weakly coupled 1H-13C spin pairs. ..
  33. Van Metre P, Mahler B. The contribution of particles washed from rooftops to contaminant loading to urban streams. Chemosphere. 2003;52:1727-41 pubmed
    ..The contribution from atmospheric deposition of particles onto rooftops to total watershed loads in stormwater was estimated to be greatest for mercury, contributing about 46 percent. ..
  34. Ogura K, Sohtome T, Sugiyama A, Okuda H, Hiratsuka A, Watabe T. Rat liver cytosolic hydroxysteroid sulfotransferase (sulfotransferase a) catalyzing the formation of reactive sulfate esters from carcinogenic polycyclic hydroxymethylarenes. Mol Pharmacol. 1990;37:848-54 pubmed
    ..The marked sex difference in STa level was in good accordance with the previous demonstration that cytosol from the liver of female rats catalyzed sulfation of 5-HCR to a greater extent than did cytosol from the liver of male rats. ..
  35. Chen R, Chou M, Ueng T. Induction of cytochrome P450 1A1 in human hepatoma HepG2 cells by 6-nitrochrysene. Toxicol Lett. 2000;117:69-77 pubmed
    ..The ability of 6-NC to induce liver and lung CYP1A1 may be an important factor to consider in assessing 6-NC metabolism and toxicity in humans. ..
  36. Choi H, Spengler J. Source attribution of personal exposure to airborne polycyclic aromatic hydrocarbon mixture using concurrent personal, indoor, and outdoor measurements. Environ Int. 2014;63:173-81 pubmed publisher
    ..B[ghi]P, B[a]P, D[a,h]A, and IP, PAHs with some of the highest carcinogenic and mutagenic potencies, are considerably enriched by cigarette smoke in addition to the outdoor sources. ..
  37. Gauthier E, Déziel E, Villemur R, Juteau P, Lepine F, Beaudet R. Initial characterization of new bacteria degrading high-molecular weight polycyclic aromatic hydrocarbons isolated from a 2-year enrichment in a two-liquid-phase culture system. J Appl Microbiol. 2003;94:301-11 pubmed
    ..New HMW PAH-degrading microorganisms and a better understanding of the mechanisms involved in HMW PAH degradation in TLP cultures. ..
  38. Smith M, Flowers T, Duncan H, Saito H. Study of PAH dissipation and phytoremediation in soils: comparing freshly spiked with weathered soil from a former coking works. J Hazard Mater. 2011;192:1219-25 pubmed publisher
    ..Therefore, predictions of PAH dissipation from laboratory amended soil do not reflect the true situation in the field. ..
  39. Li J, Chen H, Tang M, Shi X, Amin S, Desai D, et al. PI-3K and Akt are mediators of AP-1 induction by 5-MCDE in mouse epidermal Cl41 cells. J Cell Biol. 2004;165:77-86 pubmed
    ..These results demonstrate that 5-MCDE is able to induce AP-1 activation, and the AP-1 induction is specifically through a PI-3K/Akt-dependent and p70(S6K)-independent pathway. ..
  40. Lopez Tocon I, Otero J, Arenas J, García Ramos J, Sanchez Cortes S. Trace detection of triphenylene by surface enhanced Raman spectroscopy using functionalized silver nanoparticles with bis-acridinium lucigenine. Langmuir. 2010;26:6977-81 pubmed publisher
    ..The dependence of the Raman signal of TP on LG concentration has been checked, and trace concentrations of TP have been detected by this technique which therefore can be used as a chemical sensor of organic pollutants. ..
  41. Luo W, Li J, Zhang D, Cai T, Song L, Yin X, et al. Bid mediates anti-apoptotic COX-2 induction through the IKKbeta/NFkappaB pathway due to 5-MCDE exposure. Curr Cancer Drug Targets. 2010;10:96-106 pubmed
    ..Collectively, our results demonstrate that Bid is critical for COX-2 induction through the IKKbeta/NFkappaB pathway, which mediates its anti-apoptotic function, in cell response to low doses of 5-MCDE exposure. ..
  42. Uno S, Koyama J, Kokushi E, Monteclaro H, Santander S, Cheikyula J, et al. Monitoring of PAHs and alkylated PAHs in aquatic organisms after 1 month from the Solar I oil spill off the coast of Guimaras Island, Philippines. Environ Monit Assess. 2010;165:501-15 pubmed publisher
    ..These differences had two possible causes, that is, the differences between fish and shellfish could be attributed to the uptake routes and/or their metabolizing abilities. ..
  43. Mueller S, Katzenellenbogen J, Korach K. Endogenous estrogen receptor beta is transcriptionally active in primary ovarian cells from estrogen receptor knockout mice. Steroids. 2004;69:681-6 pubmed
    ..In conclusion, this study demonstrates that endogenously expressed ERbeta is capable of regulating gene transcription independent of ERalpha. ..
  44. Husain M. Measurement and theoretical characterization of electronic absorption spectrum of neutral chrysene (C18H12)and its positive ion in H3BO3 matrix. Spectrochim Acta A Mol Biomol Spectrosc. 2007;68:156-64 pubmed
    ..005 a.u. The lasing action in neutral chrysene and in its cationic form is also discussed for the first time. ..
  45. Pangrekar J, Kole P, Honey S, Kumar S, Sikka H. Metabolism of chrysene by brown bullhead liver microsomes. Toxicol Sci. 2003;71:67-73 pubmed
  46. Fernandes D, Porte C. Hydroxylated PAHs alter the synthesis of androgens and estrogens in subcellular fractions of carp gonads. Sci Total Environ. 2013;447:152-9 pubmed publisher
    ..3 ?M). The study highlights the potential of hydroxylated-polycyclic aromatic hydrocarbons, and particularly 9-hydroxyphenanthrene, to disrupt the synthesis of androgens and estrogens in carp gonads. ..
  47. Obiri S, Cobbina S, Armah F, Luginaah I. Assessment of cancer and noncancer health risks from exposure to PAHs in street dust in the Tamale Metropolis, Ghana. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2013;48:408-16 pubmed publisher
  48. Flesher J, Horn J, Lehner A. Comparative carcinogenicity of picene and dibenz[a,h]anthracene in the rat. Biochem Biophys Res Commun. 2002;290:275-9 pubmed
    ..It follows from these results that the predictions of the unified theory for the appearance of carcinogenic properties following administration of picene and dibenz[a,h]anthracene to test animals have been confirmed. ..
  49. Venkata Mohan S, Purushotham Reddy B, Sarma P. Ex situ slurry phase bioremediation of chrysene contaminated soil with the function of metabolic function: process evaluation by data enveloping analysis (DEA) and Taguchi design of experimental methodology (DOE). Bioresour Technol. 2009;100:164-72 pubmed publisher
  50. Alonso E, Tapie N, Budzinski H, Lemenach K, Peluhet L, Tarazona J. A model for estimating the potential biomagnification of chemicals in a generic food web: preliminary development. Environ Sci Pollut Res Int. 2008;15:31-40 pubmed
    ..In comparison to other previously published biomagnification models, the present one covers the time variation of bioaccumulation using just a few toxicokinetic parameters. ..
  51. Luster Teasley S, Yao J, Herner H, Trosko J, Masten S. Ozonation of chrysene: evaluation of byproduct mixtures and identification of toxic constituent. Environ Sci Technol. 2002;36:869-76 pubmed
    ..2-(2'-Formyl) phenyl-1-naphthaldehyde was determined to be the compound causing GJIC inhibition in sample fractions and byproduct mixtures. ..
  52. Khan Q, Anderson L. Hydrocarbon carcinogens evade cellular defense mechanism of G1 arrest in nontransformed and malignant lung cell lines. Toxicol Appl Pharmacol. 2001;173:105-13 pubmed
    ..The stealth effect of evasion of G1 arrest may contribute to initiation of lung adenocarcinomas and to progression of tumors. A role in resistance to chemotherapy by certain drugs is also likely. ..
  53. Miller J, Olejnik D. Photolysis of polycyclic aromatic hydrocarbons in water. Water Res. 2001;35:233-43 pubmed
    ..BAP and CHR are decomposed by a mechanism different than FLU. Quantum yields of the photolytic decomposition of BAP, CHR and FLU were determined and equal 0.014, 0.0031 and 0.0038, respectively. ..