Benzo(c)phenanthrene
Benzo(c)phenanthrene structure
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Common Name | Benzo(c)phenanthrene | ||
|---|---|---|---|---|
| CAS Number | 195-19-7 | Molecular Weight | 228.288 | |
| Density | 1.2±0.1 g/cm3 | Boiling Point | 436.7±12.0 °C at 760 mmHg | |
| Molecular Formula | C18H12 | Melting Point | 158-160℃ | |
| MSDS | Chinese USA | Flash Point | 209.1±13.7 °C | |
| Symbol |
GHS07 |
Signal Word | Warning | |
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Benzo[c]phenanthrene adducts and nogalamycin inhibit DNA transesterification by vaccinia topoisomerase.
J. Biol. Chem. 279(22) , 23335-42, (2004) Vaccinia DNA topoisomerase forms a covalent DNA-(3'-phosphotyrosyl)-enzyme intermediate at a specific target site 5'-C(+5)C(+4)C(+3)T(+2)T(+1)p downward arrow N(-1) in duplex DNA. Here we study the effects of position-specific DNA intercalators on the rate an... |
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In vitro and in vivo modulations of benzo[c]phenanthrene-DNA adducts by DNA mismatch repair system.
Nucleic Acids Res. 31(22) , 6428-34, (2003) Benzo[c]phenanthrene dihydrodiol epoxide (B[c] PhDE) is well known as an important environmental chemical carcinogen that preferentially modifies DNA in adenine residues. However, the molecular mechanism by which B[c]PhDE induces tumorigenesis is not fully un... |
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Structure/reactivity relationships in the benzo[c]phenanthrene skeleton: stable ion and electrophilic substitution (nitration, bromination) study of substituted analogues, novel carbocations and substituted derivatives.
J. Org. Chem. 72(9) , 3232-41, (2007) A series of novel carbocations were generated by low-temperature protonation of substituted benzo[c]phenanthrenes, B[c]Phs, and their charge delocalization pathways were elucidated by NMR on the basis of the magnitude of Deltadelta13C values. It has been show... |
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Benzo[a]pyrene and benz[c]phenanthrene: the effect of structure on the binding of water molecules to the diol epoxides.
Chem. Res. Toxicol. 15(8) , 1069-79, (2002) The interactions with water of the diol epoxides (DEs) of both a planar and a nonplanar PAH have been examined using molecular dynamics. To determine probable water locations around the DE for later use in the study of DE protonation, molecular dynamics simul... |
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Influence of adduct position and sequence length on the ligation of oligonucleotides containing benzo[c]phenanthrene diol epoxide-deoxyadenosine adducts into M13mp7L2.
Mutagenesis 16(1) , 65-9, (2001) The adduct that would arise from cis opening of (+)-(1S,2R,3R, 4S)-3,4-dihydroxy-1,2-epoxy-benzo[c]phenan-threne (benzo[c]phenanthrene diol epoxide-2, where the benzylic hydroxyl group and the epoxide oxygen are trans) by the exocyclic N6-amino group of deoxy... |
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Studies of the binding of diolepoxide metabolites of polycyclic aromatic hydrocarbons to DNA using electrofluorescence polarization spectroscopy.
Carcinogenesis 17(3) , 605-8, (1996) In the electrofluorescence method, a solution of DNA with covalently bound polycyclic hydrocarbons is placed in an electric field, and changes in the intensity of polarized fluorescence are observed. Under the correct conditions, these charges can be used to ... |
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Conformational searches elucidate effects of stereochemistry on structures of deoxyadenosine covalently bound to tumorigenic metabolites of benzo[C] phenanthrene.
Front. Biosci. 9 , 2807-18, (2004) Remarkably different conformations can result when DNA binds with stereoisomeric compounds containing differing absolute configurations of substituents about chiral carbon atoms. Furthermore, the biochemical functions of covalent adducts with DNA are strongly... |
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Bacteriophage T7 RNA polymerase transcription elongation is inhibited by site-specific, stereospecific benzo[c]phenanthrene diol epoxide DNA lesions.
Biochemistry 40(17) , 5200-7, (2001) Benzo[c]phenanthrene diol epoxide (B[c]PhDE), the ultimate carcinogenic metabolite of the environmental pollutant benzo[c]phenanthrene, reacts with DNA primarily at the exocyclic amino groups of purines, forming B[c]PhDE-DNA adducts that differ in their stere... |
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C-terminal region amino acid substitutions contribute to catalytic differences between murine class alpha glutathione transferases mGSTA1-1 and mGSTA2-2 toward anti-diol epoxide isomers of benzo[c]phenanthrene.
Biochemistry 40(24) , 7047-53, (2001) The molecular basis for catalytic differences between structurally closely related murine class alpha glutathione (GSH) transferases mGSTA1-1 and mGSTA2-2 in the GSH conjugation of anti-diol epoxide isomers of benzo[c]phenanthrene (anti-B[c]PDE) was investiga... |
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Ab initio and experimental studies on structure and vibrational spectra of some partially reduced benzo[c]phenanthrenes.
Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 72(1) , 82-101, (2009) A systematic study has been conducted on the conformation, electronic structure and vibrational spectra of benzo[c]phenanthrene and some of its partially reduced derivatives by experimental infrared spectroscopic and quantum chemical techniques. Electrostatic... |