DIBENZO(A,L)PYRENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H14
Molecular Weight	302.368
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1=CC2=CC3=C4C5=C(C=CC=C5C=C3)C6=C(C=CC=C6)C4=C2C=C1

InChI

InChIKey=JNTHRSHGARDABO-UHFFFAOYSA-N

InChI=1S/C24H14/c1-2-8-18-16(6-1)14-17-13-12-15-7-5-11-20-19-9-3-4-10-21(19)24(18)23(17)22(15)20/h1-14H

HIDE SMILES / InChI

Molecular Formula	C24H14
Molecular Weight	302.368
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Long-term effects of a standardized complex mixture of urban dust particulate on the metabolic activation of carcinogenic polycyclic aromatic hydrocarbons in human cells in culture.	2005 Dec	16162842
Improved measurement of dibenzo[a,l]pyrene-induced abasic sites by the aldehyde-reactive probe assay.	2005 Dec 30	16298157
Harvey-ras gene expression and epidermal cell proliferation in dibenzo[a,l]pyrene-treated early preneoplastic SENCAR mouse skin.	2005 Sep	16117800
Dibenzo[a,l]pyrene induced DNA adduct formation in lung tissue in vivo.	2005 Sep 8	16051029
Facile interstrand migration of the hydrocarbon moiety of a dibenzo[a,l]pyrene 11,12-diol 13,14-epoxide adduct at N2 of deoxyguanosine in a duplex oligonucleotide.	2006 Aug 9	16881636
Investigation of the genotoxicity of dibenzo[c,p]chrysene in human carcinoma MCF-7 cells in culture.	2006 Dec 15	17094953
Determination of dibenzopyrenes in standard reference materials (SRM) 1649a, 1650, and 2975 using ultrasonically assisted extraction and LC-GC-MS.	2006 Jan	16333601
In utero exposure of mice to dibenzo[a,l]pyrene produces lymphoma in the offspring: role of the aryl hydrocarbon receptor.	2006 Jan 15	16424006
Single-laboratory validation of a gas chromatography-mass spectrometry method for quantitation of 15 European priority polycyclic aromatic hydrocarbons in spiked smoke flavourings.	2006 Jan 27	16343513
Genotoxic effects of benzo[a]pyrene and dibenzo[a,l]pyrene in a human lung cell line.	2006 Jan-Feb	16510357
Modulation of gene expression and DNA adduct formation in HepG2 cells by polycyclic aromatic hydrocarbons with different carcinogenic potencies.	2006 Mar	16269432
Activation of ERK1/2 and p38 kinases by polycyclic aromatic hydrocarbons in rat liver epithelial cells is associated with induction of apoptosis.	2006 Mar 15	16005925
On the species-specific biotransformation of dibenzo[a,l]pyrene.	2006 May 15	16581046
Method validation for determination of the 15 European-priority polycyclic aromatic hydrocarbons in primary smoke condensates by gas chromatography/mass spectrometry: interlaboratory study.	2006 May-Jun	16792075
Indole-3-carbinol in the maternal diet provides chemoprotection for the fetus against transplacental carcinogenesis by the polycyclic aromatic hydrocarbon dibenzo[a,l]pyrene.	2006 Oct	16704990
Inhibition of human cytochrome p450 1b1 further clarifies its role in the activation of dibenzo[a,l]pyrene in cells in culture.	2007	17623886
Protective effect of dietary tomatine against dibenzo[a,l]pyrene (DBP)-induced liver and stomach tumors in rainbow trout.	2007 Dec	17979099
Binary PAH mixtures cause additive or antagonistic effects on gene expression but synergistic effects on DNA adduct formation.	2007 Dec	17690111
Diesel exhaust influences carcinogenic PAH-induced genotoxicity and gene expression in human breast epithelial cells in culture.	2007 Dec 1	17612574
Identification and determination of highly carcinogenic dibenzopyrene isomers in air particulate samples from a street canyon, a rooftop, and a subway station in Stockholm.	2007 Feb 1	17328176
The characterization of (+/-)-anti-benzo[a]pyrene diolepoxide-DNA adducts and (+/-)-anti-dibenzo[a,l]pyrene diolepoxide--DNA adducts in the same DNA sample using solid-matrix phosphorescence.	2007 Feb 12	17386581
Modulation of gene expression and DNA-adduct formation in precision-cut liver slices exposed to polycyclic aromatic hydrocarbons of different carcinogenic potency.	2007 Jan	17151004
Urban dust particulate matter alters PAH-induced carcinogenesis by inhibition of CYP1A1 and CYP1B1.	2007 Jan	17060372
Efficient syntheses of C(8)-aryl adducts of adenine and guanine formed by reaction of radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons with DNA.	2007 Jun 22	17530898
The importance of carcinogen dose in chemoprevention studies: quantitative interrelationships between, dibenzo[a,l]pyrene dose, chlorophyllin dose, target organ DNA adduct biomarkers and final tumor outcome.	2007 Mar	16973675
Competitive inhibition of carcinogen-activating CYP1A1 and CYP1B1 enzymes by a standardized complex mixture of PAH extracted from coal tar.	2007 Mar 15	17187366
Characterization of naphtho[1,2-a]pyrene and naphtho[1,2-e]pyrene DNA adducts in C3H10T1/2 fibroblasts.	2007 Mar 18	16814461
Cytotoxicity and mutagenicity of dibenzo[a,l]pyrene and (+/-)-dibenzo[a,l]pyrene-11,12-dihydrodiol in V79MZ cells co-expressing either hCYP1A1 or hCYP1B1 together with human glutathione-S-transferase A1.	2007 Nov 1	17509623
Mdm2 as a sensitive and mechanistically informative marker for genotoxicity induced by benzo[a]pyrene and dibenzo[a,l]pyrene.	2008 Apr	18096571
Anti-diol epoxide of benzo[a]pyrene induces transient Mdm2 and p53 Ser15 phosphorylation, while anti-diol epoxide of dibenzo[a,l]pyrene induces a nontransient p53 Ser15 phosphorylation.	2008 Apr	17932951
Differential response of human and rat epoxide hydrolase to polycyclic aromatic hydrocarbon exposure: studies using precision-cut tissue slices.	2008 Apr 2	18336844
Lymphoma and lung cancer in offspring born to pregnant mice dosed with dibenzo[a,l]pyrene: the importance of in utero vs. lactational exposure.	2008 Dec 15	18848954
RNA from brush oral cytology to measure squamous cell carcinoma gene expression.	2008 Feb	18197850
Up-regulation of CYP1A/B in rat lung and liver, and human liver precision-cut slices by a series of polycyclic aromatic hydrocarbons; association with the Ah locus and importance of molecular size.	2008 Feb	17920237
DNA adducts formation and induction of apoptosis in rat liver epithelial 'stem-like' cells exposed to carcinogenic polycyclic aromatic hydrocarbons.	2008 Feb 1	17961608
The role of polycyclic aromatic hydrocarbon-DNA adducts in inducing mutations in mouse skin.	2008 Jan 8	17931959
Fetal mouse Cyp1b1 and transplacental carcinogenesis from maternal exposure to dibenzo(a,l)pyrene.	2008 Jul	19138945
Up-regulation of the glutathione S-transferase system in human liver by polycyclic aromatic hydrocarbons; comparison with rat liver and lung.	2008 Jul	18388359
Proteomic analysis of MCF-7 cells treated with benzo[a]pyrene, dibenzo[a,l]pyrene, coal tar extract, and diesel exhaust extract.	2008 Jul 10	18495319
The influence of diesel exhaust on polycyclic aromatic hydrocarbon-induced DNA damage, gene expression, and tumor initiation in Sencar mice in vivo.	2008 Jun 28	18353537
Dietary berries and ellagic acid prevent oxidative DNA damage and modulate expression of DNA repair genes.	2008 Mar	19325752
Low-dose dietary chlorophyll inhibits multi-organ carcinogenesis in the rainbow trout.	2008 Mar	18069110
Synthesis of dibenzo[def,p]chrysene, its active metabolites, and their 13C-labeled analogues.	2008 Mar 20	18284245
Polycyclic aromatic hydrocarbon emission profiles and removal efficiency by electrostatic precipitator and wetfine scrubber in an iron ore sintering plant.	2008 Nov	19044155
On the impact of the molecule structure in chemical carcinogenesis.	2009	19157061
Analysis of polycyclic aromatic hydrocarbons in atmospheric particulate samples by microwave-assisted extraction and liquid chromatography.	2009 Feb	19173323
Identifying efficacious approaches to chemoprevention with chlorophyllin, purified chlorophylls and freeze-dried spinach in a mouse model of transplacental carcinogenesis.	2009 Feb	19073876
H2AX phosphorylation in A549 cells induced by the bulky and stable DNA adducts of benzo[a]pyrene and dibenzo[a,l]pyrene diol epoxides.	2009 Jan 15	18848825
Rainbow trout (Oncorhynchus mykiss) and ultra-low dose cancer studies.	2009 Mar	19135172
Differential protection by human glutathione S-transferase P1 against cytotoxicity of benzo[a]pyrene, dibenzo[a,l]pyrene, or their dihydrodiol metabolites, in bi-transgenic cell lines that co-express rat versus human cytochrome P4501A1.	2009 May 15	19330882

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:41:40 GMT 2023` Edited by `admin` on `Fri Dec 15 17:41:40 GMT 2023`
Record UNII	G3X629VE4A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIBENZO(A,L)PYRENE

Systematic Name

English

1,2,9,10-DIBENZOPYRENE

Common Name

English

2,3:4,5-DIBENZPYRENE

Common Name

English

1,2:3,4-DIBENZOPYRENE

Common Name

English

4,5,6,7-DIBENZPYRENE

Common Name

English

DIBENZO(A,L)PYRENE [HSDB]

Common Name

English

DIBENZO(A,L)PYRENE [IARC]

Common Name

English

DIBENZO(DEF,P)CHRYSENE

Systematic Name

English

DB(A,L)P

Common Name

English

NSC-90324

Code

English

BA 51-090462

Code

English

Code System Code Type Description

NCI_THESAURUS

C1069