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=C(C=C1)C3=C4C(C=CC5=CC=CC(C6=CC=CC=C36)=C45)=C2

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
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.	2009-05-15	19330882
Rainbow trout (Oncorhynchus mykiss) and ultra-low dose cancer studies.	2009-03	19135172
Analysis of polycyclic aromatic hydrocarbons in atmospheric particulate samples by microwave-assisted extraction and liquid chromatography.	2009-02	19173323
Identifying efficacious approaches to chemoprevention with chlorophyllin, purified chlorophylls and freeze-dried spinach in a mouse model of transplacental carcinogenesis.	2009-02	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.	2009-01-15	18848825
On the impact of the molecule structure in chemical carcinogenesis.	2009	19157061
Lymphoma and lung cancer in offspring born to pregnant mice dosed with dibenzo[a,l]pyrene: the importance of in utero vs. lactational exposure.	2008-12-15	18848954
Estimating individual-level exposure to airborne polycyclic aromatic hydrocarbons throughout the gestational period based on personal, indoor, and outdoor monitoring.	2008-11	19057704
Polycyclic aromatic hydrocarbon emission profiles and removal efficiency by electrostatic precipitator and wetfine scrubber in an iron ore sintering plant.	2008-11	19044155
Interactions between polycyclic aromatic hydrocarbons in binary mixtures: effects on gene expression and DNA adduct formation in precision-cut rat liver slices.	2008-11	18711122
Mutations induced by benzo[a]pyrene and dibenzo[a,l]pyrene in lacI transgenic B6C3F1 mouse lung result from stable DNA adducts.	2008-11	18573814
Both replication bypass fidelity and repair efficiency influence the yield of mutations per target dose in intact mammalian cells induced by benzo[a]pyrene-diol-epoxide and dibenzo[a,l]pyrene-diol-epoxide.	2008-08-02	18479980
Chemoprevention of dibenzo[a,l]pyrene transplacental carcinogenesis in mice born to mothers administered green tea: primary role of caffeine.	2008-08	18635525
Proteomic analysis of MCF-7 cells treated with benzo[a]pyrene, dibenzo[a,l]pyrene, coal tar extract, and diesel exhaust extract.	2008-07-10	18495319
Fetal mouse Cyp1b1 and transplacental carcinogenesis from maternal exposure to dibenzo(a,l)pyrene.	2008-07	19138945
Up-regulation of the glutathione S-transferase system in human liver by polycyclic aromatic hydrocarbons; comparison with rat liver and lung.	2008-07	18388359
The influence of diesel exhaust on polycyclic aromatic hydrocarbon-induced DNA damage, gene expression, and tumor initiation in Sencar mice in vivo.	2008-06-28	18353537
Differential response of human and rat epoxide hydrolase to polycyclic aromatic hydrocarbon exposure: studies using precision-cut tissue slices.	2008-04-02	18336844
Mdm2 as a sensitive and mechanistically informative marker for genotoxicity induced by benzo[a]pyrene and dibenzo[a,l]pyrene.	2008-04	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.	2008-04	17932951
Synthesis of dibenzo[def,p]chrysene, its active metabolites, and their 13C-labeled analogues.	2008-03-20	18284245
Dietary berries and ellagic acid prevent oxidative DNA damage and modulate expression of DNA repair genes.	2008-03	19325752
Low-dose dietary chlorophyll inhibits multi-organ carcinogenesis in the rainbow trout.	2008-03	18069110
DNA adducts formation and induction of apoptosis in rat liver epithelial 'stem-like' cells exposed to carcinogenic polycyclic aromatic hydrocarbons.	2008-02-01	17961608
RNA from brush oral cytology to measure squamous cell carcinoma gene expression.	2008-02	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.	2008-02	17920237
The role of polycyclic aromatic hydrocarbon-DNA adducts in inducing mutations in mouse skin.	2008-01-08	17931959
Diesel exhaust influences carcinogenic PAH-induced genotoxicity and gene expression in human breast epithelial cells in culture.	2007-12-01	17612574
Protective effect of dietary tomatine against dibenzo[a,l]pyrene (DBP)-induced liver and stomach tumors in rainbow trout.	2007-12	17979099
Binary PAH mixtures cause additive or antagonistic effects on gene expression but synergistic effects on DNA adduct formation.	2007-12	17690111
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.	2007-11-01	17509623
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.	2007-06-22	17530898
Characterization of naphtho[1,2-a]pyrene and naphtho[1,2-e]pyrene DNA adducts in C3H10T1/2 fibroblasts.	2007-03-18	16814461
Competitive inhibition of carcinogen-activating CYP1A1 and CYP1B1 enzymes by a standardized complex mixture of PAH extracted from coal tar.	2007-03-15	17187366
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.	2007-03	16973675
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.	2007-02-12	17386581
Identification and determination of highly carcinogenic dibenzopyrene isomers in air particulate samples from a street canyon, a rooftop, and a subway station in Stockholm.	2007-02-01	17328176
Modulation of gene expression and DNA-adduct formation in precision-cut liver slices exposed to polycyclic aromatic hydrocarbons of different carcinogenic potency.	2007-01	17151004
Urban dust particulate matter alters PAH-induced carcinogenesis by inhibition of CYP1A1 and CYP1B1.	2007-01	17060372
Inhibition of human cytochrome p450 1b1 further clarifies its role in the activation of dibenzo[a,l]pyrene in cells in culture.	2007	17623886
Investigation of the genotoxicity of dibenzo[c,p]chrysene in human carcinoma MCF-7 cells in culture.	2006-12-15	17094953
Indole-3-carbinol in the maternal diet provides chemoprotection for the fetus against transplacental carcinogenesis by the polycyclic aromatic hydrocarbon dibenzo[a,l]pyrene.	2006-10	16704990
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.	2006-08-09	16881636
Method validation for determination of the 15 European-priority polycyclic aromatic hydrocarbons in primary smoke condensates by gas chromatography/mass spectrometry: interlaboratory study.	2006-06-24	16792075
On the species-specific biotransformation of dibenzo[a,l]pyrene.	2006-05-15	16581046
Genotoxic effects of benzo[a]pyrene and dibenzo[a,l]pyrene in a human lung cell line.	2006-03-03	16510357
Single-laboratory validation of a gas chromatography-mass spectrometry method for quantitation of 15 European priority polycyclic aromatic hydrocarbons in spiked smoke flavourings.	2006-01-27	16343513
In utero exposure of mice to dibenzo[a,l]pyrene produces lymphoma in the offspring: role of the aryl hydrocarbon receptor.	2006-01-15	16424006
Determination of dibenzopyrenes in standard reference materials (SRM) 1649a, 1650, and 2975 using ultrasonically assisted extraction and LC-GC-MS.	2006-01	16333601
Improved measurement of dibenzo[a,l]pyrene-induced abasic sites by the aldehyde-reactive probe assay.	2005-12-30	16298157

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:50:34 GMT 2025` Edited by `admin` on `Mon Mar 31 18:50:34 GMT 2025`
Record UNII	G3X629VE4A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIBENZO(A,L)PYRENE

Systematic Name

English

BA 51-090462

Preferred 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

Code System Code Type Description

NCI_THESAURUS

C1069