29 Citations (Scopus)

Abstract

Dibenzo[a,l]pyrene (DB[a,l]P) is the most potent carcinogen among dibenzo[a]pyrenes. DB[a,l]P is more tumorigenic than 7,12-dimethylbenz[a]anthracene, DB[a,l]P 11,12-dihydrodiol, and 100–200 times more tumorigenic than benzo[a]pyrene. DB[a,l]P is also extremely toxic. Dose-response studies were conducted in the skin of female SENCAR mice by initiation-promotion to compare the tumorigenicity of DB[a,l]P to that of (±)-trans-DB[a,L]P-11,12-dihydrodiol, (±)-anti-DB[a,l]P diol epoxide (anti-DB[a,l]P and (±)-syn-DB[a,l]PDE. Mice were initiated with 12, 4 or 1.33 nmol of compound and promoted with tetradecanoyl phorbol acetate. DB[a,l]P at 12, 4 or 1.33 nmol induced 9.3, 7.1 or 5.2 tumors per mouse (t/m), respectively. DB[a,l]P-11,12-dihydrodiol induced 4.6, 4.3 or 2.8 t/m. Anti-DB[a,l]PDE resulted in 2.0, 0.7 or 0.7 t/m vs 1.8, 1.5 or 1.8 with syn-DB[a,l]PDE. The experiment confirms that DB[a,l]P is more potent than DB[a,l]P-11,12-dihydrodiol and shows that the two diol epoxides are less tumorigenic than their 11,12-dihydrodiol precursor. At low doses syn-DB[a,l]PDE is a stronger tumor initiator than its congener anti-DB[a,l]PDE.

Original languageEnglish (US)
Pages (from-to)177-183
Number of pages7
JournalPolycyclic Aromatic Compounds
Volume6
Issue number1-4
DOIs
StatePublished - Jan 1 1994

Fingerprint

Aromatic Hydrocarbons
Aromatic hydrocarbons
Pyrene
Tumors
Epoxy Compounds
Carcinogens
Pyrenes
Poisons
Benzo(a)pyrene
Anthracene
Skin
Acetates
pyrene
dibenzo(a,l)pyrene 11,12-dihydrodiol
Experiments
trans-1,2-dihydro-1,2-naphthalenediol

Keywords

  • Tumorigenicity carcinogenicity dibenzo[a,l]pyrene
  • dibenzo[a,l]pyrene metabolites

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

Dibenzo[fl,/]pyrene : The Most Potent Carcinogenic Aromatic Hydrocarbon. / Cavalieri, Ercole; Higginbotham, Sheila; Rogan, Eleanor G.

In: Polycyclic Aromatic Compounds, Vol. 6, No. 1-4, 01.01.1994, p. 177-183.

Research output: Contribution to journalArticle

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abstract = "Dibenzo[a,l]pyrene (DB[a,l]P) is the most potent carcinogen among dibenzo[a]pyrenes. DB[a,l]P is more tumorigenic than 7,12-dimethylbenz[a]anthracene, DB[a,l]P 11,12-dihydrodiol, and 100–200 times more tumorigenic than benzo[a]pyrene. DB[a,l]P is also extremely toxic. Dose-response studies were conducted in the skin of female SENCAR mice by initiation-promotion to compare the tumorigenicity of DB[a,l]P to that of (±)-trans-DB[a,L]P-11,12-dihydrodiol, (±)-anti-DB[a,l]P diol epoxide (anti-DB[a,l]P and (±)-syn-DB[a,l]PDE. Mice were initiated with 12, 4 or 1.33 nmol of compound and promoted with tetradecanoyl phorbol acetate. DB[a,l]P at 12, 4 or 1.33 nmol induced 9.3, 7.1 or 5.2 tumors per mouse (t/m), respectively. DB[a,l]P-11,12-dihydrodiol induced 4.6, 4.3 or 2.8 t/m. Anti-DB[a,l]PDE resulted in 2.0, 0.7 or 0.7 t/m vs 1.8, 1.5 or 1.8 with syn-DB[a,l]PDE. The experiment confirms that DB[a,l]P is more potent than DB[a,l]P-11,12-dihydrodiol and shows that the two diol epoxides are less tumorigenic than their 11,12-dihydrodiol precursor. At low doses syn-DB[a,l]PDE is a stronger tumor initiator than its congener anti-DB[a,l]PDE.",
keywords = "Tumorigenicity carcinogenicity dibenzo[a,l]pyrene, dibenzo[a,l]pyrene metabolites",
author = "Ercole Cavalieri and Sheila Higginbotham and Rogan, {Eleanor G}",
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T1 - Dibenzo[fl,/]pyrene

T2 - The Most Potent Carcinogenic Aromatic Hydrocarbon

AU - Cavalieri, Ercole

AU - Higginbotham, Sheila

AU - Rogan, Eleanor G

PY - 1994/1/1

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N2 - Dibenzo[a,l]pyrene (DB[a,l]P) is the most potent carcinogen among dibenzo[a]pyrenes. DB[a,l]P is more tumorigenic than 7,12-dimethylbenz[a]anthracene, DB[a,l]P 11,12-dihydrodiol, and 100–200 times more tumorigenic than benzo[a]pyrene. DB[a,l]P is also extremely toxic. Dose-response studies were conducted in the skin of female SENCAR mice by initiation-promotion to compare the tumorigenicity of DB[a,l]P to that of (±)-trans-DB[a,L]P-11,12-dihydrodiol, (±)-anti-DB[a,l]P diol epoxide (anti-DB[a,l]P and (±)-syn-DB[a,l]PDE. Mice were initiated with 12, 4 or 1.33 nmol of compound and promoted with tetradecanoyl phorbol acetate. DB[a,l]P at 12, 4 or 1.33 nmol induced 9.3, 7.1 or 5.2 tumors per mouse (t/m), respectively. DB[a,l]P-11,12-dihydrodiol induced 4.6, 4.3 or 2.8 t/m. Anti-DB[a,l]PDE resulted in 2.0, 0.7 or 0.7 t/m vs 1.8, 1.5 or 1.8 with syn-DB[a,l]PDE. The experiment confirms that DB[a,l]P is more potent than DB[a,l]P-11,12-dihydrodiol and shows that the two diol epoxides are less tumorigenic than their 11,12-dihydrodiol precursor. At low doses syn-DB[a,l]PDE is a stronger tumor initiator than its congener anti-DB[a,l]PDE.

AB - Dibenzo[a,l]pyrene (DB[a,l]P) is the most potent carcinogen among dibenzo[a]pyrenes. DB[a,l]P is more tumorigenic than 7,12-dimethylbenz[a]anthracene, DB[a,l]P 11,12-dihydrodiol, and 100–200 times more tumorigenic than benzo[a]pyrene. DB[a,l]P is also extremely toxic. Dose-response studies were conducted in the skin of female SENCAR mice by initiation-promotion to compare the tumorigenicity of DB[a,l]P to that of (±)-trans-DB[a,L]P-11,12-dihydrodiol, (±)-anti-DB[a,l]P diol epoxide (anti-DB[a,l]P and (±)-syn-DB[a,l]PDE. Mice were initiated with 12, 4 or 1.33 nmol of compound and promoted with tetradecanoyl phorbol acetate. DB[a,l]P at 12, 4 or 1.33 nmol induced 9.3, 7.1 or 5.2 tumors per mouse (t/m), respectively. DB[a,l]P-11,12-dihydrodiol induced 4.6, 4.3 or 2.8 t/m. Anti-DB[a,l]PDE resulted in 2.0, 0.7 or 0.7 t/m vs 1.8, 1.5 or 1.8 with syn-DB[a,l]PDE. The experiment confirms that DB[a,l]P is more potent than DB[a,l]P-11,12-dihydrodiol and shows that the two diol epoxides are less tumorigenic than their 11,12-dihydrodiol precursor. At low doses syn-DB[a,l]PDE is a stronger tumor initiator than its congener anti-DB[a,l]PDE.

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KW - dibenzo[a,l]pyrene metabolites

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