The true dibenzo [a, l] pyrene, a new, potent carcinogen

Lacassagne, A; Buu‐Hoï, Ng. Ph.; Zajdela, F; Vingiello, Frank A.

doi:10.1007/bf00593423

Cited by 26 publications

(6 citation statements)

References 4 publications

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“…Note that US EPA [ 17 ] cited [ 55 ], who reported that in studies conducted prior to 1966, the compound reported as dibenzo[a,l]pyrene (DBalP) was actually dibenzo[a,e]fluoranthene (DBaeF). Consequently, US EPA [ 17 ] listed DBaeF instead of DBalP as was originally assigned by Hoffman and Wynder [ 35 ].…”

Section: Resultsmentioning

confidence: 99%

The Long Goodbye: Finally Moving on from the Relative Potency Approach to a Mixtures Approach for Polycyclic Aromatic Hydrocarbons (PAHs)

Haber

Pecquet

Vincent

et al. 2022

IJERPH

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For the past several decades, a relative potency approach has been used to estimate the human health risks from exposure to polycyclic aromatic hydrocarbon (PAH) mixtures. Risk estimates are derived using potency equivalence factors (PEFs; also called relative potency factors [RPFs]), based on the ratio of selected PAHs to benzo[a]pyrene (BaP), expressed qualitatively by orders of magnitude. To quantify PEFs for 18 selected carcinogenic PAHs, a systematic approach with a priori and dose response criteria was developed, building on draft work by the US EPA in 2010 and its review by US EPA Science Advisory Board (SAB) in 2011. An exhaustive search for carcinogenicity studies that included both target PAHs and BaP with environmentally relevant exposure routes found only 48 animal bioassay datasets (mostly pre-1992 based on skin painting). Only eight datasets provided adequate low-response data, and of these only four datasets were appropriate for modeling to estimate PEFs; only benzo[b]fluoranthene and cyclopenta[c,d]pyrene had a PEF that could be quantified. Thus, current knowledge of PAH carcinogenicity is insufficient to support quantitative PEFs for PAH mixtures. This highlights the long-acknowledged need for an interdisciplinary approach to estimate risks from PAH mixtures. Use of alternative and short-term toxicity testing methods, improved mixture characterization, understanding the fate and bioavailability of PAH mixtures, and understanding exposure route-related differences in carcinogenicity are discussed as ways to improve the understanding of the risks of PAHs.

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Section: Resultsmentioning

confidence: 99%

The Long Goodbye: Finally Moving on from the Relative Potency Approach to a Mixtures Approach for Polycyclic Aromatic Hydrocarbons (PAHs)

Haber

Pecquet

Vincent

et al. 2022

IJERPH

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“…NMR of 7-OH-DB[a,e]P: 7.53 (d, 1 H, J = 8.5 Hz, 8-H), 7.64-7.73 (m, 2 , 11-H, 12-H), 7.82-7.86 (m, 2 , 2-H, 3-H), 8.40-8.43 (m, 1 , 1-H), 8.63 (d, 1 H, J = 9.3 Hz, 6-H), 8.72-8.75 (m, 1 , 10-H), 8.81 (d" 1H,J = 8.5 Hz, 9-H), 8.97-9.00 (m, 1 , 13-H), 9.10 (d, 1 H, J = 8.5 Hz, 5-H), 9.10-9.13 (m, 1 H, 4-H), 9.41 (s, 1H, 14-H). NMR of 9-OH-DB[a,e]P: 7.64-7.67 (m, 1 H, 8'-H), 7.77, 7.80 (m, 2 , 2'-H, 3'-H), 8.15 (d, 1 H, J = 8.7 Hz, 7'-H), 8.22 (d, 1H,J = 9.1 Hz, 6'-H), 8.36-8.39 (m, 1 H, l'-H), 8.90 (d, 1 H, J = 9.1 Hz, 5'-H), 9.04-9.07 (m, 1 H, 4'-H), 9.30 , 11-H), 8.76 (s, 1 , 10-H), 9.06-9.13 (m, 3 H, 1-H, 4-H, 5-H), 9.17 1H,J = 8.5 Hz, 9-H), 7.63-7.77 (m, 5 H, 2-H, 3-H, 6-H, 12-H, 13-H), 7.86 (d, 1 H, J = 7.2 Hz, 7-H), 8.11-8.14 (m, 1 , 11-H), 8.17 (s, 1 , 10-H), 8.73 (d, 1 H, J = 8.3 Hz, 5-H), 8.84-8.90 (m, 3 H, 1-H, 4-H, 14-H). MS: m/z (relative intensity) 336.1140 (38.0, M), in agreement with an elemental formula of C^H^O^3 18.1047 (100, M -H20); 289.1007 (51.6, M -CH302).…”

Section: Methodsmentioning

confidence: 99%

“…This compound has not been considered a very significant environmental carcinogen for two reasons. First, tumorigenicity tests prior to 1968 incorrectly used the weakly active dibenzo[a,e]fluoranthene instead of DB[a,/]P itself (8,9). Second, analytical data quantitating its presence in cigarette smoke and other environmental hazards have not been pursued.…”

Section: Introductionmentioning

confidence: 99%

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Metabolism and mutagenicity of dibenzo[a,e]pyrene and the very potent environmental carcinogen dibenzo[a,l]pyrene

Devanesan¹,

Cremonesi²,

Nunnally³

et al. 1990

Chem. Res. Toxicol.

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Dibenzo[a,l]pyrene (DB[a,l]P) is one of the most potent carcinogens ever tested in mouse skin and rat mammary gland. DB[a,l]P is present in cigarette smoke and, presumably, in other environmental pollutants. Metabolism and mutagenicity studies of this compound compared to the weak carcinogen dibenzo[a,e]pyrene (DB[a,e]P) can provide preliminary evidence on its mechanism of carcinogenesis. The mutagenicity of DB[a,l]P, DB[a,e]P, and benzo[a]pyrene (BP) was compared in the Ames assay with Aroclor-induced rat liver S-9. BP was the strongest mutagen. In strain TA100, DB[a,l]P and DB[a,e]P were marginally mutagenic. In strain TA98 both compounds were mutagenic, and DB[a,l]P induced more than twice as many revertants as DB[a,e]P. The mutagenicity of DB[a,l]P does not correlate with its carcinogenicity, since DB[a,l]P is a much stronger carcinogen, but a much weaker mutagen, than BP. The NADPH-supported metabolism of DB[a,e]P and DB[a,l]P was conducted with uninduced and 3-methylcholanthrene-induced rat liver microsomes. Metabolites were analyzed by reverse-phase HPLC and identified by NMR, UV, and mass spectrometry. Uninduced microsomes produced only traces of metabolites with either compound. The major metabolites of DB[a,l]P with induced microsomes were DB[a,l]P 8,9-dihydrodiol, DB[a,l]P 11,12-dihydrodiol, 7-hydroxyDB[a,l]P, and a DB[a,l]P dione. The metabolites of DB[a,e]P with induced microsomes were DB[a,e]P 3,4-dihydrodiol, 3-hydroxyDB[a,e]P, 7-hydroxyDB[a,e]P, and 9-hydroxyDB[a,e]P. Some of these metabolites are very useful in assessing possible pathways of activation in the initiation of cancer.

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“…Found: C, 94.63; H, 5.52); ultraviolet X^ohexa". 272 µ (e 2.09 X 106), 262.5 (1.06 X 105), 329 (2.01 X 104), 314.5 (1.98 X 104), 302 (1.60 X 104); infrared Xi=r 6.2, 6.3 (aromatic C=C), 11.6, 12.4, 13.2, 13.4 µ; mass spectrum (70 eV) m/e (relative intensity) 126 (1000), 254 (906), 113 (612), 127 (580), 125 (540); nmr (C«D6) S 3.04 (CH¡>), 8.39 (H-/3, m), 7.75 (H-, m), and 7.46 (H-a3, ml.…”

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confidence: 99%