The possible role of α,β-unsaturated carbonyl compounds in mutagenesis and carcinogenesis

Eder, Erwin; Scheckenbach, Sabine; Deininger, Christoph; Hoffman, Christian

doi:10.1016/0378-4274(93)90048-3

Cited by 113 publications

(126 citation statements)

References 37 publications

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“…coli PQ37 Not specified Weakly positive j (Eder et al, 1993) (Shinohara et al, 1986) EFSA Journal 2011; 9(10):2315 (Eder et al, 1993) DNA damage B. subtilis H17 (rec+) and M45 (rec-) 550, 5500 or 55000 µg/disc Negative Positive b,l (Shinohara et al, 1986) Chromosomal aberration CHO cells 0-112.6 mmol/l (0-13220 µg/ml) (Mortelmans et al, 1986) 13.022 1513…”

Section: Resultsmentioning

confidence: 99%

“…Evaluated in E. coli PQ37 under the conditions of the SOS chromotest, 3-(2-furyl)acrolein .034] tested negative (Eder et al, 1991); however, in a subsequent evaluation, 3-(2-furyl)acrolein .034] as well as 2-furyl methyl ketone (2-acetylfuran) .054] were slightly positive in the SOS chromotest without metabolic activation, as evidenced by 1.72-and 1.75-fold increases, respectively, in the SOS induction factor over a background value of 1 (results were considered to be significant if the induction factor was at least 1.5) (Eder et al, 1993).…”

Section: Statusmentioning

confidence: 99%

“…A second trial was not performed (Shinohara et al, 1986). Also with this substance a positive result was obtained in the rec-assay (Shinohara et al, 1986) and in an SOS-chromo test for bacterial DNA-repair (Eder et al, 1993), but the predictive value of these test systems is considered to be limited. With .054] also chromosomal aberrations in Chinese hamster ovary cells have been reported in a limited study by Stich et al (Stich et al, 1981b).…”

Section: In Vitro Studiesmentioning

confidence: 99%

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Scientific Opinion on Flavouring Group Evaluation 67, Revision 1 (FGE.67Rev.1): Consideration of 40 furan-substituted aliphatic hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and related esters, sulfides, disulfides and ethers evaluated by J

Flavourings¹

2011

EFSA Journal

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The Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids of the European Food Safety Authority was requested to consider evaluations of flavouring substances assessed since 2000 by the Joint FAO/WHO Expert Committee on Food Additives (the JECFA), and to decide whether further evaluation is necessary, as laid down in Commission Regulation (EC) No 1565/2000. The present consideration concerns a group of 33 furan‐substituted aliphatic hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and related esters, sulfides, disulfides and ethers evaluated by the JECFA. In the present version of FGE.67 eight additional substances have been included. The substances were evaluated through a stepwise approach (the Procedure) that integrates information on structure‐activity relationships, intake from current uses, toxicological threshold of concern, and available data on metabolism and toxicity. For twenty‐two substances [FL‐no: 13.029, 13.030, 13.045, 13.052, 13.054, 13.059, 13.061, 13.066, 13.069, 13.070, 13.083, 13.092, 13.101, 13.103, 13.105, 13.106, 13.107, 13.123, 13.138, 13.148, 13.163 and 13.191] a concern for genotoxicity was raised and therefore these were not evaluated using the Procedure. The Panel concluded that 8 substances [FL‐no: 13.006, 13.021, 13.022, 13.023, 13.024, 13.074, 13.116 and 13.190] do not give rise to safety concerns at the levels of dietary intake, estimated on the basis of the MSDI approach. For one substance [FL‐no: 13.058] additional toxicity data are requested. Besides the safety assessment of these substances, the specifications for the materials of commerce have been considered. For three substances [FL‐no: 13.031, 13.045 and 13.047] data on specifications / stereoisomerism are missing.

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Section: Resultsmentioning

confidence: 99%

Section: Statusmentioning

confidence: 99%

Section: In Vitro Studiesmentioning

confidence: 99%

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Scientific Opinion on Flavouring Group Evaluation 67, Revision 1 (FGE.67Rev.1): Consideration of 40 furan-substituted aliphatic hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and related esters, sulfides, disulfides and ethers evaluated by J

Flavourings¹

2011

EFSA Journal

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“…(e.g. malonaldehyde, furfural, benzaldehyde and trans,trans-2,4-hexadienal (National Toxicology Program, 1988, 1990, 1993, 2001 and other irritating substances (e.g. dihydrocoumarin, coumarin (National Toxicology Program, 1990, 1992 (Grice, 1988;Wester & Kroes, 1988;Clayson et al, 1990 (Eder et al, 1992;NTP, 2003f) and TA104 strain (Marnett et al, 1985a).…”

Section: Carcinogenicity Studiesmentioning

confidence: 99%

Flavouring Group Evaluation 203: alpha, beta‐Unsaturated aliphatic aldehydes and precursors from chemical subgroup 1.1.4 of FGE.19 with two or more conjugated double bonds and with or without additional non‐conjugated double bonds

Flavourings¹

2009

EFS2

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Based on the available data on carcinogenicity and genotoxicity there is a safety concern for hexa-2(trans),4(trans)-dienal .057] since a nonthreshold mechanism cannot be excluded. This conclusion also applies to the other substances of this FGE.Therefore, the substances of this FGE cannot be evaluated through the Procedure. The Panel requests data which clarify whether the carcinogenic effects were based on a thresholded mechanism.

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“…Vários aldeídos, como o MDA [152][153][154] ,acetaldeído 155,156 compostos dicarbonílicos 157,158 e uma série de aldeídos a-b insaturados [159][160][161][162][163][164][165][166][167] , têm sido estudados quanto a sua reatividade em relação ao DNA e têm sido identificados como eficientes agentes alquilantes de bases. Na maioria dos casos, o principal sítio reativo é o grupo amino exocíclico da guanina que é a base mais nucleofílica do DNA.…”

Section: Danos Ao Dna Promovidos Por áCido 45-dioxovaléricounclassified

Danos ao DNA promovidos por ácido 5-aminolevulínico: possível associação com o desenvolvimento de carcinoma hepatocelular em portadores de porfiria aguda intermitente

Onuki¹,

Teixeira²,

Medeiros³

et al. 2002

Quím. Nova

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Recebido em 26/6/01; aceito em 1/10/01 DNA DAMAGE INDUCED BY 5-AMINOLEVULINIC ACID: A POSSIBLE ASSOCIATION WITH THE DEVELOPMENT OF HEPATOCELLULAR CARCINOMA IN ACUTE INTERMITTENT PORPHYRIA PATIENTS. 5-Aminolevulinic acid (ALA) is a heme precursor accumulated in acute intermittent porphyria (AIP), which might be associated with hepatocellular carcinoma (HCC) in symptomatic patients. Under metal catalyzed oxidation, ALA and its cyclic dimerization product, 3,6-dihydropyrazine-2,5-dipropanoic acid, produce reactive oxygen species that damage plasmid and calf thymus DNA bases, increase the steady state level of 8-oxo-7,8-dihydro-2´-deoxyguanosine in liver DNA and promote mitochondrial DNA damage. The final product of ALA, 4,5-dioxovaleric acid (DOVA), is able to alkylate guanine moieties, producing adducts. ALA and DOVA are mutagenic in bacteria. This review shows an up-to-date literature data that reinforce the hypothesis that the DNA damage induced by ALA may be associated with the development of HCC in AIP patients.Keywords: 5-aminolevulinic acid; acute intermitent porphyria; DNA damage. PORFIRIASAs porfirias são definidas como doenças inatas ou adquiridas, relacionadas à deficiência de enzimas -inibição ou insuficiência -da via biossintética do grupo heme (Esquema 1) 1 . Esta deficiência resulta na produção excessiva e excreção de porfirinas e de seus precursores 2-6 . As porfirias são tradicionalmente classificadas com base no principal órgão que produz os metabólitos porfíricos em excesso (fígado ou os tecidos eritropoiéticos), na ocorrência ou não de ataques agudos e nas lesões cutâneas (fotossensibilidade) e/ou neurológicas produzidas 5,7,8 . Tipo de porfiria Aguda Hepática CutâneaPorfiria deficiente em ALA desidratase X X Porfiria aguda intermitente (AIP) X X Coproporfiria hereditária (HCP) X X X Porfiria variegata (VP) X X X Porfiria cutânea tarda (PCT) X X Porfiria eritropoiética congênita (CEP) X Protoporfiria eritropoiética (EPP) X A natureza molecular do defeito genético é altamente heterogê-nea e defeitos múltiplos têm sido demonstrados em cada tipo de porfiria 3,5 . Alguns modelos animais para os estudos dos diferentes tipos de porfiria já existem naturalmente, no caso de EPP e CEP e alguns foram desenvolvidos em laboratório, para EPP e porfirias hepáticas 9,10

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The possible role of α,β-unsaturated carbonyl compounds in mutagenesis and carcinogenesis

Cited by 113 publications

References 37 publications

Scientific Opinion on Flavouring Group Evaluation 67, Revision 1 (FGE.67Rev.1): Consideration of 40 furan-substituted aliphatic hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and related esters, sulfides, disulfides and ethers evaluated by J

Scientific Opinion on Flavouring Group Evaluation 67, Revision 1 (FGE.67Rev.1): Consideration of 40 furan-substituted aliphatic hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and related esters, sulfides, disulfides and ethers evaluated by J

Flavouring Group Evaluation 203: alpha, beta‐Unsaturated aliphatic aldehydes and precursors from chemical subgroup 1.1.4 of FGE.19 with two or more conjugated double bonds and with or without additional non‐conjugated double bonds

Danos ao DNA promovidos por ácido 5-aminolevulínico: possível associação com o desenvolvimento de carcinoma hepatocelular em portadores de porfiria aguda intermitente

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