BIOMAT Database Logo BIOMAT Database Logo

Genotoxic effects of the alpha, beta-unsaturated aldehydes 2-trans-butenal, 2-trans-hexenal and 2-trans, 6-cis-nonadienal. 1995

U Dittberner, and G Eisenbrand, and H Zankl
Department of Human Biology and Human Genetics, University of Kaiserslautern, Germany.

The genotoxic effects of the 2-alkenals crotonaldehyde, 2-trans-hexenal and 2-trans-6-cis-nonadienal were studied by cytogenetic methods, analyzing frequencies of sister-chromatid-exchanges, numerical and structural chromosome aberrations and micronucleus induction in human blood lymphocytes and cells of the permanent Namalva line. Crotonaldehyde and hexenal were tested in concentrations of 5 microM to 250 microM and nonadienal from 5 microM to 70 microM. Significant dose-related increases of sister-chromatid-exchanges and micronuclei were found for all three compounds. Structural chromosomal aberrations were significantly increased only by crotonaldehyde, but not by hexenal and nonadienal. In contrast numerical chromosome aberrations were not induced by crotonaldehyde whereas hexenal and nonadienal were potent inducers of aneuploidy. The micronuclei were classified by using a centromere-specific DNA probe in a fluorescence in situ hybridization assay. Hexenal and nonadienal increased the percentage of centromere-positive micronuclei, nonadienal being considerably more potent than hexenal. From these results it was concluded that crotonaldehyde acts more as a clastogen whereas hexenal and nonadienal preferentially show aneugenic effects.

UI MeSH Term Description Entries
D008214 Lymphocytes White blood cells formed in the body's lymphoid tissue. The nucleus is round or ovoid with coarse, irregularly clumped chromatin while the cytoplasm is typically pale blue with azurophilic (if any) granules. Most lymphocytes can be classified as either T or B (with subpopulations of each), or NATURAL KILLER CELLS. Lymphoid Cells,Cell, Lymphoid,Cells, Lymphoid,Lymphocyte,Lymphoid Cell
D009153 Mutagens Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. Clastogen,Clastogens,Genotoxin,Genotoxins,Mutagen
D002460 Cell Line Established cell cultures that have the potential to propagate indefinitely. Cell Lines,Line, Cell,Lines, Cell
D002869 Chromosome Aberrations Abnormal number or structure of chromosomes. Chromosome aberrations may result in CHROMOSOME DISORDERS. Autosome Abnormalities,Cytogenetic Aberrations,Abnormalities, Autosome,Abnormalities, Chromosomal,Abnormalities, Chromosome,Chromosomal Aberrations,Chromosome Abnormalities,Cytogenetic Abnormalities,Aberration, Chromosomal,Aberration, Chromosome,Aberration, Cytogenetic,Aberrations, Chromosomal,Aberrations, Chromosome,Aberrations, Cytogenetic,Abnormalities, Cytogenetic,Abnormality, Autosome,Abnormality, Chromosomal,Abnormality, Chromosome,Abnormality, Cytogenetic,Autosome Abnormality,Chromosomal Aberration,Chromosomal Abnormalities,Chromosomal Abnormality,Chromosome Aberration,Chromosome Abnormality,Cytogenetic Aberration,Cytogenetic Abnormality
D004305 Dose-Response Relationship, Drug The relationship between the dose of an administered drug and the response of the organism to the drug. Dose Response Relationship, Drug,Dose-Response Relationships, Drug,Drug Dose-Response Relationship,Drug Dose-Response Relationships,Relationship, Drug Dose-Response,Relationships, Drug Dose-Response
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000447 Aldehydes Organic compounds containing a carbonyl group in the form -CHO. Aldehyde
D012854 Sister Chromatid Exchange An exchange of segments between the sister chromatids of a chromosome, either between the sister chromatids of a meiotic tetrad or between the sister chromatids of a duplicated somatic chromosome. Its frequency is increased by ultraviolet and ionizing radiation and other mutagenic agents and is particularly high in BLOOM SYNDROME. Chromatid Exchange, Sister,Chromatid Exchanges, Sister,Exchange, Sister Chromatid,Exchanges, Sister Chromatid,Sister Chromatid Exchanges
D015162 Micronucleus Tests Induction and quantitative measurement of chromosomal damage leading to the formation of micronuclei (MICRONUCLEI, CHROMOSOME-DEFECTIVE) in cells which have been exposed to genotoxic agents or IONIZING RADIATION. Micronucleus Assays,Assay, Micronucleus,Assays, Micronucleus,Micronucleus Assay,Micronucleus Test,Test, Micronucleus,Tests, Micronucleus

Related Publications

U Dittberner, and G Eisenbrand, and H Zankl
Effects of trans-2-hexenal and cis-3-hexenal on post-harvest strawberry.
July 2019, Scientific reports,
U Dittberner, and G Eisenbrand, and H Zankl
Kinetic and Mechanistic Study of the Reactions of NO3 Radicals with Unsaturated Aldehydes: 2-Butenal, 2-Methyl-2-butenal, and 3-Methyl-2-butenal.
November 2022, The journal of physical chemistry. A,
U Dittberner, and G Eisenbrand, and H Zankl
An experimental study of the gas-phase reactions of NO3 radicals with a series of unsaturated aldehydes: trans-2-hexenal, trans-2-heptenal, and trans-2-octenal.
October 2012, The journal of physical chemistry. A,
U Dittberner, and G Eisenbrand, and H Zankl
Asymmetric formal trans-dihydroxylation and trans-aminohydroxylation of alpha,beta-unsaturated aldehydes via an organocatalytic reaction cascade.
July 2010, Journal of the American Chemical Society,
U Dittberner, and G Eisenbrand, and H Zankl
Biological interactions of alpha,beta-unsaturated aldehydes.
January 1989, Free radical biology & medicine,
U Dittberner, and G Eisenbrand, and H Zankl
Simple and alpha,beta-unsaturated aldehydes: correct prediction of genotoxic activity through structure-activity relationship models.
December 2005, Environmental and molecular mutagenesis,
U Dittberner, and G Eisenbrand, and H Zankl
alpha,beta-unsaturated aldehydes accelerate oxymyoglobin oxidation.
August 1999, Journal of agricultural and food chemistry,
U Dittberner, and G Eisenbrand, and H Zankl
Asymmetric organocatalytic beta-hydroxylation of alpha,beta-unsaturated aldehydes.
February 2007, Journal of the American Chemical Society,
U Dittberner, and G Eisenbrand, and H Zankl
Organocatalytic enantioselective aziridination of alpha,beta-unsaturated aldehydes.
January 2007, Angewandte Chemie (International ed. in English),
U Dittberner, and G Eisenbrand, and H Zankl
Organocatalytic enantioselective aminosulfenylation of alpha,beta-unsaturated aldehydes.
January 2008, Angewandte Chemie (International ed. in English),
Copied contents to your clipboard!