DNA Damage by Endogenous and Exogenous Aldehydes
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019001002000 |
Resumo: | The present overview describes the formation of deoxyribonucleic acid (DNA) adducts from endogenous and exogenous aldehydes, such as acetaldehyde, acrolein, crotonaldehyde, malonaldehyde, 4-hydroxy-2-nonenal and 2,4-decadienal. Malonaldehyde reacts with 2’-deoxyguanosine, 2’-deoxyadenosine, and 2’-deoxycytidine, yielding cyclic pyrimidopurinone and acyclic adducts. The direct addition of ɑ,β-unsaturated aldehydes to DNA bases yields cyclic substituted propano adducts, such as 1,N2-propano-2’-deoxyguanosine. Alternatively, ɑ,β-unsaturated aldehydes can be oxidized to reactive epoxides, giving ethano or etheno derivatives upon reaction with DNA. In addition, information on highly sensitive techniques, employed for the in vivo detection and quantification of DNA-aldehyde adducts, is also provided. Some of these DNA-aldehyde lesions have been shown to be highly mutagenic. In fact, lipid peroxidation and exogenous aldehyde exposure could potentially account for the observed carcinogenicity of urban air pollution and cigarette smoke exposure. |
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DNA Damage by Endogenous and Exogenous AldehydesaldehydesDNA adductsDNA damageThe present overview describes the formation of deoxyribonucleic acid (DNA) adducts from endogenous and exogenous aldehydes, such as acetaldehyde, acrolein, crotonaldehyde, malonaldehyde, 4-hydroxy-2-nonenal and 2,4-decadienal. Malonaldehyde reacts with 2’-deoxyguanosine, 2’-deoxyadenosine, and 2’-deoxycytidine, yielding cyclic pyrimidopurinone and acyclic adducts. The direct addition of ɑ,β-unsaturated aldehydes to DNA bases yields cyclic substituted propano adducts, such as 1,N2-propano-2’-deoxyguanosine. Alternatively, ɑ,β-unsaturated aldehydes can be oxidized to reactive epoxides, giving ethano or etheno derivatives upon reaction with DNA. In addition, information on highly sensitive techniques, employed for the in vivo detection and quantification of DNA-aldehyde adducts, is also provided. Some of these DNA-aldehyde lesions have been shown to be highly mutagenic. In fact, lipid peroxidation and exogenous aldehyde exposure could potentially account for the observed carcinogenicity of urban air pollution and cigarette smoke exposure.Sociedade Brasileira de Química2019-10-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019001002000Journal of the Brazilian Chemical Society v.30 n.10 2019reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20190056info:eu-repo/semantics/openAccessMedeiros,Marisa H. G.eng2019-10-17T00:00:00Zoai:scielo:S0103-50532019001002000Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2019-10-17T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
DNA Damage by Endogenous and Exogenous Aldehydes |
title |
DNA Damage by Endogenous and Exogenous Aldehydes |
spellingShingle |
DNA Damage by Endogenous and Exogenous Aldehydes Medeiros,Marisa H. G. aldehydes DNA adducts DNA damage |
title_short |
DNA Damage by Endogenous and Exogenous Aldehydes |
title_full |
DNA Damage by Endogenous and Exogenous Aldehydes |
title_fullStr |
DNA Damage by Endogenous and Exogenous Aldehydes |
title_full_unstemmed |
DNA Damage by Endogenous and Exogenous Aldehydes |
title_sort |
DNA Damage by Endogenous and Exogenous Aldehydes |
author |
Medeiros,Marisa H. G. |
author_facet |
Medeiros,Marisa H. G. |
author_role |
author |
dc.contributor.author.fl_str_mv |
Medeiros,Marisa H. G. |
dc.subject.por.fl_str_mv |
aldehydes DNA adducts DNA damage |
topic |
aldehydes DNA adducts DNA damage |
description |
The present overview describes the formation of deoxyribonucleic acid (DNA) adducts from endogenous and exogenous aldehydes, such as acetaldehyde, acrolein, crotonaldehyde, malonaldehyde, 4-hydroxy-2-nonenal and 2,4-decadienal. Malonaldehyde reacts with 2’-deoxyguanosine, 2’-deoxyadenosine, and 2’-deoxycytidine, yielding cyclic pyrimidopurinone and acyclic adducts. The direct addition of ɑ,β-unsaturated aldehydes to DNA bases yields cyclic substituted propano adducts, such as 1,N2-propano-2’-deoxyguanosine. Alternatively, ɑ,β-unsaturated aldehydes can be oxidized to reactive epoxides, giving ethano or etheno derivatives upon reaction with DNA. In addition, information on highly sensitive techniques, employed for the in vivo detection and quantification of DNA-aldehyde adducts, is also provided. Some of these DNA-aldehyde lesions have been shown to be highly mutagenic. In fact, lipid peroxidation and exogenous aldehyde exposure could potentially account for the observed carcinogenicity of urban air pollution and cigarette smoke exposure. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-10-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019001002000 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019001002000 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20190056 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.30 n.10 2019 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
_version_ |
1750318182156992512 |