Site-specific synthesis and reactivity of oligonucleotides containing stereochemically defined 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal.
Identifieur interne : 002454 ( PubMed/Corpus ); précédent : 002453; suivant : 002455Site-specific synthesis and reactivity of oligonucleotides containing stereochemically defined 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal.
Auteurs : Hao Wang ; Ivan D. Kozekov ; Thomas M. Harris ; Carmelo J. RizzoSource :
- Journal of the American Chemical Society [ 0002-7863 ] ; 2003.
English descriptors
- KwdEn :
- Aldehydes (chemistry), Binding Sites, Circular Dichroism, DNA (chemistry), DNA Adducts (chemical synthesis), DNA Adducts (chemistry), Deoxyguanosine (analogs & derivatives), Deoxyguanosine (chemistry), Lipid Peroxidation, Nuclear Magnetic Resonance, Biomolecular, Oligonucleotides (chemical synthesis), Oligonucleotides (chemistry), Stereoisomerism, Substrate Specificity.
- MESH :
- chemical , analogs & derivatives : Deoxyguanosine.
- chemical , chemical synthesis : DNA Adducts, Oligonucleotides.
- chemical , chemistry : Aldehydes, DNA, DNA Adducts, Deoxyguanosine, Oligonucleotides.
- Binding Sites, Circular Dichroism, Lipid Peroxidation, Nuclear Magnetic Resonance, Biomolecular, Stereoisomerism, Substrate Specificity.
Abstract
trans-4-Hydroxynonenal (HNE) is a major peroxidation product of omega-6 polyunsaturated fatty acids. The reaction of HNE with DNA gives four diastereomeric 1,N(2)-gamma-hydroxypropano adducts of deoxyguanosine; background levels of these adducts have been detected in animal tissue. Stereospecific syntheses of these four adducts at the nucleoside level have been accomplished. In addition, a versatile strategy for their site-specific incorporation into oligonucleotides has been developed. These adducts are destabilizing as measured by melting temperature when compared to an unadducted strand. The thermal destablization of the adducted 12-mers ranged from 5 to 16 degrees C and is dependent on the absolute stereochemistry of the adduct. The HNE adducts were also examined for their ability to form interstrand DNA-DNA cross-links when incorporated into a CpG sequence. We find that only one of the HNE stereoisomers formed interstrand DNA-DNA cross-links.
DOI: 10.1021/ja0288800
PubMed: 12733907
Links to Exploration step
pubmed:12733907Le document en format XML
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<author><name sortKey="Wang, Hao" sort="Wang, Hao" uniqKey="Wang H" first="Hao" last="Wang">Hao Wang</name>
<affiliation><nlm:affiliation>Department of Chemistry and Center in Molecular Toxicology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA.</nlm:affiliation>
</affiliation>
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<author><name sortKey="Kozekov, Ivan D" sort="Kozekov, Ivan D" uniqKey="Kozekov I" first="Ivan D" last="Kozekov">Ivan D. Kozekov</name>
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<author><name sortKey="Harris, Thomas M" sort="Harris, Thomas M" uniqKey="Harris T" first="Thomas M" last="Harris">Thomas M. Harris</name>
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<author><name sortKey="Rizzo, Carmelo J" sort="Rizzo, Carmelo J" uniqKey="Rizzo C" first="Carmelo J" last="Rizzo">Carmelo J. Rizzo</name>
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<author><name sortKey="Wang, Hao" sort="Wang, Hao" uniqKey="Wang H" first="Hao" last="Wang">Hao Wang</name>
<affiliation><nlm:affiliation>Department of Chemistry and Center in Molecular Toxicology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA.</nlm:affiliation>
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<term>Binding Sites</term>
<term>Circular Dichroism</term>
<term>DNA (chemistry)</term>
<term>DNA Adducts (chemical synthesis)</term>
<term>DNA Adducts (chemistry)</term>
<term>Deoxyguanosine (analogs & derivatives)</term>
<term>Deoxyguanosine (chemistry)</term>
<term>Lipid Peroxidation</term>
<term>Nuclear Magnetic Resonance, Biomolecular</term>
<term>Oligonucleotides (chemical synthesis)</term>
<term>Oligonucleotides (chemistry)</term>
<term>Stereoisomerism</term>
<term>Substrate Specificity</term>
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<term>Deoxyguanosine</term>
<term>Oligonucleotides</term>
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<term>Circular Dichroism</term>
<term>Lipid Peroxidation</term>
<term>Nuclear Magnetic Resonance, Biomolecular</term>
<term>Stereoisomerism</term>
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<front><div type="abstract" xml:lang="en">trans-4-Hydroxynonenal (HNE) is a major peroxidation product of omega-6 polyunsaturated fatty acids. The reaction of HNE with DNA gives four diastereomeric 1,N(2)-gamma-hydroxypropano adducts of deoxyguanosine; background levels of these adducts have been detected in animal tissue. Stereospecific syntheses of these four adducts at the nucleoside level have been accomplished. In addition, a versatile strategy for their site-specific incorporation into oligonucleotides has been developed. These adducts are destabilizing as measured by melting temperature when compared to an unadducted strand. The thermal destablization of the adducted 12-mers ranged from 5 to 16 degrees C and is dependent on the absolute stereochemistry of the adduct. The HNE adducts were also examined for their ability to form interstrand DNA-DNA cross-links when incorporated into a CpG sequence. We find that only one of the HNE stereoisomers formed interstrand DNA-DNA cross-links.</div>
</front>
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<Abstract><AbstractText>trans-4-Hydroxynonenal (HNE) is a major peroxidation product of omega-6 polyunsaturated fatty acids. The reaction of HNE with DNA gives four diastereomeric 1,N(2)-gamma-hydroxypropano adducts of deoxyguanosine; background levels of these adducts have been detected in animal tissue. Stereospecific syntheses of these four adducts at the nucleoside level have been accomplished. In addition, a versatile strategy for their site-specific incorporation into oligonucleotides has been developed. These adducts are destabilizing as measured by melting temperature when compared to an unadducted strand. The thermal destablization of the adducted 12-mers ranged from 5 to 16 degrees C and is dependent on the absolute stereochemistry of the adduct. The HNE adducts were also examined for their ability to form interstrand DNA-DNA cross-links when incorporated into a CpG sequence. We find that only one of the HNE stereoisomers formed interstrand DNA-DNA cross-links.</AbstractText>
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