Reactions in Nitroimidazole and Methylnitroimidazole Triggered by Low-Energy (0-8 eV) Electrons.
Identifieur interne : 002629 ( Ncbi/Merge ); précédent : 002628; suivant : 002630Reactions in Nitroimidazole and Methylnitroimidazole Triggered by Low-Energy (0-8 eV) Electrons.
Auteurs : Katrin Tanzer [Autriche] ; Linda Feketeová [France] ; Benjamin Puschnigg [Autriche] ; Paul Scheier [Autriche] ; Eugen Illenberger [Allemagne] ; Stephan Denifl [Autriche]Source :
- The journal of physical chemistry. A [ 1520-5215 ] ; 2015.
Descripteurs français
- KwdFr :
- MESH :
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Anions, Hydrogen, Hydroxyl Radical, Nitroimidazoles, Radiation-Sensitizing Agents.
- Electrons, Molecular Structure, Spectrum Analysis.
Abstract
Low-energy electrons (0-8 eV) effectively decompose 4-nitroimidazole (4NI) and the two methylated isomers 1-methyl-5-nitroimidazole and 1-methyl-4-nitroimidazole via dissociative electron attachment (DEA). The involved unimolecular decompositions range from simple bond cleavages (loss of H(•), formation of NO2(-)) to complex reactions possibly leading to a complete degradation of the target molecule (formation of CN(-), etc.). At energies below 2 eV, the entire rich chemistry induced by DEA is completely quenched by methylation, as demonstrated in a previous communication (Tanzer, K.; Feketeová, L.; Puschnigg, B.; Scheier, P.; Illenberger. E.; Denifl, S. Angew. Chem., Int. Ed. 2014, 53, 12240). The observation that in 4NI neutral radicals and radical anions are formed via DEA at high efficiency already at threshold (0 eV) may have significant implications for the development of nitroimidazole-based radiosensitizers in tumor radiation therapy.
DOI: 10.1021/acs.jpca.5b02721
PubMed: 26020684
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uniqKey="Feketeova L" first="Linda" last="Feketeová">Linda Feketeová</name><affiliation wicri:level="1"><nlm:affiliation>‡Université de Lyon; Université Claude Bernard Lyon1; Institut de Physique Nucléaire de Lyon, CNRS/IN2P3 UMR 5822, 43 Bd du 11 novembre 1918, 69622 Villeurbanne Cedex, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>‡Université de Lyon; Université Claude Bernard Lyon1; Institut de Physique Nucléaire de Lyon, CNRS/IN2P3 UMR 5822, 43 Bd du 11 novembre 1918, 69622 Villeurbanne Cedex</wicri:regionArea><wicri:noRegion>69622 Villeurbanne Cedex</wicri:noRegion><wicri:noRegion>69622 Villeurbanne Cedex</wicri:noRegion></affiliation></author><author><name sortKey="Puschnigg, Benjamin" sort="Puschnigg, Benjamin" uniqKey="Puschnigg B" first="Benjamin" last="Puschnigg">Benjamin Puschnigg</name><affiliation wicri:level="1"><nlm:affiliation>†Institut für Ionenphysik und Angewandte Physik and Center of Molecular Biosciences, Leopold Franzens Universität Innsbruck, Technikerstrasse 25, 6020 Innsbruck, Austria.</nlm:affiliation><country xml:lang="fr">Autriche</country><wicri:regionArea>†Institut für Ionenphysik und Angewandte Physik and Center of Molecular Biosciences, Leopold Franzens Universität Innsbruck, Technikerstrasse 25, 6020 Innsbruck</wicri:regionArea><wicri:noRegion>6020 Innsbruck</wicri:noRegion></affiliation></author><author><name sortKey="Scheier, Paul" sort="Scheier, Paul" uniqKey="Scheier P" first="Paul" last="Scheier">Paul Scheier</name><affiliation wicri:level="1"><nlm:affiliation>†Institut für Ionenphysik und Angewandte Physik and Center of Molecular Biosciences, Leopold Franzens Universität Innsbruck, Technikerstrasse 25, 6020 Innsbruck, Austria.</nlm:affiliation><country xml:lang="fr">Autriche</country><wicri:regionArea>†Institut für Ionenphysik und Angewandte Physik and Center of Molecular Biosciences, Leopold Franzens Universität Innsbruck, Technikerstrasse 25, 6020 Innsbruck</wicri:regionArea><wicri:noRegion>6020 Innsbruck</wicri:noRegion></affiliation></author><author><name sortKey="Illenberger, Eugen" sort="Illenberger, Eugen" uniqKey="Illenberger E" first="Eugen" last="Illenberger">Eugen Illenberger</name><affiliation wicri:level="3"><nlm:affiliation>∥Institut für Chemie und Biochemie-Physikalische und Theoretische Chemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany.</nlm:affiliation><country xml:lang="fr">Allemagne</country><wicri:regionArea>∥Institut für Chemie und Biochemie-Physikalische und Theoretische Chemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin</wicri:regionArea><placeName><region type="land" nuts="3">Berlin</region><settlement type="city">Berlin</settlement></placeName></affiliation></author><author><name sortKey="Denifl, Stephan" sort="Denifl, Stephan" uniqKey="Denifl S" first="Stephan" last="Denifl">Stephan Denifl</name><affiliation wicri:level="1"><nlm:affiliation>†Institut für Ionenphysik und Angewandte Physik and Center of Molecular Biosciences, Leopold Franzens Universität Innsbruck, Technikerstrasse 25, 6020 Innsbruck, Austria.</nlm:affiliation><country xml:lang="fr">Autriche</country><wicri:regionArea>†Institut für Ionenphysik und Angewandte Physik and Center of Molecular Biosciences, Leopold Franzens Universität Innsbruck, Technikerstrasse 25, 6020 Innsbruck</wicri:regionArea><wicri:noRegion>6020 Innsbruck</wicri:noRegion></affiliation></author></analytic><series><title level="j">The journal of physical chemistry. A</title><idno type="eISSN">1520-5215</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Anions (chemistry)</term><term>Electrons</term><term>Hydrogen (chemistry)</term><term>Hydroxyl Radical (chemistry)</term><term>Molecular Structure</term><term>Nitroimidazoles (chemistry)</term><term>Radiation-Sensitizing Agents (chemistry)</term><term>Spectrum Analysis</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Analyse spectrale</term><term>Anions ()</term><term>Hydrogène ()</term><term>Nitroimidazoles ()</term><term>Radical hydroxyle ()</term><term>Radiosensibilisants ()</term><term>Structure moléculaire</term><term>Électrons</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Anions</term><term>Hydrogen</term><term>Hydroxyl Radical</term><term>Nitroimidazoles</term><term>Radiation-Sensitizing Agents</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Electrons</term><term>Molecular Structure</term><term>Spectrum Analysis</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Analyse spectrale</term><term>Anions</term><term>Hydrogène</term><term>Nitroimidazoles</term><term>Radical hydroxyle</term><term>Radiosensibilisants</term><term>Structure moléculaire</term><term>Électrons</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Low-energy electrons (0-8 eV) effectively decompose 4-nitroimidazole (4NI) and the two methylated isomers 1-methyl-5-nitroimidazole and 1-methyl-4-nitroimidazole via dissociative electron attachment (DEA). The involved unimolecular decompositions range from simple bond cleavages (loss of H(•), formation of NO2(-)) to complex reactions possibly leading to a complete degradation of the target molecule (formation of CN(-), etc.). At energies below 2 eV, the entire rich chemistry induced by DEA is completely quenched by methylation, as demonstrated in a previous communication (Tanzer, K.; Feketeová, L.; Puschnigg, B.; Scheier, P.; Illenberger. E.; Denifl, S. Angew. Chem., Int. Ed. 2014, 53, 12240). The observation that in 4NI neutral radicals and radical anions are formed via DEA at high efficiency already at threshold (0 eV) may have significant implications for the development of nitroimidazole-based radiosensitizers in tumor radiation therapy.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">26020684</PMID><DateCreated><Year>2015</Year><Month>06</Month><Day>25</Day></DateCreated><DateCompleted><Year>2016</Year><Month>03</Month><Day>21</Day></DateCompleted><DateRevised><Year>2015</Year><Month>06</Month><Day>25</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-5215</ISSN><JournalIssue CitedMedium="Internet"><Volume>119</Volume><Issue>25</Issue><PubDate><Year>2015</Year><Month>Jun</Month><Day>25</Day></PubDate></JournalIssue><Title>The journal of physical chemistry. A</Title><ISOAbbreviation>J Phys Chem A</ISOAbbreviation></Journal><ArticleTitle>Reactions in Nitroimidazole and Methylnitroimidazole Triggered by Low-Energy (0-8 eV) Electrons.</ArticleTitle><Pagination><MedlinePgn>6668-75</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/acs.jpca.5b02721</ELocationID><Abstract><AbstractText>Low-energy electrons (0-8 eV) effectively decompose 4-nitroimidazole (4NI) and the two methylated isomers 1-methyl-5-nitroimidazole and 1-methyl-4-nitroimidazole via dissociative electron attachment (DEA). The involved unimolecular decompositions range from simple bond cleavages (loss of H(•), formation of NO2(-)) to complex reactions possibly leading to a complete degradation of the target molecule (formation of CN(-), etc.). At energies below 2 eV, the entire rich chemistry induced by DEA is completely quenched by methylation, as demonstrated in a previous communication (Tanzer, K.; Feketeová, L.; Puschnigg, B.; Scheier, P.; Illenberger. E.; Denifl, S. Angew. Chem., Int. Ed. 2014, 53, 12240). The observation that in 4NI neutral radicals and radical anions are formed via DEA at high efficiency already at threshold (0 eV) may have significant implications for the development of nitroimidazole-based radiosensitizers in tumor radiation therapy.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Tanzer</LastName><ForeName>Katrin</ForeName><Initials>K</Initials><AffiliationInfo><Affiliation>†Institut für Ionenphysik und Angewandte Physik and Center of Molecular Biosciences, Leopold Franzens Universität Innsbruck, Technikerstrasse 25, 6020 Innsbruck, Austria.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Feketeová</LastName><ForeName>Linda</ForeName><Initials>L</Initials><AffiliationInfo><Affiliation>‡Université de Lyon; Université Claude Bernard Lyon1; Institut de Physique Nucléaire de Lyon, CNRS/IN2P3 UMR 5822, 43 Bd du 11 novembre 1918, 69622 Villeurbanne Cedex, France.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>§ARC Centre of Excellence for Free Radical Chemistry and Biotechnology, School of Chemistry and Bio21 Institute of Molecular Science and Biotechnology, The University of Melbourne, 30 Flemington Road, Victoria 3010, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Puschnigg</LastName><ForeName>Benjamin</ForeName><Initials>B</Initials><AffiliationInfo><Affiliation>†Institut für Ionenphysik und Angewandte Physik and Center of Molecular Biosciences, Leopold Franzens Universität Innsbruck, Technikerstrasse 25, 6020 Innsbruck, Austria.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Scheier</LastName><ForeName>Paul</ForeName><Initials>P</Initials><AffiliationInfo><Affiliation>†Institut für Ionenphysik und Angewandte Physik and Center of Molecular Biosciences, Leopold Franzens Universität Innsbruck, Technikerstrasse 25, 6020 Innsbruck, Austria.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Illenberger</LastName><ForeName>Eugen</ForeName><Initials>E</Initials><AffiliationInfo><Affiliation>∥Institut für Chemie und Biochemie-Physikalische und Theoretische Chemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Denifl</LastName><ForeName>Stephan</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>†Institut für Ionenphysik und Angewandte Physik and Center of Molecular Biosciences, Leopold Franzens Universität Innsbruck, Technikerstrasse 25, 6020 Innsbruck, Austria.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate 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Feketeová</name></noRegion></country><country name="Allemagne"><region name="Berlin"><name sortKey="Illenberger, Eugen" sort="Illenberger, Eugen" uniqKey="Illenberger E" first="Eugen" last="Illenberger">Eugen Illenberger</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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