Reactions in Tirapazamine Induced by the Attachment of Low-Energy Electrons: Dissociation Versus Roaming of OH

Detalhes bibliográficos
Autor(a) principal: Arthur-Baidoo, Eugene
Data de Publicação: 2020
Outros Autores: Ameixa, João, Ziegler, Patrick, Ferreira da Silva, Filipe, Ončák, Milan, Denifl, Stephan
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10362/115244
Resumo: Vienna (P30332) PD/BD/114447/2016 PTDC/FIS-AQM/31215/2017 PD/00193/2012 UID/Multi/ 04378/2019 UID/FIS/00068/2019
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spelling Reactions in Tirapazamine Induced by the Attachment of Low-Energy Electrons: Dissociation Versus Roaming of OHdissociative electron attachmentgas-phasehypoxic cytotoxinsradiosensitizerstirapazamineCatalysisChemistry(all)Vienna (P30332) PD/BD/114447/2016 PTDC/FIS-AQM/31215/2017 PD/00193/2012 UID/Multi/ 04378/2019 UID/FIS/00068/2019Tirapazamine (TPZ) has been tested in clinical trials on radio-chemotherapy due to its potential highly selective toxicity towards hypoxic tumor cells. It was suggested that either the hydroxyl radical or benzotriazinyl radical may form as bioactive radical after the initial reduction of TPZ in solution. In the present work, we studied low-energy electron attachment to TPZ in the gas phase and investigated the decomposition of the formed TPZ− anion by mass spectrometry. We observed the formation of the (TPZ–OH)− anion accompanied by the dissociation of the hydroxyl radical as by far the most abundant reaction pathway upon attachment of a low-energy electron. Quantum chemical calculations suggest that NH2 pyramidalization is the key reaction coordinate for the reaction dynamics upon electron attachment. We propose an OH roaming mechanism for other reaction channels observed, in competition with the OH dissociation.CeFITec – Centro de Física e Investigação TecnológicaDF – Departamento de FísicaRUNArthur-Baidoo, EugeneAmeixa, JoãoZiegler, PatrickFerreira da Silva, FilipeOnčák, MilanDenifl, Stephan2021-04-08T22:16:41Z2020-09-212020-09-21T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article5application/pdfhttp://hdl.handle.net/10362/115244eng1433-7851PURE: 19997852https://doi.org/10.1002/anie.202006675info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-03-11T04:57:52Zoai:run.unl.pt:10362/115244Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:42:43.110779Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Reactions in Tirapazamine Induced by the Attachment of Low-Energy Electrons: Dissociation Versus Roaming of OH
title Reactions in Tirapazamine Induced by the Attachment of Low-Energy Electrons: Dissociation Versus Roaming of OH
spellingShingle Reactions in Tirapazamine Induced by the Attachment of Low-Energy Electrons: Dissociation Versus Roaming of OH
Arthur-Baidoo, Eugene
dissociative electron attachment
gas-phase
hypoxic cytotoxins
radiosensitizers
tirapazamine
Catalysis
Chemistry(all)
title_short Reactions in Tirapazamine Induced by the Attachment of Low-Energy Electrons: Dissociation Versus Roaming of OH
title_full Reactions in Tirapazamine Induced by the Attachment of Low-Energy Electrons: Dissociation Versus Roaming of OH
title_fullStr Reactions in Tirapazamine Induced by the Attachment of Low-Energy Electrons: Dissociation Versus Roaming of OH
title_full_unstemmed Reactions in Tirapazamine Induced by the Attachment of Low-Energy Electrons: Dissociation Versus Roaming of OH
title_sort Reactions in Tirapazamine Induced by the Attachment of Low-Energy Electrons: Dissociation Versus Roaming of OH
author Arthur-Baidoo, Eugene
author_facet Arthur-Baidoo, Eugene
Ameixa, João
Ziegler, Patrick
Ferreira da Silva, Filipe
Ončák, Milan
Denifl, Stephan
author_role author
author2 Ameixa, João
Ziegler, Patrick
Ferreira da Silva, Filipe
Ončák, Milan
Denifl, Stephan
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv CeFITec – Centro de Física e Investigação Tecnológica
DF – Departamento de Física
RUN
dc.contributor.author.fl_str_mv Arthur-Baidoo, Eugene
Ameixa, João
Ziegler, Patrick
Ferreira da Silva, Filipe
Ončák, Milan
Denifl, Stephan
dc.subject.por.fl_str_mv dissociative electron attachment
gas-phase
hypoxic cytotoxins
radiosensitizers
tirapazamine
Catalysis
Chemistry(all)
topic dissociative electron attachment
gas-phase
hypoxic cytotoxins
radiosensitizers
tirapazamine
Catalysis
Chemistry(all)
description Vienna (P30332) PD/BD/114447/2016 PTDC/FIS-AQM/31215/2017 PD/00193/2012 UID/Multi/ 04378/2019 UID/FIS/00068/2019
publishDate 2020
dc.date.none.fl_str_mv 2020-09-21
2020-09-21T00:00:00Z
2021-04-08T22:16:41Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10362/115244
url http://hdl.handle.net/10362/115244
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1433-7851
PURE: 19997852
https://doi.org/10.1002/anie.202006675
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 5
application/pdf
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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