Converging fate of the oxidation and reduction of 8-thioguanosine

Autores
Taras Goslinska, Katarzyna; Vetica, Fabrizio; Barata Vallejo, Sebastian; Triantakostanti, Virginia; Marciniak, Bronislaw; Chatgilialoglu, Chryssostomos
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Thione-containing nucleobases have attracted the attention of the scientific community for their application in oncology, virology, and transplantology. The detailed understanding of the reactivity of the purine derivative 8-thioguanosine (8-TG) with reactive oxygen species (ROS) and free radicals is crucial for its biological relevance. An extensive investigation on the fate of 8-TG under both reductive and oxidative conditions is here reported, and it was tested by employing steady-state photooxidation, laser flash photolysis, as well as γ-radiolysis in aqueous solutions. The characterization of the 8-TG T1 excited state by laser flash photolysis and the photooxidation experiments confirmed that singlet oxygen is a crucial intermediate in the formation of the unexpected reduced product guanosine, without the formation of the usual oxygenated sulfinic or sulfonic acids. Furthermore, a thorough screening of different radiolytic conditions upon γ-radiation afforded the reduced product. These results were rationalized by performing control experiments in the predominant presence of each reactive species formed by radiolysis of water, and the mechanistic pathway scenario was postulated on these bases.
Fil: Taras Goslinska, Katarzyna. Adam Mickiewicz University; Polonia
Fil: Vetica, Fabrizio. Consiglio Nazionale delle Ricerche; Italia
Fil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Triantakostanti, Virginia. Consiglio Nazionale delle Ricerche; Italia
Fil: Marciniak, Bronislaw. Adam Mickiewicz University; Polonia
Fil: Chatgilialoglu, Chryssostomos. Consiglio Nazionale delle Ricerche; Italia
Materia
FREE RADICALS
LASER FLASH PHOTOLYSIS
NUCLEOSIDES
PHOTOLYSIS
REACTION MECHANISM
SINGLET OXYGEN
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/155549
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Converging fate of the oxidation and reduction of 8-thioguanosineTaras Goslinska, KatarzynaVetica, FabrizioBarata Vallejo, SebastianTriantakostanti, VirginiaMarciniak, BronislawChatgilialoglu, ChryssostomosFREE RADICALSLASER FLASH PHOTOLYSISNUCLEOSIDESPHOTOLYSISREACTION MECHANISMSINGLET OXYGENhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Thione-containing nucleobases have attracted the attention of the scientific community for their application in oncology, virology, and transplantology. The detailed understanding of the reactivity of the purine derivative 8-thioguanosine (8-TG) with reactive oxygen species (ROS) and free radicals is crucial for its biological relevance. An extensive investigation on the fate of 8-TG under both reductive and oxidative conditions is here reported, and it was tested by employing steady-state photooxidation, laser flash photolysis, as well as γ-radiolysis in aqueous solutions. The characterization of the 8-TG T1 excited state by laser flash photolysis and the photooxidation experiments confirmed that singlet oxygen is a crucial intermediate in the formation of the unexpected reduced product guanosine, without the formation of the usual oxygenated sulfinic or sulfonic acids. Furthermore, a thorough screening of different radiolytic conditions upon γ-radiation afforded the reduced product. These results were rationalized by performing control experiments in the predominant presence of each reactive species formed by radiolysis of water, and the mechanistic pathway scenario was postulated on these bases.Fil: Taras Goslinska, Katarzyna. Adam Mickiewicz University; PoloniaFil: Vetica, Fabrizio. Consiglio Nazionale delle Ricerche; ItaliaFil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Triantakostanti, Virginia. Consiglio Nazionale delle Ricerche; ItaliaFil: Marciniak, Bronislaw. Adam Mickiewicz University; PoloniaFil: Chatgilialoglu, Chryssostomos. Consiglio Nazionale delle Ricerche; ItaliaMolecular Diversity Preservation International2019-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/155549Taras Goslinska, Katarzyna; Vetica, Fabrizio; Barata Vallejo, Sebastian; Triantakostanti, Virginia; Marciniak, Bronislaw; et al.; Converging fate of the oxidation and reduction of 8-thioguanosine; Molecular Diversity Preservation International; Molecules; 24; 17; 8-20191420-3049CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3390/molecules24173143info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/24/17/3143info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:39:29Zoai:ri.conicet.gov.ar:11336/155549instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:39:29.342CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Converging fate of the oxidation and reduction of 8-thioguanosine
title Converging fate of the oxidation and reduction of 8-thioguanosine
spellingShingle Converging fate of the oxidation and reduction of 8-thioguanosine
Taras Goslinska, Katarzyna
FREE RADICALS
LASER FLASH PHOTOLYSIS
NUCLEOSIDES
PHOTOLYSIS
REACTION MECHANISM
SINGLET OXYGEN
title_short Converging fate of the oxidation and reduction of 8-thioguanosine
title_full Converging fate of the oxidation and reduction of 8-thioguanosine
title_fullStr Converging fate of the oxidation and reduction of 8-thioguanosine
title_full_unstemmed Converging fate of the oxidation and reduction of 8-thioguanosine
title_sort Converging fate of the oxidation and reduction of 8-thioguanosine
dc.creator.none.fl_str_mv Taras Goslinska, Katarzyna
Vetica, Fabrizio
Barata Vallejo, Sebastian
Triantakostanti, Virginia
Marciniak, Bronislaw
Chatgilialoglu, Chryssostomos
author Taras Goslinska, Katarzyna
author_facet Taras Goslinska, Katarzyna
Vetica, Fabrizio
Barata Vallejo, Sebastian
Triantakostanti, Virginia
Marciniak, Bronislaw
Chatgilialoglu, Chryssostomos
author_role author
author2 Vetica, Fabrizio
Barata Vallejo, Sebastian
Triantakostanti, Virginia
Marciniak, Bronislaw
Chatgilialoglu, Chryssostomos
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv FREE RADICALS
LASER FLASH PHOTOLYSIS
NUCLEOSIDES
PHOTOLYSIS
REACTION MECHANISM
SINGLET OXYGEN
topic FREE RADICALS
LASER FLASH PHOTOLYSIS
NUCLEOSIDES
PHOTOLYSIS
REACTION MECHANISM
SINGLET OXYGEN
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Thione-containing nucleobases have attracted the attention of the scientific community for their application in oncology, virology, and transplantology. The detailed understanding of the reactivity of the purine derivative 8-thioguanosine (8-TG) with reactive oxygen species (ROS) and free radicals is crucial for its biological relevance. An extensive investigation on the fate of 8-TG under both reductive and oxidative conditions is here reported, and it was tested by employing steady-state photooxidation, laser flash photolysis, as well as γ-radiolysis in aqueous solutions. The characterization of the 8-TG T1 excited state by laser flash photolysis and the photooxidation experiments confirmed that singlet oxygen is a crucial intermediate in the formation of the unexpected reduced product guanosine, without the formation of the usual oxygenated sulfinic or sulfonic acids. Furthermore, a thorough screening of different radiolytic conditions upon γ-radiation afforded the reduced product. These results were rationalized by performing control experiments in the predominant presence of each reactive species formed by radiolysis of water, and the mechanistic pathway scenario was postulated on these bases.
Fil: Taras Goslinska, Katarzyna. Adam Mickiewicz University; Polonia
Fil: Vetica, Fabrizio. Consiglio Nazionale delle Ricerche; Italia
Fil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Triantakostanti, Virginia. Consiglio Nazionale delle Ricerche; Italia
Fil: Marciniak, Bronislaw. Adam Mickiewicz University; Polonia
Fil: Chatgilialoglu, Chryssostomos. Consiglio Nazionale delle Ricerche; Italia
description Thione-containing nucleobases have attracted the attention of the scientific community for their application in oncology, virology, and transplantology. The detailed understanding of the reactivity of the purine derivative 8-thioguanosine (8-TG) with reactive oxygen species (ROS) and free radicals is crucial for its biological relevance. An extensive investigation on the fate of 8-TG under both reductive and oxidative conditions is here reported, and it was tested by employing steady-state photooxidation, laser flash photolysis, as well as γ-radiolysis in aqueous solutions. The characterization of the 8-TG T1 excited state by laser flash photolysis and the photooxidation experiments confirmed that singlet oxygen is a crucial intermediate in the formation of the unexpected reduced product guanosine, without the formation of the usual oxygenated sulfinic or sulfonic acids. Furthermore, a thorough screening of different radiolytic conditions upon γ-radiation afforded the reduced product. These results were rationalized by performing control experiments in the predominant presence of each reactive species formed by radiolysis of water, and the mechanistic pathway scenario was postulated on these bases.
publishDate 2019
dc.date.none.fl_str_mv 2019-08
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/155549
Taras Goslinska, Katarzyna; Vetica, Fabrizio; Barata Vallejo, Sebastian; Triantakostanti, Virginia; Marciniak, Bronislaw; et al.; Converging fate of the oxidation and reduction of 8-thioguanosine; Molecular Diversity Preservation International; Molecules; 24; 17; 8-2019
1420-3049
CONICET Digital
CONICET
url http://hdl.handle.net/11336/155549
identifier_str_mv Taras Goslinska, Katarzyna; Vetica, Fabrizio; Barata Vallejo, Sebastian; Triantakostanti, Virginia; Marciniak, Bronislaw; et al.; Converging fate of the oxidation and reduction of 8-thioguanosine; Molecular Diversity Preservation International; Molecules; 24; 17; 8-2019
1420-3049
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules24173143
info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/24/17/3143
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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