Pterin-Thymidine Adducts: From Their Photochemical Synthesis to Their Photosensitizing Properties

[EN] Pterin (Ptr) is the model compound of aromatic pterins, which are efficient photosensitizers present in human skin and are able to oxidize biomolecules upon UVA irradiation. Photosensitization involves chemical alteration of a biomolecule as a result of the initial absorption of radiation by an...

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Autores: Godoy Ortega, Gricelda, Lorente, Carolina, Thomas, Andrés H., Rodríguez Muñiz, Gemma María|||0000-0001-8989-2401, Lhiaubet, Virginie Lyria|||0000-0002-8205-8892
Tipo de recurso: artículo
Fecha de publicación:2025
País:España
Institución:Universitat Politècnica de València (UPV)
Repositorio:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
Idioma:inglés
OAI Identifier:oai:riunet.upv.es:10251/221729
Acceso en línea:https://riunet.upv.es/handle/10251/221729
Access Level:acceso abierto
Palabra clave:Pterin
UVA irradiation
Thymidine
Anaerobic conditions
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dc.title.none.fl_str_mv Pterin-Thymidine Adducts: From Their Photochemical Synthesis to Their Photosensitizing Properties
title Pterin-Thymidine Adducts: From Their Photochemical Synthesis to Their Photosensitizing Properties
spellingShingle Pterin-Thymidine Adducts: From Their Photochemical Synthesis to Their Photosensitizing Properties
Godoy Ortega, Gricelda
Pterin
UVA irradiation
Thymidine
Anaerobic conditions
title_short Pterin-Thymidine Adducts: From Their Photochemical Synthesis to Their Photosensitizing Properties
title_full Pterin-Thymidine Adducts: From Their Photochemical Synthesis to Their Photosensitizing Properties
title_fullStr Pterin-Thymidine Adducts: From Their Photochemical Synthesis to Their Photosensitizing Properties
title_full_unstemmed Pterin-Thymidine Adducts: From Their Photochemical Synthesis to Their Photosensitizing Properties
title_sort Pterin-Thymidine Adducts: From Their Photochemical Synthesis to Their Photosensitizing Properties
dc.creator.none.fl_str_mv Godoy Ortega, Gricelda
Lorente, Carolina
Thomas, Andrés H.
Rodríguez Muñiz, Gemma María|||0000-0001-8989-2401
Lhiaubet, Virginie Lyria|||0000-0002-8205-8892
author Godoy Ortega, Gricelda
author_facet Godoy Ortega, Gricelda
Lorente, Carolina
Thomas, Andrés H.
Rodríguez Muñiz, Gemma María|||0000-0001-8989-2401
Lhiaubet, Virginie Lyria|||0000-0002-8205-8892
author_role author
author2 Lorente, Carolina
Thomas, Andrés H.
Rodríguez Muñiz, Gemma María|||0000-0001-8989-2401
Lhiaubet, Virginie Lyria|||0000-0002-8205-8892
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Instituto Universitario Mixto de Tecnología Química
Generalitat Valenciana
Agencia Estatal de Investigación
European Regional Development Fund
Universidad Nacional de La Plata, Argentina
Consejo Superior de Investigaciones Científicas
Agencia Nacional de Promoción Científica y Tecnológica, Argentina
Consejo Nacional de Investigaciones Científicas y Técnicas, Argentina
Repositorio Institucional de la Universitat Politècnica de València Riunet
dc.subject.none.fl_str_mv Pterin
UVA irradiation
Thymidine
Anaerobic conditions
topic Pterin
UVA irradiation
Thymidine
Anaerobic conditions
description [EN] Pterin (Ptr) is the model compound of aromatic pterins, which are efficient photosensitizers present in human skin and are able to oxidize biomolecules upon UVA irradiation. Photosensitization involves chemical alteration of a biomolecule as a result of the initial absorption of radiation by another chemical species, the photosensitizer. Under anaerobic conditions, Ptr reacts with thymine (T) to form photoadducts (T-Ptr). In this work, we present a method to prepare and purify T-Ptr adducts, using 2 '-deoxythymidine 5 '-monophosphate (dTMP) and single stranded oligonucleotide 5 '-d(TTTTT)-3 ' (dT5), and investigate their photosensitizing properties. Interestingly, the Ptr moiety, when attached to T, retains its photophysical properties. The adduct dTMP-Ptr, upon excitation, forms singlet and triplet excited states, the latter being capable of transferring energy to dissolved O2 and generating singlet oxygen, with an efficiency similar to Ptr. In air-equilibrated solutions, both dTMP-Ptr and dT5-Ptr adducts can photosensitize the oxidation of tryptophan and 2 '-deoxyguanosine 5 '-monophosphate, two of the main targets of photosensitization in biological systems, with efficiencies close to that of free Ptr. The mechanisms involved in the oxidation of biomolecules can be either type I (electron transfer) or type II (singlet oxygen).
publishDate 2025
dc.date.none.fl_str_mv 2025
2025-04-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://riunet.upv.es/handle/10251/221729
url https://riunet.upv.es/handle/10251/221729
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023 PID2021-128348NB-I00 TRANSFERENCIA DE ENERGIA TRIPLETE-TRIPLETE A LARGA DISTANCIA EN SISTEMAS MODELO DE ADN
Universidad Nacional de La Plata, Argentina https://doi.org/10.13039/501100003947 11%2FX840
Agencia Nacional de Promoción Científica y Tecnológica, Argentina https://doi.org/10.13039/501100003074 PICT 2019-3416
Consejo Nacional de Investigaciones Científicas y Técnicas, Argentina https://doi.org/10.13039/501100002923 P-UE 2017 22920170100100CO
Consejo Nacional de Investigaciones Científicas y Técnicas, Argentina https://doi.org/10.13039/501100002923 GI11220200100877CO
Comisión Sectorial de Investigación Científica, Uruguay https://doi.org/10.13039/501100003339 COOPB22038
Generalitat Valenciana https://doi.org/10.13039/501100003359 CIAICO%2F2021%2F061
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Reserva de todos los derechos
http://rightsstatements.org/vocab/InC/1.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Reserva de todos los derechos
http://rightsstatements.org/vocab/InC/1.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/octet-stream
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
instname:Universitat Politècnica de València (UPV)
instname_str Universitat Politècnica de València (UPV)
reponame_str RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
collection RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
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spelling Pterin-Thymidine Adducts: From Their Photochemical Synthesis to Their Photosensitizing PropertiesGodoy Ortega, GriceldaLorente, CarolinaThomas, Andrés H.Rodríguez Muñiz, Gemma María|||0000-0001-8989-2401Lhiaubet, Virginie Lyria|||0000-0002-8205-8892PterinUVA irradiationThymidineAnaerobic conditions[EN] Pterin (Ptr) is the model compound of aromatic pterins, which are efficient photosensitizers present in human skin and are able to oxidize biomolecules upon UVA irradiation. Photosensitization involves chemical alteration of a biomolecule as a result of the initial absorption of radiation by another chemical species, the photosensitizer. Under anaerobic conditions, Ptr reacts with thymine (T) to form photoadducts (T-Ptr). In this work, we present a method to prepare and purify T-Ptr adducts, using 2 '-deoxythymidine 5 '-monophosphate (dTMP) and single stranded oligonucleotide 5 '-d(TTTTT)-3 ' (dT5), and investigate their photosensitizing properties. Interestingly, the Ptr moiety, when attached to T, retains its photophysical properties. The adduct dTMP-Ptr, upon excitation, forms singlet and triplet excited states, the latter being capable of transferring energy to dissolved O2 and generating singlet oxygen, with an efficiency similar to Ptr. In air-equilibrated solutions, both dTMP-Ptr and dT5-Ptr adducts can photosensitize the oxidation of tryptophan and 2 '-deoxyguanosine 5 '-monophosphate, two of the main targets of photosensitization in biological systems, with efficiencies close to that of free Ptr. The mechanisms involved in the oxidation of biomolecules can be either type I (electron transfer) or type II (singlet oxygen).The present work was partially supported by Consejo Nacional de Investigaciones Cientificas y Tecnicas (CONICET, Grants P-UE 2017 22920170100100CO, Grant PIP 2021-2023 GI 11220200100877CO), Agencia de Promocion de la Investigacion, el Desarrollo Tecnologico y la Innovacion (Agencia I+D+i, Grants PICT 2019-3416), Universidad Nacional de La Plata (UNLP, Grant 11/X840). The authors thank CONICET and CSIC for supporting their collaboration through a Project of International Cooperation (Programme 2023). Also, financial support from CSIC (i-COOP, ref COOPB22038) and the Spanish (project PID2021-128348NB-I00) funded by MCIN/AEI/10.13039/501100011033/and "FEDER a way of making Europe" and regional (CIAICO/2021/061) governments is acknowledged. G.G.-O. thanks CONICET for doctoral research fellowship. Authors thank Jesuan J. Farias for the preparation of the standard of NFKyn. C.L. and A.H.T. are research members of CONICET. V.L.-V. and G.M.R.-M. are research members of CSIC.American Chemical SocietyInstituto Universitario Mixto de Tecnología QuímicaGeneralitat ValencianaAgencia Estatal de InvestigaciónEuropean Regional Development FundUniversidad Nacional de La Plata, ArgentinaConsejo Superior de Investigaciones CientíficasAgencia Nacional de Promoción Científica y Tecnológica, ArgentinaConsejo Nacional de Investigaciones Científicas y Técnicas, ArgentinaRepositorio Institucional de la Universitat Politècnica de València Riunet20252025-04-01journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfapplication/octet-streamhttps://riunet.upv.es/handle/10251/221729reponame:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valénciainstname:Universitat Politècnica de València (UPV)InglésengAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023 PID2021-128348NB-I00 TRANSFERENCIA DE ENERGIA TRIPLETE-TRIPLETE A LARGA DISTANCIA EN SISTEMAS MODELO DE ADNUniversidad Nacional de La Plata, Argentina https://doi.org/10.13039/501100003947 11%2FX840Agencia Nacional de Promoción Científica y Tecnológica, Argentina https://doi.org/10.13039/501100003074 PICT 2019-3416Consejo Nacional de Investigaciones Científicas y Técnicas, Argentina https://doi.org/10.13039/501100002923 P-UE 2017 22920170100100COConsejo Nacional de Investigaciones Científicas y Técnicas, Argentina https://doi.org/10.13039/501100002923 GI11220200100877COComisión Sectorial de Investigación Científica, Uruguay https://doi.org/10.13039/501100003339 COOPB22038Generalitat Valenciana https://doi.org/10.13039/501100003359 CIAICO%2F2021%2F061open accesshttp://purl.org/coar/access_right/c_abf2Reserva de todos los derechoshttp://rightsstatements.org/vocab/InC/1.0/info:eu-repo/semantics/openAccessoai:riunet.upv.es:10251/2217292026-06-13T07:49:27Z
score 15,811543

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