Interaction and photodynamic activity of cationic porphyrin derivatives bearing different patterns of charge distribution with GMP and DNA

Autores
Caminos, Daniel Alberto; Durantini, Edgardo Néstor
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The interaction of amphiphilic cationic porphyrins, containing different patterns of meso-substitution by 4-(3-N,N,N-trimethylammoniumpropoxy)phenyl (A) and 4-(trifluoromethyl)phenyl (B) groups, with guanosine 5′-monophosphate (GMP) and calf thymus DNA have been studied by optical methods in phosphate buffer solution. The properties of these synthetic porphyrins were compared with those of representative standard of anionic 5,10,15,20-tetra(4-sulphonatophenyl)porphyrin (TPPS44−) and cationic 5,10,15,20-tetra(4-N,N,N-trimethylammonium phenyl)porphyrin (TMAP4+). Stable complexes with GMP were found for cationic porphyrins, except for monocationic AB3+. The binding constant (KGMP ∼ 104 M−1) follows the order: A3B3+ ∼ ABAB2+ > A44+ ∼ TMAP4+. Also, interaction with DNA was observed for all evaluated cationic porphyrins. For these related cationic porphyrins, the binding constant (KDNA ∼ 105 M−1) increases with the number of cationic charges. On the other hand, the photodynamic activity of porphyrins was analyzed in solution of GMP and DNA. Monocationic AB3+ is a less effective sensitizer to oxidize GMP in comparison with the other cationic porphyrins, in agreement with the lack of detected interaction with this nucleotide. The electrophoretic analysis of DNA indicates that photocleavage takes place when the samples are exposed to photoexcited tricationic and tetracationic porphyrins. In the presence of sodium azide the DNA decomposition was diminished. Also, reduction in the DNA photocleavage was observed under anoxic condition, indicating that oxygen is essential for DNA photocleavage sensitized by these cationic porphyrins. In addition, an increase in DNA degradation was not observed in deuteriated water. Therefore, an important contribution of type I photoreaction processes could be occurring in the DNA photodamage sensitized by these cationic porphyrins. These results provide a better understanding of the characteristics needed for sensitizers to produce efficient DNA photocleavage.
Fil: Caminos, Daniel Alberto. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Durantini, Edgardo Néstor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Materia
Cationic porphyrin
Photodynamic activity
Photosensitizer
DNA
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/240865
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/240865
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Interaction and photodynamic activity of cationic porphyrin derivatives bearing different patterns of charge distribution with GMP and DNACaminos, Daniel AlbertoDurantini, Edgardo NéstorCationic porphyrinPhotodynamic activityPhotosensitizerDNAhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The interaction of amphiphilic cationic porphyrins, containing different patterns of meso-substitution by 4-(3-N,N,N-trimethylammoniumpropoxy)phenyl (A) and 4-(trifluoromethyl)phenyl (B) groups, with guanosine 5′-monophosphate (GMP) and calf thymus DNA have been studied by optical methods in phosphate buffer solution. The properties of these synthetic porphyrins were compared with those of representative standard of anionic 5,10,15,20-tetra(4-sulphonatophenyl)porphyrin (TPPS44−) and cationic 5,10,15,20-tetra(4-N,N,N-trimethylammonium phenyl)porphyrin (TMAP4+). Stable complexes with GMP were found for cationic porphyrins, except for monocationic AB3+. The binding constant (KGMP ∼ 104 M−1) follows the order: A3B3+ ∼ ABAB2+ > A44+ ∼ TMAP4+. Also, interaction with DNA was observed for all evaluated cationic porphyrins. For these related cationic porphyrins, the binding constant (KDNA ∼ 105 M−1) increases with the number of cationic charges. On the other hand, the photodynamic activity of porphyrins was analyzed in solution of GMP and DNA. Monocationic AB3+ is a less effective sensitizer to oxidize GMP in comparison with the other cationic porphyrins, in agreement with the lack of detected interaction with this nucleotide. The electrophoretic analysis of DNA indicates that photocleavage takes place when the samples are exposed to photoexcited tricationic and tetracationic porphyrins. In the presence of sodium azide the DNA decomposition was diminished. Also, reduction in the DNA photocleavage was observed under anoxic condition, indicating that oxygen is essential for DNA photocleavage sensitized by these cationic porphyrins. In addition, an increase in DNA degradation was not observed in deuteriated water. Therefore, an important contribution of type I photoreaction processes could be occurring in the DNA photodamage sensitized by these cationic porphyrins. These results provide a better understanding of the characteristics needed for sensitizers to produce efficient DNA photocleavage.Fil: Caminos, Daniel Alberto. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Durantini, Edgardo Néstor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaElsevier Science SA2008-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/240865Caminos, Daniel Alberto; Durantini, Edgardo Néstor; Interaction and photodynamic activity of cationic porphyrin derivatives bearing different patterns of charge distribution with GMP and DNA; Elsevier Science SA; Journal of Photochemistry and Photobiology A: Chemistry; 198; 2-3; 8-2008; 274-2811010-6030CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2008.04.005info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1010603008001780info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:21:35Zoai:ri.conicet.gov.ar:11336/240865instacron: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:34982025-10-22 11:21:36.294CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Interaction and photodynamic activity of cationic porphyrin derivatives bearing different patterns of charge distribution with GMP and DNA
title Interaction and photodynamic activity of cationic porphyrin derivatives bearing different patterns of charge distribution with GMP and DNA
spellingShingle Interaction and photodynamic activity of cationic porphyrin derivatives bearing different patterns of charge distribution with GMP and DNA
Caminos, Daniel Alberto
Cationic porphyrin
Photodynamic activity
Photosensitizer
DNA
title_short Interaction and photodynamic activity of cationic porphyrin derivatives bearing different patterns of charge distribution with GMP and DNA
title_full Interaction and photodynamic activity of cationic porphyrin derivatives bearing different patterns of charge distribution with GMP and DNA
title_fullStr Interaction and photodynamic activity of cationic porphyrin derivatives bearing different patterns of charge distribution with GMP and DNA
title_full_unstemmed Interaction and photodynamic activity of cationic porphyrin derivatives bearing different patterns of charge distribution with GMP and DNA
title_sort Interaction and photodynamic activity of cationic porphyrin derivatives bearing different patterns of charge distribution with GMP and DNA
dc.creator.none.fl_str_mv Caminos, Daniel Alberto
Durantini, Edgardo Néstor
author Caminos, Daniel Alberto
author_facet Caminos, Daniel Alberto
Durantini, Edgardo Néstor
author_role author
author2 Durantini, Edgardo Néstor
author2_role author
dc.subject.none.fl_str_mv Cationic porphyrin
Photodynamic activity
Photosensitizer
DNA
topic Cationic porphyrin
Photodynamic activity
Photosensitizer
DNA
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The interaction of amphiphilic cationic porphyrins, containing different patterns of meso-substitution by 4-(3-N,N,N-trimethylammoniumpropoxy)phenyl (A) and 4-(trifluoromethyl)phenyl (B) groups, with guanosine 5′-monophosphate (GMP) and calf thymus DNA have been studied by optical methods in phosphate buffer solution. The properties of these synthetic porphyrins were compared with those of representative standard of anionic 5,10,15,20-tetra(4-sulphonatophenyl)porphyrin (TPPS44−) and cationic 5,10,15,20-tetra(4-N,N,N-trimethylammonium phenyl)porphyrin (TMAP4+). Stable complexes with GMP were found for cationic porphyrins, except for monocationic AB3+. The binding constant (KGMP ∼ 104 M−1) follows the order: A3B3+ ∼ ABAB2+ > A44+ ∼ TMAP4+. Also, interaction with DNA was observed for all evaluated cationic porphyrins. For these related cationic porphyrins, the binding constant (KDNA ∼ 105 M−1) increases with the number of cationic charges. On the other hand, the photodynamic activity of porphyrins was analyzed in solution of GMP and DNA. Monocationic AB3+ is a less effective sensitizer to oxidize GMP in comparison with the other cationic porphyrins, in agreement with the lack of detected interaction with this nucleotide. The electrophoretic analysis of DNA indicates that photocleavage takes place when the samples are exposed to photoexcited tricationic and tetracationic porphyrins. In the presence of sodium azide the DNA decomposition was diminished. Also, reduction in the DNA photocleavage was observed under anoxic condition, indicating that oxygen is essential for DNA photocleavage sensitized by these cationic porphyrins. In addition, an increase in DNA degradation was not observed in deuteriated water. Therefore, an important contribution of type I photoreaction processes could be occurring in the DNA photodamage sensitized by these cationic porphyrins. These results provide a better understanding of the characteristics needed for sensitizers to produce efficient DNA photocleavage.
Fil: Caminos, Daniel Alberto. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Durantini, Edgardo Néstor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
description The interaction of amphiphilic cationic porphyrins, containing different patterns of meso-substitution by 4-(3-N,N,N-trimethylammoniumpropoxy)phenyl (A) and 4-(trifluoromethyl)phenyl (B) groups, with guanosine 5′-monophosphate (GMP) and calf thymus DNA have been studied by optical methods in phosphate buffer solution. The properties of these synthetic porphyrins were compared with those of representative standard of anionic 5,10,15,20-tetra(4-sulphonatophenyl)porphyrin (TPPS44−) and cationic 5,10,15,20-tetra(4-N,N,N-trimethylammonium phenyl)porphyrin (TMAP4+). Stable complexes with GMP were found for cationic porphyrins, except for monocationic AB3+. The binding constant (KGMP ∼ 104 M−1) follows the order: A3B3+ ∼ ABAB2+ > A44+ ∼ TMAP4+. Also, interaction with DNA was observed for all evaluated cationic porphyrins. For these related cationic porphyrins, the binding constant (KDNA ∼ 105 M−1) increases with the number of cationic charges. On the other hand, the photodynamic activity of porphyrins was analyzed in solution of GMP and DNA. Monocationic AB3+ is a less effective sensitizer to oxidize GMP in comparison with the other cationic porphyrins, in agreement with the lack of detected interaction with this nucleotide. The electrophoretic analysis of DNA indicates that photocleavage takes place when the samples are exposed to photoexcited tricationic and tetracationic porphyrins. In the presence of sodium azide the DNA decomposition was diminished. Also, reduction in the DNA photocleavage was observed under anoxic condition, indicating that oxygen is essential for DNA photocleavage sensitized by these cationic porphyrins. In addition, an increase in DNA degradation was not observed in deuteriated water. Therefore, an important contribution of type I photoreaction processes could be occurring in the DNA photodamage sensitized by these cationic porphyrins. These results provide a better understanding of the characteristics needed for sensitizers to produce efficient DNA photocleavage.
publishDate 2008
dc.date.none.fl_str_mv 2008-08
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/11336/240865
Caminos, Daniel Alberto; Durantini, Edgardo Néstor; Interaction and photodynamic activity of cationic porphyrin derivatives bearing different patterns of charge distribution with GMP and DNA; Elsevier Science SA; Journal of Photochemistry and Photobiology A: Chemistry; 198; 2-3; 8-2008; 274-281
1010-6030
CONICET Digital
CONICET
url http://hdl.handle.net/11336/240865
identifier_str_mv Caminos, Daniel Alberto; Durantini, Edgardo Néstor; Interaction and photodynamic activity of cationic porphyrin derivatives bearing different patterns of charge distribution with GMP and DNA; Elsevier Science SA; Journal of Photochemistry and Photobiology A: Chemistry; 198; 2-3; 8-2008; 274-281
1010-6030
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2008.04.005
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1010603008001780
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science SA
publisher.none.fl_str_mv Elsevier Science SA
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 12.982451

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