Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups

Autores
Cormick, Maria Paula; Rovera, Marisa; Durantini, Edgardo Néstor
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A novel Zn(II) phthalocyanine derivative (ZnPcF) bearing four antifungal structures of fluconazole was synthesized by a two-step procedure starting from 4-nitrophthalonitrile. First, phthalonitrile-azole derivative was prepared by a nucleophilic ipso-nitro substitution reaction between 4-nitrophthalonitrile and fluconazole. The cyclotetramerization of phthalonitrile-azole with Zn(II) acetate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) results in the formation of the ZnPcF as a mixtures of constitutional isomers with 27% yield. Absorption and fluorescence spectroscopic studies were analyzed in different media. The results show that ZnPcF is lowly soluble in polar solvents or in reverse micellar systems. However, addition of HCl produce an increase in the monomerization of ZnPcF in N,N-dimethylformamide (DMF)/water (10% v/v) and in benzene/benzyl-n-hexadecyldimethyl ammonium chloride (BHDC, 0.1 M)/water (W0=10). A value of 0.19 was calculated for the fluorescence quantum yield (fF) of this photosensitizer in DMF/water (10%)/HCl 1.2 mM. The photodynamic activity of ZnPcF was evaluated using 9,10-dimethylanthracene (DMA). An enhancement in the singlet molecular oxygen, O2(1Dg), production was obtained in acidified DMF/water or BHDC micellar system, which represent an appropriate system to induce monomerization of ZnPcF. Preliminary studies to evaluate the photodynamic activity of ZnPcF were tested against a typical yeast Candida albicans. These results indicated that ZnPcF is an interesting antifungal agent because it has antimycotic activity in dark and its efficiency increases in the presence of light due to the photodynamic inactivation caused by the photosensitizer moiety.
Fil: Cormick, Maria Paula. 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; Argentina
Fil: Rovera, Marisa. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; Argentina
Fil: Durantini, Edgardo Néstor. 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; Argentina
Materia
Phthalocyanine
Floconazole
Photodynamic inactivation
Yeast
Candida albicans
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/242103
Acceder
id CONICETDig_7a9082d1ca52572e348de537d62f98fa
oai_identifier_str oai:ri.conicet.gov.ar:11336/242103
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groupsCormick, Maria PaulaRovera, MarisaDurantini, Edgardo NéstorPhthalocyanineFloconazolePhotodynamic inactivationYeastCandida albicanshttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1A novel Zn(II) phthalocyanine derivative (ZnPcF) bearing four antifungal structures of fluconazole was synthesized by a two-step procedure starting from 4-nitrophthalonitrile. First, phthalonitrile-azole derivative was prepared by a nucleophilic ipso-nitro substitution reaction between 4-nitrophthalonitrile and fluconazole. The cyclotetramerization of phthalonitrile-azole with Zn(II) acetate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) results in the formation of the ZnPcF as a mixtures of constitutional isomers with 27% yield. Absorption and fluorescence spectroscopic studies were analyzed in different media. The results show that ZnPcF is lowly soluble in polar solvents or in reverse micellar systems. However, addition of HCl produce an increase in the monomerization of ZnPcF in N,N-dimethylformamide (DMF)/water (10% v/v) and in benzene/benzyl-n-hexadecyldimethyl ammonium chloride (BHDC, 0.1 M)/water (W0=10). A value of 0.19 was calculated for the fluorescence quantum yield (fF) of this photosensitizer in DMF/water (10%)/HCl 1.2 mM. The photodynamic activity of ZnPcF was evaluated using 9,10-dimethylanthracene (DMA). An enhancement in the singlet molecular oxygen, O2(1Dg), production was obtained in acidified DMF/water or BHDC micellar system, which represent an appropriate system to induce monomerization of ZnPcF. Preliminary studies to evaluate the photodynamic activity of ZnPcF were tested against a typical yeast Candida albicans. These results indicated that ZnPcF is an interesting antifungal agent because it has antimycotic activity in dark and its efficiency increases in the presence of light due to the photodynamic inactivation caused by the photosensitizer moiety.Fil: Cormick, Maria Paula. 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; ArgentinaFil: Rovera, Marisa. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; ArgentinaFil: Durantini, Edgardo Néstor. 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; ArgentinaElsevier Science SA2008-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/242103Cormick, Maria Paula; Rovera, Marisa; Durantini, Edgardo Néstor; Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups; Elsevier Science SA; Journal of Photochemistry and Photobiology A: Chemistry; 194; 2-3; 2-2008; 220-2291010-6030CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1010603007004297info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2007.08.013info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:46:32Zoai:ri.conicet.gov.ar:11336/242103instacron: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:34982025-09-03 09:46:32.731CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups
title Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups
spellingShingle Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups
Cormick, Maria Paula
Phthalocyanine
Floconazole
Photodynamic inactivation
Yeast
Candida albicans
title_short Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups
title_full Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups
title_fullStr Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups
title_full_unstemmed Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups
title_sort Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups
dc.creator.none.fl_str_mv Cormick, Maria Paula
Rovera, Marisa
Durantini, Edgardo Néstor
author Cormick, Maria Paula
author_facet Cormick, Maria Paula
Rovera, Marisa
Durantini, Edgardo Néstor
author_role author
author2 Rovera, Marisa
Durantini, Edgardo Néstor
author2_role author
author
dc.subject.none.fl_str_mv Phthalocyanine
Floconazole
Photodynamic inactivation
Yeast
Candida albicans
topic Phthalocyanine
Floconazole
Photodynamic inactivation
Yeast
Candida albicans
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A novel Zn(II) phthalocyanine derivative (ZnPcF) bearing four antifungal structures of fluconazole was synthesized by a two-step procedure starting from 4-nitrophthalonitrile. First, phthalonitrile-azole derivative was prepared by a nucleophilic ipso-nitro substitution reaction between 4-nitrophthalonitrile and fluconazole. The cyclotetramerization of phthalonitrile-azole with Zn(II) acetate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) results in the formation of the ZnPcF as a mixtures of constitutional isomers with 27% yield. Absorption and fluorescence spectroscopic studies were analyzed in different media. The results show that ZnPcF is lowly soluble in polar solvents or in reverse micellar systems. However, addition of HCl produce an increase in the monomerization of ZnPcF in N,N-dimethylformamide (DMF)/water (10% v/v) and in benzene/benzyl-n-hexadecyldimethyl ammonium chloride (BHDC, 0.1 M)/water (W0=10). A value of 0.19 was calculated for the fluorescence quantum yield (fF) of this photosensitizer in DMF/water (10%)/HCl 1.2 mM. The photodynamic activity of ZnPcF was evaluated using 9,10-dimethylanthracene (DMA). An enhancement in the singlet molecular oxygen, O2(1Dg), production was obtained in acidified DMF/water or BHDC micellar system, which represent an appropriate system to induce monomerization of ZnPcF. Preliminary studies to evaluate the photodynamic activity of ZnPcF were tested against a typical yeast Candida albicans. These results indicated that ZnPcF is an interesting antifungal agent because it has antimycotic activity in dark and its efficiency increases in the presence of light due to the photodynamic inactivation caused by the photosensitizer moiety.
Fil: Cormick, Maria Paula. 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; Argentina
Fil: Rovera, Marisa. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; Argentina
Fil: Durantini, Edgardo Néstor. 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; Argentina
description A novel Zn(II) phthalocyanine derivative (ZnPcF) bearing four antifungal structures of fluconazole was synthesized by a two-step procedure starting from 4-nitrophthalonitrile. First, phthalonitrile-azole derivative was prepared by a nucleophilic ipso-nitro substitution reaction between 4-nitrophthalonitrile and fluconazole. The cyclotetramerization of phthalonitrile-azole with Zn(II) acetate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) results in the formation of the ZnPcF as a mixtures of constitutional isomers with 27% yield. Absorption and fluorescence spectroscopic studies were analyzed in different media. The results show that ZnPcF is lowly soluble in polar solvents or in reverse micellar systems. However, addition of HCl produce an increase in the monomerization of ZnPcF in N,N-dimethylformamide (DMF)/water (10% v/v) and in benzene/benzyl-n-hexadecyldimethyl ammonium chloride (BHDC, 0.1 M)/water (W0=10). A value of 0.19 was calculated for the fluorescence quantum yield (fF) of this photosensitizer in DMF/water (10%)/HCl 1.2 mM. The photodynamic activity of ZnPcF was evaluated using 9,10-dimethylanthracene (DMA). An enhancement in the singlet molecular oxygen, O2(1Dg), production was obtained in acidified DMF/water or BHDC micellar system, which represent an appropriate system to induce monomerization of ZnPcF. Preliminary studies to evaluate the photodynamic activity of ZnPcF were tested against a typical yeast Candida albicans. These results indicated that ZnPcF is an interesting antifungal agent because it has antimycotic activity in dark and its efficiency increases in the presence of light due to the photodynamic inactivation caused by the photosensitizer moiety.
publishDate 2008
dc.date.none.fl_str_mv 2008-02
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/11336/242103
Cormick, Maria Paula; Rovera, Marisa; Durantini, Edgardo Néstor; Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups; Elsevier Science SA; Journal of Photochemistry and Photobiology A: Chemistry; 194; 2-3; 2-2008; 220-229
1010-6030
CONICET Digital
CONICET
url http://hdl.handle.net/11336/242103
identifier_str_mv Cormick, Maria Paula; Rovera, Marisa; Durantini, Edgardo Néstor; Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups; Elsevier Science SA; Journal of Photochemistry and Photobiology A: Chemistry; 194; 2-3; 2-2008; 220-229
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/url/https://www.sciencedirect.com/science/article/pii/S1010603007004297
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2007.08.013
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
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 13.13397

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