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dc.contributor.author
Cormick, Maria Paula
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dc.contributor.author
Rovera, Marisa
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dc.contributor.author
Durantini, Edgardo Néstor
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dc.date.available
2024-08-08T12:35:25Z
dc.date.issued
2008-02
dc.identifier.citation
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
dc.identifier.issn
1010-6030
dc.identifier.uri
http://hdl.handle.net/11336/242103
dc.description.abstract
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.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Elsevier Science SA
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dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Phthalocyanine
dc.subject
Floconazole
dc.subject
Photodynamic inactivation
dc.subject
Yeast
dc.subject
Candida albicans
dc.subject.classification
Biología Celular, Microbiología
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dc.subject.classification
Ciencias Biológicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2024-08-07T11:17:07Z
dc.journal.volume
194
dc.journal.number
2-3
dc.journal.pagination
220-229
dc.journal.pais
Países Bajos
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dc.journal.ciudad
Amsterdam
dc.description.fil
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
dc.description.fil
Fil: Rovera, Marisa. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; Argentina
dc.description.fil
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
dc.journal.title
Journal of Photochemistry and Photobiology A: Chemistry
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1010603007004297
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.jphotochem.2007.08.013
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