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dc.contributor.author
Spesia, Mariana Belen
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dc.contributor.author
Durantini, Edgardo Néstor
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dc.date.available
2024-07-29T11:59:34Z
dc.date.issued
2008-06
dc.identifier.citation
Spesia, Mariana Belen; Durantini, Edgardo Néstor; Synthesis and antibacterial photosensitizing properties of a novel tricationic subphthalocyanine derivative; Elsevier; Dyes and Pigments; 77; 1; 6-2008; 229-237
dc.identifier.issn
0143-7208
dc.identifier.uri
http://hdl.handle.net/11336/241094
dc.description.abstract
A novel chloro[2,9,16(2,9,17)-trikis-4-(N-methylpyridyloxy)]subphthalocyaninnato boron(III) iodide (SubOPc3+) has been synthesized by boron trichloride-induced cyclotrimerization of 4-(4-pyridyloxy)phthalonitrile in 1-chloronaphthalene. This approach produced a regioisomers mixture of chloro[2,9,16(2,9,17)-trikis-4-(pyridyloxy)]subphthalocyaninnato boron(III) (SubOPc) with 19% yield. Exhaustive methylation of SubOPc with methyl iodide yielded 92% of tricationic SubOPc3+. The spectroscopic and photodynamic properties of the SubOPc3+ were compared with its homologous non-charged SubOPc and with subphthalocyanine (SubPc). The cationic SubOPc3+ is essentially aggregated in solution of different solvents and it is partially dissolved as monomer in aqueous sodium dodecyl sulfate (SDS) 2% w/v. The photodynamic effect was strongly dependent of the medium, increasing in an appropriated surrounding microenvironment. The photodynamic inactivation produced by these subphthalocyanines was for first time investigated in vitro on a typical Gram-negative bacterium, Escherichia coli. Cationic SubOPc3+ is rapidly bound to E. coli cells reaching a value of ~2 nmol/106 cells after 5 min of incubation with 4 mM of sensitizer in dark. Photosensitized inactivation of E. coli cellular suspensions by SubOPc3+ exhibits a ~2.5 log decrease of cell survival (99.7 % of cellular inactivation), when the cultures are irradiated for 30 min. The growth of E. coli cells was completely arrested when the cultures were exposed to 8 mM of cationic subphthalocyanine and irradiated, whereas a negligible effect was found for the non-charged SubOPc. Also, SubOPc3+ remains a high activity to inactivate E. coli cells immobilized on agar surfaces. Therefore, the reported results indicate that tricationic subphthalocyanines are interesting photosensitizers with useful antibacterial activity.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Elsevier
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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
Subphthalocyanine
dc.subject
Photosensitizer
dc.subject
Bacteria
dc.subject
Photodynamic inactivation
dc.subject.classification
Química Orgánica
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Synthesis and antibacterial photosensitizing properties of a novel tricationic subphthalocyanine derivative
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2024-07-25T14:30:05Z
dc.journal.volume
77
dc.journal.number
1
dc.journal.pagination
229-237
dc.journal.pais
Países Bajos
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dc.journal.ciudad
Amsterdam
dc.description.fil
Fil: Spesia, Mariana Belen. 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: 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
Dyes and Pigments
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0143720807001179
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.dyepig.2007.05.008
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