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dc.contributor.author
Caminos, Daniel Alberto
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dc.contributor.author
Durantini, Edgardo Néstor
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dc.date.available
2024-08-07T11:25:14Z
dc.date.issued
2005-02
dc.identifier.citation
Caminos, Daniel Alberto; Durantini, Edgardo Néstor; Synthesis of asymmetrically meso -substituted porphyrins bearing amino groups as potential cationic photodynamic agents; World Sci Publ Co Inc; Journal Of Porphyrins And Phthalocyanines; 09; 05; 2-2005; 334-342
dc.identifier.issn
1088-4246
dc.identifier.uri
http://hdl.handle.net/11336/241964
dc.description.abstract
Novel asymmetrically meso-substituted porphyrins bearing amino groups have been synthesized as precursors of cationic photodynamic agents. The amphiphilic character of these porphyrins was increased by the presence of a high lipophilic trifluoromethyl group. Different patterns of porphyrin structures were obtained from meso-4-[(3-N,N-dimethylaminopropoxy)phenyl] dipyrromethane 1, which was formed by the condensation of 4-(3-N,N-dimethylaminopropoxy) benzaldehyde with a large excess of pyrrole. This reaction takes place at high temperature with a yield of 59%. This reaction was also attempted under acid-catalyzed condensation at room temperature. However, under these conditions, the amino group reduces the catalyst and the reaction does not take place. To obtain porphyrins, dipyrromethane 1 was condensed with aldehydes in the presence of trifluoroacetic acid (TFA) under different conditions. First, 1 reacted with 4-(3-N,N-dimethylaminopropoxy)benzaldehyde in dichloromethane catalyzed by TFA (~4 times TFA/1 molar ratio) to obtain 6.2% of 5,10,15,20-tetrakis(4-[3-N,N-dimethylaminopropoxy]phenyl)porphyrin (A4-porphyrin). Under similar conditions, reaction of 1 with 4-(trifluoromethyl)benzaldehyde produces 5,15-di(4-[3-N,N-dimethylaminopropoxy]phenyl)-10,20- di(4-trifluoromethylphenyl)porphyrin (A2B2-porphyrin) with a 4.8% yield. This procedure also yields a mixture of porphyrins, which were formed due to acidolysis of 1. When a minor amount of TFA was used in acetonitrile, the yield of A2B2-porphyrin was very poor (~0.4%). On the other hand, condensation of 1 with 4-trifluoromethylbenzaldehyde and 4-(3-N,N-dimethylaminopropoxy)benzaldehyde catalyzed by TFA (~2 times TFA/1 molar ratio) in acetonitrile yields 9.3% of 5-(4-trifluoromethylphenyl)-10,15,20- tris(4-[3-N,N-dimethylaminopropoxy]phenyl)porphyrin (A3B-porphyrin). A2B2 and A4 porphyrins were also isolated with 6.0 and 2.0%, respectively. Finally, exhaustive methylation of amino porphyrins produces cationic sensitizers (>94% yield). Absorption and fluorescence spectroscopic studies of these sensitizers were compared in N,N-dimethylformamide. In these porphyrins, the cationic centers are isolated from the porphyrin ring by a propoxy bridge. Thus, the cationic charges have minimal influence on the photophysical properties of the sensitizers. In addition, this chain provides a higher mobility of the charge, which could facilitate interaction with the outer membrane of the Gram-negative bacteria. These amphiphilic cationic porphyrins are promising photosensitizers with potential applications in bacterial inactivation by photodynamic therapy.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
World Sci Publ Co Inc
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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
Amino porphyrin
dc.subject
Dipyrromethane
dc.subject
Anphiphilic structure
dc.subject
Photosensitizer
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 of asymmetrically meso -substituted porphyrins bearing amino groups as potential cationic photodynamic agents
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2024-08-06T11:14:36Z
dc.journal.volume
09
dc.journal.number
05
dc.journal.pagination
334-342
dc.journal.pais
Estados Unidos
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dc.description.fil
Fil: Caminos, Daniel Alberto. 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
dc.description.fil
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
dc.journal.title
Journal Of Porphyrins And Phthalocyanines
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.worldscientific.com/doi/abs/10.1142/S1088424605000423
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1142/S1088424605000423
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