Can Porphyrin-Triphenylphosphonium Conjugates Enhance the Photosensitizer Performance Toward Bacterial Strains?
ACS Appl Bio Mater
; 7(8): 5541-5552, 2024 Aug 19.
Article
en En
| MEDLINE
| ID: mdl-39008849
ABSTRACT
Antimicrobial photodynamic treatment (aPDT) offers an alternative option for combating microbial pathogens, and in this way, addressing the challenges of growing antimicrobial resistance. In this promising and effective approach, cationic porphyrins and related macrocycles have emerged as leading photosensitizers (PS) for aPDT. In general, their preparation occurs via N-alkylation of nitrogen-based moieties with alkyl halides, which limits the ability to fine-tune the features of porphyrin-based PS. Herein, is reported that the conjugation of porphyrin macrocycles with triphenylphosphonium units created a series of effective cationic porphyrin-based PS for aPDT. The presence of positive charges at both the porphyrin macrocycle and triphenylphosphonium moieties significantly enhances the photodynamic activity of porphyrin-based PS against both Gram-positive and Gram-negative bacterial strains. Moreover, bacterial photoinactivation is achieved with a notable reduction in irradiation time, exceeding 50%, compared to 5,10,15,20-tetrakis(1-methylpyridinium-4-yl)porphyrin (TMPyP), used as the reference and known as good PS. The improved capability of the porphyrin macrocycle to generate singlet oxygen combined with the enhanced membrane interaction promoted by the presence of triphenylphosphonium moieties represents a promising approach to developing porphyrin-based PS with enhanced photosensitizing activity.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Compuestos Organofosforados
/
Porfirinas
/
Ensayo de Materiales
/
Fármacos Fotosensibilizantes
/
Antibacterianos
Idioma:
En
Revista:
ACS Appl Bio Mater
Año:
2024
Tipo del documento:
Article
País de afiliación:
Portugal
Pais de publicación:
Estados Unidos