INVESTIGADORES
ALVAREZ Maria Gabriela
artículos
Título:
Porphyrin-Schiff Base Conjugates Bearing Basic Amino Groups as Antimicrobial Phototherapeutic Agents
Autor/es:
PÉREZ, M. EUGENIA ; DURANTINI, JAVIER E.; REYNOSO, EUGENIA; ALVAREZ, M. GABRIELA; MILANESIO, M. ELISA; DURANTINI, EDGARDO N.
Revista:
MOLECULES
Editorial:
MOLECULAR DIVERSITY PRESERVATION INTERNATIONAL-MDPI
Referencias:
Año: 2021 vol. 26
ISSN:
1420-3049
Resumen:
New porphyrin Schiff base conjugates bearing one (6) and two (7) basic amino groups were syn-thesized by condensation between tetrapyrrolic macrocycle-containing amine functions and 4-(3-(N,N-dimethylamino)propoxy)benzaldehyde. This approach allowed us to easily obtain por-phyrins substituted by positive charge precursor groups in aqueous media. These compounds showed the typical Soret and four Q absorption bands with red fluorescence emission in N,N-dimethylformamide. Porphyrins 6 and 7 photosensitized the generation of O2(1Δg) and the photo-oxidation of L-tryptophan. The decomposition of this amino acid was mainly me-diated by a type II photoprocess. Moreover, the addition of KI strongly quenched the photody-namic action through a reaction with O2(1Δg) to produce iodine. The photodynamic inactivation capacity induced by porphyrins 6 and 7 was evaluated in Staphylococcus aureus, Escherichia coli, and Candida albicans. Furthermore, the photoinactivation of these microorganisms was improved using potentiation with iodide anions. These porphyrins containing basic aliphatic amino groups can be protonated in biological systems, which provides an amphiphilic character to the tetrapyrrolic macrocycle. This effect allows one to increase the interaction with the cell wall, thus improving photocytotoxic activity against microorganisms.