An insight into the synthesis of cationic porphyrin-imidazole derivatives and their photodynamic inactivation efficiency against Escherichia coli. (July 2020)

• Record Type: Journal Article
• Authors: Moreira, Xavier; Santos, Patrícia; Faustino, M. Amparo F.; Raposo, M. Manuela M.; Costa, Susana P.G.; Moura, Nuno M.M.; Gomes, Ana T.P.C.; Almeida, Adelaide; Neves, M.G.P.M.S.
• Is Part Of: Dyes and pigments. Volume 178(2020)
• Publication Date: 2020-07
• Subjects: Porphyrin -- N-Heterocycles -- Photosensitizer -- Antimicrobial photodynamic therapy -- Gram-negative E. coli; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2020.108330
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: New porphyrin-imidazole derivatives were synthesised by Radziszewski reaction between 2-formyl-5, 10, 15, 20-tetraphenylporphyrin 1 and several (hetero)aromatic 1, 2-diones, which after cationization afforded promising monocationic photosensitizers 3a-d . Singlet oxygen studies have demonstrated that all the cationic porphyrin-imidazole conjugates 3a–d were capable to produce cytotoxic species. These photosensitizers were able to photoinactivate Eschericha coli and their inactivation profile was improved in the presence of KI. Graphical abstract: Image 1 Highlights: β-functionalized porphyrinic derivatives bearing imidazole were prepared by a Radziszewski reaction. The alkylation/cationization of the imidazole ring was efficiently achieved affording the mono-charged β-porphyrinic derivatives. All the new derivatives are able to generate singlet oxygen. The cationic porphyrin-imidazole showed the ability to be used as photosensitizer in the photoinactivation of bioluminescent E. coli . The efficiency of the photosensitizer is meaningfully improved in the presence of KI.