Synthesis and characterization of photoactive porphyrin and poly(2-hydroxyethyl methacrylate) based materials with bactericidal properties


Poly(2-hydroxyethyl methacrylate)-based materials bearing porphyrinic units were prepared, characterized and their ability to inactivate Escherichia coli and Staphylococcus aureus bacteria was evaluated. Porphyrins containing methacrylate moieties were prepared by the sequential nucleophilic substitution of the para-fluorine atoms in 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (P1) with 2-hydroxyethyl methacrylate (HEMA). Two distinct materials were obtained, namely PHEMA-Porph by in situ non-covalent incorporation of P1 (porphyrin with no methacrylic unit) during the free radical polymerization of HEMA, and PHEMA-co-Porph by the covalent coupling of P2 (porphyrin containing one methacrylic unit) with HEMA via free radical polymerization. Both PHEMA-co-Porph and PHEMA-Porph showed to be fluorescent and photostable under visible light and to have the capacity to generate singlet oxygen. The evaluation of the photodynamic inactivation (PDI) exhibited by the two photoactive materials towards the selected bacteria showed that, apart from the higher performance of PHEMA-co-Porph, both can be reused at least three times without significant loss of their efficacy towards E. coli. In this sense, these photoactive polymeric materials bearing porphyrinic units have potential as photosensitizers for photodynamic inactivation of both Gram-positive and Gram-negative bacteria. (C) 2019 Elsevier Ltd. All rights reserved.



subject category

Materials Science


Castro, KADF; Moura, NMM; Simoes, MMQ; Cavaleiro, JAS; Faustino, MDF; Cunha, A; Paz, FAA; Mendes, RF; Almeida, A; Freire, CSR; Vilela, C; Silvestre, AJD; Nakagaki, S; Neves, MDPMS

our authors


The authors are grateful to the Conselho Nacional de Desenvolvimento Cientifico e Tecnologico, Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior, to the University of Aveiro and to the FCT/MCT for the financial support for QOPNA research Unit (FCT UID/QUI/00062/2019), (FCOMP-01-0124-FEDER-037296), CESAM (UUID/AMB/50017 - POCI-01-0145-FEDER-007638), CICECO - Aveiro Institute of Materials (FCT Ref. UID/CTM/50011/2019), and the project (FCT-PTDC/ASP-PES/29576/2017), through national funds and, where applicable, co-financed by FEDER, within the PT2020 Partnership Agreement, and to the Portuguese NMR Network. K.A.D.F. Castro also thanks CNPq for her post-doctoral scholarship (Process: 201107/2014-7). The research contracts of N. M. M. Moura (REF.-048-88-ARH/2018) and C. Vilela are funded by national funds (OE), through FCT - Fundacao para a Ciencia e a Tecnologia, I.P., in the scope of the framework contract foreseen in the numbers 4, 5 and 6 of the article 23, of the Decree-Law 57/2016, of August 29, changed by Law 57/2017, of July 19. FCT is also acknowledge for the doctoral grant to R.F. Mendes (SFRH/BD/84231/2012) and the research contract under Stimulus of Scientific Employment 2017 to C.S.R. Freire (CEECIND/00464/2017). We would like to thank Jose M.G. Pererira for digital photographs.

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