Versatile thiopyridyl/pyridinone porphyrins combined with potassium iodide and thiopyridinium/methoxypyridinium porphyrins on E. coli photoinactivation

Detalhes bibliográficos
Autor(a) principal: Calmeiro, Joana M.D.
Data de Publicação: 2020
Outros Autores: Gamelas, Sara R.D., Gomes, Ana T.P.C., Faustino, Maria A.F., Neves, Maria G.P.M.S., Almeida, Adelaide, Tomé, João P.C., Lourenço, Leandro M.O.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10773/37610
Resumo: Porphyrins (Pors) are well-known photoactive molecules with recognized features to be explored as photosensitisers in the photodynamic inactivation (PDI) of microorganisms. The use of appropriate moieties like pyridinium groups is a remarkable strategy to add peripheral and internal positive charges in the Por structure making them more effective PSs against Gram-negative bacteria like Escherichia coli (E. coli). In this context, an easy synthetic access to obtain cationic Zn(II) porphyrins bearing thiopyridinium and inverted methoxypyridinium units (ZnPors 1c and 2c) was developed and their photo-physical and photo-chemical properties were evaluated. The photodynamic effectiveness of these complexes against a E. coli strain was also studied and compared with the efficacy of the corresponding free-bases (Pors 1b and 2b) and of the neutral precursors (Pors 1, 1a, 2, 2a), these last ones in the absence and in the presence of potassium iodide salt (KI). The obtained results demonstrate high PDI efficiency with the cationic free-base 1b and the ZnPor 2c; both derivatives were able to photoinactivate E. coli till the detection limit of the method at a concentration of 1.0 μM after 20 and 15 min of white light irradiation (25 mW cm−2), respectively. Interestingly, under the same experimental conditions (1.0 μM and white light), the neutral Pors (1, 1a, 2 and 2a) with addition of KI salt show a fast inactivation rate, reaching the detection limit of the method after 5 min of irradiation.
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spelling Versatile thiopyridyl/pyridinone porphyrins combined with potassium iodide and thiopyridinium/methoxypyridinium porphyrins on E. coli photoinactivationPorphyrins (Pors) are well-known photoactive molecules with recognized features to be explored as photosensitisers in the photodynamic inactivation (PDI) of microorganisms. The use of appropriate moieties like pyridinium groups is a remarkable strategy to add peripheral and internal positive charges in the Por structure making them more effective PSs against Gram-negative bacteria like Escherichia coli (E. coli). In this context, an easy synthetic access to obtain cationic Zn(II) porphyrins bearing thiopyridinium and inverted methoxypyridinium units (ZnPors 1c and 2c) was developed and their photo-physical and photo-chemical properties were evaluated. The photodynamic effectiveness of these complexes against a E. coli strain was also studied and compared with the efficacy of the corresponding free-bases (Pors 1b and 2b) and of the neutral precursors (Pors 1, 1a, 2, 2a), these last ones in the absence and in the presence of potassium iodide salt (KI). The obtained results demonstrate high PDI efficiency with the cationic free-base 1b and the ZnPor 2c; both derivatives were able to photoinactivate E. coli till the detection limit of the method at a concentration of 1.0 μM after 20 and 15 min of white light irradiation (25 mW cm−2), respectively. Interestingly, under the same experimental conditions (1.0 μM and white light), the neutral Pors (1, 1a, 2 and 2a) with addition of KI salt show a fast inactivation rate, reaching the detection limit of the method after 5 min of irradiation.Elsevier2023-05-09T14:36:00Z2020-10-01T00:00:00Z2020-10info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10773/37610eng0143-720810.1016/j.dyepig.2020.108476Calmeiro, Joana M.D.Gamelas, Sara R.D.Gomes, Ana T.P.C.Faustino, Maria A.F.Neves, Maria G.P.M.S.Almeida, AdelaideTomé, João P.C.Lourenço, Leandro M.O.info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-02-22T12:12:46Zoai:ria.ua.pt:10773/37610Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:08:13.479057Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Versatile thiopyridyl/pyridinone porphyrins combined with potassium iodide and thiopyridinium/methoxypyridinium porphyrins on E. coli photoinactivation
title Versatile thiopyridyl/pyridinone porphyrins combined with potassium iodide and thiopyridinium/methoxypyridinium porphyrins on E. coli photoinactivation
spellingShingle Versatile thiopyridyl/pyridinone porphyrins combined with potassium iodide and thiopyridinium/methoxypyridinium porphyrins on E. coli photoinactivation
Calmeiro, Joana M.D.
title_short Versatile thiopyridyl/pyridinone porphyrins combined with potassium iodide and thiopyridinium/methoxypyridinium porphyrins on E. coli photoinactivation
title_full Versatile thiopyridyl/pyridinone porphyrins combined with potassium iodide and thiopyridinium/methoxypyridinium porphyrins on E. coli photoinactivation
title_fullStr Versatile thiopyridyl/pyridinone porphyrins combined with potassium iodide and thiopyridinium/methoxypyridinium porphyrins on E. coli photoinactivation
title_full_unstemmed Versatile thiopyridyl/pyridinone porphyrins combined with potassium iodide and thiopyridinium/methoxypyridinium porphyrins on E. coli photoinactivation
title_sort Versatile thiopyridyl/pyridinone porphyrins combined with potassium iodide and thiopyridinium/methoxypyridinium porphyrins on E. coli photoinactivation
author Calmeiro, Joana M.D.
author_facet Calmeiro, Joana M.D.
Gamelas, Sara R.D.
Gomes, Ana T.P.C.
Faustino, Maria A.F.
Neves, Maria G.P.M.S.
Almeida, Adelaide
Tomé, João P.C.
Lourenço, Leandro M.O.
author_role author
author2 Gamelas, Sara R.D.
Gomes, Ana T.P.C.
Faustino, Maria A.F.
Neves, Maria G.P.M.S.
Almeida, Adelaide
Tomé, João P.C.
Lourenço, Leandro M.O.
author2_role author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Calmeiro, Joana M.D.
Gamelas, Sara R.D.
Gomes, Ana T.P.C.
Faustino, Maria A.F.
Neves, Maria G.P.M.S.
Almeida, Adelaide
Tomé, João P.C.
Lourenço, Leandro M.O.
description Porphyrins (Pors) are well-known photoactive molecules with recognized features to be explored as photosensitisers in the photodynamic inactivation (PDI) of microorganisms. The use of appropriate moieties like pyridinium groups is a remarkable strategy to add peripheral and internal positive charges in the Por structure making them more effective PSs against Gram-negative bacteria like Escherichia coli (E. coli). In this context, an easy synthetic access to obtain cationic Zn(II) porphyrins bearing thiopyridinium and inverted methoxypyridinium units (ZnPors 1c and 2c) was developed and their photo-physical and photo-chemical properties were evaluated. The photodynamic effectiveness of these complexes against a E. coli strain was also studied and compared with the efficacy of the corresponding free-bases (Pors 1b and 2b) and of the neutral precursors (Pors 1, 1a, 2, 2a), these last ones in the absence and in the presence of potassium iodide salt (KI). The obtained results demonstrate high PDI efficiency with the cationic free-base 1b and the ZnPor 2c; both derivatives were able to photoinactivate E. coli till the detection limit of the method at a concentration of 1.0 μM after 20 and 15 min of white light irradiation (25 mW cm−2), respectively. Interestingly, under the same experimental conditions (1.0 μM and white light), the neutral Pors (1, 1a, 2 and 2a) with addition of KI salt show a fast inactivation rate, reaching the detection limit of the method after 5 min of irradiation.
publishDate 2020
dc.date.none.fl_str_mv 2020-10-01T00:00:00Z
2020-10
2023-05-09T14:36:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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url http://hdl.handle.net/10773/37610
dc.language.iso.fl_str_mv eng
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10.1016/j.dyepig.2020.108476
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dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
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