Synthesis, characterization and biological evaluation of cationic porphyrin-terpyridine derivatives

Nuno M.M. Moura, Catarina I.V. Ramos, Inês Linhares, Sérgio M. Santos, M. Amparo F. Faustino, Adelaide Almeida, José A.S. Cavaleiro, Francisco M.L. Amado, Carlos Lodeiro, M. Graça P.M.S. Neves

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

A simple access to a new series of cationic porphyrin-terpyridine derivatives is described. The key step to obtain the required neutral precursors as major products involved a Kröhnke type approach. The methodology allowed also the isolation of the respective benzoporphyrins and porphyrin-chalcone type derivatives, and in one case a new 2-(2,4-terpyridin-6-yl)-porphyrin. The quaternization of the pyridyl groups was performed in the presence of the adequate alkyl iodide affording the dicationic derivatives in excellent yields. All the new conjugates were fully characterised and it was found that the cationic isomers can be efficiently differentiated by ESI-MS, as their behaviour can be intensively studied by mass spectrometry. The new methylated cationic porphyrin-terpyridine derivatives demonstrate an ability to generate singlet oxygen and their efficacy to photoinactivate bioluminescent Gram-negative E. coli was evaluated. A reduction in the bioluminescence signal, up to 5.4 log, was obtained with the most efficient photosensitiser.

Original languageEnglish
Pages (from-to)110674-110685
Number of pages12
JournalRSC Advances
Volume6
Issue number112
DOIs
Publication statusPublished - 1 Jan 2016

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Porphyrins
Derivatives
Bioluminescence
Chalcone
Singlet Oxygen
Photosensitizing Agents
Photosensitizers
Iodides
Isomers
Escherichia coli
Mass spectrometry
Oxygen

Keywords

  • BIOLUMINESCENT ESCHERICHIA-COLI
  • PHOTODYNAMIC INACTIVATION
  • ANTIMICROBIAL PHOTOINACTIVATION

Cite this

Moura, N. M. M., Ramos, C. I. V., Linhares, I., Santos, S. M., Faustino, M. A. F., Almeida, A., ... Neves, M. G. P. M. S. (2016). Synthesis, characterization and biological evaluation of cationic porphyrin-terpyridine derivatives. RSC Advances, 6(112), 110674-110685. https://doi.org/10.1039/c6ra25373c
Moura, Nuno M.M. ; Ramos, Catarina I.V. ; Linhares, Inês ; Santos, Sérgio M. ; Faustino, M. Amparo F. ; Almeida, Adelaide ; Cavaleiro, José A.S. ; Amado, Francisco M.L. ; Lodeiro, Carlos ; Neves, M. Graça P.M.S. / Synthesis, characterization and biological evaluation of cationic porphyrin-terpyridine derivatives. In: RSC Advances. 2016 ; Vol. 6, No. 112. pp. 110674-110685.
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abstract = "A simple access to a new series of cationic porphyrin-terpyridine derivatives is described. The key step to obtain the required neutral precursors as major products involved a Kr{\"o}hnke type approach. The methodology allowed also the isolation of the respective benzoporphyrins and porphyrin-chalcone type derivatives, and in one case a new 2-(2,4-terpyridin-6-yl)-porphyrin. The quaternization of the pyridyl groups was performed in the presence of the adequate alkyl iodide affording the dicationic derivatives in excellent yields. All the new conjugates were fully characterised and it was found that the cationic isomers can be efficiently differentiated by ESI-MS, as their behaviour can be intensively studied by mass spectrometry. The new methylated cationic porphyrin-terpyridine derivatives demonstrate an ability to generate singlet oxygen and their efficacy to photoinactivate bioluminescent Gram-negative E. coli was evaluated. A reduction in the bioluminescence signal, up to 5.4 log, was obtained with the most efficient photosensitiser.",
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Moura, NMM, Ramos, CIV, Linhares, I, Santos, SM, Faustino, MAF, Almeida, A, Cavaleiro, JAS, Amado, FML, Lodeiro, C & Neves, MGPMS 2016, 'Synthesis, characterization and biological evaluation of cationic porphyrin-terpyridine derivatives', RSC Advances, vol. 6, no. 112, pp. 110674-110685. https://doi.org/10.1039/c6ra25373c

Synthesis, characterization and biological evaluation of cationic porphyrin-terpyridine derivatives. / Moura, Nuno M.M.; Ramos, Catarina I.V.; Linhares, Inês; Santos, Sérgio M.; Faustino, M. Amparo F.; Almeida, Adelaide; Cavaleiro, José A.S.; Amado, Francisco M.L.; Lodeiro, Carlos; Neves, M. Graça P.M.S.

In: RSC Advances, Vol. 6, No. 112, 01.01.2016, p. 110674-110685.

Research output: Contribution to journalArticle

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AU - Moura, Nuno M.M.

AU - Ramos, Catarina I.V.

AU - Linhares, Inês

AU - Santos, Sérgio M.

AU - Faustino, M. Amparo F.

AU - Almeida, Adelaide

AU - Cavaleiro, José A.S.

AU - Amado, Francisco M.L.

AU - Lodeiro, Carlos

AU - Neves, M. Graça P.M.S.

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PY - 2016/1/1

Y1 - 2016/1/1

N2 - A simple access to a new series of cationic porphyrin-terpyridine derivatives is described. The key step to obtain the required neutral precursors as major products involved a Kröhnke type approach. The methodology allowed also the isolation of the respective benzoporphyrins and porphyrin-chalcone type derivatives, and in one case a new 2-(2,4-terpyridin-6-yl)-porphyrin. The quaternization of the pyridyl groups was performed in the presence of the adequate alkyl iodide affording the dicationic derivatives in excellent yields. All the new conjugates were fully characterised and it was found that the cationic isomers can be efficiently differentiated by ESI-MS, as their behaviour can be intensively studied by mass spectrometry. The new methylated cationic porphyrin-terpyridine derivatives demonstrate an ability to generate singlet oxygen and their efficacy to photoinactivate bioluminescent Gram-negative E. coli was evaluated. A reduction in the bioluminescence signal, up to 5.4 log, was obtained with the most efficient photosensitiser.

AB - A simple access to a new series of cationic porphyrin-terpyridine derivatives is described. The key step to obtain the required neutral precursors as major products involved a Kröhnke type approach. The methodology allowed also the isolation of the respective benzoporphyrins and porphyrin-chalcone type derivatives, and in one case a new 2-(2,4-terpyridin-6-yl)-porphyrin. The quaternization of the pyridyl groups was performed in the presence of the adequate alkyl iodide affording the dicationic derivatives in excellent yields. All the new conjugates were fully characterised and it was found that the cationic isomers can be efficiently differentiated by ESI-MS, as their behaviour can be intensively studied by mass spectrometry. The new methylated cationic porphyrin-terpyridine derivatives demonstrate an ability to generate singlet oxygen and their efficacy to photoinactivate bioluminescent Gram-negative E. coli was evaluated. A reduction in the bioluminescence signal, up to 5.4 log, was obtained with the most efficient photosensitiser.

KW - BIOLUMINESCENT ESCHERICHIA-COLI

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KW - ANTIMICROBIAL PHOTOINACTIVATION

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Moura NMM, Ramos CIV, Linhares I, Santos SM, Faustino MAF, Almeida A et al. Synthesis, characterization and biological evaluation of cationic porphyrin-terpyridine derivatives. RSC Advances. 2016 Jan 1;6(112):110674-110685. https://doi.org/10.1039/c6ra25373c