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Medicinal Chemistry Research

, Volume 27, Issue 5, pp 1478–1484 | Cite as

Optimal axial alkylpyridinium-bonded tricationic P-porphyrin in photodynamic inactivation of Escherichia coli

  • Jin Matsumoto
  • Masahide Yasuda
Original Research
  • 66 Downloads

Abstract

Alkylpyridinium (Apy)-bonded porphyrins have received considerable attention as singlet-oxygen (1O2) sensitizers for photodynamic inactivation (PDI). It is expected that the introduction of Apy makes porphyrins water-soluble and enhances the affinity of porphyrins to DNA. Here, we focused on Apy-bonded P-porphyrins that were prepared through the modification of axial ligands of meso-tetraphenylporphyrinatophosphorus by the Apy’s group and linkers. These water-soluble porphyrins (1) were applied to sensitize the inactivation of Escherichia coli under visible-light irradiation, since there are only few 1O2 sensitizers that can efficiently inactivate E. coli at low concentrations. The PDI activities were evaluated using the half-life (T1/2 in min) of E. coli and the minimum effective concentrations ([P]) of the porphyrin sensitizers. It was found that the PDI activity towards E. coli depends on the alkyl chain length of Apy. The [P] value for E. coli was optimized to be 0.25 μM of bis[5-(3- ethyl-1-pyridinio)-3-oxapentyloxo]tetraphenylporphyrinatophosphorus dibromide chloride (1b). Since the previous results on the optimized [P] value for S. cerevisiae was 50 nM for 1b, it was found that the [P] value for E. coli was larger than that for S. cerevisiae.

Keywords

Photoinactivation P-porphyrins Alkylpyridinium Escherichia coli 

Notes

Acknowledgements

This research was supported by a Grant-in-Aid for Scientific Research (C) (16K05847) from the Japan Society for the Promotion of Science (JSPS).

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

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© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Applied Chemistry, Faculty of EngineeringUniversity of MiyazakiMiyazakiJapan

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