Quenching of singlet oxygen by pyocyanin and related phenazines

Krzysztof J. Reszka, Piotr J. Bilski, Bradley E. Britigan

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Pseudomonas aeruginosa is a human pathogen, which causes infections of various organs, including lung, skin and eye, particularly in individuals who are immunocompromised. Pyocyanin (1-hydroxy-5-methylphenazine), a cytotoxic pigment secreted by the bacterium, is among the factors that contribute to virulence of this pathogen. We have previously shown that rose bengal and riboflavin photosensitize oxidation of pyocyanin to a product(s) with diminished reactivity and toxicity. Singlet oxygen was suggested as the major oxidant, based on the inhibitory effect of sodium azide. In the present study, we used the time resolved technique to investigate direct interaction of pyocyanin and related phenazines (1-hydroxyphenazine [1-OH-Phen], 1-methoxy-5-methylphenazine [1-MeO-PCN] and phenazine methosulfate [PMS]) with 1O2. The rate constants for the 1O2 quenching (physical + chemical) by pyocyanin and 1-OH-Phen in D2O buffer (pD ∼7.2) have been determined to be 4.8 × 108 and 6.8 × 108 M-1 s-1, respectively. 1-MeO-PCN and PMS were markedly less efficient 1O2 quenchers. Among the phenazines studied only phenazine methosulfate photogenerated 1O2 (Φ(1O2) = 0.56 in acetonitrile). Interaction of 1O2 with pyocyanin and other related phenazines produced by the bacteria may be important in determining the potential utility of photochemical/pharmacological approaches to eradicate P. aeruginosa from infected tissues.

Original languageEnglish (US)
Pages (from-to)742-746
Number of pages5
JournalPhotochemistry and Photobiology
Volume86
Issue number4
DOIs
StatePublished - Jul 1 2010

Fingerprint

Pyocyanine
Phenazines
Singlet Oxygen
pathogens
bacteria
Methylphenazonium Methosulfate
Quenching
quenching
virulence
riboflavin
sodium azides
pseudomonas
Pregnenolone Carbonitrile
oxygen
infectious diseases
pigments
toxicity
organs
lungs
acetonitrile

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry

Cite this

Quenching of singlet oxygen by pyocyanin and related phenazines. / Reszka, Krzysztof J.; Bilski, Piotr J.; Britigan, Bradley E.

In: Photochemistry and Photobiology, Vol. 86, No. 4, 01.07.2010, p. 742-746.

Research output: Contribution to journalArticle

Reszka, Krzysztof J. ; Bilski, Piotr J. ; Britigan, Bradley E. / Quenching of singlet oxygen by pyocyanin and related phenazines. In: Photochemistry and Photobiology. 2010 ; Vol. 86, No. 4. pp. 742-746.
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