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Chemical Compound Review:

CPD-9546 10H-phenazin-2-one

Synonyms: AG-J-34288, CHEMBL2071427, SureCN2367791, NSC-509501, AC1Q6AZH, ...

Bäumer, S. et al., Maddula, V.S. et al., Ide, T. et al., Baumer, S. et al., Tietze, M. et al., et al.

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Disease relevance of AIDS019756

The biological control bacterium Pseudomonas chlororaphis (aureofaciens) strain 30-84 employs two quorum sensing (QS) systems: PhzR/PhzI regulates the production of the antibiotics phenazine-1-carboxylic acid, 2-hydroxy-phenazine-1-carboxylic acid, and 2-hydroxy-phenazine, whereas CsaR/CsaI regulates currently unknown aspects of the cell surface [1].

High impact information on AIDS019756

Here it is shown that cofactor F(420)H(2)-dependent reduction of 2-hydroxyphenazine as catalyzed by the membrane-bound enzyme is coupled to proton translocation across the cytoplasmic membrane, exhibiting a stoichiometry of 0.9 H(+) translocated per two electrons transferred [2].
Cyclization of the diphenylamines by various methods, including the intramolecular Pd(0)-catalyzed N-arylation, produces 2-methoxyphenazine which can easily be deprotected to give 2-hydroxyphenazine [3].
The membrane-bound H2:heterodisulfide oxidoreductase system of the methanogenic archaeon Methanosarcina mazei Gö1 catalyzed the H2-dependent reduction of 2-hydroxyphenazine and the dihydro-2-hydroxyphenazine-dependent reduction of the heterodisulfide of HS-CoM and HS-CoB (CoM-S-S-CoB) [4].
F420H2-dependent CoB-S-S-CoM reduction as catalyzed by the F420H2:heterodisulfide oxidoreductase from Methanosarcina strains was observed in a defined system containing purified F420H2 dehydrogenase from Methanosarcina mazei Gö1, 2-hydroxyphenazine and purified heterodisulfide reductase from Methanosarcina thermophila [5].
In case of the F420H2 dehydrogenase electron transport from FAD or from FeS centers to 2-hydroxyphenazine is inhibited [6].

Gene context of AIDS019756

The F420H2:heterodisulfide oxidoreductase system from Methanosarcina species. 2-Hydroxyphenazine mediates electron transfer from F420H2 dehydrogenase to heterodisulfide reductase [5].

References

Quorum Sensing and Phenazines are Involved in Biofilm Formation by Pseudomonas chlororaphis (aureofaciens) Strain 30-84. Maddula, V.S., Zhang, Z., Pierson, E.A., Pierson, L.S. Microb. Ecol. (2006) [Pubmed]
The F420H2 dehydrogenase from Methanosarcina mazei is a Redox-driven proton pump closely related to NADH dehydrogenases. Baumer, S., Ide, T., Jacobi, C., Johann, A., Gottschalk, G., Deppenmeier, U. J. Biol. Chem. (2000) [Pubmed]
Efficient methods for the synthesis of 2-hydroxyphenazine based on the Pd-catalyzed N-arylation of aryl bromides. Tietze, M., Iglesias, A., Merisor, E., Conrad, J., Klaiber, I., Beifuss, U. Org. Lett. (2005) [Pubmed]
Energy conservation by the H2:heterodisulfide oxidoreductase from Methanosarcina mazei Gö1: identification of two proton-translocating segments. Ide, T., Bäumer, S., Deppenmeier, U. J. Bacteriol. (1999) [Pubmed]
The F420H2:heterodisulfide oxidoreductase system from Methanosarcina species. 2-Hydroxyphenazine mediates electron transfer from F420H2 dehydrogenase to heterodisulfide reductase. Bäumer, S., Murakami, E., Brodersen, J., Gottschalk, G., Ragsdale, S.W., Deppenmeier, U. FEBS Lett. (1998) [Pubmed]
Inhibition of membrane-bound electron transport of the methanogenic archaeon Methanosarcina mazei Gö1 by diphenyleneiodonium. Brodersen, J., Bäumer, S., Abken, H.J., Gottschalk, G., Deppenmeier, U. Eur. J. Biochem. (1999) [Pubmed]

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