Phenazine 1-carboxamide

Phenazines — The phenazines are biosynthesized by the shikimic acid pathway, through the intermediate chorismic acid. The process was studied using different strains of Pseudomonas species, the major producers of phenazines. The best-known phenazine, pyocyanine, seems to be produced from the intermediate phenazine-1-carboxylic acid (PCA). Although intensive biochemical studies were done, not all the details and the intermediates of conversion of chorismic acid to PCA are known. In the first step, PCA is N-methylated by a SAM-dependent methyltransferase. The second step is a hydroxylative decarboxylation catalyzed by a flavoprotein monooxygenase dependent on NADH. PCA is also the precursor of phenazine-1-carboxamide and 1-hydroxyphenazine from Pseudomonas species. - - ... 

Mavrodi, D.V. et al., Functional analysis of genes for biosynthesis of pyocianin and phenazine-1-carboxamide from Pseudomonas aeruginosa PAOl, J- Bacterial, 183, 6454, 2001. 

Tjeerd van Rij E, G Girard, BJJ Lugtenberg, GV Bloemberg (2005) Influence of fusaric acid on phenazine-1-carboxamide synthesis and gene expression of Pseudomonas chlororaphis strain PCL1391. Microbiology (UK) 151 2805-2814. 

Phenazine-1-carboxamide undergoes rearrangement to the 1-amino derivative (see Houben-Weyl, Vol. 11/1, p 890) and the thermal decomposition of 2-azidophenazine affords phenazin-2-amine in good yield in different solvents. Catalytic hydrogenation of 2-nitro-phenazin-6-amine yields phenazine-2,6-diamine (3, yield 98% mp 221... 

Besides the already-mentioned chlororaphine (2, a 1 1 complex of phenazine-1-carboxamide and its 5,10-dihydro derivative Figure and iodinin... 

Fig. 2.4 Mediators can achieve high power densities in MFCs. (A) Solvent extracts from an MFC showing characteristic biue-green coiors, typicai of phenazines such as pyocyanin and phenazine-1-carboxamide produced by bacteria such as Pseudomonas aeruginosa] (B) a recirculation tube stained blue, likely by adsorbed mediators (C) cation exchange membrane of 4 anodic chambers containing P. aeruginosa that produced different phenazines the mediators partially sorbed onto the membrane. [Photographs by K. Rabaey.]...

Phenazine-l-carboxamide (137) is known as oxychlororaphine and has been isolated from cultures of Pseudomonas chlororaphisit has some limited inhibitory properties, but the inhibitory action of phenazines is generally disappointing. Some phenazine derivatives have insecticidal properties thus, phenazine itself has been found to be toxic to the clothes moth, the Hawaiian beet webworm, the rice weevil and larva of the codling moth, but under trial conditions its toxicity to plant material, as evidenced by severe burning of foliage, was found to be too high to make it of practical value. 

Chin-A-Woeng TFC, D van den Broek, G de Voer, KMGK van der Drift, S Tuinman, JE Thomas-Oates, BJJ Lugtenberg, GV Bloemberg (2001) Phenazine-l-carboxamide production in the biocontrol strain Pseudomonas chlororaphis PC L 1391 is regulated by multiple factors secreted into the growth medium. Mol Plant-Microbe Interact 14 869-879. 

Chin-A-Woeng TFC, GV Bloemberg, IHM Mulders, LC Dekkers, BJJ Lugtenberg (2000) Root comonization by phenazine-l-carboxamide-producing bacterium Pseudomonas chlororaphis PCL 1391 is essential for biocontrol of tomato foot and root rot. Mol Plant-Microbe Interact 13 1340-1345. 

Mavrodi DV, RE Bonall, SMK Delaney, MJ Soule, G Phillips, LS Thomashow (2001) Eunctional analysis of genes for biosynthesis of pyocyanin and phenazine-l-carboxamide from Pseudomonas aeruginosa PAGE J Bacterial 183 6454-6465. 

Tjeerd van Rij E, M Wesselink, TEC Chin-A-Woeng, GV Bloemberg, BJJ Lugtenberg (2004) Influence of environmental conditions on the production of phenazine-l-carboxamide by Pseudomonas chlororaphis PCL 1391. Mol Plant-Microbe Interact 17 557-566. 

A series of bis[(phenazine-l-carboxamide)propyl]methylamines (XVIII) was synthesized by Spicer et al. [43] and their cytotoxicities evaluated against a panel of tumor cell lines. From the cytotoxic data of these compounds against P388, LLc, and JLc cancer cells, QSAR Eqs. 18, 19, and 20 were developed, respectively [44]. 

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