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2538-68-3,MFCD00185184
Catalog No.:AA00BFDG

2538-68-3 | Phenazine-1-carboxylic acid

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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00BFDG
Chemical Name:
Phenazine-1-carboxylic acid
CAS Number:
2538-68-3
Molecular Formula:
C13H8N2O2
Molecular Weight:
224.2148
MDL Number:
MFCD00185184
SMILES:
OC(=O)c1cccc2c1nc1ccccc1n2
NSC Number:
15851
Properties
Computed Properties
 
Complexity:
308  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
1  
XLogP3:
2.2  

Literature

Title: 5-Methyl phenazine-1-carboxylic acid: a novel bioactive metabolite by a rhizosphere soil bacterium that exhibits potent antimicrobial and anticancer activities.

Journal: Chemico-biological interactions 20150425

Title: Trapped intermediates in crystals of the FMN-dependent oxidase PhzG provide insight into the final steps of phenazine biosynthesis.

Journal: Acta crystallographica. Section D, Biological crystallography 20130801

Title: Aerobic denitration of 2,4,6-trinitrotoluene in the presence of phenazine compounds and reduced pyridine nucleotides.

Journal: Environmental science & technology 20121002

Title: Insights into a divergent phenazine biosynthetic pathway governed by a plasmid-born esmeraldin gene cluster.

Journal: Chemistry & biology 20120921

Title: Simply enhancing throughput of free-flow electrophoresis via organic-aqueous environment for purification of weak polarity solute of phenazine-1-carboxylic acid in fermentation of Pseudomonas sp. M18.

Journal: Electrophoresis 20120901

Title: Geranylphenazinediol, an acetylcholinesterase inhibitor produced by a Streptomyces species.

Journal: Journal of natural products 20120727

Title: Population structure and diversity of phenazine-1-carboxylic acid producing fluorescent Pseudomonas spp. from dryland cereal fields of central Washington State (USA).

Journal: Microbial ecology 20120701

Title: Quantitative investigation of resolution increase of free-flow electrophoresis via simple interval sample injection and separation.

Journal: Electrophoresis 20120701

Title: Elucidation of antifungal metabolites produced by Pseudomonas aurantiaca IB5-10 with broad-spectrum antifungal activity.

Journal: Journal of microbiology and biotechnology 20120301

Title: Chromophenazines from the terrestrial Streptomyces sp. Ank 315.

Journal: Journal of natural products 20120127

Title: Metabolic profiling and biological activities of bioactive compounds produced by Pseudomonas sp. strain ICTB-745 isolated from Ladakh, India.

Journal: Journal of microbiology and biotechnology 20120101

Title: Modeling physiological processes that relate toxicant exposure and bacterial population dynamics.

Journal: PloS one 20120101

Title: Synthesis and antibacterial activity against ralstonia solanacearum for novel hydrazone derivatives containing a pyridine moiety.

Journal: Chemistry Central journal 20120101

Title: Co-cultures of Pseudomonas aeruginosa and Roseobacter denitrificans reveal shifts in gene expression levels compared to solo cultures.

Journal: TheScientificWorldJournal 20120101

Title: Enhanced production of a novel cyclic hexapeptide antibiotic (NW-G01) by Streptomyces alboflavus 313 using response surface methodology.

Journal: International journal of molecular sciences 20120101

Title: The transcriptional regulator CzcR modulates antibiotic resistance and quorum sensing in Pseudomonas aeruginosa.

Journal: PloS one 20120101

Title: Transcriptional activation of pyoluteorin operon mediated by the LysR-type regulator PltR bound at a 22 bp lys box in Pseudomonas aeruginosa M18.

Journal: PloS one 20120101

Title: Bioelectricity enhancement via overexpression of quorum sensing system in Pseudomonas aeruginosa-inoculated microbial fuel cells.

Journal: Biosensors & bioelectronics 20111215

Title: Biological control of take-all by fluorescent Pseudomonas spp. from Chinese wheat fields.

Journal: Phytopathology 20111201

Title: Molecular identification of antagonistic bacteria from Tehran soils and evaluation of their inhibitory activities toward pathogenic fungi.

Journal: Iranian journal of microbiology 20110901

Title: The direct electrocatalysis of phenazine-1-carboxylic acid excreted by Pseudomonas alcaliphila under alkaline condition in microbial fuel cells.

Journal: Bioresource technology 20110701

Title: Phenazine-1-carboxylic acid is a more important contributor to biocontrol Fusarium oxysporum than pyrrolnitrin in Pseudomonas fluorescens strain Psd.

Journal: Microbiological research 20110520

Title: Stacking and determination of phenazine-1-carboxylic acid with low pKa in soil via moving reaction boundary formed by alkaline and double acidic buffers in capillary electrophoresis.

Journal: Analytical and bioanalytical chemistry 20110401

Title: Enhanced production of 2-hydroxyphenazine in Pseudomonas chlororaphis GP72.

Journal: Applied microbiology and biotechnology 20110101

Title: The ability of Pseudomonas sp. LBUM 223 to produce phenazine-1-carboxylic acid affects the growth of Streptomyces scabies, the expression of thaxtomin biosynthesis genes and the biological control potential against common scab of potato.

Journal: FEMS microbiology ecology 20110101

Title: Izumiphenazine D, a new phenazoquinoline N-oxide from Streptomyces sp. IFM 11204.

Journal: Chemical & pharmaceutical bulletin 20110101

Title: Regulatory feedback loop of two phz gene clusters through 5'-untranslated regions in Pseudomonas sp. M18.

Journal: PloS one 20110101

Title: Genetic approach for the fast discovery of phenazine producing bacteria.

Journal: Marine drugs 20110101

Title: Atomic resolution structure of EhpR: phenazine resistance in Enterobacter agglomerans Eh1087 follows principles of bleomycin/mitomycin C resistance in other bacteria.

Journal: BMC structural biology 20110101

Title: Genomic analysis and temperature-dependent transcriptome profiles of the rhizosphere originating strain Pseudomonas aeruginosa M18.

Journal: BMC genomics 20110101

Title: Bioactive pigments from marine bacteria: applications and physiological roles.

Journal: Evidence-based complementary and alternative medicine : eCAM 20110101

Title: Screening of Rhizobacteria for Their Plant Growth Promotion Ability and Antagonism Against Damping off and Root Rot Diseases of Broad Bean (Vicia faba L.).

Journal: Indian journal of microbiology 20110101

Title: Phenazine-1-carboxylic acid derivatives: design, synthesis and biological evaluation against Rhizoctonia solani Kuhn.

Journal: Bioorganic & medicinal chemistry letters 20101215

Title: Purification of low-concentration phenazine-1-carboxylic acid from fermentation broth of Pseudomonas sp. M18 via free flow electrophoresis with gratis gravity.

Journal: Electrophoresis 20101001

Title: Engineering a novel self-powering electrochemical biosensor.

Journal: Systems and synthetic biology 20100901

Title: Medium optimization for phenazine-1-carboxylic acid production by a gacA qscR double mutant of Pseudomonas sp. M18 using response surface methodology.

Journal: Bioresource technology 20100601

Title: Dermacozines, a new phenazine family from deep-sea dermacocci isolated from a Mariana Trench sediment.

Journal: Organic & biomolecular chemistry 20100521

Title: Enhancement of phenazine-1-carboxylic acid production using batch and fed-batch culture of gacA inactivated Pseudomonas sp. M18G.

Journal: Bioresource technology 20100501

Title: Optimization of phenazine-1-carboxylic acid production by a gacA/qscR-inactivated Pseudomonas sp. M18GQ harboring pME6032Phz using response surface methodology.

Journal: Applied microbiology and biotechnology 20100501

Title: Metabolism and function of phenazines in bacteria: impacts on the behavior of bacteria in the environment and biotechnological processes.

Journal: Applied microbiology and biotechnology 20100501

Title: Synthesis and fungicidal activity of novel aminophenazine-1-carboxylate derivatives.

Journal: Journal of agricultural and food chemistry 20100324

Title: Rapid monitoring of mRNA levels with a molecular beacon during microbial fermentation.

Journal: Journal of biotechnology 20100201

Title: Phenazines are not essential for Pseudomonas chlororaphis PA23 biocontrol of Sclerotinia sclerotiorum, but do play a role in biofilm formation.

Journal: FEMS microbiology ecology 20100101

Title: Complete genome sequence of the multiresistant taxonomic outlier Pseudomonas aeruginosa PA7.

Journal: PloS one 20100101

Title: Scarless and sequential gene modification in Pseudomonas using PCR product flanked by short homology regions.

Journal: BMC microbiology 20100101

Title: The distinct quorum sensing hierarchy of las and rhl in Pseudomonas sp. M18.

Journal: Current microbiology 20091201

Title: Characterization of a phenazine and hexanoyl homoserine lactone producing Pseudomonas aurantiaca strain PB-St2, isolated from sugarcane stem.

Journal: Journal of microbiology and biotechnology 20091201

Title: Utilizing RNA/DNA hybridization to directly quantify mRNA levels in microbial fermentation samples.

Journal: Journal of microbiological methods 20091101

Title: LysR family transcriptional regulator PqsR as repressor of pyoluteorin biosynthesis and activator of phenazine-1-carboxylic acid biosynthesis in Pseudomonas sp. M18.

Journal: Journal of biotechnology 20090810

Title: Lines of evidence for horizontal gene transfer of a phenazine producing operon into multiple bacterial species.

Journal: Journal of molecular evolution 20090201

Title: Antifungal activity of selected indigenous pseudomonas and bacillus from the soybean rhizosphere.

Journal: International journal of microbiology 20090101

Title: PhzA/B catalyzes the formation of the tricycle in phenazine biosynthesis.

Journal: Journal of the American Chemical Society 20081217

Title: Exploring antagonistic metabolites of established biocontrol agent of marine origin.

Journal: Applied biochemistry and biotechnology 20081201

Title: Characterization of Streptomyces spp. isolated from the sea surface microlayer in the Trondheim Fjord, Norway.

Journal: Marine drugs 20081201

Title: [Quorum sensing systems of regulation, synthesis of phenazine antibiotics, and antifungal (corrected) activity in rhizospheric bacterium Pseudomonas chlororaphis 449].

Journal: Genetika 20081201

Title: [Effects of insertional inactivation of gacS gene on two secondary metabolites in Psedomonas chlororaphis G-05].

Journal: Wei sheng wu xue bao = Acta microbiologica Sinica 20081201

Title: Genetic and functional diversity among fluorescent pseudomonads isolated from the rhizosphere of banana.

Journal: Microbial ecology 20081001

Title: Antimicrobial activity of Paenibacillus polymyxa SCE2 against some mycotoxin-producing fungi.

Journal: Journal of applied microbiology 20081001

Title: Use of Pseudomonas species producing phenazine-based metabolites in the anodes of microbial fuel cells to improve electricity generation.

Journal: Applied microbiology and biotechnology 20081001

Title: Metabolic degradation of phenazine-1-carboxylic acid by the strain Sphingomonas sp. DP58: the identification of two metabolites.

Journal: Biodegradation 20080901

Title: Rapid quantitative analysis of phenazine-1-carboxylic acid and 2-hydroxyphenazine from fermentation culture of Pseudomonas chlororaphis GP72 by capillary zone electrophoresis.

Journal: Talanta 20080715

Title: Medium factor optimization and fermentation kinetics for phenazine-1-carboxylic acid production by Pseudomonas sp. M18G.

Journal: Biotechnology and bioengineering 20080601

Title: Efficient purification of the biosurfactant viscosin from Pseudomonas libanensis strain M9-3 and its physicochemical and biological properties.

Journal: Journal of natural products 20080601

Title: Crystal structure of the pyocyanin biosynthetic protein PhzS.

Journal: Biochemistry 20080513

Title: Positive regulation of pyoluteorin biosynthesis in Pseudomonas sp. M18 by quorum-sensing regulator VqsR.

Journal: Journal of microbiology and biotechnology 20080501

Title: QscR acts as an intermediate in gacA-dependent regulation of PCA biosynthesis in Pseudomonas sp. M-18.

Journal: Current microbiology 20080401

Title: Redox reactions of phenazine antibiotics with ferric (hydr)oxides and molecular oxygen.

Journal: Environmental science & technology 20080401

Title: PltR expression modulated by the global regulators GacA, RsmA, LasI and RhlI in Pseudomonas sp. M18.

Journal: Research in microbiology 20080301

Title: Optimization of critical medium components using response surface methodology for phenazine-1-carboxylic acid production by Pseudomonas sp. M-18Q.

Journal: Journal of bioscience and bioengineering 20080301

Title: Las-like quorum-sensing system negatively regulates both pyoluteorin and phenazine-1-carboxylic acid production in Pseudomonas sp. M18.

Journal: Science in China. Series C, Life sciences 20080201

Title: Optimization of nutrient components for enhanced phenazine-1-carboxylic acid production by gacA-inactivated Pseudomonas sp. M18G using response surface method.

Journal: Applied microbiology and biotechnology 20080101

Title: Evidence of recent interkingdom horizontal gene transfer between bacteria and Candida parapsilosis.

Journal: BMC evolutionary biology 20080101

Title: [New amides of phenazine-1-carboxylic acid: antimicrobial activity and structure-activity relationship].

Journal: Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20080101

Title: Assessment of genetic and functional diversity of phosphate solubilizing fluorescent pseudomonads isolated from rhizospheric soil.

Journal: BMC microbiology 20080101

Title: Isolation, identification, and degradation characteristics of phenazine-1-carboxylic acid-degrading strain Sphingomonas sp. DP58.

Journal: Current microbiology 20071001

Title: Biosurfactants are involved in the biological control of Verticillium microsclerotia by Pseudomonas spp.

Journal: Journal of applied microbiology 20071001

Title: [Autoinduction of pyoluteorin and correlation between phenazine-1-carboxylic acid and pyoluteorin in Pseudomonas sp. M18].

Journal: Wei sheng wu xue bao = Acta microbiologica Sinica 20070601

Title: Correlation between antifungal agent phenazine-1-carboxylic acid and pyoluteorin biosynthesis in Pseudomonas sp. M18.

Journal: Current microbiology 20070401

Title: Characterization of a phenazine-producing strain Pseudomonas chlororaphis GP72 with broad-spectrum antifungal activity from green pepper rhizosphere.

Journal: Current microbiology 20070401

Title: [Construction of Pseudomonas sp. M18 qscR- mutant and its regulation on biosynthesis of PCA and Plt].

Journal: Wei sheng wu xue bao = Acta microbiologica Sinica 20070401

Title: RpoS as an intermediate in RsmA-dependent regulation of secondary antifungal metabolites biosynthesis in Pseudomonas sp. M18.

Journal: FEMS microbiology letters 20070301

Title: Structural and functional analysis of the pyocyanin biosynthetic protein PhzM from Pseudomonas aeruginosa.

Journal: Biochemistry 20070220

Title: Widespread pyocyanin over-production among isolates of a cystic fibrosis epidemic strain.

Journal: BMC microbiology 20070101

Title: [Effects of sigma38 subunit deletion of RNA polymerase on antibiotics biosynthesis in pseudomonas].

Journal: Wei sheng wu xue bao = Acta microbiologica Sinica 20061201

Title: The purification, crystallization and preliminary structural characterization of FAD-dependent monooxygenase PhzS, a phenazine-modifying enzyme from Pseudomonas aeruginosa.

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications 20061001

Title: The purification, crystallization and preliminary structural characterization of PhzM, a phenazine-modifying methyltransferase from Pseudomonas aeruginosa.

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications 20060901

Title: [Analysis of mechanism and relationship of GacA and RsmA, two regulators of antibiotics production in Pseudomonas sp. M18].

Journal: Wei sheng wu xue bao = Acta microbiologica Sinica 20060801

Title: [Negative regulation on PCA production is not correlated with positive regulation on BHL and HHL synthesis by gacA in Pseudomonas sp. M18].

Journal: Wei sheng wu xue bao = Acta microbiologica Sinica 20060601

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Detection of antibiotic-related genes from bacterial biocontrol agents with polymerase chain reaction.

Journal: Canadian journal of microbiology 20060501

Title: Biocontrol of avocado dematophora root rot by antagonistic Pseudomonas fluorescens PCL1606 correlates with the production of 2-hexyl 5-propyl resorcinol.

Journal: Molecular plant-microbe interactions : MPMI 20060401

Title: Inhibition of Salmonella enterica by plant-associated pseudomonads in vitro and on sprouting alfalfa seed.

Journal: Journal of food protection 20060401

Title: Genetic diversity of phenazine- and pyoluteorin-producing pseudomonads isolated from green pepper rhizosphere.

Journal: Archives of microbiology 20060301

Title: Gluconic acid: an antifungal agent produced by Pseudomonas species in biological control of take-all.

Journal: Phytochemistry 20060301

Title: Regulatory roles of psrA and rpoS in phenazine-1-carboxamide synthesis by Pseudomonas chlororaphis PCL1391.

Journal: Microbiology (Reading, England) 20060101

Title: [Lectins modulate the cytostatic action of the composite bioregulators-conjugates of azaanalogues of pyrimidine and phenazine-1-carboxilic acid in Bacillus subtilis test-system].

Journal: Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20060101

Title: Ascomycete communities in the rhizosphere of field-grown wheat are not affected by introductions of genetically modified Pseudomonas putida WCS358r.

Journal: Environmental microbiology 20051101

Title: Pyocyanin and its precursor phenazine-1-carboxylic acid increase IL-8 and intercellular adhesion molecule-1 expression in human airway epithelial cells by oxidant-dependent mechanisms.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20050915

Title: [Differential effect of temperature on Plt and PCA synthesis in a rsmA inactivated mutant strain of Pseudomonas sp. M-18].

Journal: Sheng wu gong cheng xue bao = Chinese journal of biotechnology 20050101

Title: The TyrA family of aromatic-pathway dehydrogenases in phylogenetic context.

Journal: BMC biology 20050101

Title: [Differential regulation of phenazine-1-carboxylic acid and pyoluteorin production mediated by inactivated gacA in Pseudomonas sp. M18].

Journal: Wei sheng wu xue bao = Acta microbiologica Sinica 20041201

Title: Structure of the phenazine biosynthesis enzyme PhzG.

Journal: Acta crystallographica. Section D, Biological crystallography 20041101

Title: Structure and function of the phenazine biosynthesis protein PhzF from Pseudomonas fluorescens 2-79.

Journal: Biochemistry 20041005

Title: Phenazine-1-carboxylic acid is negatively regulated and pyoluteorin positively regulated by gacA in Pseudomonas sp. M18.

Journal: FEMS microbiology letters 20040801

Title: Transformation of Pseudomonas fluorescens with genes for biosynthesis of phenazine-1-carboxylic acid improves biocontrol of rhizoctonia root rot and in situ antibiotic production.

Journal: FEMS microbiology ecology 20040801

Title: Minimal changes in rhizobacterial population structure following root colonization by wild type and transgenic biocontrol strains.

Journal: FEMS microbiology ecology 20040801

Title: Overexpression, purification and crystallization of PhzA, the first enzyme of the phenazine biosynthesis pathway of Pseudomonas fluorescens 2-79.

Journal: Acta crystallographica. Section D, Biological crystallography 20040601

Title: Identification and characterization of pltZ, a gene involved in the repression of pyoluteorin biosynthesis in Pseudomonas sp. M18.

Journal: FEMS microbiology letters 20040319

Title: The purification, crystallization and preliminary structural characterization of PhzF, a key enzyme in the phenazine-biosynthesis pathway from Pseudomonas fluorescens 2-79.

Journal: Acta crystallographica. Section D, Biological crystallography 20040101

Title: Phenazine-1-carboxylic acid, a secondary metabolite of Pseudomonas aeruginosa, alters expression of immunomodulatory proteins by human airway epithelial cells.

Journal: American journal of physiology. Lung cellular and molecular physiology 20030901

Title: Isolation and in vitro and in vivo activity against Phytophthora capsici and Colletotrichum orbiculare of phenazine-1-carboxylic acid from Pseudomonas aeruginosa strain GC-B26.

Journal: Pest management science 20030801

Title: [Gene cloning of rpoD and its impact on biosynthesis of antibiotics in Fluorescent pseudomonas M18].

Journal: Wei sheng wu xue bao = Acta microbiologica Sinica 20030601

Title: Effect of genotype and root colonization in biological control of fusarium wilts in pigeonpea and chickpea by Pseudomonas aeruginosa PNA1.

Journal: Canadian journal of microbiology 20030201

Title: [The production of antifungal metabolites by Pseudomonas chlororaphis grown on different nutrient sources].

Journal: Mikrobiologiia 20030101

Title: Field releases of genetically modified micro-organisms.

Journal: Environmental biosafety research 20030101

Title: Enhancement of population densities of fluorescent pseudomonads in the rhizosphere of tomato plants by addition of acibenzolar-S-methyl.

Journal: Canadian journal of microbiology 20021201

Title: Fungal ABC transporters and microbial interactions in natural environments.

Journal: Molecular plant-microbe interactions : MPMI 20021101

Title: Endophenazines A-D, new phenazine antibiotics from the arthropod associated endosymbiont Streptomyces anulatus. I. Taxonomy, fermentation, isolation and biological activities.

Journal: The Journal of antibiotics 20020901

Title: Effects of Pseudomonas putida modified to produce phenazine-1-carboxylic acid and 2,4-diacetylphloroglucinol on the microflora of field grown wheat.

Journal: Antonie van Leeuwenhoek 20020801

Title: [The production of phenazine antibiotics by the Pseudomonas aureofaciens strain with plasmid-controlled resistance to cobalt and nickel].

Journal: Mikrobiologiia 20020101

Title: [Determination of phenazine-1-carboxylic acid in anti-fungal agent M18 by high performance liquid chromatography].

Journal: Se pu = Chinese journal of chromatography 20011101

Title: Introduction of the phzH gene of Pseudomonas chlororaphis PCL1391 extends the range of biocontrol ability of phenazine-1-carboxylic acid-producing Pseudomonas spp. strains.

Journal: Molecular plant-microbe interactions : MPMI 20010801

Title: Cloning and sequencing of a novel human gene which encodes a putative hydroxylase.

Journal: Journal of human genetics 20010101

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Tags:2538-68-3 Molecular Formula|2538-68-3 MDL|2538-68-3 SMILES|2538-68-3 Phenazine-1-carboxylic acid