PYRROLNITRIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H6Cl2N2O2
Molecular Weight	257.073
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[O-][N+](=O)C1=C(Cl)C=CC=C1C2=CNC=C2Cl

InChI

InChIKey=QJBZDBLBQWFTPZ-UHFFFAOYSA-N

InChI=1S/C10H6Cl2N2O2/c11-8-3-1-2-6(10(8)14(15)16)7-4-13-5-9(7)12/h1-5,13H

HIDE SMILES / InChI

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/4310080
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/5785951

Pyrrolnitrin is an antifungal antibiotic and is most active against dermatophytic fungi, especially the species of Trichophyton. Fist, physical and chemical properties of pyrrolnitrin was described by Arima et al. It is synthesized from tryptophan, and the synthesis is probably initiated by a chloroperoxidase enzyme system acting on tryptophan. The present report deals with the mechanism of action of pyrrolnitrin. Pseudomonas pyrrocinia and other Pseudomonas species produce pyrrolnitrin from tryptophan as secondary metabolite. Pyrrolnitrin inhibits fungal growth by inhibiting the respiratory electron transport system.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
respiratory electron transport chain 1 Target ID: GO:0022904 Sources: http://www.ncbi.nlm.nih.gov/pubmed/4310080	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Mycoses 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5785951	Curative		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Beneficial bacteria of agricultural importance.	2010-11	20635120
T4 genes in the marine ecosystem: studies of the T4-like cyanophages and their role in marine ecology.	2010-10-28	21029435
Gene expression enabling synthetic diversification of natural products: chemogenetic generation of pacidamycin analogs.	2010-09-08	20712319
The ternary complex of PrnB (the second enzyme in the pyrrolnitrin biosynthesis pathway), tryptophan, and cyanide yields new mechanistic insights into the indolamine dioxygenase superfamily.	2010-07-02	20421301
Chemical, physical and biological approaches to prevent ochratoxin induced toxicoses in humans and animals.	2010-07	22069658
Combination of fluorescent reporters for simultaneous monitoring of root colonization and antifungal gene expression by a biocontrol pseudomonad on cereals with flow cytometry.	2010-07	20521957
Evaluation of multiple plant growth promoting traits of an isolate of Pseudomonas fluorescens strain Psd.	2010-06	20882763
Effects of pesticides on the bacterial production of pyrrolnitrin.	2010-05-12	20373823
Phenazines are not essential for Pseudomonas chlororaphis PA23 biocontrol of Sclerotinia sclerotiorum, but do play a role in biofilm formation.	2010-01	19889032
Proteomic detection of non-annotated protein-coding genes in Pseudomonas fluorescens Pf0-1.	2009-12-24	20041161
Microsatellite stability in the plant pathogen Botrytis cinerea after exposure to different selective pressures.	2009-11-30	21036339
Effects of nutrients on quorum signals and secondary metabolite productions of Burkholderia sp. O33.	2009-10	19884772
Specific rhizosphere bacterial and fungal groups respond differently to elevated atmospheric CO(2).	2009-10	19536195
Design, synthesis, and fungicidal activity of novel analogues of pyrrolnitrin.	2009-09-09	19681615
Production of the antifungal compound pyrrolnitrin is quorum sensing-regulated in members of the Burkholderia cepacia complex.	2009-06	19220396
Synthesis of pyrrolnitrin and related halogenated phenylpyrroles.	2009-03-05	19196161
Differential effectiveness of Serratia plymuthica IC1270-induced systemic resistance against hemibiotrophic and necrotrophic leaf pathogens in rice.	2009-01-22	19161601
Mobile genetic elements in the genome of the beneficial rhizobacterium Pseudomonas fluorescens Pf-5.	2009-01-13	19144133
Genomics of pyrrolnitrin biosynthetic loci: evidence for conservation and whole-operon mobility within gram-negative bacteria.	2009-01	18793314
Antifungal activity of selected indigenous pseudomonas and bacillus from the soybean rhizosphere.	2009	20016811
Assessment of genetic and functional diversity of phosphate solubilizing fluorescent pseudomonads isolated from rhizospheric soil.	2008-12-20	19099598
Genetic and functional diversity among fluorescent pseudomonads isolated from the rhizosphere of banana.	2008-10	18347847
Halogenase genes in nonribosomal peptide synthetase gene clusters of Microcystis (cyanobacteria): sporadic distribution and evolution.	2008-09	18614525
Characterization of a new isolate of Pseudomonas fluorescens strain Psd as a potential biocontrol agent.	2008-08	18565138
Novel oxidized derivatives of antifungal pyrrolnitrin from the bacterium Burkholderia cepacia K87.	2008-07	18776654
Sensing of oxygen in microtiter plates: a novel tool for screening drugs against pathogenic yeasts.	2008-07	18297273
Overlapping protein-encoding genes in Pseudomonas fluorescens Pf0-1.	2008-06-13	18551168
Acetylcholinesterase-inhibiting activity of pyrrole derivatives from a novel marine gliding bacterium, Rapidithrix thailandica.	2008	19172195
The second enzyme in pyrrolnitrin biosynthetic pathway is related to the heme-dependent dioxygenase superfamily.	2007-10-30	17924666
Characterization of CMR5c and CMR12a, novel fluorescent Pseudomonas strains from the cocoyam rhizosphere with biocontrol activity.	2007-10	17897205
Quorum-sensing signaling is required for production of the antibiotic pyrrolnitrin in a rhizospheric biocontrol strain of Serratia plymuthica.	2007-05	17355597
Preliminary crystallographic characterization of PrnB, the second enzyme in the pyrrolnitrin biosynthetic pathway.	2006-11-01	17077497
Probing the substrate specificity of aminopyrrolnitrin oxygenase (PrnD) by mutational analysis.	2006-09	16923884
Detection of antibiotic-related genes from bacterial biocontrol agents with polymerase chain reaction.	2006-05	16699573
Evaluation of Bacterial Antagonists for Biological Control of Broccoli Head Rot Caused by Pseudomonas fluorescens.	2006-04	18943423
Recent developments in enzymatic chlorination.	2006-04	16572225
Mechanistic studies on the conversion of arylamines into arylnitro compounds by aminopyrrolnitrin oxygenase: identification of intermediates and kinetic studies.	2006-01-16	16342311
Reconstitution and characterization of aminopyrrolnitrin oxygenase, a Rieske N-oxygenase that catalyzes unusual arylamine oxidation.	2005-11-04	16150698
Residue level, persistence, and storage performance of citrus fruit treated with fludioxonil.	2005-08-24	16104790
Three Prochlorococcus cyanophage genomes: signature features and ecological interpretations.	2005-05	15828858
Use of green fluorescent protein-based reporters to monitor balanced production of antifungal compounds in the biocontrol agent Pseudomonas fluorescens CHA0.	2005	15960662
[Tryptophan 7-halogenase from Pseudomonas aureofaciens ACN strain: gene cloning and sequencing and the enzyme expression].	2004-10-08	15469014
A novel halogenase gene from the pentachloropseudilin producer Actinoplanes sp. ATCC 33002 and detection of in vitro halogenase activity.	2004-08-15	15321684
Crystallization and X-ray diffraction of a halogenating enzyme, tryptophan 7-halogenase, from Pseudomonas fluorescens.	2004-08	15272170
Cloning and sequencing of the gene of tryptophan-7-halogenase from Pseudomonas fluorescens strain CHA0.	2004-06	15236607
PCR-based identification and characterization of Burkholderia cepacia complex bacteria from clinical and environmental sources.	2004	15482431
Polymorphisms within the prnD and pltC genes from pyrrolnitrin and pyoluteorin-producing Pseudomonas and Burkholderia spp.	2003-02-01	19719693
Genetic Diversity of phlD from 2,4-Diacetylphloroglucinol-Producing Fluorescent Pseudomonas spp.	2001-01	18944276
Pyrrolnitrin and related pyrroles endowed with antibacterial activities against Mycobacterium tuberculosis.	1998-10-20	9873650
Screening for new compounds with antiherpes activity.	1984-10	6517562

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Pyrrolnitrin caused drastic swelling of mitochondria in isotonic solutions of alkali metal salts and of sucrose without any addition of substrate for the respiratory chain in mitochondria. The swelling induced by pyrrolnitrin was characterized by a biphasic swelling process; a very fast initial swelling and thereafter a very slow speed secondary swelling. The increase of pyrrolnitrin concentration exponentially increased the magnitude of over-all rapid swelling. Pyrrolnitrin enhance the latent ATPase activity of mitochondria at the similar range of concentrations to those needed for the induction of the swelling. The concentrations of pyrrolnitrin where mitochondrial swelling was induced were found to be far lower than those needed for the exhibition of inhibitory effect on the electron transport system of mitochondria.

Name

Type

Language

NSC-107654

Preferred Name

English

PYRROLNITRIN

Official Name

English

pyrrolnitrin [INN]

Common Name

English

PYRROLNITRIN [MART.]

Common Name

English

1H-PYRROLE, 3-CHLORO-4-(3-CHLORO-2-NITROPHENYL)-

Systematic Name

English

PYRROLNITRIN [JAN]

Common Name

English

3-Chloro-4-(3-chloro-2-nitrophenyl)pyrrole

Systematic Name

English

Pyrrolnitrin [WHO-DD]

Common Name

English

PYRROLNITRIN [USAN]

Common Name

English

PYRROLNITRIN [MI]

Common Name

English

Classification Tree Code System Code

WHO-ATC

D01AA07