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P8861

Sigma-Aldrich

Pyrrolnitrin from Pseudomonas cepacia

≥98% (HPLC), solid

Synonym(s):

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

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About This Item

CAS Number:
1018-71-9
EC Number:
213-812-7
MDL number:
MFCD00865605
UNSPSC Code:
12352200
PubChem Substance ID:
24898985
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

200

Assay

≥98% (HPLC)

form

solid

antibiotic activity spectrum

fungi

Mode of action

enzyme | inhibits

shipped in

wet ice

storage temp.

−20°C

SMILES string

[O-][N+](=O)c1c(Cl)cccc1-c2c[nH]cc2Cl

InChI

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

InChI key

QJBZDBLBQWFTPZ-UHFFFAOYSA-N

Specificity

The purified antibiotic has strong antifungal activity and is less efficient against bacteria or yeast.

Application

Pyrrolnitrin from Pseudomonas cepacia has been used as a standard in the detection of pyrrolnitrin in Serratia marcescens cell culture extract.[1]

Biochem/physiol Actions

Pyrrolnitrin blocks the terminal electron transport between succinate or reduced NADH and coenzyme Q. In mitochondria preparations of S. cerevisiae, the antibiotic inhibited succinate oxidase, NADH oxidase, succinate cythochrome C reductase, and NADH-cytochrome C reductase. Pyrrolnitrin is involved in many cellular processes such as oxidative stress, electron transport, DNA and RNA synthesis.
Pyrrolnitrin is a metabolite, produced by Pseudomonas sp.[2]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000245427
0000240719
0000284651
0000281003

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Magdalena M Rose et al.
Environmental microbiology, 23(9), 5525-5540 (2021-08-05)
The unicellular alga Chlamydomonas reinhardtii and the bacterium Pseudomonas protegens serve as a model to study the interactions between photosynthetic and heterotrophic microorganisms. P. protegens secretes the cyclic lipopeptide orfamide A that interferes with cytosolic Ca2+ homeostasis in C. reinhardtii
El-Banna, N., and Winkelmann, G.
Applied Microbiology, 85, 69-69 (1998)
Chernin, L., et al.
Current Microbiology, 32, 208-208 (1996)
Natural Antimicrobials for the Minimal Processing of Foods, 201-201 (2003)
Suppression of damping-off of cucumber caused by Pythium ultimum with live cells and extracts of Serratia marcescens N4-5
Roberts DP, et al.
Soil Biology and Biochemistry, 39(9), 2275-2288 (2007)

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