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P8861

Sigma-Aldrich

Pyrrolnitrin from Pseudomonas cepacia

≥98% (HPLC), solid

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Synonym(s):
3-Chloro-4-(3-chloro-2-nitrophenyl)pyrrole
CAS Number:
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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1 of 4

This Item
SML1057SML0122R1033
Sigma-Aldrich

Sigma-Aldrich

SML1057

NPP

Sigma-Aldrich

Sigma-Aldrich

SML0122

Pit-1

RN-1747 ≥98% (HPLC)

Sigma-Aldrich

R1033

RN-1747

form

solid

form

powder

form

powder

form

powder

shipped in

wet ice

shipped in

-

shipped in

-

shipped in

-

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

antibiotic activity spectrum

fungi

antibiotic activity spectrum

-

antibiotic activity spectrum

-

antibiotic activity spectrum

-

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.

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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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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
Chernin, L., et al.
Current Microbiology, 32, 208-208 (1996)
El-Banna, N., and Winkelmann, G.
Applied Microbiology, 85, 69-69 (1998)
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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