Pyrrolnitrin | CAS# 1018-71-9 | antifungal antibiotic

Pyrrolnitrin
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 415012

CAS#: 1018-71-9

Description: Pyrrolnitrin is an antifungal antibiotic isolated from Pseudomonas pyrrocinia. It is effective mainly against Trichophyton, Microsporium, Epidermophyton, and Penicillium.

Chemical Structure

Pyrrolnitrin

CAS# 1018-71-9

Instruction

Theoretical Analysis

MedKoo Cat#: 415012
Name: Pyrrolnitrin
CAS#: 1018-71-9
Chemical Formula: C10H6Cl2N2O2
Exact Mass: 255.98
Molecular Weight: 257.070
Elemental Analysis: C, 46.72; H, 2.35; Cl, 27.58; N, 10.90; O, 12.45

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 550	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Pyrrolnitrin; NSC107654; NSC-107654; NSC 107654

IUPAC/Chemical Name: 1H-Pyrrole, 3-chloro-4-(3-chloro-2-nitrophenyl)-

InChi Key: QJBZDBLBQWFTPZ-UHFFFAOYSA-N

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

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

Appearance: Solid powder

Purity: >97% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 257.07 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Pawar S, Chaudhari A, Prabha R, Shukla R, Singh DP. Microbial Pyrrolnitrin: Natural Metabolite with Immense Practical Utility. Biomolecules. 2019 Sep 3;9(9):443. doi: 10.3390/biom9090443. PMID: 31484394; PMCID: PMC6769897.

2: Pawar S, Chaudhari A. Pyrrolnitrin from Rhizospheric Serratia marcescens NCIM 5696: Optimization of Process Parameters Using Statistical Tools and Seed- Applied Bioprotectants for Vigna radiata (L.) Against Fusarium oxysporum MTCC 9913. Appl Biochem Biotechnol. 2020 Mar;190(3):803-825. doi: 10.1007/s12010-019-03123-w. Epub 2019 Sep 7. PMID: 31493159.

3: Wu X, Chi X, Wang Y, Zhang K, Kai L, He Q, Tang J, Wang K, Sun L, Hao X, Xie W, Ge Y. vfr, A Global Regulatory Gene, is Required for Pyrrolnitrin but not for Phenazine-1-carboxylic Acid Biosynthesis in Pseudomonas chlororaphis G05. Plant Pathol J. 2019 Aug;35(4):351-361. doi: 10.5423/PPJ.OA.01.2019.0011. Epub 2019 Aug 1. PMID: 31481858; PMCID: PMC6706016.

4: Huang R, Feng Z, Chi X, Sun X, Lu Y, Zhang B, Lu R, Luo W, Wang Y, Miao J, Ge Y. Pyrrolnitrin is more essential than phenazines for Pseudomonas chlororaphis G05 in its suppression of Fusarium graminearum. Microbiol Res. 2018 Oct;215:55-64. doi: 10.1016/j.micres.2018.06.008. Epub 2018 Jun 18. PMID: 30172309.

5: van Pée KH, Ligon JM. Biosynthesis of pyrrolnitrin and other phenylpyrrole derivatives by bacteria. Nat Prod Rep. 2000 Apr;17(2):157-64. doi: 10.1039/a902138h. PMID: 10821110.

6: Keum YS, Zhu YZ, Kim JH. Structure-inhibitory activity relationships of pyrrolnitrin analogues on its biosynthesis. Appl Microbiol Biotechnol. 2011 Feb;89(3):781-9. doi: 10.1007/s00253-010-2872-0. Epub 2010 Sep 24. PMID: 20865257.

7: Luo W, Miao J, Feng Z, Lu R, Sun X, Zhang B, Ding W, Lu Y, Wang Y, Chi X, Ge Y. Construction of a β-galactosidase-gene-based fusion is convenient for screening candidate genes involved in regulation of pyrrolnitrin biosynthesis in Pseudomonas chlororaphis G05. J Gen Appl Microbiol. 2019 Jan 24;64(6):259-268. doi: 10.2323/jgam.2018.01.003. Epub 2018 May 28. PMID: 29806629.

8: Zhang J, Mavrodi DV, Yang M, Thomashow LS, Mavrodi OV, Kelton J, Weller DM. Pseudomonas synxantha 2-79 Transformed with Pyrrolnitrin Biosynthesis Genes Has Improved Biocontrol Activity Against Soilborne Pathogens of Wheat and Canola. Phytopathology. 2020 May;110(5):1010-1017. doi: 10.1094/PHYTO-09-19-0367-R. Epub 2020 Mar 24. PMID: 32065038; PMCID: PMC7238759.

9: Keum YS, Lee HR, Kim JH. Effects of pesticides on the bacterial production of pyrrolnitrin. J Agric Food Chem. 2010 May 12;58(9):5531-7. doi: 10.1021/jf904195j. PMID: 20373823.

10: el-Banna N, Winkelmann G. Pyrrolnitrin from Burkholderia cepacia: antibiotic activity against fungi and novel activities against streptomycetes. J Appl Microbiol. 1998 Jul;85(1):69-78. doi: 10.1046/j.1365-2672.1998.00473.x. PMID: 9721657.

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