Pyoluteorin | CAS#25683-07-2 | Antifungal agent

MedKoo Cat#: 558450 | Name: Pyoluteorin

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Description:

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

Pyoluteorin is an antifungal agent composed of a 4,5-dichlorinated pyrrole group linked to a resorcinol moiety. The pyoluteorin biosynthetic gene cluster in Pseudomonas fluorescens Pf-5 encodes the halogenase PltA, which has been previously demonstrated to perform both chlorinations in vitro. Pyoluteorin protects various plants from diseases caused by soilborne pathogenic fungi.

Chemical Structure

Pyoluteorin

CAS#25683-07-2

Theoretical Analysis

MedKoo Cat#: 558450

Name: Pyoluteorin

CAS#: 25683-07-2

Chemical Formula: C11H7Cl2NO3

Exact Mass: 270.9803

Molecular Weight: 272.08

Elemental Analysis: C, 48.56; H, 2.59; Cl, 26.06; N, 5.15; O, 17.64

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 500.00	2 Weeks

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Related CAS #

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Synonym

Pyoluteorin; NSC 143092; NSC143092; NSC143092;

IUPAC/Chemical Name

Ketone, 4,5-dichloropyrrol-2-yl 2,6-dihydroxyphenyl

InChi Key

JPGWTZORMBTNMF-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H7Cl2NO3/c12-5-4-6(14-11(5)13)10(17)9-7(15)2-1-3-8(9)16/h1-4,14-16H

SMILES Code

O=C(C1=CC(Cl)=C(Cl)N1)C2=C(O)C=CC=C2O

Appearance

Solid powder

Purity

>98% (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

Soluble in DMSO

Shelf Life

>3 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

2934.99.03.00

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Pyoluteorin demonstrates antibiotic, antifungal, and herbicidal activity. Pyoluteorin production is influenced by positive autoregulation and has been shown to function as a signal molecule negatively regulating additional secondary metabolites produced by Pseudomonas.

In vitro activity:

Pyoluteorin showed significant anti-tumor effects on human non-small cell lung cancer cell lines H1299 (IC50 = 1.57 µM) and H2030 (IC50 = 1.94 µM). Pyoluteorin could induce apoptosis and autophagy as evidence by the upregulation of caspase3 activity, the accumulation of LC3 and expression of apoptosis, or autophagy related proteins. Pyoluteorin induced autophagy through the c-Jun N-terminal kinase/B-cell lymphoma-2 (JNK/Bcl-2) signal pathway. Reference: Biol Pharm Bull. 2021;44(7):976-983. https://pubmed.ncbi.nlm.nih.gov/34193693/

In vivo activity:

To be determined

Preparing Stock Solutions

The following data is based on the product molecular weight 272.08 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:

1. Fan D, Yu S, Yang Y, Qu S. Pyoluteorin Induces Apoptosis and Autophagy in NSCLC Cells. Biol Pharm Bull. 2021;44(7):976-983. doi: 10.1248/bpb.b21-00120. PMID: 34193693. 2. Brodhagen M, Henkels MD, Loper JE. Positive autoregulation and signaling properties of pyoluteorin, an antibiotic produced by the biological control organism Pseudomonas fluorescens Pf-5. Appl Environ Microbiol. 2004 Mar;70(3):1758-66. doi: 10.1128/AEM.70.3.1758-1766.2004. PMID: 15006802; PMCID: PMC368289.

In vitro protocol:

In vivo protocol:

To be determined

1: Pang AH, Garneau-Tsodikova S, Tsodikov OV. Crystal structure of halogenase PltA from the pyoluteorin biosynthetic pathway. J Struct Biol. 2015 Dec;192(3):349-357. doi: 10.1016/j.jsb.2015.09.013. Epub 2015 Sep 28. PubMed PMID: 26416533. 2: Doi K, Gowda K, Liu Q, Lin JM, Sung SS, Dower C, Claxton D, Loughran TP Jr, Amin S, Wang HG. Pyoluteorin derivatives induce Mcl-1 degradation and apoptosis in hematological cancer cells. Cancer Biol Ther. 2014;15(12):1688-99. doi: 10.4161/15384047.2014.972799. PubMed PMID: 25535900; PubMed Central PMCID: PMC4623387. 3: Yan Q, Philmus B, Hesse C, Kohen M, Chang JH, Loper JE. The Rare Codon AGA Is Involved in Regulation of Pyoluteorin Biosynthesis in Pseudomonas protegens Pf-5. Front Microbiol. 2016 Apr 19;7:497. doi: 10.3389/fmicb.2016.00497. eCollection 2016. PubMed PMID: 27148187; PubMed Central PMCID: PMC4836200. 4: Jaremko MJ, Lee DJ, Opella SJ, Burkart MD. Structure and Substrate Sequestration in the Pyoluteorin Type II Peptidyl Carrier Protein PltL. J Am Chem Soc. 2015 Sep 16;137(36):11546-9. doi: 10.1021/jacs.5b04525. Epub 2015 Sep 4. PubMed PMID: 26340431; PubMed Central PMCID: PMC4847951. 5: Vinay JU, Naik MK, Rangeshwaran R, Chennappa G, Shaikh SS, Sayyed RZ. Detection of antimicrobial traits in fluorescent pseudomonads and molecular characterization of an antibiotic pyoluteorin. 3 Biotech. 2016 Dec;6(2):227. doi: 10.1007/s13205-016-0538-z. Epub 2016 Oct 20. PubMed PMID: 28330299; PubMed Central PMCID: PMC5073079. 6: Kidarsa TA, Goebel NC, Zabriskie TM, Loper JE. Phloroglucinol mediates cross-talk between the pyoluteorin and 2,4-diacetylphloroglucinol biosynthetic pathways in Pseudomonas fluorescens Pf-5. Mol Microbiol. 2011 Jul;81(2):395-414. doi: 10.1111/j.1365-2958.2011.07697.x. Epub 2011 May 26. PubMed PMID: 21564338. 7: Brodhagen M, Paulsen I, Loper JE. Reciprocal regulation of pyoluteorin production with membrane transporter gene expression in Pseudomonas fluorescens Pf-5. Appl Environ Microbiol. 2005 Nov;71(11):6900-9. PubMed PMID: 16269724; PubMed Central PMCID: PMC1287665. 8: Li S, Huang X, Wang G, Xu Y. Transcriptional activation of pyoluteorin operon mediated by the LysR-type regulator PltR bound at a 22 bp lys box in Pseudomonas aeruginosa M18. PLoS One. 2012;7(6):e39538. doi: 10.1371/journal.pone.0039538. Epub 2012 Jun 25. PubMed PMID: 22761817; PubMed Central PMCID: PMC3382589. 9: Nowak-Thompson B, Chaney N, Wing JS, Gould SJ, Loper JE. Characterization of the pyoluteorin biosynthetic gene cluster of Pseudomonas fluorescens Pf-5. J Bacteriol. 1999 Apr;181(7):2166-74. PubMed PMID: 10094695; PubMed Central PMCID: PMC93630. 10: Brodhagen M, Henkels MD, Loper JE. Positive autoregulation and signaling properties of pyoluteorin, an antibiotic produced by the biological control organism Pseudomonas fluorescens Pf-5. Appl Environ Microbiol. 2004 Mar;70(3):1758-66. PubMed PMID: 15006802; PubMed Central PMCID: PMC368289. 11: Ge YH, Zhao YH, Chen LJ, Miao J, Wen L. [Autoinduction of pyoluteorin and correlation between phenazine-1-carboxylic acid and pyoluteorin in Pseudomonas sp. M18]. Wei Sheng Wu Xue Bao. 2007 Jun;47(3):441-6. Chinese. PubMed PMID: 17672302. 12: Hassan MN, Afghan S, Hafeez FY. Biological control of red rot in sugarcane by native pyoluteorin-producing Pseudomonas putida strain NH-50 under field conditions and its potential modes of action. Pest Manag Sci. 2011 Sep;67(9):1147-54. doi: 10.1002/ps.2165. Epub 2011 Apr 14. PubMed PMID: 21495154. 13: Zhang J, Wang W, Lu X, Xu Y, Zhang X. The stability and degradation of a new biological pesticide, pyoluteorin. Pest Manag Sci. 2010 Mar;66(3):248-52. doi: 10.1002/ps.1856. PubMed PMID: 19834883. 14: Ramette A, Frapolli M, Fischer-Le Saux M, Gruffaz C, Meyer JM, Défago G, Sutra L, Moënne-Loccoz Y. Pseudomonas protegens sp. nov., widespread plant-protecting bacteria producing the biocontrol compounds 2,4-diacetylphloroglucinol and pyoluteorin. Syst Appl Microbiol. 2011 May;34(3):180-8. doi: 10.1016/j.syapm.2010.10.005. Epub 2011 Mar 9. PubMed PMID: 21392918. 15: Chen J, Wang W, Xu Y, Zhang X. Slow-release formulation of a new biological pesticide, pyoluteorin, with mesoporous silica. J Agric Food Chem. 2011 Jan 12;59(1):307-11. doi: 10.1021/jf103640t. Epub 2010 Dec 8. PubMed PMID: 21141897. 16: Kilani-Feki O, Khiari O, Culioli G, Ortalo-Magné A, Zouari N, Blache Y, Jaoua S. Antifungal activities of an endophytic Pseudomonas fluorescens strain Pf1TZ harbouring genes from pyoluteorin and phenazine clusters. Biotechnol Lett. 2010 Sep;32(9):1279-85. doi: 10.1007/s10529-010-0286-9. Epub 2010 May 11. PubMed PMID: 20458521. 17: Huang XQ, Ge YH, Zhang XH, Xu YQ. [Transcriptional repression of pltZ on pyoluteorin ABC transporter of Pseudomonas sp. M18]. Wei Sheng Wu Xue Bao. 2005 Jun;45(3):344-8. Chinese. PubMed PMID: 15989223. 18: Thomas MG, Burkart MD, Walsh CT. Conversion of L-proline to pyrrolyl-2-carboxyl-S-PCP during undecylprodigiosin and pyoluteorin biosynthesis. Chem Biol. 2002 Feb;9(2):171-84. PubMed PMID: 11880032. 19: Ge Y, Huang X, Wang S, Zhang X, Xu Y. Phenazine-1-carboxylic acid is negatively regulated and pyoluteorin positively regulated by gacA in Pseudomonas sp. M18. FEMS Microbiol Lett. 2004 Aug 1;237(1):41-7. PubMed PMID: 15268936. 20: Nowak-Thompson B, Gould SJ, Loper JE. Identification and sequence analysis of the genes encoding a polyketide synthase required for pyoluteorin biosynthesis in Pseudomonas fluorescens Pf-5. Gene. 1997 Dec 19;204(1-2):17-24. PubMed PMID: 9434161.