Shanghai Nianxing Industrial Co., Ltd
China
Product Name: Pyoluteorin
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Purity: 98.0%
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DC Chemicals Limited
China
Product Name: Pyoluteorin
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Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: Methanone,(4,5-dichloro-1H-pyrrol-2-yl)(2,6-dihydroxyphenyl)-
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Purity: 98.0%
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25683-07-2

25683-07-2 structure

Name: Pyoluteorin
Chemical Name: (4,5-dichloro-1H-pyrrol-2-yl)-(2,6-dihydroxyphenyl)methanone
CAS Number: 25683-07-2
Molecular Formula: C₁₁H₇Cl₂NO₃
Molecular Weight: 272.08400
Catalog: Signaling Pathways Anti-infection Fungal
Create Date: 2016-05-19 12:56:39
Modify Date: 2024-01-07 14:16:55
Pyoluteorin is an antibiotic that inhibits Oomycete fungi, including the plant pathogen Pythium ultimum, and suppresses plant diseases caused by this fungus[1]. Pyoluteorin induces human triple-negative breast cancer MDA-MB-231 cells apoptosis in vitro. Pyoluteorin can be used for the research of human triple-negative breast cancer[2].

Name	(4,5-dichloro-1H-pyrrol-2-yl)-(2,6-dihydroxyphenyl)methanone
Synonyms	Pyoluteorin KETONE,4,5-DICHLOROPYRROL-2-YL 2,6-DIHYDROXYPHENYL Methanone,(4,5-dichloro-1H-pyrrol-2-yl)(2,6-dihydroxyphenyl) (4,5-Dichlor-pyrrol-2-yl)-(2,6-dihydroxy-phenyl)-keton (4,5-dichloro-pyrrol-2-yl)-(2,6-dihydroxy-phenyl)-methanone (4,5-dichloro-pyrrol-2-yl)-(2,6-dihydroxy-phenyl)-ketone WLN: T5MJ BG CG EVR BQ FQ

Description	Pyoluteorin is an antibiotic that inhibits Oomycete fungi, including the plant pathogen Pythium ultimum, and suppresses plant diseases caused by this fungus[1]. Pyoluteorin induces human triple-negative breast cancer MDA-MB-231 cells apoptosis in vitro. Pyoluteorin can be used for the research of human triple-negative breast cancer[2].
Related Catalog	Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Research Areas >> Infection Signaling Pathways >> Anti-infection >> Fungal
In Vitro	Pyoluteorin is an antifungal compound composed of a bichlorinated pyrrole linked to a resorcinol moiety, were identified within a 24-kb genomic region of Pseudomonas fluorescens Pf-5[1]. Pyoluteorin has significant cytotoxicity towards MCF-7 (IC50=1.84 μM). Pyoluteorin also displays significantly selective cytotoxicity against BT474, HCC1954, MAD-MB-468, MDA-MB-231, and MCF-10A cells with IC50s of 9.75±0.16, 0.94±0.01, 3.89±0.08, 0.97±0.01, and 57.01±0.76 μM, respectively[2]. Pyoluteorin (0.1-10 μM; for 24 hours) induces change of apoptosis-related protein expressions. Pyoluteorin-induced cell apoptosis in MDA-MB-231 is related to Bcl-2 family proteins and caspase cascade[2]. Pyoluteorin (0.1-10 μM; for 24 h) induces cell cycle arrest and apoptosis in human triple-negative breast cancer cells MDA-MB-231[2]. Cell Proliferation Assay[2] Cell Line: Human triple-negative breast cancer cell MDA-MB-231 Concentration: 0, 0.032, 0.16, 0.8, 4, 20, 100 μM Incubation Time: 24, 48, 72 hours Result: Inhibited cells proliferation in a dose- and time-dependent manner. Western Blot Analysis[2] Cell Line: MDA-MB-231 cells Concentration: 0.1, 0.3, 1, 3, 10 μM Incubation Time: 24 hours Result: The levels of the anti-apoptotic proteins Bcl-2, Bcl-XL and PARP were obviously decreased while the pro-apoptotic proteins BAX and caspase 3 were increased in a dose-dependent manner.
References	[1]. B Nowak-Thompson, et al. Characterization of the pyoluteorin biosynthetic gene cluster of Pseudomonas fluorescens Pf-5. J Bacteriol. 1999 Apr;181(7):2166-74. [2]. Ting Ding, et al. Pyoluteorin induces cell cycle arrest and apoptosis in human triple-negative breast cancer cells MDA-MB-231. J Pharm Pharmacol. 2020 Jul;72(7):969-978.

Density	1.632g/cm3
Boiling Point	436.9ºC at 760mmHg
Molecular Formula	C₁₁H₇Cl₂NO₃
Molecular Weight	272.08400
Flash Point	218ºC
Exact Mass	270.98000
PSA	73.32000
LogP	2.96370
Vapour Pressure	3.06E-08mmHg at 25°C
Index of Refraction	1.694

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OB1804400

CHEMICAL NAME :: Ketone, 4,5-dichloropyrrol-2-yl 2,6-dihydroxyphenyl

CAS REGISTRY NUMBER :: 25683-07-2

BEILSTEIN REFERENCE NO. :: 0234664

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C11-H7-Cl2-N-O3

MOLECULAR WEIGHT :: 272.09

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 125 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 5,48,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 45 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 5,48,1981

HS Code	2933990090