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2-Methyl-3-amyl-6-methoxyprodigiosene

Product Name
2-Methyl-3-amyl-6-methoxyprodigiosene
CAS No.
56144-17-3
Chemical Name
2-Methyl-3-amyl-6-methoxyprodigiosene
Synonyms
Prodigiosin HCl;Prodigiosine hydrochloride;Prodigiosin hydrochloride ;Prodigiosin hydrochloride from Serratia marcescens, >=98% (HPLC), powder
CBNumber
CB32750423
Molecular Formula
C20H26ClN3O
Formula Weight
359.9
MOL File
56144-17-3.mol
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2-Methyl-3-amyl-6-methoxyprodigiosene Property

storage temp. 
-20°C
solubility 
DMSO: soluble
form 
powder
color 
Purple to purplish red
biological source
Serratia marcescens
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Safety

WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
P0103
Product name
Prodigiosin hydrochloride
Purity
from Serratia marcescens, ≥98% (HPLC), powder
Packaging
100μg
Price
$457
Updated
2025/07/31
American Custom Chemicals Corporation
Product number
MTB0000973
Product name
2,2'-BI-1H-PYRROLE-4-METHOXY-5-(5-METHYL-4-PENTYL-2H-PYRROL-2-YLIDENE)METHYL HYDROCHLORIDE
Purity
95.00%
Packaging
5MG
Price
$502.61
Updated
2021/12/16
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2-Methyl-3-amyl-6-methoxyprodigiosene Chemical Properties,Usage,Production

Uses

Prodigiosin (Prodigiosine) hydrochloride is a red pigment produced by bacteria as a bioactive secondary metabolite. Prodigiosin hydrochloride is a potent proapoptotic agent, and inhibits Wnt/β-catenin pathway. Prodigiosin hydrochloride has antibacterial, antifungal, antiprotozoal, antimalarial, immunosuppressive, and anticancer properties[1][2].

General Description

Prodigiosin is a red pigment with common pyrrolyl pyrromethene skeleton and is biosynthesized by Serratia marcescens and other bacteria.

Biochem/physiol Actions

Prodigiosin, a tripyrrole red pigment biosynthesized by Serratia marcescens and other bacteria, exhibits antibacterial, anticancer, cytotoxic, immunosuppressive, and antiproliferative activities. Prodigiosin induces apoptosis in hematopoietic cancer cells and cells derived from other human cancers, including gastric and colon with no marked toxicity in nonmalignant cell lines. Morphological analysis of prodigiosin-treated cells demonstrated that prodigiosin induces cell shrinkage, chromatin condensation, reorganization of actin microfilament architecture, and detachment of cells from the cell culture substrate. Different targets and mechanisms of action are described for prodigiosin, including induction of single- and double-strand DNA breaks, modulation of pH, regulation of mitogen-activated protein kinase, and inhibition of cell cycle progression.

in vivo

Prodigiosin (5 mg/kg; intraperitoneal injection; twice weekly; for 3 weeks) treatment significantly inhibits tumor growth. Prodigiosin treatment decreases tumor cell density and expression of the proliferation marker Ki-67[1].

Animal Model:Female BALB/c nude mice injected with MDA-MB-231 cells[1]
Dosage: 5 mg/kg
Administration:Intraperitoneal injection; twice weekly; for 3 weeks
Result:Significantly inhibited tumor growth in mice.

IC 50

Plasmodium

References

[1] Wang Z, et al. Prodigiosin inhibits Wnt/β-catenin signaling and exerts anticancer activity in breast cancer cells. Proc Natl Acad Sci U S A. 2016 Nov 15;113(46):13150-13155. DOI:10.1073/pnas.1616336113
[2] Woodhams DC, et al. Prodigiosin, Violacein, and Volatile Organic Compounds Produced by Widespread Cutaneous Bacteria of Amphibians Can Inhibit Two Batrachochytrium Fungal Pathogens. Microb Ecol. 2018 May;75(4):1049-1062. DOI:10.1007/s00248-017-1095-7

2-Methyl-3-amyl-6-methoxyprodigiosene Preparation Products And Raw materials

Raw materials

Preparation Products

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2-Methyl-3-amyl-6-methoxyprodigiosene Suppliers

Sigma-Aldrich
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021-61415566 800-8193336
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orderCN@merckgroup.com
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BOC Sciences
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Energy Chemical
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Merck KGaA
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Adooq Bioscience LLC
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Nantong HI-FUTURE Biology Co., Ltd.
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Guangzhou Baide Biotechnology Co., Ltd.
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56144-17-3, 2-Methyl-3-amyl-6-methoxyprodigioseneRelated Search:


  • Prodigiosin hydrochloride
  • Prodigiosin hydrochloride from Serratia marcescens, >=98% (HPLC), powder
  • Prodigiosine hydrochloride
  • Prodigiosin HCl
  • 56144-17-3