CAS 82-89-3

Prodigiosin

Description:

Prodigiosin is a red, pigmented compound produced by certain bacteria, notably *Serratia marcescens*. It is classified as a tripyrrole alkaloid and is known for its striking red color, which is attributed to its unique chemical structure comprising three pyrrole rings linked by methylene bridges. Prodigiosin exhibits a range of biological activities, including antibacterial, antifungal, and antiprotozoal properties, making it of interest in pharmaceutical research. Its mechanism of action is thought to involve interference with cellular processes, such as the inhibition of cell division and induction of apoptosis in certain cancer cells. Additionally, prodigiosin has been studied for its potential as an immunosuppressive agent and its role in microbial communication. The compound is soluble in organic solvents but has limited solubility in water, which can affect its bioavailability. Due to its diverse biological activities and potential applications, prodigiosin continues to be a subject of scientific investigation in various fields, including microbiology and medicinal chemistry.

Formula: C₂₀H₂₅N₃O

InChI: InChI=1S/C20H25N3O/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17/h7,9-13,21,23H,4-6,8H2,1-3H3

InChI key: InChIKey=SZXDNGVQRDTJSD-UHFFFAOYSA-N

SMILES: C(C1=C(OC)C=C(N1)C2=CC=CN2)=C3C=C(CCCCC)C(C)=N3

Synonyms:

• 2,2'-Bi-1H-pyrrole, 4-methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)- (9CI)
• 2,2'-Bipyrrole, 4-methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)-
• 2,2'-Bipyrrole, 4-methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)-(VAN) (8CI)
• 2,2′-Bi-1H-pyrrole, 4-methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-
• 2-Methyl-3-amyl-6-methoxyprodigiosene
• 4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2,2′-bi-1H-pyrrole
• 82-89-3
• NSC 47147
• Prodigiosin
• Prodigiosine
• 5-26-03-00352 (Beilstein Handbook Reference)

Prodigiosin

CAS: 82-89-3

Formula: C₂₀H₂₅N₃O

Purity: %

Color and Shape: Solid

Molecular weight: 323.4320

Ref: IN-DA00G3A1

4-Methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)-1H,1'H-2,2'-bipyrrole

CAS: 82-89-3

4-Methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)-1H,1'H-2,2'-bipyrrole

Formula: C₂₀H₂₅N₃O

Purity: >98%

Molecular weight: 323.44

Ref: 54-OR1065237

Prodigiosin

CAS: 82-89-3

Prodigiosin is a natural red pigment and secondary metabolite that inhibits the Wnt/β-catenin pathway and exhibits antibacterial activities.

Formula: C₂₀H₂₅N₃O

Purity: 99.99%

Color and Shape: Red Solid

Molecular weight: 323.44

Ref: TM-T16580

Prodigiosin

CAS: 82-89-3

Formula: C₂₀H₂₅N₃O

Purity: ≥ 95.0%

Color and Shape: Dark red solid

Molecular weight: 323.4

Ref: 7W-GL3187

Prodigiosin

Controlled Product

CAS: 82-89-3

Formula: C₂₀H₂₅N₃O

Color and Shape: Neat

Molecular weight: 323.432

Ref: TR-P755330

Prodigiosin-d3

Controlled Product

CAS: 82-89-3

Formula: C₂₀D₃H₂₂N₃O

Color and Shape: Neat

Molecular weight: 326.45

Ref: TR-P755332

Prodigiosin

CAS: 82-89-3

Prodigiosin is a natural red pigment that is produced by a variety of bacteria, including Serratia marcescens. It has been shown to have transcriptional regulatory activity on pro-inflammatory cytokine, IL-2 receptor, and wild-type strain. Prodigiosin has also been shown to have genotoxic activity in colorectal adenocarcinoma cells. The mechanism of this genotoxicity may be due to its ability to form DNA adducts and cause strand breaks. Prodigiosin also induces antibody responses in mice infected with Shigella flexneri. This compound has been shown to induce carcinoma cell lines through surface methodology and molecular docking analysis.

Formula: C₂₀H₂₅N₃O

Purity: Min. 95%

Molecular weight: 323.43 g/mol

Ref: 3D-AAA08289