ChemicalBook > CAS DataBase List > PRODIGIOSIN

PRODIGIOSIN

Product Name: PRODIGIOSIN
CAS No.: 82-89-3
Chemical Name: PRODIGIOSIN
Synonyms: Nsc47147;Aids010622;Aids-010622;PRODIGIOSIN;Prodigiosine;Prodigiosin, apoptotic agent;2-Methyl-3-amyl-6-methoxyprodigiosene;Prodigiosin Serratia marcescens;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]-2,2'-bi[1H-pyrrol]
CBNumber: CB5156304
Molecular Formula: C20H25N3O
Formula Weight: 323.43
MOL File: 82-89-3.mol

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PRODIGIOSIN Property

Melting point:: 151-152°
Boiling point:: 554.3±50.0 °C(Predicted)
Density: 1.12±0.1 g/cm3(Predicted)
storage temp.: -20C
solubility: Acetonitrile: Soluble; Ethanol: Soluble; Methanol: Soluble
form: Dark red solid
pka: 17.09±0.50(Predicted)
color: Dark red
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
InChIKey: SZXDNGVQRDTJSD-UHFFFAOYSA-N
SMILES: N1C(C=C2C=C(CCCCC)C(C)=N2)=C(OC)C=C1C1=CC=CN1

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 529685
Product name: Prodigiosin Serratia marcescens - CAS 82-89-3 - Calbiochem
Purity: Acell-permeabletripyrrolealkaloidcompoundthatdisplaysimmunosuppressivean
Packaging: 200μg
Price: $192
Updated: 2025/07/31

Cayman Chemical

Product number: 19464
Product name: Prodigiosin
Purity: ≥95%
Packaging: 250μg
Price: $81
Updated: 2024/03/01

Cayman Chemical

Product number: 19464
Product name: Prodigiosin
Purity: ≥95%
Packaging: 500μg
Price: $152
Updated: 2024/03/01

Cayman Chemical

Product number: 19464
Product name: Prodigiosin
Purity: ≥95%
Packaging: 1mg
Price: $254
Updated: 2024/03/01

Usbiological

Product number: 045166
Product name: Prodigiosin
Packaging: 250ug
Price: $307
Updated: 2021/12/16

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PRODIGIOSIN Chemical Properties,Usage,Production

Uses

Prodigiosin is an intensely red, pyrrole pigment produced by several bacteria, most notably Serratia marcescens. Prodigiosin has a broad biological profile with activity against fungi, tumour cell lines and malaria. It was shown to be an immunosuppressant in 2007. Prodigiosin acts via caspase inhibition to induce of apoptosis in human primary cancer cells. Prodigiosin also acts as an inducer of p21WAF1/CIP1 expression via transforming growth factor-β receptor pathway, and activates NAG-1 via glycogen synthase kinase-3β.

Uses

Prodigiosin is an intensely red pyrrole pigment produced by several bacteria, most notably Serratia marcescens. Prodigiosin has a broad biological profile with activity against fungi, tumor cell lines and malaria. It was shown to be an immunosuppressant in 2007. Prodigiosin acts via caspase inhibition to induce of apoptosis in human primary cancer cells. Prodigiosin also acts as an inducer of p21WAF1/CIP1 expression via transforming growth factor-β receptor pathway, and activates NAG-1 via glycogen synthase kinase-3β.

Uses

Prodigiosin is a naturally occurring pigment which occurs as a product of Serratia marcescens. Pink colored pigment.

Definition

ChEBI: A member of the class of tripyrroles that is a red-coloured pigment with antibiotic properties produced by Serratia marcescens.

General Description

A cell-permeable tripyrrole alkaloid compound that displays immunosuppressive and anti-tumor properties irrespective of p53 status and multidrug resistance. Shown to selectively upregulate p21^WAF/CIP1 and NAG-1 (nonsteroidal anti-inflammatory drug-activated gene 1) and downregulate survivin expression levels, induce mitochondria-mediated apoptosis and cell cycle arrest in tumor cells. Prevents FADD phosphorylation (IC₅₀ = 2.0 μM in A549-FKR cells) through inhibition of FADD-kinase CK1α (IC₅₀ ~ 6.0 μM in SW620-BGCR cells) and augments cisplatin (Cat. No. 232120)-induced apoptosis. Blocks NF-κB activation by decreasing pIκBα (by 63% at 3 μM) and IκBα levels in A549 cells, and shrinks tumor growth in A549-FKR tumor xenograft mouse model (3 mg/kg, i.p., o.d.).

Enzyme inhibitor

This red bacterial pigment (FWfree-base = 323.44 g/mol; melting point = 151- 152°C) is an antibiotic produced by Serratia marcescens (formerly Chromobacterium prodigiosum). Prodigiosin is the parent member of a class of pyrrole-containing natural products that exhibit immunosuppressive, cytotoxic, and apoptotic activity and can facilitate copper-promoted oxidative double-strand DNA cleavage through reductive activation of Cu2+. They also uncouple lysosomal vacuolar-type ATPases by promoting H+/Cl– symport activity. The solid pigment is dark red and displays a green reflex. Acidic aqueous solutions are also red, but neutral or alkaline solutions are orange-yellow. Target(s): DNA topoisomerase I; DNA topoisomerase II; FoF1 ATPase, or H+-transporting two-sector ATPase, as an uncoupler; H+/K+-ATPase, as an uncoupler; proton translocation, as an uncoupler; and Serratia marcescens nuclease.

storage

+4°C

PRODIGIOSIN Preparation Products And Raw materials

Raw materials

Preparation Products

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82-89-3, PRODIGIOSINRelated Search:

MELANIN indigoidine Indigo actinorhodin Melamine Zeaxanthin violacein flaviolin Pseudoalteromonas nigrifaciens 1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide 2,2'-BIPYRROL PRODIGIOSIN

PRODIGIOSIN

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

3-Methoxy-2-(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl-5-(1H-pyrrol-2-yl)-1H-pyrrole

4-Methoxy-5-(4-pentyl-5-methyl-2H-pyrrole-2-ylidenemethyl)-2,2'-bi[1H-pyrrole]

4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2,2'-bi[1H-pyrrol]

4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2,2'-bi[1H-pyrrole]

Prodigiosine

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

Aids010622

Aids-010622

Nsc47147

2,2'-Bi-1H-pyrrole,4-Methoxy-5-[(5-Methyl-4-pentyl-2H-pyrrol-2-ylidene)Methyl]-prodigiosinⅡ≤

2,2'-Bi-1H-pyrrole,4-Methoxy-5-[(5-Methyl-4-pentyl-2H-pyrrol-2-ylidene)Methyl]-

2-Methyl-3-amyl-6-methoxyprodigiosene

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

Prodigiosin, apoptotic agent

Prodigiosin <i>Serratia marcescens</i>

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

82-89-3