| Identification | Back Directory | [Name]
PRODIGIOSIN | [CAS]
82-89-3 | [Synonyms]
Nsc47147
Aids010622
Aids-010622
PRODIGIOSIN
Prodigiosine
2-Methyl-3-amyl-6-methoxyprodigiosene
4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl], 2,2'bipyrrole
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]
2,2'-Bi-1H-pyrrole,4-Methoxy-5-[(5-Methyl-4-pentyl-2H-pyrrol-2-ylidene)Methyl]-
(E)-4-methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)-1H,1'H-2,2'-bipyrrole
(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
2,2'-Bi-1H-pyrrole,4-Methoxy-5-[(5-Methyl-4-pentyl-2H-pyrrol-2-ylidene)Methyl]-prodigiosinⅡ≤ | [Molecular Formula]
C20H25N3O | [MDL Number]
MFCD01740630 | [MOL File]
82-89-3.mol | [Molecular Weight]
323.43 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 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. | [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 p21WAF/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 |
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| Company Name: |
China Langchem Inc.
|
| Telephone: |
0086-21-58956006 |
| Website: |
www.chemicalbook.com/ShowSupplierProductsList19141/0_EN.htm |
| Company Name: |
Lynnchem
|
| Telephone: |
86-(0)29-85992781 17792393971 |
| Website: |
http://www.lynnchem.com/ |
| Company Name: |
Shanghai Bank Pharma Limited
|
| Telephone: |
2221346380 17701603001 |
| Website: |
www.chemicalbook.com/showsupplierproductslist20106/0_en.htm |
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