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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
TRC
Product number
P755330
Product name
Prodigiosin
Packaging
1mg
Price
$115
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 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

PRODIGIOSIN Preparation Products And Raw materials

Raw materials

Preparation Products

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PRODIGIOSIN Suppliers

China 76 Germany 1 India 1 United Kingdom 1 United States 8 Global 87
Nantong Hi-Future Biotechnology Co., Ltd
Tel
18051384581
Email
sales@chemhifuture.com
Country
China
ProdList
2998
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58
Syntechem Co.,Ltd
Tel
Fax
E-Mail Inquiry
Email
info@syntechem.com
Country
China
ProdList
12984
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57
China Langchem Inc.
Tel
0086-21-58956006
Fax
0086-21-58956100
Country
China
ProdList
7811
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57
Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
400-6206333 13167063860
Fax
021-50323701
Email
anhua.mao@aladdin-e.com
Country
China
ProdList
25003
Advantage
65
Shanghai Tauto Biotech Co., Ltd.
Tel
021-51320588
Fax
0086-21-51320502
Email
tauto@tautobiotech.com
Country
China
ProdList
3988
Advantage
66
Bide Pharmatech Ltd.
Tel
400-164-7117 13681763483
Fax
+86-21-61629029
Email
product02@bidepharm.com
Country
China
ProdList
39966
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60
ChemStrong Scientific Co.,Ltd
Tel
0755-0755-66853366 13670046396
Fax
0755-28363542
Email
sales@chem-strong.com
Country
China
ProdList
18333
Advantage
56
Shanghai Lollane Biological Technology Co.,Ltd.
Tel
021-52996696，15000506266 15000506266
Fax
+86-21-52996696
Country
China
ProdList
4757
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55
Shanghai EFE Biological Technology Co., Ltd.
Tel
021-65675885 18964387627
Fax
021-65675885
Email
info@efebio.com
Country
China
ProdList
9803
Advantage
58
Shanghai YuanYe Biotechnology Co., Ltd.
Tel
021-61312847; 18021002903
Fax
QQ:3008007432
Email
3008007409@qq.com
Country
China
ProdList
71826
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60

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