Prodigiosin
Product Code: AG-CN2-0105
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0105-C250 | 250 ug | £70.00 |
Quantity:
| AG-CN2-0105-M001 | 1 mg | £190.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
NSC 47147; BRN 4526727
Appearance:
Dark red solid.
CAS:
82-89-3
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Protect from light.
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/b16-12+
InChiKey:
SZXDNGVQRDTJSD-FOWTUZBSSA-N
Long Description:
Chemical. CAS: 82-89-3. Formula: C20H25N3O. MW: 323.4. Isolated from gamma-proteobacterium strain MS-02-063. Red-pigmented antibiotic. Antimalarial. Immunosuppressive. Apoptosis inducer. Cytotoxic. Induces phosphorylation of p38-MAPK. Antimetastatic. Tumor invasion inhibitor. Induces p21WAF1/CIP1 expression. Anticancer compound. gp91(phox) and iNOS expression inhibitor. mTORC1 and mTORC2 complex inhibitor. Down-regulates SKP2 to induce p27(KIP1) stabilization.
MDL:
MFCD01740630
Molecular Formula:
C20H25N3O
Molecular Weight:
323.4
Package Type:
Vial
Product Description:
Red-pigmented antibiotic [1]. Antimalarial [2, 13]. Immunosuppressive [3, 7, 11, 12]. Apoptosis inducer [4-6, 15]. Cytotoxic. Induces phosphorylation of p38-MAPK [8]. Antimetastatic. Tumor invasion inhibitor [9]. Induces p21WAF1/CIP1 expression [10]. Anticancer compound [11, 12, 15]. gp91(phox) and iNOS expression inhibitor [14]. mTORC1 and mTORC2 complex inhibitor [16]. Down-regulates SKP2 to induce p27(KIP1) stabilization [17]. Blocking autophagosome-lysosome fusion [19].
Purity:
>95% (HPLC)
SMILES:
CCCCCC1=CC(=C/C2=C(OC)C=C(N2)C2=CC=CN2)N=C1C
Solubility Chemicals:
Soluble in methanol, ethanol, chloroform, ethyl acetate, hexane, acetone or acetonitrile. Insoluble in water.
Source / Host:
Isolated from gamma-proteobacterium strain MS-02-063.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 3 years after receipt when stored at -20°C.
References
The Antibiotic Activity of Violacein, Prodigiosin, and Phthiocol: H.C. Lichstein & V.F. Van De Sand; J. Bacteriol. 52, 145 (1946) | Antimalarial activity of prodigiosin: A.J. Castro; Nature 213, 903 (1967) | T-cell specific immunosuppression by prodigiosin isolated from Serratia marcescens: S.B. Han, et al.; Int. J. Immunopharmacol. 20, 1 (1998) | Prodigiosin from the supernatant of Serratia marcescens induces apoptosis in haematopoietic cancer cell lines: B. Montaner, et al.; Br. J. Pharmacol. 131, 585 (2000) | Prodigiosin-induced apoptosis in human colon cancer cells: B. Montaner & R. Perez-Tomas; Life Sci. 68, 2025 (2001) | Prodigiosin induces cell death and morphological changes indicative of apoptosis in gastric cancer cell line HGT-1: C. Diaz-Ruiz, et al.; Histol. Histopathol. 16, 415 (2001) | Prodigiosin blocks T cell activation by inhibiting interleukin-2Ralpha expression and delays progression of autoimmune diabetes and collagen-induced arthritis: S.B. Han, et al.; JPET 299, 415 (2001) | The cytotoxic prodigiosin induces phosphorylation of p38-MAPK but not of SAPK/JNK: B. Montaner & R. Perez-Tomas; Toxicol. Lett. 129, 93 (2002) | Antimetastatic effect of prodigiosin through inhibition of tumor invasion: J. Zhang, et al.; Biochem. Pharmacol. 69, 407 (2005) | The anticancer agent prodigiosin induces p21WAF1/CIP1 expression via transforming growth factor-beta receptor pathway: V. Soto-Cerrato, et al.; Biochem. Pharmacol. 74, 1340 (2007) | Prodigiosins as anti cancer agents: living upto their name: R. Pandey, et al.; Curr. Pharm. Des. 15, 732 (2009) | New insights on the antitumoral properties of prodiginines: R. Perez-Tomas & M. Vinas; Curr. Med. Chem. 17, 2222 (2010) | Prodigiosin produced by Serratia marcescens NMCC46 as a mosquito larvicidal agent against Aedes aegypti and Anopheles stephensi: C.D. Patil, et al.; Parasitol. Res. 109, 1179 (2011) | Prodigiosin inhibits gp91(phox) and iNOS expression to protect mice against the oxidative/nitrosative brain injury induced by hypoxia-ischemia: C.C. Chang, et al.; Toxicol. Appl. Pharmacol. 257, 137 (2011) | Prodigiosin, the red pigment of Serratia marcescens, shows cytotoxic effects and apoptosis induction in HT-29 and T47D cancer cell lines: D. Dalili, et al; Nat. Prod. Res. 26, 2078 (2011) | Identification of dual mTORC1 and mTORC2 inhibitors in melanoma cells: prodigiosin vs. obatoclax: M. Espona-Fiedler, et al.; Biochem. Pharmacol. 83, 489 (2012) | Prodigiosin down-regulates SKP2 to induce p27(KIP1) stabilization and antiproliferation in human lung adenocarcinoma cells: H.Y. Hsieh, et al.; Br. J. Pharmacol. 166, 2095 (2012) | Sensitivity of Bacillus oleronius, a bacterium that is associated with rosacea, to prodigiosin: M.V. Sayger, et al.; Science Matters (2020) | Prodigiosin impairs autophagosome-lysosome fusion that sensitizes colorectal cancer cells to 5-fluorouracil-induced cell death: C. Zhao, et al.; Cancer Lett. 481, 15 (2020)
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