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Prodigiosin

AG-CN2-0105-C250 250 µg INQ
AG-CN2-0105-M001 1 mg INQ
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Additional Information

Product Data
Synonyms NSC 47147; BRN 4526727
Properties
Formula C20H25N3O
MW 323.4
Merck Index 14: 7767
CAS 82-89-3
Source/Host Isolated from γ-proteobacterium strain MS-02-063.
Purity ≥95% (HPLC)
Appearance Dark red solid.
Solubility Soluble in methanol, ethanol, chloroform, ethyl acetate, hexane, acetone or acetonitrile. Insoluble in water.
Origin Manufactured by BioLinks K.K. with courtesy strain from The Kitasato Institute.
InChi Key SZXDNGVQRDTJSD-FOWTUZBSSA-N
Product Type Chemical
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Protect from light.
Use/Stability Stable for at least 3 years after receipt when stored at -20°C.
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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].

Product References

  1. The Antibiotic Activity of Violacein, Prodigiosin, and Phthiocol: H.C. Lichstein & V.F. Van De Sand; J. Bacteriol. 52, 145 (1946)
  2. Antimalarial activity of prodigiosin: A.J. Castro; Nature 213, 903 (1967)
  3. T-cell specific immunosuppression by prodigiosin isolated from Serratia marcescens: S.B. Han, et al.; Int. J. Immunopharmacol. 20, 1 (1998)
  4. Prodigiosin from the supernatant of Serratia marcescens induces apoptosis in haematopoietic cancer cell lines: B. Montaner, et al.; Br. J. Pharmacol. 131, 585 (2000)
  5. Prodigiosin-induced apoptosis in human colon cancer cells: B. Montaner & R. Perez-Tomas; Life Sci. 68, 2025 (2001)
  6. 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)
  7. 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)
  8. The cytotoxic prodigiosin induces phosphorylation of p38-MAPK but not of SAPK/JNK: B. Montaner & R. Perez-Tomas; Toxicol. Lett. 129, 93 (2002)
  9. Antimetastatic effect of prodigiosin through inhibition of tumor invasion: J. Zhang, et al.; Biochem. Pharmacol. 69, 407 (2005)
  10. 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)
  11. Prodigiosins as anti cancer agents: living upto their name: R. Pandey, et al.; Curr. Pharm. Des. 15, 732 (2009)
  12. New insights on the antitumoral properties of prodiginines: R. Perez-Tomas & M. Vinas; Curr. Med. Chem. 17, 2222 (2010)
  13. 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)
  14. 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)
  15. 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. (Epub ahead of print) (2011)
  16. Identification of dual mTORC1 and mTORC2 inhibitors in melanoma cells: prodigiosin vs. obatoclax: M. Espona-Fiedler, et al.; Biochem. Pharmacol. 83, 489 (2012)
  17. 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)
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