A natural red pigment and antibiotic
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Prodigiosin

Item No. 19464

Technical Information
Formal Name
4-methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2,2'-bi-1H-pyrrole
CAS Number
82-89-3
Synonyms
  • BRN 4526727
  • NSC 47147
Molecular Formula
C20H25N3O
Formula Weight
Purity
≥95%
A solid
Acetonitrile: SolubleEthanol: SolubleMethanol: Soluble
SMILES
CC1=N/C(C=C1CCCCC)=C/C(N2)=C(OC)C=C2C3=CC=CN3
InChi Code
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+
InChi Key
SZXDNGVQRDTJSD-FOWTUZBSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Prodigiosin is a natural red bacterial pigment that has antibiotic, antitumor, and immunosuppressant properties.1 It blocks T cell proliferation at a concentration of 30 ng/ml, by interfering with IL-2 receptor expression.2 Prodigiosin induces apoptosis in cancer cells by diverse mechanisms and rescues deficient p53 signaling.3,4,5 Prodigiosin derivatives can uncouple vacuolar H+-ATPase and inhibit osteoclast function.6 Prodigiosin is cytolytic against the red tide dinoflagellate Cochlodinium at very low concentrations (1 ppb), suggesting an application in controlling algal blooms.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kim, D., Kim, J.F., Yim, J.H., et alRed to red - the marine bacterium Hahella chejuensis and its product prodigiosin for mitigation of harmful algal blooms. J. Microbiol. Biotechnol. 18(10), 1621-1629 (2008).

    2. Han, S.B., Park, S.H., Jeon, Y.J., et alProdigiosin blocks T cell activation by inhibiting interleukin-2Rα expression and delays progression of autoimmune diabetes and collagen-induced arthritis. J. Pharmacol. Exp. Ther. 299(2), 415-425 (2001).

    3. Soto-Cerrato, V., Viñals, F., Lambert, J.R., et alProdigiosin induces the proapoptotic gene NAG-1 via glycogen synthase kinase-3β activity in human breast cancer cells. Mol. Cancer Ther. 6(1), 362-369 (2016).

    4. Hong, B., Prabhu, V.V., Zhang, S., et alProdigiosin rescues deficient p53 signaling and antitumor effects via upregulating p73 and disrupting its interaction with mutant p53. Cancer Res. 74(4), 1153-1165 (2014).

    5. Hosseini, A., Espona-Fiedler, M., Soto-Cerrato, V., et alMolecular interactions of prodiginines with the BH3 domain of anti-apoptotic Bcl-2 family members. PLoS One 8(2), (2013).

    6. Woo, J.T., Yonezawa, T., Cha, B.Y., et alPharmacological topics of bone metabolism: Antiresorptive microbial compounds that inhibit osteoclast differentiation, function, and survival. J. Pharmacol. Sci. 106(4), 547-554 (2008).