Specifications
Chemical identification
Synonyms:
Disambiguation: Do not confuse with Prodigiozan, another antibiotic from the same source.
Chemical names: 2,2'-Bi-1H-pyrrole, 4-methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-, hydrochloride (1:1)
Parent CAS: 82-89-3 (Free base form)
IUPAC: (2Z)-3-methoxy-2-[(5-methyl-4-pentyl-1H-pyrrol-2-yl)methylidene]-5-(1H-pyrrol-2-yl)pyrrole;hydrochloride
RTECS DW2977000 refers to prodigiosin free base
Prodigiosin is a antibiotic from Serratia marcescens and some other bacterial species. It displays a wide range of biological activities, making it a promissing candidate drug. Among these are antimalarial, antifungal, anti-cancer, immunosuppressant, and antibiotic properties.
Further Information
(Data from literature including scientific publications and books, patents and other vendors)Prodigiosin is soluble in acetonitrile, ethanol, methanol, chloroform, and DMSO. It is insoluble in water.
UNSPSC
- 51000000 Drugs and Pharmaceutical Products
- 51200000 Immunomodulating drugs
For research only!
Composition
Supply related information
Publications
- 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. 26, 2078 (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)
- 18. Sensitivity of Bacillus oleronius, a bacterium that is associated with rosacea, to prodigiosin: M.V. Sayger, et al.; Science Matters (2020)
- 19. Prodigiosin impairs autophagosome-lysosome fusion that sensitizes colorectal cancer cells to 5-fluorouracilinduced cell death: C. Zhao, et al.; Cancer Lett. 481, 15 (2020)