Description: 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.
Solubility ( literature ): (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.
Applications: For research only!
Composition: Ingredient type Fermentek product
Disclaimer: For Research use only, Not for Human or Drug use, Not extracted from humans or animals, Refer to MSDS for further safety and handling instructions
Names and identifiers: 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) 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
Pub 1: 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)
Source: Serratia marcescens
Chemical name: 4-Methoxy-5-[(E)-(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-1H,1'H-2,2'-bipyrrole
InChl Key: UQRGJSTXVCWXNU-JHMJKTBASA-N