Undecylprodigiosin

Specifications / Handling

More Information
Product Details
Synonyms	Undecylprodiginine; Prodigiosin 25C
Product Type	Chemical
Properties
Formula	C₂₅H₃₅N₃O . HCl
MW	393.6 . 36.5
CAS	56247-02-0 \| 52340-48-4 (parent)
Source/Host Chemicals	Isolated from Streptomyces parvulus.
Purity Chemicals	≥95% (HPLC, NMR)
Appearance	Red solid.
Solubility	Soluble in DMSO, methanol, acetone or chloroform.
Identity	Determined by ¹H-NMR.
Declaration	Manufactured by BioViotica.
InChi Key	ZZRPZWXEPLULCE-XWASNXTISA-N
Smiles	COC1=CC(C2=CC=CN2)=N/C1=C\C3=CC=C(CCCCCCCCCCC)N3.Cl
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 1 year after receipt when stored at -20°C. Store solutions at -20°C in the dark.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Tripyrrolic pigment like prodigiosin.
Antimalarial agent.
Apoptosis inducer.
Anticancer agent with multiple modes of action.
Immunosuppressant in non-toxic concentrations.
Bone resorption inhibitor.
Antiulcer agent.

Product References

A new prodiginine (prodigiosin-like) pigment from Streptomyces. Antimalarial activity of several prodiginines: N. N. Gerber; J. Antibiot. 28, 194 (1975)
Undecylprodigiosin: H. H. Wassermann, et al.; Tetrahedron 32, 1851 (1976)
Characterization of the new immunosuppressive drug undecylprodigiosin in human lymphocytes: retinoblastoma protein, cyclin-dependent kinase-2, and cyclin-dependent kinase-4 as molecular targets: S. Songia, et al.; J. Immunol. 158, 3987 (1997)
Chemistry and biology of roseophilin and the prodigiosin alkaloids: a survey of the last 2500 years: A. Fürstner; Angew. Chem. Int. Ed. 42, 3582 (2003)
The prodigiosins: a new family of anticancer drugs: B. Montaner & R. Pérez-Tomás; Curr. Cancer Drug Targets 3, 57 (2003) (Review)
Potent in vitro anticancer activity of metacycloprodigiosin and undecylprodigiosin from a sponge-derived actinomycete Saccharopolyspora sp. nov: R. Liu, et al.; Arch. Pharm. Res. 28, 1341 (2005)
The biosynthesis and regulation of bacterial prodiginines: N. R. Williamson, et al.; Nat. Rev. Microbiol. 4, 887 (2006) (Review)
Undecylprodigiosin selectively induces apoptosis in human breast carcinoma cells independent of p53: T.-F. Ho, et al.; Toxicol. Appl. Pharmacol. 225, 318 (2007)
Prodigiosin synthesis with electron rich 2,2`-bipyrroles: B. Jolicoeur & W. D. Lubell; Can. J. Chem. 86, 213 (2008)
Antimalarial activity of natural and synthetic prodiginines: K. Papireddy, et al.; J. Med. Chem. 54, 5296 (2011)
Streptomyces sp. JS520 produces exceptionally high quantities of undecylprodigiosin with antibacterial, antioxidative, and UV-protective properties: N. Stankovic, et al.; Appl. Microbiol. Biotechnol. 96, 1217 (2012)
Undecylprodigiosin induced apoptosis in P388 cancer cells is associated with its binding to ribosome: P. Liu, et al.; PLoS One 8, e65381 (2013)
Properties and applications of undecylprodigiosin and other bacterial prodigiosins: N. Stankovic, et al.; Appl. Microbiol. Biot. 98, 3841 (2014)
Undecylprodigiosin conjugated monodisperse gold nanoparticles efficiently cause apoptosis in colon cancer cells in vitro: J. Nikodinovic-Runic, et al.; J. Mater. Chem. B: Mat. Biol. Med. 2, 3271 (2014)
Stereochemistry and Mechanism of undecylprodigiosin Oxidative Carbocyclization to Streptorubin B by the rieske oxygenase RedG: D.M. Withall, et al.; JACS 137, 7889 (2015)
The Streptomyces metabolite anhydroexfoliamycin ameliorates hallmarks of Alzheimer's disease in vitro and in vivo: M. Leiros, et al.; Neuroscience (Amsterdam, Netherlands) 305, 26 (2015)
Biological effects of bacterial pigment undecylprodigiosin on human blood cells treated with atmospheric gas plasma in vitro: S. Lazovic, et al.; Exp. Toxicol. Pathol. 69, 55 (2017)

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