A bacterial metabolite with diverse biological activities
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Streptochlorin

Item No. 27605

Technical Information
Formal Name
3-(4-chloro-5-oxazolyl)-1H-indole
CAS Number
120191-51-7
Synonyms
  • SF 2583A
Molecular Formula
C11H7ClN2O
Formula Weight
Purity
≥98%
A solid
DMSO: SolubleMethanol: Soluble
λmax
222, 272, 288 nm
SMILES
ClC(N=CO1)=C1C2=CNC3=CC=CC=C32
InChi Code
InChI=1S/C11H7ClN2O/c12-11-10(15-6-14-11)8-5-13-9-4-2-1-3-7(8)9/h1-6,13H
InChi Key
BKYJGKRXUHPPLR-UHFFFAOYSA-N
Origin
Bacterium/Streptomyces roseolilacinus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Streptochlorin is a bacterial metabolite originally isolated from Streptomyces sp. SF2583 that has diverse biological activities, including antiangiogenic, antiproliferative, and anti-allergic properties.1,2,3,4 It inhibits TNF-α-induced NF-κB transcriptional activity and decreases proliferation of human umbilical vein endothelial cells (HUVECs) when used at concentrations ranging from 5 to 20 µM.2 Streptochlorin (12 µg/ml) decreases viability of, as well as induces apoptosis and increases the production of reactive oxygen species (ROS) in, Hep3B human hepatocellular carcinoma cells.3 It does not induce cytotoxicity in RBL-2H3 mast cells at concentrations up to 100 µM.4 Streptochlorin prevents degranulation in antigen-stimulated mast cells, as well as inhibits Syk kinase and the Src family kinases LYN and Fyn and reduces the secretion of TNF-α and IL-4 induced by dinitrophenyl-human serum album (DNP-HSA) in RBL-2H3 mast cells. It also decreases swelling and reduces scratching behavior in a mouse model of allergic dermatitis induced by dinitrofluorobenzene (DNFB).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hiroomi, W., Shoichi, A., Junko, Y., et alA new antibiotic SF2583A, 4-chloro-5-(3'-indolyl)oxazole, produced by Streptomyces. Meiji Seika Kenkyu Nenpo 27, 55-62 (1988).

    2. Choi, I.-K., Shin, H.J., H.-S., L., et alStreptochlorin, a marine natural product, inhibits NF-κB activation and suppresses angiogenesis in vitro. J. Microbiol. Biotechnol. 17(8), 1338-13343 (2007).

    3. Shin, D.Y., Shin, H.J., Kim, G.-Y., et alStreptochlorin isolated from Streptomyces sp. Induces apoptosis in human hepatocarcinoma cells through a reactive oxygen species-mediated mitochondrial pathway. J. Microbiol. Biotechnol. 18(11), 1862-1868 (2008).

    4. Lee, S.-H., Shin, H.J., Kim, D.-Y., et alStreptochlorin suppresses allergic dermatitis and mast cell activation via regulation of Lyn/Fyn and Syk signaling pathways in cellular and mouse models. PLoS One 8(9), e74194 (2013).