Synonym
SF 2583A, Streptochlorin
IUPAC/Chemical Name
3-(4-chloro-5-oxazolyl)-1H-indole
InChi Key
BKYJGKRXUHPPLR-UHFFFAOYSA-N
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
SMILES Code
ClC(N=CO1)=C1C2=CNC3=CC=CC=C32
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Streptochlorin has antitrypanosomal activity with an IC50 value of 230 ng/ml for GUTat 3.1.
In vitro activity:
This study reports that streptochlorin possess anti-allergic properties, and its underlying mechanism might be through the inhibition of the Lyn/Fyn and Syk signaling pathways. Streptochlorin inhibited degranulation and production of tumor necrosis factor-α and IL-4 by antigen-stimulated mast cells. Streptochlorin also inhibited the phosphorylation of Akt and MAPKs, including p38, ERK, and JNK. Streptochlorin also reduced the phosphorylation of Syk in RBL-2H3 cells and inhibited the activity of Lyn and Fyn.
Reference: PLoS One. 2013 Sep 27;8(9):e74194. https://pubmed.ncbi.nlm.nih.gov/24086321/
In vivo activity:
Streptochlorin is a promising chemotherapeutic agent for cholangiocarcinoma treatment. Streptochlorin effectively regulated metastasis of HuCC-T1 cells in a mouse model of liver metastasis. In a tumor xenograft study using SNU478 cells, streptochlorin significantly inhibited tumor growth without changes in body weight when compared with the control.
Reference: Drug Des Devel Ther. 2015 Apr 16;9:2201-14. https://pubmed.ncbi.nlm.nih.gov/25931814/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
218.64
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Lee SH, Shin HJ, Kim DY, Shim DW, Kim TJ, Ye SK, Won HS, Koppula S, Kang TB, Lee KH. Streptochlorin suppresses allergic dermatitis and mast cell activation via regulation of Lyn/Fyn and Syk signaling pathways in cellular and mouse models. PLoS One. 2013 Sep 27;8(9):e74194. doi: 10.1371/journal.pone.0074194. PMID: 24086321; PMCID: PMC3785495.
2. Shin DY, Shin HJ, Kim GY, Cheong J, Choi IW, Kim SK, Moon SK, Kang HS, Choi YH. Streptochlorin isolated from Streptomyces sp. Induces apoptosis in human hepatocarcinoma cells through a reactive oxygen species-mediated mitochondrial pathway. J Microbiol Biotechnol. 2008 Nov;18(11):1862-8. doi: 10.4014/jmb.0800.124. PMID: 19047834.
3. Kwak TW, Shin HJ, Jeong YI, Han ME, Oh SO, Kim HJ, Kim DH, Kang DH. Anticancer activity of streptochlorin, a novel antineoplastic agent, in cholangiocarcinoma. Drug Des Devel Ther. 2015 Apr 16;9:2201-14. doi: 10.2147/DDDT.S80205. PMID: 25931814; PMCID: PMC4404940.
4. Shim DW, Shin HJ, Han JW, Shin WY, Sun X, Shim EJ, Kim TJ, Kang TB, Lee KH. Anti-inflammatory effect of Streptochlorin via TRIF-dependent signaling pathways in cellular and mouse models. Int J Mol Sci. 2015 Mar 26;16(4):6902-10. doi: 10.3390/ijms16046902. PMID: 25822875; PMCID: PMC4424995.
In vitro protocol:
1. Lee SH, Shin HJ, Kim DY, Shim DW, Kim TJ, Ye SK, Won HS, Koppula S, Kang TB, Lee KH. Streptochlorin suppresses allergic dermatitis and mast cell activation via regulation of Lyn/Fyn and Syk signaling pathways in cellular and mouse models. PLoS One. 2013 Sep 27;8(9):e74194. doi: 10.1371/journal.pone.0074194. PMID: 24086321; PMCID: PMC3785495.
2. Shin DY, Shin HJ, Kim GY, Cheong J, Choi IW, Kim SK, Moon SK, Kang HS, Choi YH. Streptochlorin isolated from Streptomyces sp. Induces apoptosis in human hepatocarcinoma cells through a reactive oxygen species-mediated mitochondrial pathway. J Microbiol Biotechnol. 2008 Nov;18(11):1862-8. doi: 10.4014/jmb.0800.124. PMID: 19047834.
In vivo protocol:
1. Kwak TW, Shin HJ, Jeong YI, Han ME, Oh SO, Kim HJ, Kim DH, Kang DH. Anticancer activity of streptochlorin, a novel antineoplastic agent, in cholangiocarcinoma. Drug Des Devel Ther. 2015 Apr 16;9:2201-14. doi: 10.2147/DDDT.S80205. PMID: 25931814; PMCID: PMC4404940.
2. Shim DW, Shin HJ, Han JW, Shin WY, Sun X, Shim EJ, Kim TJ, Kang TB, Lee KH. Anti-inflammatory effect of Streptochlorin via TRIF-dependent signaling pathways in cellular and mouse models. Int J Mol Sci. 2015 Mar 26;16(4):6902-10. doi: 10.3390/ijms16046902. PMID: 25822875; PMCID: PMC4424995.
1. Hiroomi, W., Shoichi, A., Junko, Y., et al. A 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 al. Streptochlorin, 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 al. Streptochlorin 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 al. Streptochlorin 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).
