Streptochlorin
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| Category | Antibiotics |
| Catalog number | BBF-04316 |
| CAS | 120191-51-7 |
| Molecular Weight | 218.64 |
| Molecular Formula | C11H7ClN2O |
| Purity | ≥98% |
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Description
Streptochlorin is a metabolite originally isolated from Streptomyces sp. It exhibits antiangiogenesis, antiproliferation and antiallergic activities. It inhibits TNF-α-induced NF-κB activation.
Specification
| Synonyms | SF 2583A; 3-(4-chloro-5-oxazolyl)-1H-indole; Antibiotic SF 2583A |
| Storage | Store at -20°C |
| IUPAC Name | 4-chloro-5-(1H-indol-3-yl)-1,3-oxazole |
| Canonical SMILES | C1=CC=C2C(=C1)C(=CN2)C3=C(N=CO3)Cl |
| InChI | 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 |
Properties
| Appearance | Solid Powder |
| Boiling Point | 419.6±35.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
| Solubility | Soluble in Methanol, DMSO |
Reference Reading
1. Synthesis and antifungal activity of novel indole-replaced streptochlorin analogues
Nick Mulholland, David Beattie, Ming-Zhi Zhang, Sarah Turner, Guang-Fu Yang, John Clough, Chen-Yang Jia, Wei-Hua Zhang, Yu-Cheng Gu Eur J Med Chem . 2017 Jan 27;126:669-674. doi: 10.1016/j.ejmech.2016.12.001.
Based on examples of the successful applications in drug discovery of bioisosterism, a series of streptochlorin analogues in which indole has been replaced by other heterocycles has been designed and synthesized, as a continuation of our studies aimed at the discovery of novel streptochlorin analogues with improved antifungal activity. Biological testing showed that most of the indole-replaced streptochlorin analogues were inactive, though compound 6f had a broad spectrum of antifungal activity with significant activity against Alternaria solani. The SAR study demonstrated that indole ring is an essential moiety for the antifungal activity of streptochlorin analogues, promoting the idea of indole ring as a framework that might be exploited in the future.
2. Streptochlorin suppresses allergic dermatitis and mast cell activation via regulation of Lyn/Fyn and Syk signaling pathways in cellular and mouse models
Hee Jae Shin, Hyung-Sik Won, Seung-Hwan Lee, Kwang-Ho Lee, Dong-Young Kim, Tack-Joong Kim, Sushruta Koppula, Tae-Bong Kang, Do-Wan Shim, Sang-Kyu Ye PLoS One . 2013 Sep 27;8(9):e74194. doi: 10.1371/journal.pone.0074194.
Allergic diseases are chronic inflammatory conditions with specific immune and inflammatory mechanisms. Scientific interest in understanding the mechanisms and discovering novel agents for the prevention and treatment of allergic disease is increasing. Streptochlorin, a small compound derived from marine actinomycete possesses anti-angiogenic and anti-tumor activities. However, the anti-allergic effects and underlying mechanisms remain to be elucidated. In the present study, we investigated the effect of streptochlorin on allergic responses in vitro and in vivo. 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 the mitogen-activated protein kinases (MAPKs), including p38, ERK, and JNK. Further, streptochlorin reduced the phosphorylation of Syk in RBL-2H3 cells and inhibited the activity of Lyn and Fyn. Furthermore, administration of streptochlorin suppressed the allergic reactions in both passive cutaneous anaphylaxis reaction and 2, 4-dinitrofluorobenzene (DNFB)-induced allergic dermatitis in mice model. Considering the data obtained, we report for the first time that streptochlorin possess anti-allergic properties. The underlying mechanism of streptochlorin in exhibiting potent anti-allergic activity might be through the inhibition of the Lyn/Fyn and Syk signaling pathways.
3. Streptochlorin analogues as potential antifungal agents: Design, synthesis, antifungal activity and molecular docking study
Dai-Chuan Huang, Xinya Han, Chang Liu, Jun-Yang Tan, Nick Mulholland, Ya Gao, Haifeng Zhang, Bing Jin, Yun Deng, Ming-Zhi Zhang, Qinfei Xia, Abdallah S Ali, Shu-Ke Guo, Dale Guo, Zi-Long Song, Yu-Cheng Gu, Jing-Rui Liu, Run-Ling Qiu Bioorg Med Chem . 2021 Apr 1;35:116073. doi: 10.1016/j.bmc.2021.116073.
Streptochlorin is a small molecule of indole alkaloid isolated from marine Streptomyces sp., it is a promising lead compound due to its potent bioactivity in preventing many phytopathogens in our previous study, but further structural modifications are required to improve its antifungal activity. Our work in this paper focused on the replacement of oxazole ring in streptochlorin with the imidazole ring, to discover novel analogues. Based on this design strategy, three series of streptochlorin analogues were efficiently synthesized through sequential Vilsmeier-Haack reaction, Van Leusen imidazole synthesis and halogenation reaction. Some of the analogues displayed excellent activity in the primary assays, and this is highlighted by compounds 4g and 4i, the growth inhibition against Alternaria Leaf Spot and Rhizoctorzia solani under 50 μg/mL are 97.5% and 90.3%, respectively, even more active than those of streptochlorin, pimprinine and Osthole. Molecular docking models indicated that streptochlorin binds with Thermus thermophiles Leucyl-tRNA Synthetase in a similar mode to AN2690, offering a perspective on the mode of action study for antifungal activities of streptochlorin derivatives. Further study is still ongoing with the aim of discovering synthetic analogues, with improved antifungal activity and clear mode of action.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
