Epoxyquinomicin C
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00858 |
| CAS | 200496-85-1 |
| Molecular Weight | 291.26 |
| Molecular Formula | C14H13NO6 |
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Description
Epoxyquinomicin C is the active substance produced by Amycolatopsis sp. MK299-95F4. Inhibitor of histidine decarboxylase.
Specification
| Synonyms | Benzamide, 2-hydroxy-N-(2-hydroxy-6-(hydroxymethyl)-5-oxo-7-oxabicyclo(4.1.0)hept-3-en-3-yl)-, (1R-(1-alpha,2-alpha,6-alpha))-; 2-hydroxy-N-[(1R,2S,6R)-2-hydroxy-6-(hydroxymethyl)-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzamide |
| IUPAC Name | 2-hydroxy-N-[(1R,2S,6R)-2-hydroxy-6-(hydroxymethyl)-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzamide |
| Canonical SMILES | C1=CC=C(C(=C1)C(=O)NC2=CC(=O)C3(C(C2O)O3)CO)O |
| InChI | InChI=1S/C14H13NO6/c16-6-14-10(18)5-8(11(19)12(14)21-14)15-13(20)7-3-1-2-4-9(7)17/h1-5,11-12,16-17,19H,6H2,(H,15,20)/t11-,12+,14-/m0/s1 |
| InChI Key | JNDISHBDOZQLTR-SCRDCRAPSA-N |
Properties
| Appearance | White Powder |
| Melting Point | 168-172°C |
| Solubility | Soluble in Methanol, methyl ether, ethyl acetate |
Reference Reading
1. Dehydroxymethylepoxyquinomicin, a novel nuclear factor-κB inhibitor, reduces chemokines and adhesion molecule expression induced by IL-1β in human corneal fibroblasts
Sosuke Inokawa, Takayo Watanabe, Hiroshi Keino, Yasuhiko Sato, Akito Hirakata, Annabelle A Okada, Ken Fukuda, Atsuki Fukushima, Kazuo Umezawa Graefes Arch Clin Exp Ophthalmol. 2015 Apr;253(4):557-63. doi: 10.1007/s00417-014-2879-9. Epub 2014 Dec 18.
Purpose: Dehydroxymethylepoxyquinomicin (DHMEQ) is derived from the antibiotic, epoxyquinomicin C, and is a novel low molecular weight nuclear factor-κB (NF-κB) inhibitor. We investigated the effects of DHMEQ on the expression of chemokines and the intercellular adhesion molecule (ICAM)-1 induced by proinflammatory cytokines in cultures of the human corneal fibroblasts (HCFs). Methods: The cytotoxicity of DHMEQ on cultured HCFs was evaluated by cell proliferation assays. Cultures were exposed to interleukin (IL)-1β, and the production of IL-8 and monocyte chemoattractant protein (MCP)-1 was assessed by enzyme-linked immunosorbent assay. The degree of expression of ICAM-1 was measured by flow cytometry. The translocation of NF-κB p65 into the nucleus of HCFs was assessed by immunocytochemistry. Results: DHMEQ was not toxic to cultured HCFs at doses up to 10 μg/ml. DHMEQ significantly suppressed the production of both IL-8 and MCP-1 in IL-1β-stimulated HCFs. In addition, DHMEQ down-regulated ICAM-1 expression in IL-1β-stimulated HCFs in a dose-dependent manner. DHMEQ inhibited the IL-1β-induced nuclear accumulation of p65, a component of NF-κB, in HCFs. Conclusions: The suppression of inflammatory chemokines IL-8 and MCP-1 and inhibition of the expression of ICAM-1 in cultured HCFs by DHMEQ indicates that DHMEQ may have a therapeutic potential for treating ICAM-1 and chemokine-mediated corneal inflammatory disorders.
2. Inhibition of Late and Early Phases of Cancer Metastasis by the NF-κB Inhibitor DHMEQ Derived from Microbial Bioactive Metabolite Epoxyquinomicin: A Review
Yinzhi Lin, Tamami Ukaji, Naoki Koide, Kazuo Umezawa Int J Mol Sci. 2018 Mar 3;19(3):729. doi: 10.3390/ijms19030729.
We previously designed and synthesized dehydroxyepoxyquinomicin (DHMEQ) as an inhibitor of NF-κB based on the structure of microbial secondary metabolite epoxyquinomicin C. DHMEQ showed anti-inflammatory and anticancer activity in various in vivo disease models without toxicity. On the other hand, the process of cancer metastasis consists of cell detachment from the primary tumor, invasion, transportation by blood or lymphatic vessels, invasion, attachment, and formation of secondary tumor. Cell detachment from the primary tumor and subsequent invasion are considered to be early phases of metastasis, while tumor cell attachment to the tissue and secondary tumor formation the late phases. The assay system for the latter phase was set up with intra-portal-vein injection of pancreatic cancer cells. Intraperitoneal administration of DHMEQ was found to inhibit liver metastasis possibly by decreasing the expression of MMP-9 and IL-8. Also, when the pancreatic cancer cells treated with DHMEQ were inoculated into the peritoneal cavity of mice, the metastatic foci formation was inhibited. These results indicate that DHMEQ is likely to inhibit the late phase of metastasis. Meanwhile, we have recently employed three-dimensional (3D) culture of breast cancer cells for the model of early phase metastasis, since the 3D invasion just includes cell detachment and invasion into the matrix. DHMEQ inhibited the 3D invasion of breast cancer cells at 3D-nontoxic concentrations. In this way, DHMEQ was shown to inhibit the late and early phases of metastasis. Thus, DHMEQ is likely to be useful for the suppression of cancer metastasis.
3. Inhibition of matrix metalloproteinase expression and cellular invasion by NF-κB inhibitors of microbial origin
Kazuo Umezawa, Yinzhi Lin Biochim Biophys Acta Proteins Proteom. 2020 Jun;1868(6):140412. doi: 10.1016/j.bbapap.2020.140412. Epub 2020 Mar 14.
Matrix metalloproteinases (MMPs) are zinc-dependent extracellular matrix remodeling endopeptidases. MMPs cleave various matrix proteins such as collagen, elastin, gelatin and casein. MMPs are often implicated in pathological processes, such as cancer progression including metastasis. Meanwhile, microorganisms produce various secondary metabolites having unique structures. We designed and synthesized dehydroxymethylepoxyquinomicin (DHMEQ) based on the structure of epoxyquinomicin C derived from Amycolatopsis as an inhibitor of NF-κB. This compound inhibited cancer cell migration and invasion. Since DHMEQ is comparatively unstable in the body, we designed and synthesized a stable DHMEQ analog, SEMBL. SEMBL also inhibited cancer cell migration and invasion. We also looked for inhibitors of cancer cell migration and invasion from microbial culture filtrates. As a result, we isolated a known compound, ketomycin, from Actinomycetes. DHMEQ, SEMBL, and ketomycin are all NF-κB inhibitors, and inhibited the expression of MMPs in the inhibition of cellular migration and invasion. These are all compounds with comparatively low toxicity, and may be useful for the development of anti-metastasis agents.
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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 ╳
