Epoxyquinomicin A
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| Category | Antibiotics |
| Catalog number | BBF-00856 |
| CAS | 175448-31-4 |
| Molecular Weight | 323.68 |
| Molecular Formula | C14H10ClNO6 |
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Description
Epoxyquinomicin A is an antibiotic produced by Amycolatopsis sp. MK299-95F4. It has moderate antibacterial activity against Pasteurella. It has a strong inhibitory activity of arthritis induced by oral collagen and is cytotoxic to several tumor cells.
Specification
| Synonyms | Benzamide, 3-chloro-2-hydroxy-N-(6-(hydroxymethyl)-2,5-dioxo-7-oxoabicyclo(4.1.0)hept-3-en-3-yl)-, (1S)- |
| IUPAC Name | 3-chloro-2-hydroxy-N-[(1S,6R)-6-(hydroxymethyl)-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzamide |
| Canonical SMILES | C1=CC(=C(C(=C1)Cl)O)C(=O)NC2=CC(=O)C3(C(C2=O)O3)CO |
| InChI | InChI=1S/C14H10ClNO6/c15-7-3-1-2-6(10(7)19)13(21)16-8-4-9(18)14(5-17)12(22-14)11(8)20/h1-4,12,17,19H,5H2,(H,16,21)/t12-,14+/m1/s1 |
| InChI Key | WJXATQQNIQELOK-OCCSQVGLSA-N |
Properties
| Appearance | Light Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 636.5°C at 760 mmHg |
| Melting Point | 168-173°C |
| Density | 1.71 g/cm3 |
Reference Reading
1. Epoxyquinomicins A, B, C and D, new antibiotics from Amycolatopsis. III. Physico-chemical properties and structure determination
N Matsumoto, T Tsuchida, R Sawa, H Iinuma, H Nakamura, H Naganawa, T Sawa, T Takeuchi J Antibiot (Tokyo). 1997 Nov;50(11):912-5. doi: 10.7164/antibiotics.50.912.
The structures of epoxyquinomicins A (1), B (2), C (3) and D (4) were determined by spectroscopic studies. Compound 1 was determined to be (5R,6S)-2-(3-chloro-2-hydroxybenzoylamino)-5-hydroxymethyl-5,6-epo xy- 2-cyclohexene-1,4-dione. Compound 2 was revealed to be the dechlorinated derivative of 1. Compounds 3 and 4 were determined to be the reduced derivative of 2 and 1, respectively.
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. TGF-β-induced epithelial-mesenchymal transition of A549 lung adenocarcinoma cells is enhanced by pro-inflammatory cytokines derived from RAW 264.7 macrophage cells
Mikiko Kawata, Daizo Koinuma, Tomohiro Ogami, Kazuo Umezawa, Caname Iwata, Tetsuro Watabe, Kohei Miyazono J Biochem. 2012 Feb;151(2):205-16. doi: 10.1093/jb/mvr136. Epub 2011 Dec 7.
Cancer cells undergo epithelial-mesenchymal transition (EMT) during invasion and metastasis. Although transforming growth factor-β (TGF-β) and pro-inflammatory cytokines have been implicated in EMT, the underlying molecular mechanisms remain to be elucidated. Here, we studied the effects of proinflammatory cytokines derived from the mouse macrophage cell line RAW 264.7 on TGF-β-induced EMT in A549 lung cancer cells. Co-culture and treatment with conditioned medium of RAW 264.7 cells enhanced a subset of TGF-β-induced EMT phenotypes in A549 cells, including changes in cell morphology and induction of mesenchymal marker expression. These effects were increased by the treatment of RAW 264.7 cells with lipopolysaccharide, which also induced the expression of various proinflammatory cytokines, including TNF-α and IL-1β. The effects of conditioned medium of RAW 264.7 cells were partially inhibited by a TNF-α neutralizing antibody. Dehydroxy methyl epoxyquinomicin, a selective inhibitor of NFκB, partially inhibited the enhancement of fibronectin expression by TGF-β, TNF-α, and IL-1β, but not of N-cadherin expression. Effects of other pharmacological inhibitors also suggested complex regulatory mechanisms of the TGF-β-induced EMT phenotype by TNF-α stimulation. These findings provide direct evidence of the effects of RAW 264.7-derived TNF-α on TGF-β-induced EMT in A549 cells, which is transduced in part by NFκB signalling.
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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
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
