Ketomycin
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| Category | Antibiotics |
| Catalog number | BBF-01892 |
| CAS | 23364-22-9 |
| Molecular Weight | 154.16 |
| Molecular Formula | C8H10O3 |
| Purity | ≥98% |
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Description
It is produced by the strain of Str. sp. Tu99, Ketomycin is resistant to subtilis on the synthetic medium.
Specification
| Synonyms | Antibiotic R-3; Antibiotic T 86A; Cyclohexenyl-1-glyoxalic acid; (R)-alpha-Oxo-3-cyclohexene-1-acetic acid; BRN 2964900 |
| IUPAC Name | 2-[(1R)-cyclohex-3-en-1-yl]-2-oxoacetic acid |
| Canonical SMILES | C1CC(CC=C1)C(=O)C(=O)O |
| InChI | InChI=1S/C8H10O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-2,6H,3-5H2,(H,10,11)/t6-/m0/s1 |
| InChI Key | XJVDGWZMESEVTD-LURJTMIESA-N |
Properties
| Appearance | Flaky Crystalline |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 253.3°C at 760 mmHg |
| Melting Point | 50-51°C |
| Density | 1.227 g/cm3 |
Reference Reading
1. Polyketomycin, a new antibiotic from Streptomyces sp. MK277-AF1. I. Taxonomy, production, isolation, physico-chemical properties and biological activities
I Momose, W Chen, N Kinoshita, H Iinuma, M Hamada, T Takeuchi J Antibiot (Tokyo). 1998 Jan;51(1):21-5. doi: 10.7164/antibiotics.51.21.
A new antibiotic designated polyketomycin was isolated from the culture broth of Streptomyces sp. MK277-AF1. It was purified by ethyl acetate extraction, Sephadex LH-20 column chromatography and centrifugal partition chromatography (CPC). It inhibited growth of Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA). Its MICs were less than 0.2 microgram/ml. Polyketomycin exhibited cytotoxic activity against nine tumor cell lines at concentrations of 0.9-5.2 micrograms/ml.
2. 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.
3. Isolation of ketomycin from Actinomycetes as an inhibitor of 2D and 3D cancer cell invasion
Yinzhi Lin, Yue Chen, Tamami Ukaji, Shoshiro Okada, Kazuo Umezawa J Antibiot (Tokyo). 2019 Mar;72(3):148-154. doi: 10.1038/s41429-018-0129-9. Epub 2018 Dec 3.
Inhibitors of cancer cell migration and invasion should be useful to inhibit metastasis. Then, we have screened microbial culture filtrates for the inhibitors of cancer cell migration. As a result, we isolated an antibiotic ketomycin from a culture filtrate of Actinomycetes SF2912 as an inhibitor of cancer cell migration. It is a known antibiotic, but its biological activity on mammalian cells has not been reported. Ketomycin inhibited cellular migration and invasion in human breast carcinoma MDA-MB-231 and MCF-7 cells at the non-toxic concentrations. Ketomycin decreased the expressions of MMP-9 and MMP-11 in MDA-MB-231 cells. Knockdown of each gene by siRNA inhibited the cellular migration and invasion. Ketomycin was then found to inhibit the cellular NF-κB activity that may be involved in the upstream signaling. For the mechanism of NF-κB inhibition, ketomycin inhibited autophosphorylation of IKK-α/IKK-β. Ketomycin also inhibited the 3D-invasion of MDA-MB-231 cells at the non-toxic concentrations. Thus, ketomycin having a comparatively simple structure may become a seed of anti-metastasis agent.
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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 ╳
