Nanaomycin A
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| Category | Antibiotics |
| Catalog number | BBF-02570 |
| CAS | 52934-83-5 |
| Molecular Weight | 302.28 |
| Molecular Formula | C16H14O6 |
| Purity | 98% |
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Description
Nanaomycin A is an antibiotic produced by Str. rosa subsp. notoensis. It has anti-gram-positive bacteria, mycobacteria, mycoplasma and fungi activity.
Specification
| Synonyms | Nanafrocin; Rosanomycin A; Nanafrocine |
| Storage | Store at -20°C |
| IUPAC Name | 2-[(1S,3R)-9-hydroxy-1-methyl-5,10-dioxo-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetic acid |
| Canonical SMILES | CC1C2=C(CC(O1)CC(=O)O)C(=O)C3=C(C2=O)C(=CC=C3)O |
| InChI | InChI=1S/C16H14O6/c1-7-13-10(5-8(22-7)6-12(18)19)15(20)9-3-2-4-11(17)14(9)16(13)21/h2-4,7-8,17H,5-6H2,1H3,(H,18,19)/t7-,8+/m0/s1 |
| InChI Key | ZCJHPTKRISJQTN-JGVFFNPUSA-N |
Properties
| Appearance | Orange Needle Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycoplasma; mycobacteria |
| Boiling Point | 601.5±55.0°C at 760 mmHg |
| Melting Point | 178-180°C |
| Density | 1.5±0.1 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1.New compounds, nanaomycin F and G, discovered by physicochemical screening from a culture broth of Streptomyces rosa subsp. notoensis OS-3966.
Nakashima T1, Boonsnongcheep P2, Kimura T3, Iwatsuki M4, Sato N5, Nonaka K4, Prathanturarug S2, Takahashi Y6, Ōmura S6. J Biosci Bioeng. 2015 Nov;120(5):596-600. doi: 10.1016/j.jbiosc.2015.03.018. Epub 2015 Jun 20.
Two new compounds, nanaomycin F and G, were isolated by physicochemical screening method from cultured broth of Streptomyces rosa subsp. notoensis OS-3966, which is known to produce nanaomycin A, B, C, D, and E. Nanaomycin F is a new nanaomycin analog, a 4a-hydroxyl analog of nanaomycin B. Nanaomycin G has a unique skeleton with 1-indanone infused with a tetrahydropyran ring. Nanaomycin A possesses broad antimicrobial activity but nanaomycin F and G demonstrated no bioactivity against all bacteria and fungi tested in this study. In addition, in both nanaomycin F and G, the production of superoxide radicals was majorly decreased in comparison to nanaomycin A. It was considered that the antimicrobial properties were lost as a result of the decrease in production of the superoxide radicals.
2.Polymyxin B identified as an inhibitor of alternative NADH dehydrogenase and malate: quinone oxidoreductase from the Gram-positive bacterium Mycobacterium smegmatis.
Mogi T1, Murase Y, Mori M, Shiomi K, Omura S, Paranagama MP, Kita K. J Biochem. 2009 Oct;146(4):491-9. doi: 10.1093/jb/mvp096. Epub 2009 Jun 29.
Tuberculosis is the leading cause of death due to a single infectious agent in the world and the emergence of multidrug-resistant strains prompted us to develop new drugs with novel targets and mechanism. Here, we screened a natural antibiotics library with Mycobacterium smegmatis membrane-bound dehydrogenases and identified polymyxin B (cationic decapeptide) and nanaomycin A (naphtoquinone derivative) as inhibitors of alternative NADH dehydrogenase [50% inhibitory concentration (IC(50)) values of 1.6 and 31 microg/ml, respectively] and malate: quinone oxidoreductase (IC(50) values of 4.2 and 49 microg/ml, respectively). Kinetic analysis on inhibition by polymyxin B showed that the primary site of action was the quinone-binding site. Because of the similarity in K(m) value for ubiquinone-1 and inhibitor sensitivity, we examined amino acid sequences of actinobacterial enzymes and found possible binding sites for L-malate and quinones. Proposed mechanisms of polymyxin B and nanaomycin A for the bacteriocidal activity were the destruction of bacterial membranes and production of reactive oxygen species, respectively, while this study revealed their inhibitory activity on bacterial membrane-bound dehydrogenases.
3.A rapid screening system evaluates novel inhibitors of DNA methylation and suggests F-box proteins as potential therapeutic targets for high-risk neuroblastoma.
Penter L1, Maier B2, Frede U3, Hackner B4, Carell T4, Hagemeier C3, Truss M5. Target Oncol. 2015 Dec;10(4):523-33. doi: 10.1007/s11523-014-0354-5. Epub 2015 Jan 6.
After extensive research on radiochemotherapy, 5-year survival rates of children with high risk neuroblastoma still do not exceed 50%, owing to adverse side-effects exemplified by doxorubicin-induced cardiomyopathy. A promising new approach is the combination of conventional therapies with specific modulation of cell signaling pathways promoting therapeutic resistance, such as inhibition of aberrant kinase activity or re-expression of silenced tumor suppressor genes by means of chromatin remodeling. In this regard, we established a system that allows to identify potential drug targets as well as to validate respective candidate inhibitors in high-risk neuroblastoma model cell lines. Cell culture, drug exposure, shRNA-mediated knockdown and phenotype analysis are integrated into an efficient and versatile single well-based protocol. By utilizing this system, we assessed RG108, SGI-1027 and nanaomycin A, three novel DNA methyltransferase inhibitors that have not been tested in neuroblastoma cell lines so far, for their potential of synergistic anti-tumor activity in combination with doxorubicin.
4.Selective and potent in vitro antitrypanosomal activities of ten microbial metabolites.
Otoguro K1, Ishiyama A, Namatame M, Nishihara A, Furusawa T, Masuma R, Shiomi K, Takahashi Y, Yamada H, Omura S. J Antibiot (Tokyo). 2008 Jun;61(6):372-8. doi: 10.1038/ja.2008.52.
More than 400 compounds isolated from soil microorganisms, and catalogued in the antibiotic library of the Kitasato Institute for Life Sciences, were screened against African trypanosomes. Ten compounds were found to have selective and potent antitrypanosomal activity in vitro: aureothin, cellocidin, destomycin A, echinomycin, hedamycin, irumamycin, LL-Z 1272beta, O-methylnanaomycin A, venturicidin A and virustomycin A. Results of the in vitro assays using the GUTat 3.1 strain of Trypanosomal brucei brucei and the STIB900 strain of T. b. rhodesiense are presented. Cytotoxicity was determined using a human MRC-5 cell line. This is the first report of antitrypanosomal activities of the 10 microbial metabolites listed above.
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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 ╳
