Nybomycin

For research use only. Not for therapeutic Use.

  • CAT Number: R004321
  • CAS Number: 30408-30-1
  • Molecular Formula: C16H14N2O4
  • Molecular Weight: 298.29
  • Purity: 95%
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Nybomycin(Cat No.:R004321)is a potent, naturally occurring antibiotic derived from Streptomyces species, known for its broad-spectrum activity against a variety of bacterial and fungal pathogens. It exerts its antimicrobial effects by inhibiting protein synthesis through interference with bacterial ribosomes. Nybomycin has shown potential in treating infections caused by multi-drug resistant organisms, particularly in clinical settings. Additionally, its unique mechanism of action and minimal cross-resistance make it a promising candidate for further research in the development of novel antibiotics for resistant pathogens.


Catalog Number R004321
CAS Number 30408-30-1
Molecular Formula C16H14N2O4
Purity 95%
Target Antibiotic
Appearance Tan to dark tan solid
Storage -20°C
Analysis method HPLC
IUPAC Name 6-(hydroxymethyl)-3,10-dimethyl-15-oxa-3,13-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(16),2(7),5,8,10-pentaene-4,12-dione
InChI InChI=1S/C16H14N2O4/c1-8-3-13(21)18-7-22-16-14-11(5-10(8)15(16)18)9(6-19)4-12(20)17(14)2/h3-5,19H,6-7H2,1-2H3
InChIKey HKMUGCUFXWTNSP-UHFFFAOYSA-N
SMILES CC1=CC(=O)N2COC3=C2C1=CC4=C3N(C(=O)C=C4CO)C
Reference

1. Biochimie. 2019 May;160:93-99. doi: 10.1016/j.biochi.2019.02.010. Epub 2019 Feb 21.<br />
Nybomycin-producing Streptomyces isolated from carpenter ant Camponotus vagus.<br />
Zakalyukina YV(1), Birykov MV(2), Lukianov DA(3), Shiriaev DI(4), Komarova ES(5), Skvortsov DA(4), Kostyukevich Y(3), Tashlitsky VN(4), Polshakov VI(6), Nikolaev E(3), Sergiev PV(7), Osterman IA(8).<br />
Author information:<br />
(1)Department of Soil Science, Lomonosov Moscow State University, Moscow, 119234 Russia. (2)Department of Biology, Lomonosov Moscow State University, Moscow, 119234 Russia. (3)Skolkovo Institute of Science and Technology, Skolkovo, Moscow Region, 143025, Russia. (4)Department of Chemistry and A.N. Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, Moscow, 119992, Russia. (5)Skolkovo Institute of Science and Technology, Skolkovo, Moscow Region, 143025, Russia; Faculty of Bioengineering and Bioinformatics, Lomonosov Moscow State University, Moscow, 119234 Russia. (6)Center for Magnetic Tomography and Spectroscopy, Faculty of Fundamental Medicine, M.V., Russia. (7)Skolkovo Institute of Science and Technology, Skolkovo, Moscow Region, 143025, Russia; Department of Chemistry and A.N. Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, Moscow, 119992, Russia.<br />
(8)Skolkovo Institute of Science and Technology, Skolkovo, Moscow Region, 143025, Russia; Department of Chemistry and A.N. Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, Moscow, 119992, Russia. Electronic address: [email protected].<br />
A novel strain of Actinomycetes was isolated from the body of an ant (Camponotus vagus Scopoli) and its genetic and morphological properties were characterized. The 16S rDNA gene sequence analysis of the isolate revealed its high phylogenetic relationship with type strains of Streptomyces violaceochromogenes NBRC 13100T. As a result of antimicrobial activity assessment, it was found that the fermentation broth of the isolated strain both inhibited the growth and induced the SOS response in E.&nbsp;coli BW25113 &Delta;tolC strain cells. Using bioassay-guided fractionation, mass spectrometric and NMR analyses we identified the active compound to be nybomycin, a previously described antibiotic. Here we report for the first time Streptomyces producer of nybomycin in association with carpenter ants and demonstrate cytotoxic activity of nybomycin against human cell lines.<br />
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2. Mar Drugs. 2018 Nov 4;16(11):435. doi: 10.3390/md16110435.<br />
Heterologous Expression of the Nybomycin Gene Cluster from the Marine Strain Streptomyces albus subsp. chlorinus NRRL B-24108.<br />
Rodr&iacute;guez Est&eacute;vez M(1), Myronovskyi M(2), Gummerlich N(3), Nadmid S(4), Luzhetskyy A(5)(6).<br />
Author information:<br />
(1)Pharmazeutische Biotechnologie, Universit&auml;t des Saarlandes, 66123 Saarbr&uuml;cken, Germany. [email protected]. (2)Pharmazeutische Biotechnologie, Universit&auml;t des Saarlandes, 66123 Saarbr&uuml;cken, Germany. [email protected]. (3)Pharmazeutische Biotechnologie, Universit&auml;t des Saarlandes, 66123 Saarbr&uuml;cken, Germany. [email protected]. (4)Pharmazeutische Biotechnologie, Universit&auml;t des Saarlandes, 66123 Saarbr&uuml;cken, Germany. [email protected]. (5)Pharmazeutische Biotechnologie, Universit&auml;t des Saarlandes, 66123 Saarbr&uuml;cken, Germany. [email protected]. (6)Helmholtz-Institut f&uuml;r Pharmazeutische Forschung Saarland, 66123 Saarbr&uuml;cken, Germany. [email protected].<br />
Streptomycetes represent an important reservoir of active secondary metabolites with potential applications in the pharmaceutical industry. The gene clusters responsible for their production are often cryptic under laboratory growth conditions. Characterization of these clusters is therefore essential for the discovery of new microbial pharmaceutical drugs. Here, we report the identification of the previously uncharacterized nybomycin gene cluster from the marine actinomycete Streptomyces albus subsp. chlorinus through its heterologous expression. Nybomycin has previously been reported to act against quinolone-resistant Staphylococcus aureus strains harboring a mutated gyrA gene but not against those with intact gyrA. The nybomycin-resistant mutants generated from quinolone-resistant mutants have been reported to be caused by a back-mutation in the gyrA gene that restores susceptibility to quinolones. On the basis of gene function assignment from bioinformatics analysis, we suggest a model for nybomycin biosynthesis.<br />
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3. Front Chem. 2020 Jan 10;7:896. doi: 10.3389/fchem.2019.00896. eCollection 2019.<br />
Benzanthric Acid, a Novel Metabolite From Streptomyces albus Del14 Expressing the Nybomycin Gene Cluster.<br />
Rodr&iacute;guez Est&eacute;vez M(1), Gummerlich N(1), Myronovskyi M(1), Zapp J(2), Luzhetskyy A(1)(3).<br />
Author information:<br />
(1)Pharmaceutical Biotechnology, University of Saarland, Saarbr&uuml;cken, Germany. (2)Department of Pharmacy, Institute of Pharmaceutical Biology, University of Saarland, Saarbr&uuml;cken, Germany. (3)Helmholtz Institute for Pharmaceutical Research Saarland, Saarbr&uuml;cken, Germany.<br />
Streptomycetes constitute a diverse bacterial group able to produce a wide variety of secondary metabolites with potential applications in the pharmacy industry. However, the genes responsible for the biosynthesis of these compounds are very frequently inactive or expressed at very low levels under standard laboratory cultivation conditions. Therefore, the activation or upregulation of secondary metabolite biosynthesis genes is a crucial step for the discovery of new bioactive natural products. We have recently reported the discovery of the biosynthetic genes for the antibiotic nybomycin (nyb genes) in Streptomyces albus subsp. chlorinus. The nyb genes were expressed in the heterologous host Streptomyces albus Del14, which produces not only nybomycin, but also a novel compound. In this study, we describe the isolation, purification, and structure elucidation of the new substance named benzanthric acid.<br />

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