Nybomycin
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| Category | Antibiotics |
| Catalog number | BBF-02613 |
| CAS | 30408-30-1 |
| Molecular Weight | 298.29 |
| Molecular Formula | C16H14N2O4 |
| Purity | >95% by HPLC |
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Description
An unusual heterocyclic metabolite isolated from several streptomyces species; possesses antiviral and antibacterial activity.
Specification
| Synonyms | NSC613948; 8-(Hydroxymethyl)-6,11-dimethyl-2H,4H-oxazolo[5,4,3-ij]pyrido[3,2-g]quinoline-4,10(11H)-dione; 8,9-Dihydro-4-(hydroxymethyl)-6,9-dimethyl-2,8-dioxopyrido(3,2-g)quinoline-1(2H)-carboxaldehyde |
| Storage | Store at -20°C |
| 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 |
| Canonical SMILES | CC1=CC(=O)N2COC3=C2C1=CC4=C3N(C(=O)C=C4CO)C |
| 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 |
| InChI Key | HKMUGCUFXWTNSP-UHFFFAOYSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Tan to Dark Tan Solid |
| Antibiotic Activity Spectrum | mycobacteria |
| Boiling Point | 538.7°C at 760 mmHg |
| Melting Point | 325-330°C |
| Density | 1.54 g/cm3 |
| Solubility | Soluble in DMF or DMSO. Moderately soluble in methanol or ethanol. Poor water solubility. |
Reference Reading
1. Nybomycin inhibits both types of E. coli DNA gyrase - fluoroquinolone-sensitive and fluoroquinolone-resistant
Petr V Sergiev, Yuliya V Zakalyukina, Tinashe P Maviza, Dmitrii A Lukianov, Alina A Sofronova, Yan A Ivanenkov, Ilya A Osterman, Ekaterina S Komarova, Mikhail V Biryukov, Olga A Dontsova, Dmitrii I Shiriaev, Valeria I Marina, Ekaterina A Berdnikovich Antimicrob Agents Chemother . 2021 Feb 16;65(5):e00777-20. doi: 10.1128/AAC.00777-20.
Bacterial type II topoisomerases, DNA gyrase and topoisomerase IV, are targets of many antibiotics including fluoroquinolones (FQs). Unfortunately, a number of bacterial species easily acquire resistance to FQs by mutations in either DNA gyrase or topoisomerase IV genes. The emergence of resistant pathogenic strains is a global problem in healthcare, therefore, identifying alternative pathways to thwart their persistence is the current frontier in drug discovery. An attractive class of compounds is nybomycins, reported to be "reverse antibiotics" that selectively inhibit growth of some Gram-positive FQ-resistant bacteria by targeting the mutant form of DNA gyrase, while being inactive against wild-type strains with FQ-sensitive gyrases. The strong "reverse" effect was demonstrated only for a few Gram-positive organisms resistant to FQs due to the S83L/I mutation in GyrA subunit of DNA gyrase. However, the activity of nybomycins has not been extensively explored among Gram-negative species. Here, we observed that in Gram-negativeE. coliΔtolC strain with enhanced permeability, wild-type gyrase and GyrA S83L mutant, resistant to fluoroquinolones, are both similarly sensitive to nybomycin.
2. Heterologous Expression of the Nybomycin Gene Cluster from the Marine Strain Streptomyces albus subsp. chlorinus NRRL B-24108
Marta Rodríguez Estévez, Andriy Luzhetskyy, Nils Gummerlich, Maksym Myronovskyi, Suvd Nadmid Mar Drugs . 2018 Nov 4;16(11):435. doi: 10.3390/md16110435.
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 actinomyceteStreptomyces albussubsp.chlorinusthrough its heterologous expression. Nybomycin has previously been reported to act against quinolone-resistantStaphylococcus aureusstrains harboring a mutatedgyrAgene but not against those with intactgyrA. The nybomycin-resistant mutants generated from quinolone-resistant mutants have been reported to be caused by a back-mutation in thegyrAgene that restores susceptibility to quinolones. On the basis of gene function assignment from bioinformatics analysis, we suggest a model for nybomycin biosynthesis.
3. Anti-dormant mycobacterial activity and target analysis of nybomycin produced by a marine-derived Streptomyces sp
Chisu Han, Naoyuki Kotoku, Motomasa Kobayashi, Patamaporn Pruksakorn, Masayoshi Arai, Jean-Pierre Joubert, Yuji Sumii, Dayoung Shin, Prashini Moodley, Kentaro Kamiya Bioorg Med Chem . 2015 Jul 1;23(13):3534-41. doi: 10.1016/j.bmc.2015.04.033.
In the course of our search for anti-dormant Mycobacterial substances, nybomycin (1) was re-discovered from the culture broth of a marine-derived Streptomyces sp. on the bioassay-guided separation. Compound 1 showed anti-microbial activity against Mycobacterium smegmatis and Mycobacterium bovis BCG with the MIC of 1.0μg/mL under both actively growing aerobic conditions and dormancy inducing hypoxic conditions. Compound 1 is also effective to Mycobacterium tuberculosis including the clinically isolated strains. The mechanistic analysis indicated that 1 bound to DNA and induces a unique morphological change to mycobacterial bacilli leading the bacterial cell death.
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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 ╳
