Deoxynybomycin
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| Category | Antibiotics |
| Catalog number | BBF-02140 |
| CAS | 27259-98-9 |
| Molecular Weight | 282.29 |
| Molecular Formula | C16H14N2O3 |
| Purity | >98% by HPLC |
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Description
Deoxynybomycin is originally isolated from Str. hyalinum MB 891-A1 and Str. sp. A-717. It is resistant to bacteria, mycobacterium and phage.
Specification
| Synonyms | BRN 0626835; 6,8,11-Trimethyl-2H,4H-oxazolo(5,4,3-ij)pyrido(3,2-g)quinoline-4,10(11H)-dione; 5,7,10-Trimethyl-10H-1-oxa-2a,10-diaza-aceanthrylene-3,9-dione |
| IUPAC Name | 3,6,10-trimethyl-15-oxa-3,13-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1,5,7,9(16),10-pentaene-4,12-dione |
| Canonical SMILES | CC1=CC(=O)N(C2=C3C4=C(C=C12)C(=CC(=O)N4CO3)C)C |
| InChI | InChI=1S/C16H14N2O3/c1-8-4-12(19)17(3)14-10(8)6-11-9(2)5-13(20)18-7-21-16(14)15(11)18/h4-6H,7H2,1-3H3 |
| InChI Key | SBTFHJGTXHMDPR-UHFFFAOYSA-N |
Properties
| Appearance | White Acicular Crystal |
| Antibiotic Activity Spectrum | mycobacteria |
| Boiling Point | 470.2°C at 760 mmHg |
| Density | 1.44 g/cm3 |
Reference Reading
1. Deoxynybomycin is a selective anti-tumor agent inducing apoptosis and inhibiting topoisomerase I
K Egawa, T Yamori, C Nosaka, S Kunimoto, T Takeuchi, K Nos Biol Pharm Bull. 2000 Sep;23(9):1036-40. doi: 10.1248/bpb.23.1036.
Deoxynybomycin was identified as an inducer of p21the/WAF1 gene following screening using a reporter, p21/luciferase. The present study examined its anti-proliferative effect on human tumor cell lines. Deoxynybomycin selectively inhibited growth of human osteoblastic sarcoma Saos-2, gastric cancer TMK-1, and monocytic leukemia THP-1 cells, but did not affect survival of normal human fibroblasts at doses up to 5 microg/ml. Results from an assay system using a panel of 39 human cancer cell lines indicated that deoxynybomycin has selective cytotoxic activity against lung carcinoma cell lines. Deoxynybomycin induced apoptosis in Saos-2, TMK-1, and THP-1 cells as revealed by DNA fragmentation and TUNEL assays. It inhibited topoisomerase I but not topoisomerase II. These results suggest that deoxynybomycin may be useful in cancer chemotherapy.
2. Predictive compound accumulation rules yield a broad-spectrum antibiotic
Michelle F Richter, Bryon S Drown, Andrew P Riley, Alfredo Garcia, Tomohiro Shirai, Riley L Svec, Paul J Hergenrother Nature. 2017 May 18;545(7654):299-304. doi: 10.1038/nature22308. Epub 2017 May 10.
Most small molecules are unable to rapidly traverse the outer membrane of Gram-negative bacteria and accumulate inside these cells, making the discovery of much-needed drugs against these pathogens challenging. Current understanding of the physicochemical properties that dictate small-molecule accumulation in Gram-negative bacteria is largely based on retrospective analyses of antibacterial agents, which suggest that polarity and molecular weight are key factors. Here we assess the ability of over 180 diverse compounds to accumulate in Escherichia coli. Computational analysis of the results reveals major differences from the retrospective studies, namely that the small molecules that are most likely to accumulate contain an amine, are amphiphilic and rigid, and have low globularity. These guidelines were then applied to convert deoxynybomycin, a natural product that is active only against Gram-positive organisms, into an antibiotic with activity against a diverse panel of multi-drug-resistant Gram-negative pathogens. We anticipate that these findings will aid in the discovery and development of antibiotics against Gram-negative bacteria.
3. Deoxynybomycins inhibit mutant DNA gyrase and rescue mice infected with fluoroquinolone-resistant bacteria
Elizabeth I Parkinson, Joseph S Bair, Bradley A Nakamura, Hyang Y Lee, Hani I Kuttab, Emma H Southgate, Stéphane Lezmi, Gee W Lau, Paul J Hergenrother Nat Commun. 2015 Apr 24;6:6947. doi: 10.1038/ncomms7947.
Fluoroquinolones are one of the most commonly prescribed classes of antibiotics, but fluoroquinolone resistance (FQR) is widespread and increasing. Deoxynybomycin (DNM) is a natural-product antibiotic with an unusual mechanism of action, inhibiting the mutant DNA gyrase that confers FQR. Unfortunately, isolation of DNM is difficult and DNM is insoluble in aqueous solutions, making it a poor candidate for development. Here we describe a facile chemical route to produce DNM and its derivatives. These compounds possess excellent activity against FQR methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococci clinical isolates and inhibit mutant DNA gyrase in-vitro. Bacteria that develop resistance to DNM are re-sensitized to fluoroquinolones, suggesting that resistance that emerges to DNM would be treatable. Using a DNM derivative, the first in-vivo efficacy of the nybomycin class is demonstrated in a mouse infection model. Overall, the data presented suggest the promise of DNM derivatives for the treatment of FQR infections.
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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 ╳
