Nybomycin is an unusual heterocyclic metabolite isolated from several Streptomyces species, first reported in 1961 from Streptomyces niveus. Nybomycin possesses antiviral and antibacterial activity. The spectrum of Nybomycin has not been extensively studied. Nybomycins are reported to be 'reverse antibiotics' that inhibit growth of some Gram-positive fluoroquinolone-resistant bacteria by targeting the mutant form of DNA gyrase while being inactive against wild-type strains with fluoroquinolone-sensitive gyrases. In research, the compound can be used to study bacterial DNA replication and repair, and bacterial resistance.
Nybomycin is soluble in DMF or DMSO. Moderately soluble in methanol or ethanol. Poor water solubility.
| Mechanism of Action | The mode of action of Nybomycin has not been extensively studied. Fluoroquinolones inhibit topoisomerase activity, specifically type II topoisomerases, DNA gyrase, and topo IV. |
| Spectrum | Nybomycin is active against many relevant Gram-negative and Gram-positive bacteria. However, the emergence of resistant isolates is relatively high. Nybomycin also showed antimicrobial activity against Mycobacterium including M. smegmatis, M. bovis, and M. tuberculosis (ref). |
| Microbiology Applications |
Mutations conferring resistance to fluoroquinolones are located in quinolone resistance-determining regions (QRDRs) of GyrA/ParC. After it was first reported that Nybomycin was a 'reverse' antibiotic, the family was studied as an alternative scaffold for antimicrobial agents. The causative agent of Tuberculosis (TB) is Mycobacterium tuberculosis. It has the ability to become dormant, thus new compounds that are effective against both active and dormant states are needed. Authors screened marine organisms and found Nybomybin was re-discovered from the culture broth of a marine-derived Streptomyces sp. MS44. It is interesteing because Nybomycin was originally came from the terrestrial Streptomyces A717 by Srelitz et al). (Arai et al, 2015). |
| Molecular Formula | C16H14N2O4 |
| References |
Arai M et al (2015) Anti-dormant mycobacterial activity and target analysis of Nybomycin produced by a marine-derived Streptomyces sp. Bioorg. Med. Chem. 23 (13):3534-3541 Rinehart KL et al (1970) Nybomycin. III. Revised structure. J. Am. Chem. Soc. 92:6994 Strelitz F et al (1955) Nybomycin, a new antibiotic with antiphage and antibacterial properties. Proc. Natl. Acad. Sci. U.S.A. 41:620 |