| Identification | Back Directory | [Name]
BicozaMycin benzoate, FR 2054 | [CAS]
37134-40-0 | [Synonyms]
FR2054
BicycloMycin benzoate
Bicyclomycin benzoate,FR 2054
BicozaMycin benzoate, FR 2054
Bicyclomycin, 3'-benzoate (9CI) | [Molecular Formula]
C19H22N2O8 | [MDL Number]
MFCD28899082 | [MOL File]
37134-40-0.mol | [Molecular Weight]
406.39 |
| Chemical Properties | Back Directory | [Melting point ]
>123°C (dec.) | [storage temp. ]
Hygroscopic, -20°C Freezer, Under inert atmosphere | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [color ]
White |
| Hazard Information | Back Directory | [Uses]
BicozaMycin benzoate, FR 2054 is a polar metabolite first isolated from Streptomyces sapporonensis in 1972, with activity against Gram negative bacteria. The selective Gram negative profile of bicyclomycin is rare among Streptomyces metabolites, and in an effort to overcome its poor in vivo absorption, the benzoate ester was prepared by reaction with the more exposed primary alcohol. BicozaMycin benzoate, FR 2054 benzoate has limited use as a veterinary antibiotic.
| [Biological Activity]
bicyclomycin benzoate is a novel antibiotic produced by s. sapporonensi [1]. bicyclomycin shows an inhibitory effect on gram-negative bacteria, such as e. coli, klebsiella, shigella, salmonella, citrobacter, e. cloacae, and the pathogenic group of neisseria [2]. bicyclomycin benzoate is inactive against proteus, p. aeruginosa, and gram-positive bacteria [1,2]. | [in vitro]
the mig of bicyclomycin for e.coli nihj jc-2 was 25-50 μg/ml. bicyclomycin (25-50 μg/ml) completely inhibited formation of visible colonies or turbidity of this organism on agar plates, in nutrient broth, and in heart infusion broth [2]. bicyclomycin inhibited atpase activity in the presence of poly(dc) and ribo(c)10. the approximate ic50 value for inhibition of transcription termination at rho-dependent sites was 5 μm. the inhibitory effect of bicyclomycin on rho-dependent transcripts was accompanied by the appearance of a new set of transcripts. in the presence of poly(dc), bicyclomycin reversibly inhibited the ribo(c)10-stimulated atpase activity. the extrapolated ki for bicyclomycin was 2.8 μm without ribo(c)10, which was increased to 26 μm in the presence of ribo(c)10 [3]. | [in vivo]
bicyclomycin showed therapeutic activity for infections with several strains of e. coli which were resistant to the control antibiotics. the ed50 of bicyclomycin for infection with gp-resistant e.coli 312 was 3.05 (1.47-7.66) mg/mouse [2]. | [storage]
Store at -20°C | [References]
[1] miyoshi, t. ,miyairi, n.,aoki, h., et al. bicyclomycin, a new antibiotic. i. taxonomy, isolation and characterization. j.antibiot.(tokyo) 25(10), 569-575(1972).
[2] nishida, m. ,mine, y.,matsubara, t., et al. bicyclomycin, a new antibiotic. iii. in vitro and in vivo antimicrobial activity. j.antibiot.(tokyo) 25(10), 582-593(1972).
[3] magyar a, zhang x, kohn h, et al. the antibiotic bicyclomycin affects the secondary rna binding site of escherichia coli transcription termination factor rho[j]. journal of biological chemistry, 1996, 271(41): 25369-25374. |
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