| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg | |||
| Other Sizes |
| Targets |
Bicyclomycin benzoate targets the transcription termination factor Rho, a RecA-type ATPase in E. coli. By inhibiting Rho, the compound disrupts bacterial RNA synthesis. The compound also interferes with the biosynthesis of lipoprotein and its assembly to peptidoglycan in the cell envelope of E. coli. This dual mechanism of action contributes to its broad-spectrum antibacterial activity. Bicyclomycin benzoate is effective against a broad spectrum of Gram-negative bacteria, including Escherichia coli and Pseudomonas aeruginosa, as well as some Gram-positive bacteria.
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| ln Vitro |
Dicyclomycin's primary action is to obstruct lipoprotein production and assembly with peptidoglycan in the E. coli cell envelope. Coli. Dicyclomycin suppresses RNA and protein synthesis in growing E. coli at fatal concentrations. fifteen THU of coli cells [1]. In Escherichia coli, dicyclomycin targets the rho transcription termination factor. Dicyclomycin is a weak rho inhibitor that can damage the rho molecular mechanism, causing anomalous constitutively expressed proteins to be overproduced too soon, which can have harmful effects on cells and cause catastrophic outcomes [2]. Dicyclomycin has been discovered to inhibit rho poly(C)-stimulated ATP hydrolysis via a noncompetitive, reversible route with regard to ATP (Ki=20 μM) [3].
In vitro, bicyclomycin benzoate exhibits activity against a broad spectrum of Gram-negative bacteria and Gram-positive bacteria. The compound's antibacterial activity can be assessed using broth microdilution or disk diffusion methods to determine minimum inhibitory concentrations (MICs). Bicyclomycin benzoate selectively inhibits the transcription termination factor Rho in E. coli. The compound also interferes with lipoprotein biosynthesis and peptidoglycan assembly in the cell envelope. |
| ln Vivo |
Rats excreted a small amount of dicyclomycin following a single intramuscular dose of 50 mg/kg. Dicyclomycin is widely dispersed throughout the body, with the kidney exhibiting the greatest concentration of 100 mg/kg [4].
In vivo, bicyclomycin benzoate has limited use as a veterinary antibiotic. The compound is explored for its potential use in treating bacterial infections, especially those caused by Gram-negative bacteria. Its efficacy depends on the susceptibility of the infecting organism and the pharmacokinetic profile. |
| Enzyme Assay |
For non-cellular enzyme assays, bicyclomycin benzoate can be tested for inhibition of Rho ATPase activity. The enzyme is incubated with varying concentrations of the compound, and ATPase activity is measured using colorimetric or radiometric methods. The compound's binding affinity to Rho can be assessed using surface plasmon resonance or other biophysical techniques.
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| Cell Assay |
For in vitro cell-based assays, bacterial cultures are used to assess the antibacterial activity of bicyclomycin benzoate. Minimum inhibitory concentrations (MICs) are determined using broth microdilution or agar dilution methods. Time-kill assays can be performed to assess bactericidal activity.
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| Animal Protocol |
For in vivo animal studies, bicyclomycin benzoate can be administered to animal models of bacterial infection. Efficacy is assessed by measuring bacterial clearance, survival, and reduction of infection-related pathology.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of bicyclomycin benzoate include solubility in ethanol, methanol, DMF, and DMSO. The compound has a molecular weight of 406.39. As an antibiotic, its pharmacokinetic properties would depend on the route of administration and the formulation.
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| Toxicity/Toxicokinetics |
The toxicological profile of bicyclomycin benzoate has not been fully characterized. As a veterinary antibiotic, its safety profile has been evaluated in animals.
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| References |
[1]. Tanaka N, et al. Mechanism of action of bicyclomycin. J Antibiot (Tokyo). 1976 Feb;29(2):155-68.
[2]. Kohn H, et al. The molecular basis for the mode of action of bicyclomycin. Curr Drug Targets Infect Disord. 2005 Sep;5(3):273-95. [3]. Park HG, et al. Bicyclomycin and dihydrobicyclomycin inhibition kinetics of Escherichia coli rho-dependent transcription termination factor ATPase activity. Arch Biochem Biophys. 1995 Nov 10;323(2):447-54. [4]. Nishida M. et al. Bicyclomycin, a new antibiotic. IV. Absorption, excretion and tissue distribution. J Antibiot (Tokyo). 1972 Oct;25(10):594-601 |
| Additional Infomation |
Bicyclomycin benzoate is a broad-spectrum antibiotic. It selectively inhibits the transcription termination factor Rho in E. coli. The compound also interferes with lipoprotein biosynthesis and peptidoglycan assembly. It is effective against Gram-negative bacteria, including E. coli and Pseudomonas aeruginosa. Bicyclomycin benzoate has limited use as a veterinary antibiotic.
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| Molecular Formula |
C19H22N2O8
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|---|---|
| Molecular Weight |
406.3866
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| Exact Mass |
406.137
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| CAS # |
37134-40-0
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| Related CAS # |
Bicyclomycin;38129-37-2
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| PubChem CID |
91618023
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
788.6±60.0 °C at 760 mmHg
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| Flash Point |
430.7±32.9 °C
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| Vapour Pressure |
0.0±2.9 mmHg at 25°C
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| Index of Refraction |
1.640
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| LogP |
1.87
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
29
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| Complexity |
721
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| Defined Atom Stereocenter Count |
4
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| SMILES |
O1C([H])([H])C([H])([H])C(=C([H])[H])[C@]2(C(N([H])[C@@]1(C(N2[H])=O)[C@]([H])([C@](C([H])([H])[H])(C([H])([H])OC(C1C([H])=C([H])C([H])=C([H])C=1[H])=O)O[H])O[H])=O)O[H]
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| InChi Key |
YYGLCPHONATYBU-FZDIXFNVSA-N
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| InChi Code |
InChI=1S/C19H22N2O8/c1-11-8-9-29-19(16(25)20-18(11,27)15(24)21-19)14(23)17(2,26)10-28-13(22)12-6-4-3-5-7-12/h3-7,14,23,26-27H,1,8-10H2,2H3,(H,20,25)(H,21,24)/t14-,17-,18+,19-/m0/s1
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| Chemical Name |
[(2S,3S)-2,3-dihydroxy-3-[(1S,6R)-6-hydroxy-5-methylidene-8,10-dioxo-2-oxa-7,9-diazabicyclo[4.2.2]decan-1-yl]-2-methylpropyl] benzoate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~246.07 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.15 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.15 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (6.15 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4607 mL | 12.3035 mL | 24.6069 mL | |
| 5 mM | 0.4921 mL | 2.4607 mL | 4.9214 mL | |
| 10 mM | 0.2461 mL | 1.2303 mL | 2.4607 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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