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| Targets |
Pseudomonic acid C's primary target is bacterial protein synthesis. It targets bacterial ribosomes and disrupts the translation process. More specifically, it inhibits isoleucyl-tRNA synthetase, an enzyme essential for protein synthesis. By inhibiting this enzyme, it prevents the incorporation of isoleucine into proteins, leading to the inhibition of bacterial growth. This mechanism is similar to that of mupirocin (pseudomonic acid A), the major component of the antibiotic mixture.
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| ln Vitro |
In vitro, Pseudomonic acid C is an antibacterial agent with activity against various Gram-positive bacteria. It inhibits bacterial protein synthesis by targeting isoleucyl-tRNA synthetase. Its activity is characterized by its ability to inhibit the growth of susceptible bacterial strains. The compound is a minor component of the mupirocin antibiotic mixture, and its antibacterial activity is similar to that of the major component.
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| ln Vivo |
In vivo, Pseudomonic acid C is not used as a standalone antibiotic. As a minor component of mupirocin, it contributes to the overall antibacterial activity of the mixture. Mupirocin is used topically for the treatment of bacterial skin infections, including impetigo and methicillin-resistant Staphylococcus aureus (MRSA) infections. The compound is especially useful in the treatment of infections caused by resistant bacterial strains.
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| Enzyme Assay |
The in vitro antibacterial activity of Pseudomonic acid C is assessed using standard susceptibility testing methods. Minimum inhibitory concentrations (MICs) against various Gram-positive bacteria (e.g., Staphylococcus aureus, Streptococcus pyogenes) are determined using broth microdilution or agar dilution methods. Serial two-fold dilutions of the compound are prepared in appropriate growth medium. A standardized bacterial inoculum is added to each well, and the plates are incubated at 35-37°C for 18-24 hours. The MIC is determined as the lowest concentration that inhibits visible growth. For mechanistic studies, the inhibition of isoleucyl-tRNA synthetase can be assessed using cell-free enzyme assays.
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| Cell Assay |
For cellular assays, bacterial cultures of susceptible strains are grown in appropriate media. Cells are treated with various concentrations of Pseudomonic acid C (typically 0.1-100 µg/mL) for defined periods. Bacterial viability is assessed by colony counting or by measuring optical density at 600 nm. The effect on protein synthesis can be evaluated by measuring the incorporation of [³H]-leucine or [³H]-isoleucine into newly synthesized proteins. Time-kill curves are generated by sampling at multiple time points to determine the bactericidal kinetics.
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| Animal Protocol |
In vivo, Pseudomonic acid C is not administered as a standalone compound. It is used as a component of mupirocin formulations for topical application. In animal models of skin infection, mupirocin is applied topically to infected skin, and the reduction in bacterial burden is assessed. The efficacy of the compound is evaluated by measuring the reduction in colony-forming units (CFU) from skin biopsies or swabs.
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| ADME/Pharmacokinetics |
Pseudomonic acid C has a molecular weight of 484.62 g/mol and a molecular formula of C26H44O8. It is a lipophilic compound. The compound should be stored under appropriate conditions to maintain stability. Specific pharmacokinetic data is not available in the provided search results.
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| Toxicity/Toxicokinetics |
Specific toxicity data for Pseudomonic acid C is not available in the provided search results. As a minor component of mupirocin, its safety profile is expected to be similar to that of mupirocin. Mupirocin is generally well-tolerated when applied topically, with local irritation being the most common side effect. Systemic toxicity is minimal due to poor absorption through intact skin. The compound should be handled with standard laboratory safety precautions.
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| Additional Infomation |
Pseudomonas acid C is a fatty alcohol. It has been reported that Pseudomonas fluorescens contains pseudomonas acid C, and relevant data are available for reference.
Pseudomonic acid C is a minor biosynthetic component of the antibiotic mixture known as mupirocin, produced by Pseudomonas fluorescens. Mupirocin is a clinically approved antibiotic used topically for the treatment of bacterial skin infections, including impetigo and MRSA infections. Pseudomonic acid C is an analogue of Pseudomonic Acid D and belongs to the pseudomonic acid family of antibiotics. The compound is used as a research tool to study the mechanism of action of mupirocin and to investigate the biosynthesis of pseudomonic acids. It is not approved for clinical use as a standalone drug and is intended for research purposes only. It is available from chemical suppliers for research applications. |
| Molecular Formula |
C26H44O8
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|---|---|
| Molecular Weight |
484.63
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| Exact Mass |
484.304
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| CAS # |
71980-98-8
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| PubChem CID |
10413058
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| Appearance |
Colorless to light yellow viscous liquid
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| Density |
1.125g/cm3
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| Boiling Point |
656.193ºC at 760 mmHg
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| Flash Point |
210.281ºC
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| Index of Refraction |
1.516
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| LogP |
3.381
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
17
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| Heavy Atom Count |
34
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| Complexity |
659
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| Defined Atom Stereocenter Count |
6
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| SMILES |
OC(CCCCCCCCOC(/C=C(/C[C@@H]1OC[C@H](C/C=C/[C@H]([C@@H](O)C)C)[C@@H](O)[C@H]1O)\C)=O)=O
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| InChi Key |
KKMHFUKZHJOMJL-WZLBZGCNSA-N
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| InChi Code |
InChI=1S/C26H44O8/c1-18(16-24(30)33-14-9-7-5-4-6-8-13-23(28)29)15-22-26(32)25(31)21(17-34-22)12-10-11-19(2)20(3)27/h10-11,16,19-22,25-27,31-32H,4-9,12-15,17H2,1-3H3,(H,28,29)/b11-10+,18-16+/t19-,20+,21+,22+,25-,26+/m1/s1
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| Chemical Name |
9-[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(E,4R,5S)-5-hydroxy-4-methylhex-2-enyl]oxan-2-yl]-3-methylbut-2-enoyl]oxynonanoic acid
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| Synonyms |
Mupirocin calcium impurity B [EP]; Pseudomonic acid C
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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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0634 mL | 10.3171 mL | 20.6343 mL | |
| 5 mM | 0.4127 mL | 2.0634 mL | 4.1269 mL | |
| 10 mM | 0.2063 mL | 1.0317 mL | 2.0634 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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