| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 25mg |
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Usaramine is natural product of the pyrrolizidine alkaloid class, and is isolated from seeds of Crolatalaria pallida. Usaramine demonstrates a highlighted antibiofilm activity against Staphylococcus epidermidis by reducing more than 50% of biofilm formation without killing the bacteria.
| ln Vitro |
Usaramine at 1 mg/mL reduced Staphylococcus epidermidis biofilm formation by more than 50% without affecting planktonic bacterial growth. [1]
Usaramine showed no inhibition of biofilm formation against Pseudomonas aeruginosa and no bactericidal action against this strain. [1] Scanning electron microscopy (SEM) revealed that Usaramine at concentrations of 0.25 mg/mL, 0.5 mg/mL, and 1 mg/mL inhibited S. epidermidis biofilm formation, and bacterial cells remained intact with no surface damage compared to the control. [1] |
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| Cell Assay |
Staphylococcus epidermidis ATCC 35984 and Pseudomonas aeruginosa ATCC 27853 were grown on Mueller Hinton agar overnight at 37°C. Bacterial suspensions were prepared in 0.9% NaCl to a density of 3×10^8 CFU/mL. Usaramine was dissolved in DMSO (1 mg/mL) and tested for antibiofilm activity using the crystal violet assay. The adherent biofilm layer formed after 24 hours of incubation was stained with crystal violet, and absorbance was measured. Bacterial growth was evaluated by the difference between initial (t=0) and final (t=24 h) OD600 absorbance in 96-well microtiter plates. Rifampicin was used as a positive control for antibacterial activity. [1]
For scanning electron microscopy, biofilms of S. epidermidis ATCC 35984 were grown in 96-well microtiter plates containing a piece of PermanoxTM slide. After 24 hours of incubation at 37°C, samples were fixed in 2.5% glutaraldehyde for 3 hours, washed with 100 mM cacodylate buffer (pH 7.2), and dehydrated in increasing concentrations of acetone. The slides were dried by the CO2 critical point technique, fixed on aluminum stubs, covered with gold film, and examined under a scanning electron microscope. [1] |
| Toxicity/Toxicokinetics |
In scanning electron microscopy analysis, Usaramine treatment (0.25–1 mg/mL) caused no damage to the surface of Staphylococcus epidermidis cells, which remained intact compared to the control, indicating no bactericidal toxicity. [1]
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| References | |
| Additional Infomation |
LSM-2938 is a macrolide antibiotic. Usalamin has been reported to be present in Gynura divaricata, Crotalaria lanceolata, and other organisms with relevant data.
Usaramine is a pyrrolizidine alkaloid with an unsaturated C1-C2 bond. It demonstrated selective antibiofilm activity against Staphylococcus epidermidis without inhibiting planktonic cell growth, which may reduce evolutionary pressure for resistance development. No activity was observed against the Gram-negative bacterium Pseudomonas aeruginosa. The mechanism of action remains to be elucidated, but Usaramine is suggested as a prototype for new antibiofilm molecules for pharmaceutical and industrial purposes, particularly for topical use or surface coating of biomaterials. [1] |
| Molecular Formula |
C18H25NO6
|
|---|---|
| Molecular Weight |
351.3942
|
| Exact Mass |
351.168
|
| CAS # |
15503-87-4
|
| PubChem CID |
5281756
|
| Appearance |
White to off-white solid powder
|
| Density |
1.3±0.1 g/cm3
|
| Boiling Point |
583.2±50.0 °C at 760 mmHg
|
| Flash Point |
306.5±30.1 °C
|
| Vapour Pressure |
0.0±3.7 mmHg at 25°C
|
| Index of Refraction |
1.590
|
| LogP |
-0.14
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
7
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
25
|
| Complexity |
627
|
| Defined Atom Stereocenter Count |
4
|
| SMILES |
C/C=C/1\C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(CO)O)C
|
| InChi Key |
BCJMNZRQJAVDLD-FXGRWVCYSA-N
|
| InChi Code |
InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3+/t11-,14-,15-,18-/m1/s1
|
| Chemical Name |
(1R,4E,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
|
| Synonyms |
Mucronatine; (15E)-Retrorsine; Usaramin; CHEBI:9912; trans-Retrorsine; (+)-Ursamine;
|
| 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)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~284.58 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.11 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 (7.11 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 (7.11 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 | 2.8458 mL | 14.2292 mL | 28.4584 mL | |
| 5 mM | 0.5692 mL | 2.8458 mL | 5.6917 mL | |
| 10 mM | 0.2846 mL | 1.4229 mL | 2.8458 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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