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| 250mg |
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Purity: ≥95%
Lactonic (di-acetylated) Sophorolipid is a naturally occurring glycolipid generated from fermentation of sugar by yeasts including C. bombicola. This lactone form of sophorolipid has been used as a biosurfactant, possessing lower surface tension compared to the acid form of sophorolipids. As a natural antimicrobial surfactant, it can be used for oral hygiene. Lactonic sophorolipid is also a potential anticancer agent, induces apoptosis in human HepG2 cells through the caspase-3 pathway.
| Targets |
Antimicrobial surfactant
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|---|---|
| ln Vitro |
Liver cancer, one of the most common types of cancer in the world, is the second leading cause of death for cancer patients. For liver cancer, there is an urgent need for an effective treatment with no or less toxic side effects. Lactonic sophorolipids (LSL), as a potential anticancer drug, has attracted wide attention of pharmaceutical researchers with its good biological activities. The effects of LSL and cell death inhibitors were measured by MTT test on HepG2 cells. Meanwhile, the morphology of the cells was observed under a microscope. The apoptosis rate was detected by flow cytometry, and the expression levels of enzyme activity of Caspase-3 and Caspase-9 were measured by detection kits. Meanwhile, mRNA levels of Apaf-1, Caspase-3, Bax, and Bcl-2 were measured by quantitative real-time RT-PCR; protein levels of Caspase-3, Cleaved Caspase-3, Bax, and Bcl-2 were measured by western blot. LSL can inhibit the proliferation of cells, and it is possible to induce apoptosis in cells. The HepG2 cells with LSL co-culture exhibited typical apoptotic morphology, and the expression levels of enzyme activity of Caspase-3 and Caspase-9 increased (P< 0.05). We also found that LSL increases cell apoptosis rate and regulates the expression of genes and proteins associated with apoptosis through the Caspase-3 pathway. These results indicate that LSL may be one of the potential drug candidates to inhibit the proliferation and induce apoptosis in HepG2 cells.Key points• LSL, which is of good biological activities such as anti-bacterium, virus elimination, and inflammatory response elimination, has been firstly used to intervene in vitro to investigate its effect on HepG2 cell proliferation.• LSL can inhibit the proliferation of cells, and it is possible to induce apoptosis in HepG2 cells through the Caspase-3 pathway.• The mechanism of LSL action on HepG2 cell proliferation was firstly also discussed, which provides a certain experimental reference for the clinical treatment of liver cancer[2].
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| ln Vivo |
Aims: To assess the efficacy of rhamnolipid (mixture of monorhamnolipid and dirhamnolipid congeners), purified monorhamnolipid, dirhamnolipid and lactonic sophorolipid biosurfactants against pathogens important for oral hygiene.[1]
Methods and results: Acquired and produced biosurfactants were fully characterized to allow the antimicrobial activity to be assigned to the biosurfactant congeners. Antimicrobial activity was assessed using the resazurin-aided microdilution method. Mixed rhamnolipid JBR425 (MR) and lactonic sophorolipids (LSLs) demonstrated the lowest minimum inhibitory concentration (MIC) which ranged between 100 and 400 μg ml-1 against Streptococcus mutans, Streptococcus oralis, Actinomyces naeslundii, Neisseria mucosa and Streptococcus sanguinis. Combining these biosurfactants with standard antimicrobial agents namely chlorhexidine, sodium lauryl sulphate, tetracycline HCl and ciprofloxacin showed a dramatic drop in the MIC values. In addition, in vitro studies demonstrated the biosurfactants' ability to prevent and disrupt oral pathogens biofilms. The increased permeability of microorganisms treated with biosurfactant, as shown using bisbenzimide dye, in part explains the inhibition effect.[1] Conclusion: The results demonstrate that rhamnolipids and LSLs have the ability to inhibit oral pathogens both in planktonic and oral biofilm states.[1] Significance and impact of the study: The findings indicate the potential value of biosurfactants for both oral hygiene and the pharmaceutical industries since there is a serious need to reduce the reliance on synthetic antimicrobials and antibiotics.[1] |
| Enzyme Assay |
Caspase-3 and Caspase-9 enzyme activity assay[2]
The HepG2 cells were treated with the LSL (25 μg/mL) for 24 h, and then collected. Next, the cells were assayed in strict accordance with the instructions of the corresponding activity assay kits. Finally, absorbance value at 405 nm was determined by using a micro-plate reader. The protein concentration was calculated according to the manufacturer’s instructions. |
| Cell Assay |
Apoptosis inhibitor[1]
HepG2 cells were seeded in a 96-well plate at a density of 1 × 104 cells/well. Each group was cultured in a DMEM medium containing LSL (25 μg/mL) except the control group. In the treatment group, apoptosis inhibitor (0, 5, 10, 20 μM) was added. Then the cells’ survival rate of each group was tested. Necrosis inhibitor[1] HepG2 cells were seeded in a 96-well plate at a density of 1 × 104 cells/well. Each group was cultured in a DMEM medium containing LSL (25 μg/mL) except the control group. In the treatment group, necrosis inhibitor (0, 20, 40, 80 μM) was added respectively. Then the cells survival rate of each group was calculated. |
| References |
| Molecular Formula |
C34H56O14
|
|---|---|
| Molecular Weight |
688.8
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| Exact Mass |
688.367004
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| CAS # |
148409-20-5
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| PubChem CID |
117065237
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| Appearance |
Typically exists as light yellow to yellow solids at room temperature
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
843.8±65.0 °C at 760 mmHg
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| Flash Point |
256.9±27.8 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.484
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| LogP |
7.83
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| tPSA |
196.74
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| SMILES |
C[C@H]1CCCCCCC=CCCCCCCCC(=O)O[C@@H]2[C@@H](COC(=O)C)O[C@H]([C@@H]([C@H]2O)O)O[C@@H]3[C@H]([C@@H]([C@@H](COC(=O)C)O[C@H]3O1)O)O
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| InChi Key |
OGTXYHUVJIPSDT-GNUCGHNBSA-N
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| InChi Code |
InChI=1S/C34H56O14/c1-21-17-15-13-11-9-7-5-4-6-8-10-12-14-16-18-26(37)47-31-25(20-43-23(3)36)46-33(30(41)29(31)40)48-32-28(39)27(38)24(19-42-22(2)35)45-34(32)44-21/h4-5,21,24-25,27-34,38-41H,6-20H2,1-3H3/b5-4-/t21-,24+,25+,27+,28-,29+,30+,31+,32+,33-,34+/m0/s1
|
| Chemical Name |
[(1S,3R,4S,5S,6R,8R,10S,17Z,28S,29R,31R,32R)-29-(acetyloxymethyl)-4,5,31,32-tetrahydroxy-10-methyl-26-oxo-2,7,9,27,30-pentaoxatricyclo[26.2.2.03,8]dotriacont-17-en-6-yl]methyl acetate
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| Synonyms |
Lactonic Sophorolipid; Lactonic Sophorolipid; 148409-20-5; [(1S,3R,4S,5S,6R,8R,10S,17Z,28S,29R,31R,32R)-29-(acetyloxymethyl)-4,5,31,32-tetrahydroxy-10-methyl-26-oxo-2,7,9,27,30-pentaoxatricyclo[26.2.2.03,8]dotriacont-17-en-6-yl]methyl acetate; Lactonic sophorolipid, tech. grade; 1',4-Sophorolactone 6',6-diacetate from yeast; 1',4'-Sophorolactone 6',6'-diacetate from yeast
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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 : ~125 mg/mL (~181.48 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.02 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 20.8 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: ≥ 2.08 mg/mL (3.02 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.4518 mL | 7.2590 mL | 14.5180 mL | |
| 5 mM | 0.2904 mL | 1.4518 mL | 2.9036 mL | |
| 10 mM | 0.1452 mL | 0.7259 mL | 1.4518 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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