| Size | Price | Stock | Qty |
|---|---|---|---|
| 10mg |
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| 100mg | |||
| Other Sizes |
| Targets |
N-Oleoyl glycine targets cannabinoid receptor 1 (CB1 receptor) [1]
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|---|---|
| ln Vitro |
N-oleoylglycine is a lipoamino acid that stimulates adipogenesis associated with activation of CB1 receptors and Akt signaling pathways in 3T3-L1 adipocytes. N-oleoylglycine (1, 5, 10, 20, 50 μM) dose- and time-dependently stimulated 3T3-L1 adipogenesis by activating CB1R after 1-10 days of treatment. N-oleoylglycine also stimulates the Akt signaling pathway during 3T3-L1 adipocyte development [1].
N-Oleoyl glycine stimulated adipogenesis in 3T3-L1 preadipocytes in a dose-dependent manner (1, 5, 10 μM), as evidenced by increased lipid droplet accumulation (Oil Red O staining) [1] It significantly upregulated mRNA and protein expression of adipogenic markers (PPARγ, C/EBPα, aP2) in 3T3-L1 cells during adipocyte differentiation [1] The compound activated the Akt signaling pathway, increasing phosphorylation of Akt (p-Akt) in 3T3-L1 cells; this activation was time-dependent, peaking at 30 minutes after treatment [1] Pretreatment with a CB1 receptor antagonist (AM251) blocked the adipogenic effect of N-Oleoyl glycine, reducing lipid droplet formation and downregulating adipogenic markers, confirming CB1 receptor involvement [1] It did not affect the viability of 3T3-L1 cells at concentrations up to 20 μM (assessed by MTT assay) [1] |
| Cell Assay |
3T3-L1 preadipocytes were cultured in DMEM medium supplemented with 10% fetal bovine serum and antibiotics, maintained at 37°C in a 5% CO₂ incubator [1]
Adipogenic differentiation assay: - Cells were seeded in 6-well plates (for Western blot/RT-PCR) or 96-well plates (for Oil Red O staining) at a density of 2 × 10⁴ cells/well, allowed to reach confluence (day 0) [1] - Differentiation was induced by adding adipogenic induction medium (containing insulin, dexamethasone, and IBMX) along with N-Oleoyl glycine (1, 5, 10 μM); the medium was replaced every 2 days [1] - For antagonist experiments: Cells were pretreated with AM251 (1 μM) for 1 hour before adding N-Oleoyl glycine and induction medium [1] Oil Red O staining: - On day 8 of differentiation, cells were fixed with formaldehyde, stained with Oil Red O solution for 30 minutes, washed to remove excess dye [1] - Stained lipid droplets were quantified by elution with isopropanol and absorbance measurement at 510 nm [1] Western blot analysis: - Cells were harvested on day 8 (for adipogenic markers) or at specified time points (for p-Akt), lysed in RIPA buffer with protease/phosphatase inhibitors [1] - Protein concentrations were determined by BCA assay; equal amounts of protein were separated by SDS-PAGE, transferred to PVDF membranes [1] - Membranes were incubated with primary antibodies (PPARγ, C/EBPα, aP2, Akt, p-Akt, β-actin) overnight at 4°C, followed by HRP-conjugated secondary antibodies [1] - Protein bands were visualized using an enhanced chemiluminescence detection system [1] RT-PCR analysis: - Total RNA was extracted from cells on day 8 of differentiation, reverse-transcribed into cDNA [1] - PCR amplification was performed with specific primers for PPARγ, C/EBPα, aP2, and GAPDH (housekeeping gene) [1] - Relative mRNA expression levels were calculated using the comparative Ct method [1] Cell viability assay (MTT): - 3T3-L1 cells were seeded in 96-well plates, treated with N-Oleoyl glycine (0.1–20 μM) for 48 hours [1] - MTT reagent was added, incubated for 4 hours, formazan crystals were dissolved in DMSO, and absorbance was measured at 570 nm [1] |
| References | |
| Additional Infomation |
N-Oleoylglycine is a fatty acid derivative, a 9Z-octadecenoyl derivative of glycine. It is considered an intermediate in the biosynthesis of oleamide and functions as a metabolite. It is a fatty amide and also an N-acylglycine 18:1. It is functionally related to oleic acid and is the conjugate acid of N-oleoylglycine. N-Oleoylglycine is a naturally occurring lipid amino acid [1]. Its adipogenic function is mediated by phosphorylation of the CB1 receptor and subsequently the downstream Akt signaling pathway [1]. As an endogenous ligand of the CB1 receptor, it regulates adipocyte differentiation by modulating the expression of key adipogenic transcription factors [1].
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| Molecular Formula |
C20H37NO3
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|---|---|
| Molecular Weight |
339.51300
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| Exact Mass |
339.277
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| CAS # |
2601-90-3
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| PubChem CID |
6436908
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| Appearance |
White to off-white solid powder
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
525.6±43.0 °C at 760 mmHg
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| Flash Point |
271.7±28.2 °C
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| Vapour Pressure |
0.0±3.0 mmHg at 25°C
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| Index of Refraction |
1.478
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| LogP |
6.57
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
17
|
| Heavy Atom Count |
24
|
| Complexity |
340
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
CCCCCCCC/C=C\CCCCCCCC(=O)NCC(=O)O
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| InChi Key |
HPFXACZRFJDURI-KTKRTIGZSA-N
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| InChi Code |
InChI=1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(22)21-18-20(23)24/h9-10H,2-8,11-18H2,1H3,(H,21,22)(H,23,24)/b10-9-
|
| Chemical Name |
2-[[(Z)-octadec-9-enoyl]amino]acetic acid
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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. |
| 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 (~294.54 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.36 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 25.0 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 | 2.9454 mL | 14.7271 mL | 29.4542 mL | |
| 5 mM | 0.5891 mL | 2.9454 mL | 5.8908 mL | |
| 10 mM | 0.2945 mL | 1.4727 mL | 2.9454 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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