[CAS NO. 1077-28-7] α-Lipoic Acid
PRODUCTS SPECIFICATIONS [1077-28-7]
DESCRIPTION [1077-28-7]
Overview
| MDL | MFCD00005474 |
|---|---|
| Molecular Weight | 206.33 |
| Molecular Formula | C8H14O2S2 |
| SMILES | O=C(O)CCCCC1SSCC1 |
4 Publications Citing Use of MCE
Summary
α-Lipoic Acid (Thioctic acid) is an antioxidant, which is an essential cofactor of mitochondrial enzyme complexes. α-Lipoic Acid inhibits NF-κB -dependent HIV-1 LTR activation [1] [2] [3] . α-Lipoic Acid induces endoplasmic reticulum (ER) stress-mediated apoptosis in hepatoma cells [4] . α-Lipoic Acid can be used with CPUL1 (HY-151802) to construct the self-assembled nanoaggregate CPUL1-LA NA, which has improved antitumor efficacy than CPUL1 [5] .
IC50 & Target
|
Human Endogenous Metabolite |
NF-κB |
Mitochondrial bioenergetics |
HIV-1 |
In Vitro
The long terminal repeat (LTR) of HIV-1 is the target of cellular transcription factors such as NF-κB, and serves as the promoter-enhancer for the viral genome when integrated in host DNA [1] . α-Lipoic Acid (Alpha-Lipoic acid, ALA), a naturally occurring dithiol compound, plays an essential role in mitochondrial bioenergetics. α-Lipoic Acid reduces lipid accumulation in the liver by regulating the transcriptional factors SREBP-1, FoxO1, and Nrf2, and their downstream lipogenic targets via the activation of the SIRT1/LKB1/AMPK pathway. Treatment of cells with α-Lipoic Acid (250, 500 and 1000 μM) significantly increases the NAD + /NADH ratio in HepG2 cells (P<0.05 or P<0.01). Treatment with α-Lipoic Acid (50, 125, 250 and 500 μM) increases SIRT1 activity in HepG2 cells. α-Lipoic Acid (50, 125, 250, 500 and 1000 μM) increases phosphorylation of AMPK and acetyl-CoA carboxylase (ACC) in HepG2 cells in a dose-dependent fashion [1] .
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
C57BL/6J mice, divided into four groups, are fed an high-fat diet (HFD) for 24 weeks to induce nonalcoholic fatty liver disease (NAFLD) followed by daily administration of α-Lipoic Acid. Then, the effects of α-Lipoic Acid on hepatic lipid accumulation in long-term HFD-fed mice are assessed. Administration of α-Lipoic Acid (100 mg/kg or 200 mg/kg) markedly reduces visceral fat mass in mice. In addition, α-Lipoic Acid (100 mg/kg or 200 mg/kg) treatment inhibits the appetite and causes a dramatic weight loss (all P<0.05) [1] .
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Clinical Trial
| NCT Number | Sponsor | Condition | Start Date | Phase |
|---|---|---|---|---|
| NCT00004770 | National Center for Research Resources (NCRR)|University of Rochester|Office of Rare Diseases (ORD) |
Mitochondrial Myopathy
|
October 1995 | Not Applicable |
| NCT00703989 | Albert Einstein College of Medicine|Juvenile Diabetes Research Foundation|National Institutes of Health (NIH) |
Type 1 Diabetes
|
February 2005 | Not Applicable |
| NCT00328601 | MEDA Pharma GmbH & Co. KG|Viatris Inc. |
Diabetic Polyneuropathy
|
February 2005 | Phase 3 |
| NCT02056366 | The Catholic University of Korea |
Type 2 Diabetes|Cardiac Autonomic Neuropathy
|
January 2010 | Phase 4 |
| NCT00002154 | The Dana Foundation|NIH AIDS Clinical Trials Information Service |
Cognitive Disorders|HIV Infections
|
Phase 2 | |
| NCT05449171 | Lo.Li.Pharma s.r.l |
Abortion, Spontaneous
|
July 2022 | Not Applicable |
| NCT03914404 | Chonbuk National University Hospital |
Diabetic Neuropathy
|
January 26, 2016 | Phase 4 |
| NCT00977483 | MEDA Pharma GmbH & Co. KG|Clinquest, Inc.|Ergomed|Quintiles, Inc.|Viatris Inc. |
Diabetic Polyneuropathy
|
May 1998 | Phase 3 |
| NCT01808300 | Unimed Pharmaceuticals |
Healthy
|
February 2013 | Phase 1 |
| NCT02966665 | Russell Richardson|University of Utah |
Chronic Obstructive Pulmonary Disease|Pulmonary Artery Hypertension|Heart Failure|Hypertension
|
September 2008 | Phase 1 |
Appearance
Solid
Shipping
Room temperature in continental US; may vary elsewhere.
Storage
| Powder | -20°C | 3 years |
|---|---|---|
| 4°C | 2 years | |
| In solvent | -80°C | 6 months |
| -20°C | 1 month |
Solvent & Solubility
DMSO : ≥ 100 mg/mL ( 484.66 mM )
H 2 O : 0.1 mg/mL ( 0.48 mM ; Need ultrasonic)
* "≥" means soluble, but saturation unknown.
Stock Solutions
| Concentration Solvent Mass | 1 mg | 5 mg | 10 mg |
|---|
| 1 mM | 4.8466 mL | 24.2330 mL | 48.4660 mL |
| 5 mM | 0.9693 mL | 4.8466 mL | 9.6932 mL |
| 10 mM | 0.4847 mL | 2.4233 mL | 4.8466 mL |
-
1.
Add each solvent one by one: 50% PEG300 >> 50% saline
Solubility: 10 mg/mL (48.47 mM); Clear solution; Need ultrasonic
-
2.
-
3.
Add each solvent one by one: 10% DMSO >> 90% (20% SBE-β-CD in saline)
Solubility: ≥ 2.5 mg/mL (12.12 mM); Clear solution
-
4.
Add each solvent one by one: 10% DMSO >> 90% corn oil
Solubility: ≥ 2.5 mg/mL (12.12 mM); Clear solution
References
- [1] Xiao L, et al. Activity of the dietary antioxidant ergothioneine in a virus gene-based assay for inhibitors of HIV transcription. Biofactors. 2006;27(1-4):157-65.
- [2] Lei D, et al. Synergistic neuroprotective effect of rasagiline and idebenone against retinal ischemia-reperfusion injury via the Lin28-let-7-Dicer pathway. Oncotarget. 2018 Jan 30;9(15):12137-12153.
- [3] Yang Y, et al. Alpha-lipoic acid improves high-fat diet-induced hepatic steatosis by modulating the transcription factors SREBP-1, FoxO1 and Nrf2 via the SIRT1/LKB1/AMPK pathway. J Nutr Biochem. 2014 Nov;25(11):1207-1217.
- [4] Pibiri M, et al. α-Lipoic acid induces Endoplasmic Reticulum stress-mediated apoptosis in hepatoma cells. Sci Rep. 2020 Apr 28;10(1):7139.
- [5] Liu J, et al. Nanoaggregates of Disulfide-Decorated TrxR Inhibitor Promote Cellular Uptake, Selective Targeting, and Antitumor Efficacy. Langmuir, 2022.
Synonyms