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Lipoamide

Alias: NSC 90787; Lipoacin; Lipoamide
Cat No.:V16798 Purity: ≥98%
Lipoamide ((±)-α-Lipoamide) is a monocarboxylic acid amide formed by the formal condensation of the carboxyl group of lipoic acid and ammonia.
Lipoamide
Lipoamide Chemical Structure CAS No.: 940-69-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
500mg
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Product Description
Lipoamide ((±)-α-Lipoamide) is a monocarboxylic acid amide formed by the formal condensation of the carboxyl group of lipoic acid and ammonia. Lipoamide serves as a coenzyme to transfer acetyl groups and hydrogens during pyruvate deacylation.
Lipoamide (DL-α-Lipoamide) is the amide derivative of lipoic acid, a naturally occurring compound involved in mitochondrial energy metabolism. Lipoamide is a coenzyme for several dehydrogenase complexes, including pyruvate dehydrogenase and α-ketoglutarate dehydrogenase. It is a potent antioxidant that can scavenge free radicals and regenerate other antioxidants. Lipoamide is used in research to study mitochondrial function and oxidative stress.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary target of Lipoamide is the mitochondrial dehydrogenase complexes. As a coenzyme, lipoamide is covalently bound to the enzyme and participates in the transfer of acyl groups and electrons. It also acts as a potent antioxidant, scavenging reactive oxygen species (ROS) and regenerating other antioxidants, such as glutathione and vitamin C.
ln Vitro
In vitro, lipoamide has been shown to be a potent antioxidant. It scavenges ROS and reduces oxidative stress in various cell types. It also enhances the activity of mitochondrial dehydrogenase complexes. In cell-based assays, lipoamide protects cells from oxidative damage and improves mitochondrial function.
ln Vivo
In vivo, lipoamide has been studied for its potential therapeutic applications. It has been shown to have beneficial effects in animal models of diabetes, neuropathy, and neurodegenerative diseases. The compound is also used as a dietary supplement.
Enzyme Assay
In vitro enzyme or receptor binding (non-cell) assays for lipoamide involve measuring its antioxidant activity using cell-free assays such as DPPH radical scavenging or ABTS radical scavenging assays. Its ability to enhance the activity of dehydrogenase complexes can be measured using enzymatic assays with purified enzymes.
Cell Assay
In vitro cell-based assays for lipoamide are performed using various cell lines. Cells are treated with the compound, and oxidative stress, mitochondrial function, and cell viability are assessed. The compound's effects on antioxidant gene expression and enzyme activity are also measured.
Animal Protocol
In vivo animal experiments for lipoamide are conducted using rodent models of diabetes, neuropathy, and neurodegenerative diseases. The compound is administered orally or intraperitoneally, and its effects on disease pathology and oxidative stress are assessed.
ADME/Pharmacokinetics
Pharmacokinetic (PK) properties of lipoamide indicate that it is absorbed from the gastrointestinal tract. The compound has a molecular weight of 207.31 and a molecular formula of C8H15NOS2. It is a solid at room temperature. It is metabolized in the liver and excreted renally. The compound can be stored at -20°C.
Toxicity/Toxicokinetics
Toxicology (toxicology) data for lipoamide indicate that it is generally well-tolerated. Common side effects may include mild gastrointestinal disturbances. The compound has a favorable safety profile, with no significant toxicity reported at therapeutic doses.
References

[1]. Efficient reduction of lipoamide and lipoic acid by mammalian thioredoxin reductase. Biochem Biophys Res Commun. 1996 Aug 5;225(1):268-74.

[2]. Lipoamide Ameliorates Oxidative Stress via Induction of Nrf2/ARE Signaling Pathway in PC12 Cells. J Agric Food Chem. 2019 Jul 24;67(29):8227-8234.

Additional Infomation
Lipoic acid amide is a monocarboxylic acid amide formed by the condensation of the carboxyl group of lipoic acid with ammonia. It is found in humans, Saccharomyces cerevisiae, Escherichia coli, and mice as a metabolite. It belongs to the dithiocyclopentane class of monocarboxylic acid amides and is functionally related to lipoic acid. Lipoic acid amide is a metabolite found or produced in Escherichia coli (K12 strain, MG1655 strain). It has been reported to exist in humans, Apis cerevisiae, and other organisms with relevant data. Lipoic acid amide is a metabolite found or produced in Saccharomyces cerevisiae.
Other information: Lipoamide is the amide derivative of lipoic acid, a coenzyme involved in mitochondrial energy metabolism. It is also known as DL-α-Lipoamide. The compound is a potent antioxidant used in research. Its CAS number is 940-69-2.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C8H15NOS2
Molecular Weight
205.33
Exact Mass
205.06
CAS #
940-69-2
PubChem CID
863
Appearance
Light yellow to yellow solid powder
Density
1.169 g/cm3
Boiling Point
399.2ºC at 760 mmHg
Melting Point
127-129ºC(lit.)
Flash Point
195.2ºC
Index of Refraction
1.562
LogP
2.886
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
5
Heavy Atom Count
12
Complexity
152
Defined Atom Stereocenter Count
0
InChi Key
FCCDDURTIIUXBY-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)
Chemical Name
5-(dithiolan-3-yl)pentanamide
Synonyms
NSC 90787; Lipoacin; Lipoamide
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product is not stable in solution, please use freshly prepared working solution for optimal results.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ≥ 50 mg/mL (~243.50 mM)
H2O : ~0.67 mg/mL (~3.26 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.38 mg/mL (11.59 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 23.8 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 (10.13 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 20.8 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.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (10.13 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 4.8702 mL 24.3510 mL 48.7021 mL
5 mM 0.9740 mL 4.8702 mL 9.7404 mL
10 mM 0.4870 mL 2.4351 mL 4.8702 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.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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