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Glycodeoxycholic Acid

Alias: Glycodeoxycholic acid; Glycodeoxycholic acid
Glycodeoxycholic Acid is a natural product found in Streptomyces nigricans, Trypanosoma brucei and Caenorhabditis elegans.
Glycodeoxycholic Acid
Glycodeoxycholic Acid Chemical Structure CAS No.: 360-65-6
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Glycodeoxycholic Acid is a natural product found in Streptomyces nigricans, Trypanosoma brucei and Caenorhabditis elegans. Glycodeoxycholic Acid can induce hepatocyte necrosis and induce autophagy in patients with obstructive cholestasis.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Glycodeoxycholic Acid (200 μM, 24-48 h) induces stemness and chemoresistance of hepatocellular carcinoma cells via the STAT3 signaling pathway[1]. Glycodeoxycholic Acid (50 μM, pretreatment for 1 h) abolishes UCB-induced cytochrome c oxidase inhibition and significantly prevents oxidative stress, metabolic changes, and cell death[2].
ln Vivo
Glycodeoxycholic Acid (11.20 mg/kg, injected into the bile-pancreatic duct) induces acute pancreatitis in macaques[3].
Cell Assay
Cell Viability Assay[1]
Cell Types: Huh7, LM3 Concentration: 200 μM
Incubation Duration: 24, 48 h
Experimental Results: Increased cell viability treated with 5-FU and cisplatin.

Western Blot Analysis[1]
Cell Types: Huh7, LM3 Concentration: 200 μM
Incubation Duration: 24, 48 h
Experimental Results: Suppressed the expression of apoptotic genes and increased anti-apoptotic genes. Promoted the expression of Sox2, Sox9, Nanog and CD133. Down-regulated the level of E-cadherin and up-regulated vimentin. Decreased the levels of SOCS2, SOCS5, PTPN1 and PTPN11.
Animal Protocol
Animal/Disease Models:Experimental macaque model[3]
Doses: 11.20 mg/kg
Route of Administration: injected along the biliopancreatic duct
Experimental Results: Increased the levels of Serum amylase and lipase. Elevated Blood pressure and heart rate.
References

[1]. Glycochenodeoxycholic acid induces stemness and chemoresistance via the STAT3 signaling pathway in hepatocellular carcinoma cells. Aging (Albany NY). 2020 Aug 3;12(15):15546-15555.

[2]. Bilirubin selectively inhibits cytochrome c oxidase activity and induces apoptosis in immature cortical neurons: assessment of the protective effects of glycoursodeoxycholic acid. J Neurochem. 2010 Jan;112(1):56-65.

[3]. Role of glycodeoxycholic acid to induce acute pancreatitis in Macaca nemestrina. J Med Primatol. 2022 Jun;51(3):134-142. doi: 10.1111/jmp.12577. Epub 2022 Mar 20. PMID: 35306662; PMCID: PMC9310849.

Additional Infomation
Glycodeoxycholic acid is a bile acid glycine conjugate of deoxycholic acid. It has a role as a human metabolite. It is functionally related to a deoxycholic acid. It is a conjugate acid of a glycodeoxycholate.
Glycodeoxycholic acid has been reported in Streptomyces nigra, Trypanosoma brucei, and Caenorhabditis elegans with data available.
A bile salt formed in the liver by conjugation of deoxycholate with glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and choleretic.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C26H43NO5
Molecular Weight
449.62
Exact Mass
467.325
CAS #
360-65-6
PubChem CID
3035026
Appearance
Solid powder
Density
1.162 g/cm3
Boiling Point
655.6ºC at 760 mmHg
Flash Point
350.3ºC
Index of Refraction
1.546
LogP
3.92
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
6
Heavy Atom Count
32
Complexity
727
Defined Atom Stereocenter Count
10
SMILES
O([H])[C@@]1([H])C([H])([H])[C@@]2([H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]([H])(C([H])([H])C3([H])C([H])([H])C([H])([H])[C@@]2([H])[C@]2([H])C([H])([H])C([H])([H])[C@]([H])([C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C(N([H])C([H])([H])C(=O)O[H])=O)[C@]21C([H])([H])[H])O[H]
InChi Key
WVULKSPCQVQLCU-BUXLTGKBSA-N
InChi Code
InChI=1S/C26H43NO5/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17-,18+,19-,20+,21+,22+,25+,26-/m1/s1
Chemical Name
2-[[(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid
Synonyms
Glycodeoxycholic acid; Glycodeoxycholic acid
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

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 : 125 mg/mL (278.01 mM; with sonication (<60°C))
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.63 mM)(Saturation unknown) in 10% DMSO 40% PEG300 5% Tween-80 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, add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix well; then add 50 μL Tween-80 to the above system and mix well; then add 450 μL saline to make up 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 (4.63 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, add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD in saline and mix well.
*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.

Solubility in Formulation 3: ≥ 2.08 mg/mL (4.63 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, add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL corn oil and mix well.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.2241 mL 11.1205 mL 22.2410 mL
5 mM 0.4448 mL 2.2241 mL 4.4482 mL
10 mM 0.2224 mL 1.1121 mL 2.2241 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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An example of molarity calculation using the molarity calculator is shown below:
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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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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