Startseite>>Signaling Pathways>> Proteases>> Endogenous Metabolite>>Deoxycholic acid (Cholanoic Acid)

Deoxycholic acid (Cholanoic Acid) (Synonyms: Cholanoic Acid, DCA, NSC 8797)

Katalog-Nr.GC33762

Deoxycholic acid (Cholanoic Acid) is a bile acid and a byproduct of intestinal metabolism that can activate the G protein-coupled bile acid receptor TGR5.

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Deoxycholic acid (Cholanoic Acid) Chemische Struktur

Cas No.: 83-44-3

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10mM (in 1mL DMSO)
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Sample solution is provided at 25 µL, 10mM.

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Description of Deoxycholic acid (Cholanoic Acid)

Deoxycholic acid (Cholanoic Acid) is a bile acid and a byproduct of intestinal metabolism that can activate the G protein-coupled bile acid receptor TGR5[1]. Deoxycholic acid can induce tyrosine phosphorylation and activate the receptor tyrosine kinase epidermal growth factor receptor in a ligand-independent manner[2]. Deoxycholic acid is the first drug that can be used to reduce submental fat[3].

In vitro, Deoxycholic acid (0-1000µM) treatment of AR42J cells for 24h inhibited cell proliferation in a dose- and time-dependent manner, induced cell apoptosis and necrosis, and significantly increased the activities of transcription factor 2 (ATF2), interferon-stimulated response element (ISRE), NKX-2.5, androgen receptor (AR), p53, and hypoxia-inducible factor-1 (HIF-1), and reduced the activities of peroxisome proliferator-activated receptor (PPAR) and activator protein 1 (AP1)[4]. Treatment of colon cancer cells (SW480 and LoVo) with Deoxycholic acid (5, 50µM) for 30min significantly increased tyrosine phosphorylation of β-catenin, leading to the loss of E-cadherin binding to β-catenin in the cells[5]. Treatment of gastric cancer cell MGC803 cells with Deoxycholic acid (100µM) for 2h enhanced cell survival and proliferation activity under bile acid stress[6].

In vivo, Deoxycholic acid added to drinking water at a concentration of 0.2% for 12 weeks in Apcmin/+ mice increased the incidence of intestinal tumors, increased intestinal permeability and induced low-grade inflammation[7].

References:
[1] Truong J K, Dawson P A. Bile acid metabolism[J]. Biochemistry of Lipids, Lipoproteins and Membranes, 2021: 395-428.
[2] Jean-Louis S, Akare S, Ali M A, et al. Deoxycholic acid induces intracellular signaling through membrane perturbations[J]. Journal of Biological Chemistry, 2006, 281(21): 14948-14960.
[3] Farina G A, Cherubini K, de Figueiredo M A Z, et al. Deoxycholic acid in the submental fat reduction: A review of properties, adverse effects, and complications[J]. Journal of Cosmetic Dermatology, 2020, 19(10): 2497-2504.
[4] Zhang G, Zhang J, Shang D, et al. Deoxycholic acid inhibited proliferation and induced apoptosis and necrosis by regulating the activity of transcription factors in rat pancreatic acinar cell line AR42J[J]. In Vitro Cellular & Developmental Biology-Animal, 2015, 51: 851-856.
[5] Pai R, Tarnawski A S, Tran T. Deoxycholic acid activates β-catenin signaling pathway and increases colon cell cancer growth and invasiveness[J]. Molecular biology of the cell, 2004, 15(5): 2156-2163.
[6] Wang X, Sun L, Wang X, et al. Acidified bile acids enhance tumor progression and telomerase activity of gastric cancer in mice dependent on c‐Myc expression[J]. Cancer Medicine, 2017, 6(4): 788-797.
[7] Liu L, Dong W, Wang S, et al. Deoxycholic acid disrupts the intestinal mucosal barrier and promotes intestinal tumorigenesis[J]. Food & function, 2018, 9(11): 5588-5597.

Protocol of Deoxycholic acid (Cholanoic Acid)

Cell experiment [1]:

Cell lines

AR42J cells

Preparation Method

2×104 cells in the logarithmic growth phase were seeded in each well of a 96-well plate. The medium was changed on the second day, and the fused cells were maintained for 24 h with medium containing different concentrations of Deoxycholic acid (0-1000µM). Then, 10μL MTT in PBSwith a concentration of 5g/L was added into each well for 4 h at 37°C.

Reaction Conditions

0-1000µM; 24h

Applications

Deoxycholic acid inhibited AR42J cells proliferation in a dose- and time-dependent manner.

Animal experiment [2]:

Animal models

Apcmin/+ mice

Preparation Method

Four-week-old female Apcmin/+ mice were obtained and randomly divided into 2 groups (n=10): a control group (receiving sterile water) and a Deoxycholic acid group (0.2% Deoxycholic acid in sterile water). After 12 weeks, the mice were sacrificed and intestinal tissues were obtained.

Dosage form

Add 0.2% Deoxycholic acid to drinking water

Applications

Deoxycholic acid increased the multiplicity of intestinal tumors and promoted tumorigenesis in mice. Deoxycholic acid increased intestinal permeability and induced low grade inflammation in mice.

References:

[1]Zhang G, Zhang J, Shang D, et al. Deoxycholic acid inhibited proliferation and induced apoptosis and necrosis by regulating the activity of transcription factors in rat pancreatic acinar cell line AR42J[J]. In Vitro Cellular & Developmental Biology-Animal, 2015, 51: 851-856.

[2]Liu L, Dong W, Wang S, et al. Deoxycholic acid disrupts the intestinal mucosal barrier and promotes intestinal tumorigenesis[J]. Food & function, 2018, 9(11): 5588-5597.

Chemical Properties of Deoxycholic acid (Cholanoic Acid)

Cas No. 83-44-3 SDF
Überlieferungen Cholanoic Acid, DCA, NSC 8797
Canonical SMILES C[C@@]1([C@@]2([H])[C@H](C)CCC(O)=O)[C@](CC2)([H])[C@@](CC[C@@]3([H])[C@@]4(CC[C@@H](O)C3)C)([H])[C@]4([H])C[C@@H]1O
Formula C24H40O4 M.Wt 392.57
Löslichkeit DMSO : ≥ 100 mg/mL (254.73 mM) Storage Store at RT
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Deoxycholic acid (Cholanoic Acid)

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 2.5473 mL 12.7366 mL 25.4732 mL
5 mM 0.5095 mL 2.5473 mL 5.0946 mL
10 mM 0.2547 mL 1.2737 mL 2.5473 mL
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