Deoxycholic acid sodium salt (Sodium deoxycholate)
(Synonyms: 脱氧胆酸钠; Sodium deoxycholate) 目录号 : GC33768
A secondary bile acid
Cas No.:302-95-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
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Cell experiment: |
MGC803 cells are cultured in Roswell Park Memorial Institute media supplemented with 10% fetal calf serum and 100 U/mL Penicillin and 100 mg/mL Streptomycin. To generate MGC803-resistant cells, the pH value of the MGC803 culture medium is adjusted to the experimental conditions using the hydrochloric acid (A). The bile acids GCDA and Deoxycholic acid are diluted to optimal working concentrations of 100 μM (B) with culture medium, and the overall pH (A+B) is adjusted to pH 5.5, simulating the gastric environment. Initially, MGC803 cells are chronically exposed to acidified medium with bile acids (A+B) for 10 min every 24 h. The experimental time and conditions are optimized in our preliminary experiments, which show that 10 min is enough and does not result in cell damage. This procedure is repeated and it takes 60 weeks for the MGC803 cells to survive and proliferate under the exposure of A+B for 120 min. Control untreated cells are cultured in neutral RPMI medium at pH 7.4 in parallel to the resistant cells for 60 weeks. The morphological changes in MGC803 cells exposed to acidified bile acids (A+B) are documented at 30 and 60 weeks[2]. |
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References: [1]. Somm E, et al. β-Klotho deficiency protects against obesity through a crosstalk between liver, microbiota, and brown adipose tissue. JCI Insight. 2017 Apr 20;2(8). pii: 91809. |
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Deoxycholic acid (DCA) is a secondary bile acid that is formed via microbial transformation of cholic acid in the colon.1 It can be conjugated to glycine or taurine to produce glycodeoxycholic acid or taurodeoxycholic acid , respectively, in hepatocytes.1,2,3 DCA (0.2% v/v) inhibits spore germination induced by taurocholic acid in seven C. difficile strains, as well as inhibits growth and decreases the cytotoxicity of C. difficile culture supernatants to Vero cells when used at a concentration of 0.02% v/v.1 It inhibits ionizing radiation-induced p53-dependent transcription in a reporter assay using HCT116 cells when used at a concentration of 200 ?M.4 Fecal and intestinal tissue levels of DCA are increased in a rat model of high-fat diet-induced obesity compared with rats fed a normal diet.5 Increased serum DCA levels have been found in patients with colorectal cancer.6
1.Thanissery, R., Winston, J.A., and Theriot, C.M.Inhibition of spore germination, growth, and toxin activity of clinically relevant C. difficile strains by gut microbiota derived secondary bile acidsAnaerobe4586-100(2017) 2.Schmid, A., Neumann, H., Karrasch, T., et al.Bile acid metabolome after an oral lipid tolerance test by liquid chromatography-tandem mass spectrometry (LC-MS/MS)PLoS One11(2)e0148869(2016) 3.?arenac, T.M., and Mikov, M.Bile acid synthesis: From nature to the chemical modification and synthesis and their applications as drugs and nutrientsFront. Pharmacol.9939(2018) 4.Qiao, D., Gaitonde, S.V., Qi, W., et al.Deoxycholic acid suppresses p53 by stimulating proteasome-mediated p53 protein degradationCarcinogenesis22(6)957-964(2001) 5.Lin, H., An, Y., Tang, H., et al.Alterations of bile acids and gut microbiota in obesity induced by high fat diet in rat modelJ. Agric. Food Chem.67(13)3624-3632(2019) 6.Bayerd?rffer, E., Mannes, G.A., Richter, W.O., et al.Increased serum deoxycholic acid levels in men with colorectal adenomasGastroenterology104(1)145-151(1993)
| Cas No. | 302-95-4 | SDF | |
| 别名 | 脱氧胆酸钠; Sodium deoxycholate | ||
| 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.[Na+] | ||
| 分子式 | C24H39NaO4 | 分子量 | 414.55 |
| 溶解度 | DMSO : 6 mg/mL (14.47 mM) | 储存条件 | Store at 2-8°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.4123 mL | 12.0613 mL | 24.1225 mL |
| 5 mM | 0.4825 mL | 2.4123 mL | 4.8245 mL |
| 10 mM | 0.2412 mL | 1.2061 mL | 2.4123 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Why is glycocholic acid sodium salt better than Deoxycholic acid sodium salt for the preparation of mixed micelle injections?
Food Sci Nutr 2019 Sep 27;7(11):3675-3680.PMID:31763016DOI:10.1002/fsn3.1224.
Classical mixed micelle systems make excellent parenteral drug carriers for lipophilic or poorly soluble drugs, but many formulations details are not fully understood and need further study. Thus, we constructed mixed micelle systems with lecithin and either glycocholic acid sodium salt or Deoxycholic acid sodium salt in order to investigate the differences between the bile salts. Vitamin K1, a lipid-soluble drug, was encapsulated in the mixed micelles, and the influence of bile salts on the quality and stability of the mixed micelle systems was analyzed. Both bile salts displayed similar profiles, and the amounts of bile salts used in formulating clear solutions did not differ. Mixed micelle systems formed from glycocholic acid sodium were physically stable at low pH levels (5.5), whereas those formed from deoxycholic acid required higher pH (>8.5). High pH levels hurt active pharmaceutical ingredients that are prone to hydrolytic and oxidative degradation. Hence, when mixed micelle systems formed from deoxycholic acid sodium were sterilized, unexpected chemical unstability occurred. Therefore, we conclude that glycocholic acid sodium salt is more suitable than Deoxycholic acid sodium salt for the preparation of mixed micelle injections.
The human bile salt Sodium deoxycholate induces metabolic and cell envelope changes in Salmonella Typhi leading to bile resistance
J Med Microbiol 2022 Jan;71(1).PMID:35006066DOI:10.1099/jmm.0.001461.
Introduction. Salmonella enterica serovar Typhi (S. Typhi) is the etiological agent of typhoid fever. To establish an infection in the human host, this pathogen must survive the presence of bile salts in the gut and gallbladder.Hypothesis. S. Typhi uses multiple genetic elements to resist the presence of human bile.Aims. To determine the genetic elements that S. Typhi utilizes to tolerate the human bile salt Sodium deoxycholate.Methodology. A collection of S. Typhi mutant strains was evaluated for their ability to growth in the presence of Sodium deoxycholate and ox-bile. Additionally, transcriptomic and proteomic responses elicited by Sodium deoxycholate on S. Typhi cultures were also analysed.Results. Multiple transcriptional factors and some of their dependent genes involved in central metabolism, as well as in cell envelope, are required for deoxycholate resistance.Conclusion. These findings suggest that metabolic adaptation to bile is focused on enhancing energy production to sustain synthesis of cell envelope components exposed to damage by bile salts.
Oxidation of Sodium deoxycholate Catalyzed by Gold Nanoparticles and Chiral Recognition Performances of Bile Salt Micelles
Molecules 2019 Dec 9;24(24):4508.PMID:31835427DOI:10.3390/molecules24244508.
Au nanoparticles (NPs) were prepared by UV light irradiation of a mixed solution of HAuCl4 and Sodium deoxycholate (NaDC) under alkaline condition, in which NaDC served as both reducing agent and capping agent. The reaction was monitored by circular dichroism (CD) spectra, and it was found that the formed gold NPs could catalyze the oxidation of NaDC. A CD signal at ~283 nm in the UV region was observed for the oxidation product of NaDC. The intensity of the CD signal of the oxidation product was enhanced gradually with the reaction time. Electrospray ionization (ESI) mass spectra and nuclear magnetic resonance (NMR) spectra were carried out to determine the chemical composition of the oxidation product, revealing that NaDC was selectively oxidized to sodium 3-keto-12-hydroxy-cholanate (3-KHC). The chiral discrimination abilities of the micelles of NaDC and its oxidation product, 3-KHC, were investigated by using chiral model molecules R,S-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate (R,S-BNDHP). Compared with NaDC, the micelles of 3-KHC displayed higher binding ability to the chiral model molecules. In addition, the difference in binding affinity of 3-KHC micelles towards R,S-isomer was observed, and S-isomer was shown to preferentially bind to the micelles.
Light-scattering studies on bile acid salts II: pattern of self-association of Sodium deoxycholate, sodium taurodeoxycholate, and sodium glycodeoxycholate in aqueous electrolyte solutions
J Pharm Sci 1978 Jul;67(7):994-9.PMID:660526DOI:10.1002/jps.2600670734.
The pattern of self-association of the bile salts Sodium deoxycholate, sodium glycodeoxycholate, and sodium taurodeoxycholate was investigated in aqueous electrolyte solutions by the light-scattering technique. The turbidity of the bile salt solutions was obtained over the concentration range of 0-20 mg/ml at 25 degrees. These data were analyzed according to a monomer-micellar equilibrium model and a stepwise association model. Comparison of the light-scattering data with these models suggests that the monomer-micellar model may be inappropriate. Analysis of the data according to the stepwise association model suggests that the dihydroxy bile salts associate to form dimers, trimers, and tetramers in addition to a larger aggregate which varies in size depending on the degree of conjugation of the bile salt.
Using Nuclear Magnetic Resonance Spectroscopy to Probe Hydrogels Formed by Sodium deoxycholate
Langmuir 2022 May 3;38(17):5111-5118.PMID:34730971DOI:10.1021/acs.langmuir.1c02175.
Hydrogels of bile acids and their salts are promising materials for drug delivery, cellular immobilization, and other applications. However, these hydrogels are poorly understood at the molecular level, and further study is needed to allow improved materials to be created by design. We have used NMR spectroscopy to probe hydrogels formed from mixtures of formic acid and Sodium deoxycholate (NaDC), a common bile acid salt. By assaying the ratio of deoxycholate molecules that are immobilized as part of the fibrillar network of the hydrogels and those that can diffuse, we have found that 65% remain free under typical conditions. The network appears to be composed of both the acid and salt forms of deoxycholate, possibly because a degree of charge inhibits excessive aggregation and precipitation of the fibrils. Spin-spin relaxation times provided a molecular-level estimate of the temperature of gel-sol transition (42 °C), which is virtually the same as the value determined by analyzing macroscopic parameters. Saturation transfer difference (STD) NMR spectroscopy established that formic acid, which is present mainly as formate, is not immobilized as part of the gelating network. In contrast, HDO interacts with the network, which presumably has a surface with exposed hydrophilic groups that form hydrogen bonds with water. Moreover, the STD NMR experiments revealed that the network is a dynamic entity, with molecules of deoxycholate associating and dissociating reversibly. This exchange appears to occur preferentially by contact of the hydrophobic edges or faces of free molecules of deoxycholate with those of molecules immobilized as components of the network. In addition, DOSY experiments revealed that gelation has little effect on the diffusion of free NaDC and HDO.