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Glycocholic acid Sale

(Synonyms: 甘氨胆酸) 目录号 : GC34134

Glycocholic acid是一种参与脂肪乳化的结晶胆汁酸,是胆酸与甘氨酸的结合物,它以钠盐的形式存在于哺乳动物的胆汁中。

Glycocholic acid Chemical Structure

Cas No.:475-31-0

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10mM (in 1mL DMSO)
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50mg
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Sample solution is provided at 25 µL, 10mM.

Description

Glycocholic acid is a crystalline bile acid involved in fat emulsification. It is a combination of bile acid and glycine and exists in mammalian bile in the form of sodium salt[1]. Glycocholic acid has anti-tumor activity and can target resistance pumps and non-resistance pump pathways[2]. Glycocholic acid can be used as a phenotypic biomarker for cholangiocarcinoma[3]. Glycocholic acid can treat bile acid amidation defects[4].

In vitro, treatment of Caco-2 cells with Glycocholic acid (10, 100μM) for 48h significantly increased the expression of Hsp90β protein, and exerted a synergistic effect when used in combination with butyrate[5].

In vivo, Glycocholic acid (10μg/mL) was used to treat lipopolysaccharide (LPS)-induced zebrafish inflammation model by microinjection, which significantly reduced the accumulation of macrophages in zebrafish and inhibited the upregulation of interleukin-6 (IL-6), tumor necrosis factor-α (TNF-α), and cc motif chemokine ligand-2 (CCL-2)[6].

References:
[1] Holm R, Müllertz A, Mu H. Bile salts and their importance for drug absorption[J]. International Journal of Pharmaceutics, 2013, 453(1): 44-55.
[2] Lo Y L, Ho C T, Tsai F L. Inhibit multidrug resistance and induce apoptosis by using glycocholic acid and epirubicin[J]. European journal of pharmaceutical sciences, 2008, 35(1-2): 52-67.
[3] Song W S, Park H M, Ha J M, et al. Discovery of glycocholic acid and taurochenodeoxycholic acid as phenotypic biomarkers in cholangiocarcinoma[J]. Scientific Reports, 2018, 8(1): 11088.
[4] Heubi J E, Setchell K D R, Jha P, et al. Treatment of bile acid amidation defects with glycocholic acid[J]. Hepatology, 2015, 61(1): 268-274.
[5] Casselbrant A, Fändriks L, Wallenius V. Glycocholic acid and butyrate synergistically increase vitamin D-induced calcium uptake in Caco-2 intestinal epithelial cell monolayers[J]. Bone reports, 2020, 13: 100294.
[6] Ge X, Huang S, Ren C, et al. Taurocholic acid and glycocholic acid inhibit inflammation and activate farnesoid X receptor expression in LPS-stimulated zebrafish and macrophages[J]. Molecules, 2023, 28(5): 2005.

Glycocholic acid是一种参与脂肪乳化的结晶胆汁酸,是胆酸与甘氨酸的结合物,它以钠盐的形式存在于哺乳动物的胆汁中[1]。Glycocholic acid 具有抗肿瘤活性,可靶向作用于耐药泵和非耐药泵通路[2]。Glycocholic acid能够作为胆管癌的表型生物标志物[3]。Glycocholic acid 能够治疗胆汁酸酰胺化缺陷[4]

在体外,Glycocholic acid(10, 100μM)处理Caco-2细胞48h,显著增加了Hsp90β蛋白的表达,与丁酸盐联合使用发挥了协同效应[5]

在体内,Glycocholic acid(10µg/mL)通过显微注射治疗脂多糖(LPS)诱导的斑马鱼炎症模型,显著减少了斑马鱼体内巨噬细胞蓄积,抑制了白细胞介素-6(IL-6)、肿瘤坏死因子-α(TNF-α)和cc基序趋化因子配体-2(CCL-2)的上调[6]

实验参考方法

Cell experiment [1]:

Cell lines

Caco-2 cells

Preparation Method

All Caco-2 cell experiments started on day 14 after seeding. The cells were exposed for 48h with the following: 1:75 dilution (~1mM) of whole human bile (coming from one patient with unknown identity for the researchers) 10 or 100μM chenodeoxycholic acid (CDCA) as primary bile acid, 10 or 100μM lithocholic acid (LCA) as secondary bile acid, and 10 or 100μM Glycocholic acid (GCA) and taurocholic acid (TCA) as conjugated bile acid and 10mM of the short-chain fatty acid butyrate in FBS-free medium in the upper compartments. After incubation, the resistance was measured and the cells were saved for protein expression.

Reaction Conditions

10, 100μM; 48h

Applications

Glycocholic acid in combination with butyrate increased the Hsp90β protein expression significantly, at a comparable level to whole bile, while Taurocholic acid had no such effect.

Animal experiment [2]:

Animal models

Zebrafish

Preparation Method

Three days post-fertilization (dpf), zebrafish were divided into control (PBS microinjection), model (LPS microinjection), and administration (LPS microinjection+drug administration) groups. Embryos in the administration groups were pretreated with Babaodan (10µg/mL), C. bovis (10µg/mL), bile acids (including Taurodeoxycholate sodium salt (TDCA), Deoxycholic acid (DCA), Taurocholic acid Sodium Salt (TCA), Glycodeoxycholic acid (GDCA), Glycocholic acid (GCA), Cholic acid (CA), Taurochenodeoxycholic acid (TCDCA), Glycochenodeoxycholic acid (GCDCA)) (All the bile acids were administered at a concentration of 10µg/mL), and dexamethasone (DEX, 20µg/mL) (positive control), respectively. After 24h of treatment, microinjection was performed in a 1nL volume per larva with LPS at a concentration of 2.5mg/mL. The control group used phosphate-buffered saline of the same volume as LPS. Embryos were retreated with drugs for 6h right after recovery from anesthesia (0.02% tricaine).

Dosage form

10µg/mL; microinjection

Applications

Among all the bile acids, Taurocholic acid and Glycocholic acid showed the strongest effects on reducing macrophage accumulation. the LPS-stimulated upregulation of IL-6, TNF-α, and CCL-2 were significantly inhibited by either Taurocholic acid or Glycocholic acid treatment. 

References:
[1]Casselbrant A, Fändriks L, Wallenius V. Glycocholic acid and butyrate synergistically increase vitamin D-induced calcium uptake in Caco-2 intestinal epithelial cell monolayers[J]. Bone reports, 2020, 13: 100294.
[2]Ge X, Huang S, Ren C, et al. Taurocholic acid and glycocholic acid inhibit inflammation and activate farnesoid X receptor expression in LPS-stimulated zebrafish and macrophages[J]. Molecules, 2023, 28(5): 2005.

化学性质

Cas No. 475-31-0 SDF
别名 甘氨胆酸
Canonical SMILES O=C(O)CNC(CC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)=O
分子式 C26H43NO6 分子量 465.62
溶解度 DMSO : ≥ 100 mg/mL (214.77 mM) 储存条件 Store at -20°C
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1 mM 2.1477 mL 10.7384 mL 21.4767 mL
5 mM 0.4295 mL 2.1477 mL 4.2953 mL
10 mM 0.2148 mL 1.0738 mL 2.1477 mL
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