Glycochenodeoxycholic acid

Manufactured by Merck Group

Sourced in United States, United Kingdom, Belgium

Glycochenodeoxycholic acid is a bile acid compound used in various laboratory applications. It serves as a key component in research and analysis processes, particularly in the study of biological and biochemical systems. The compound has well-defined chemical properties and functions that make it a valuable tool for scientific investigations.

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Lab products found in correlation

35 protocols using glycochenodeoxycholic acid

Purification and Mutagenesis of Bile Salt Hydrolase

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Major bacterial strains and plasmids used in this study and their sources are listed in Table S1. Briefly, the E. coli recombinant strain JL885 containing pBSH expression vector (Table S1), constructed in our previous study^{19 (link)}, was used for purification of wild-type lsBSH in this study. The pBSH plasmid bearing original bsh gene from L. salivarius NRRL B-30514 was used as parent vector for site-directed mutagenesis. All compounds were purchased from Sigma-Aldrich (St. Louis, MO, USA), which include ampicillin, glycocholic acid (GCA), glycodeoxycholic acid (GDCA), glycochenodeoxycholic acid (GCDCA), taurocholic acid (TCA), taurodeoxycholic acid (TDCA), taurochenodeoxycholic acid (TCDCA).

Xu F., Hu X.J., Singh W., Geng W., Tikhonova I.G, & Lin J. (2019). The complex structure of bile salt hydrolase from Lactobacillus salivarius reveals the structural basis of substrate specificity. Scientific Reports, 9, 12438.

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Acid and Bile Tolerance of Probiotic Strain

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For acid tolerance, CNCM I-4884 suspension was adjusted to 1.0 (OD 600 nm) with phosphate buffered saline (PBS) at pH 2.0 using 1 N HCl. After 30, 60, 90 and 120 min of incubation at 37 °C, suspensions were serially diluted in PBS and plated onto MRS agar. Viable cells were counted after 48 h incubation at 37 °C. For bile salts tolerance, MRS broth was supplemented with a mix of taurocholic acid, taurochenodeoxycholic acid, glycocholic acid and glycochenodeoxycholic acid (Sigma, Saint Louis, MO, USA) at 0.05 mg/mL, 0.1 mg/mL, 0.5 mg/mL, 1 mg/mL and 2 mg/mL each. Bacterial growth was monitored at 37 °C every 30 min for 24 h by OD at 600 nm using Infinite M200 Pro spectrophotometer (TECAN, Lyon, France). The experiments were performed in three biological replicates.

Boucard A.S., Florent I., Polack B., Langella P, & Bermúdez-Humarán L.G. (2022). Genome Sequence and Assessment of Safety and Potential Probiotic Traits of Lactobacillus johnsonii CNCM I-4884. Microorganisms, 10(2), 273.

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Quantification of Bile Acids Metabolites

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ANIT, carbamazepine, mycophenolic acid, and reference standards for 18 BAs, including CA, glycocholic acid, TCA, CDCA, glycocheno deoxycholic acid, TCDCA, deoxycholic acid, glycodeoxycholic acid, taurodeoxycholic acid, UDCA, glycoursodeoxycholic acid, TUDCA, LCA, glycolithocholic acid, taurolithocholic acid, hyodeoxycholic acid, glycohyodeoxycholic acid, and taurohyodeoxycholic acid were purchased from Sigma-Aldrich (St. Louis, MO, USA). Chromatography-grade acetonitrile was purchased from Merck (Darmstadt, Germany). Water was purified using a MilliQ water system (Millipore, Bedford, MA, USA). Chromatography-grade acetic acid, formic acid, and methanol were provided by Tedia Company (Fairfield, OH, USA).

Li Y.F., Wu J.S., Li Y.Y., Dai Y., Zheng M., Zeng J.K., Wang G.F., Wang T.M., Li W.K., Zhang X.Y., Gu M., Huang C., Yang L., Wang Z.T, & Ma Y.M. (2017). Chicken bile powder protects against α-naphthylisothiocyanate-induced cholestatic liver injury in mice. Oncotarget, 8(57), 97137-97152.

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Standardized Bile Acid Analysis

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All chemicals and solvents were of the highest purity commercially available. Standard bile acids (sodium salts), including glyco cheno deoxy cholic acid (GCDCA), glyco deoxy cholic acid (GDCA), glyco cholic acid (GCA), tauro cheno deoxy cholic acid (TCDCA), tauro deoxy cholic acid (TDCA), tauro cholic acid (TCA), cheno deoxy cholic acid (CDCA), deoxy cholic acid (DCA) and cholic acid (CA), were purchased from Sigma-Aldrich (St. Louis, MO, USA). Three different oxgall powder samples were obtained from Sigma-Aldrich (Product code B3883), Oxoid (Product code LP005, Basingstoke, Hampshire, UK) and BD Difco (Product code 212820, Sparks, MD, USA). Acetonitrile and methanol (HPLC grade) were supplied by Tedia (Fairfield, OH, USA). The derivatization reagents p-bromophenacylbromide and N, N-diisopropylethylamine, and the ion-pairing reagent tetrabutylammonium hydrogen sulfate were also purchased from Sigma-Aldrich.

Hu P.L., Yuan Y.H., Yue T.L, & Guo C.F. (2018). Bile acid patterns in commercially available oxgall powders used for the evaluation of the bile tolerance ability of potential probiotics. PLoS ONE, 13(3), e0192964.

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Bile Salts Cocktail for GERD

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A bile salts cocktail, consisting of an equal molar mixture of sodium salts of glycocholic acid, taurocholic acid, glycodeoxycholic acid, deoxycholic acid (CALBIOCHEM, La Jolla, CA), and glycochenodeoxycholic acid (Sigma-Aldrich, Saint Louis, MO), was prepared to reflect the mixture of bile salts in the distal esophagus during GERD, as previously reported [9 (link), 18 (link), 19 (link)]. To mimic pathophysiology conditions of GERD, we used the bile salts cocktail in acidic medium (pH4, ABS) to treat Barrett’s epithelial cells.

Peng D., Lu H., Zhu S., Zhou Z., Hu T., Chen Z., Zaika A, & El-Rifai W. (2019). NRF2 antioxidant response protects against acidic bile salts-induced oxidative stress and DNA damage in esophageal cells. Cancer letters, 458, 46-55.

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Targeted Bile Acid Profiling

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Two-milliliter Tough Tubes with caps, ceramic beads 1.4 mm and 2.8 mm, and Omni Bead Ruptor 24 were purchased from Omni International, Kennesaw, GA, USA. Pipette tips (200 µL Genomic LR (orifice diameter 1.5) low retention) were purchased from VWR International, Radnor, PA, USA. Data were integrated with Lab Solutions 5.97 Shimadzu Corporation, Kyoto, Japan, Lab Solutions Insight LCMS. Pierce™ BCA Protein Kit was obtained by Thermo Scientific, Waltham, MA, USA. LC-MS grade isopropanol, methanol, and acetonitrile were obtained from Fischer Chemicals, Pittsburgh, PA, USA. Taurocholic acid, glycocholic acid, chenodeoxycholic acid, glycochenodeoxycholic acid, taurochenodeoxycholic acid, and their corresponding deuterium-labeled compounds, as well as hydrochloric acid 37%, ammonium formate, and formic acid were purchased from Sigma-Aldrich, Burlington, MA, USA.

Schött H.F., Chua E.W., Mir S.A., Burla B., Bendt A.K, & Wenk M.R. (2022). Evaluation of Normalization Approaches for Quantitative Analysis of Bile Acids in Human Feces. Metabolites, 12(8), 723.

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Bile Acid Compound Procurement for Analysis

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Cholic
acid (CA), deoxycholic acid (DCA),
chenodeoxycholic acid (CDCA), lithocholic acid (LCA), taurocholic
acid (TCA), taurodeoxycholic acid (TDCA), taurochenodeoxycholic acid
(TCDCA), glycocholic acid (GCA), glycochenodeoxycholic acid (GCDCA),
glycodeoxycholic acid (GDCA), 2,5-dihydroxybenzoic acid (DHB), 9-aminoacridine
(9AA), chloroform (CHCl₃), and trifluoroacetic acid (TFA)
were purchased from Sigma-Aldrich (Zwijndrecht, The Netherlands).
Methanol (MeOH) was purchased from Biosolve (Valkenswaard, The Netherlands).

Flinders B., Huizing L.R., van Heerden M., Cuyckens F., Neumann U.P., van der Laan L.J., Olde Damink S.W., Heeren R.M., Schaap F.G, & Vreeken R.J. (2018). Cross-Species Molecular Imaging of Bile Salts and Lipids in Liver: Identification of Molecular Structural Markers in Health and Disease. Analytical Chemistry, 90(20), 11835-11846.

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Quantification of Bile Acids and Cortisone

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Cholic acid (CA), glycoCholic acid (GCA), tauroCholic acid (TCA), chenodeoxyCholic acid (CDCA), glycochenodeoxyCholic acid (GCDCA), taurochenodeoxyCholic acid (TCDCA), ursodeoxyCholic acid (UDCA), glycoursodeoxyCholic acid (GUDCA), tauroursodeoxyCholic acid (TUDCA), deoxyCholic acid (DCA), glycodeoxyCholic acid (GDCA), taurodeoxyCholic acid (TDCA), taurolithoCholic acid (TLCA), and cortisone acetate were purchased from Sigma-Aldrich (St. Louis, MO, USA). α-MuriCholic acid (α-MCA) and tauromuriCholic acid (TMCA) were purchased from Steraloids Inc (Newport, RI, USA). All other reagents and solvents were of high performance liquid chromatography (HPLC) grade. Deionized water was purified using a Milli-Q system (Millipore, Bedford, MA, USA). S. baicalensis Georgi (Hebei Province), G. uralensis Fisch (Inner Mongolia of China), P. lactiflora Pall (Anhui Province), and Z. jujuba Mill (Henan Province) were authenticated by Dr. Ehu Liu (State Key Laboratory of Natural Medicine, China Pharmaceutical University, China).

Wang X., Cui D.N., Dai X.M., Wang J., Zhang W., Zhang Z.J, & Xu F.G. (2017). HuangQin Decoction Attenuates CPT-11-Induced Gastrointestinal Toxicity by Regulating Bile Acids Metabolism Homeostasis. Frontiers in Pharmacology, 8, 156.

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Hypoxia and Bile Acid Exposure in NES Cells

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For hypoxia, NES cells were incubated at 1% oxygen by nitrogen in an INVivo2 400 (LAF Technologies, Queensland, Australia) hypoxia work station. For individual experiments, cells were cultured in neutral medium (pH7) alone or with periodic exposures to acidic medium (pH 5.5) containing a mixture of conjugated bile acids (glycocholic acid, glycodeoxycholic acid [both from Calbiochem, San Diego, CA], taurocholic acid, glycochenodeoxycholic acid, taurochenodeoxycholic acid, and taurodeoxycholic acid [Sigma-Aldrich, St. Louis, MO] in a 20:6:3:15:3:1 molar concentration, total concentration 400 μM) as previously described. ^{14 (link), 16 (link)-18 (link)} Neutral or acidic bile salt medium was added for 10, 30 or 60 minutes, then replaced with growth medium. These exposure durations were chosen to simulate typical episodes of gastrooesophageal reflux. ^{19 (link), 20 (link)} All assays were performed over a 24-hour time course unless otherwise indicated.
Additional details are provided in the Supplemental Material and Methods section and in Supplemental Tables 1 and 2.

Huo X., Agoston A.T., Dunbar K.B., Cipher D.J., Zhang X., Yu C., Cheng E., Zhang Q., Pham T.H., Tambar U.K., Bruick R.K., Wang D.H., Odze R.D., Spechler S.J, & Souza R.F. (2016). Hypoxia-Inducible Factor-2α Plays a Role in Mediating Oesophagitis in Gastro-Oesophageal Reflux Disease. Gut, 66(9), 1542-1554.

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Plasma and Fecal Biomarker Analysis

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Pharmacodynamic and pharmacokinetic venous blood samples were collected in serum separator and EDTA tubes. Plasma samples were rapidly separated by centrifugation at 4°C. The serum separator tubes were left on the bench at room temperature for the blood to clot before centrifugation. Plasma and serum was stored at −70°C until they were analyzed. Faecal samples were collected while in the unit and stored at −70°C until they were analyzed.
Plasma total and active GLP-1_7–36, total PYY and GIP concentrations and plasma glucose levels were measured by BioAgilytix Labs (Durham, NC) using the assays shown in Table 1.
Venous serum samples, Entero-Test bile samples and faecal samples were analyzed for primary, secondary and conjugated bile acids. Bile acid (BA) standards, cholic acid (CA), chenodeoxycholic acid (CDCA), deoxycholic acid (DCA), glycochenodeoxycholic acid (GCDCA), glycocholic acid (GCA), glycodeoxycholic acid (GDCA), lithocholic acid (LCA), taurochenodeoxycholic acid (TCDCA), taurocholic acid (TCA), taurodeoxycholic acid (TDCA), taurolithocolic acid (TLCA), tauroursodeoxycholic acid (TUDCA) and ursodeoxycholic acid (UDCA), were purchased from Sigma Aldrich (Gillingham, UK) and were ≥95% purity. The internal standards, cholic acid (24-¹³C) and deoxycholic acid (24-¹³C), were obtained from Cambridge Isotope Laboratories (Massachusetts, USA) and were 99% pure.

Napolitano A., Miller S., Nicholls A.W., Baker D., Van Horn S., Thomas E., Rajpal D., Spivak A., Brown J.R, & Nunez D.J. (2014). Novel Gut-Based Pharmacology of Metformin in Patients with Type 2 Diabetes Mellitus. PLoS ONE, 9(7), e100778.

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