Sodium taurodeoxycholate

Catalog Number	ACM1180956-3
CAS	1180-95-6
Structure
Synonyms	2-[[(3α,5β,12α)-3,12-dihydroxy-24-oxocholan-24-yl]amino]-ethanesulfonic acid, monosodium salt
IUPAC Name	sodium;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]ethanesulfonate
Molecular Weight	522.69
Molecular Formula	C26H44NNaO6S
Canonical SMILES	CC(CCC(=O)NCCS(=O)(=O)[O-])C1CCC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)O)C.[Na+]
InChI	InChI=1S/C26H45NO6S.Na/c1-16(4-9-24(30)27-12-13-34(31,32)33)20-7-8-21-19-6-5-17-14-18(28)10-11-25(17,2)22(19)15-23(29)26(20,21)3;/h16-23,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33);/q;+1/p-1/t16-,17-,18-,19+,20-,21+,22+,23+,25+,26-;/m1./s1
InChI Key	YXHRQQJFKOHLAP-FVCKGWAHSA-M
Melting Point	168 °C (dec.) (lit.)
Purity	≥97%
Appearance	White to off-white solid
Storage	Solid
Complexity	864
Covalently-Bonded Unit Count	2
Defined Atom Stereocenter Count	10
EC Number	214-652-0
Exact Mass	521.27870358
Heavy Atom Count	35
Hydrogen Bond Acceptor Count	6
Hydrogen Bond Donor Count	3
Isomeric SMILES	C[C@H](CCC(=O)NCCS(=O)(=O)[O-])[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C.[Na+]
MDL Number	MFCD00003671
Monoisotopic Mass	521.27870358
Physical State	Freezer
Rotatable Bond Count	7
Shipping	Gel pack
Storage Conditions	-20 ºC
Topological Polar Surface Area	135 Ų

Knowledge & Learning Case Study Q&A

Influence of Sodium Taurodeoxycholate (NaTDC) on Flavonoid-Hemoglobin Interactions

Kong J, et al. Journal of Molecular Liquids, 2023, 391, 123302.

Sodium taurodeoxycholate (NaTDC) has a key role in enhancing the functional properties of the flavonoid-hemoglobin (HB) system. By strengthening the binding interactions and improving biological activities, NaTDC provides a promising approach for the design of flavonoid-based foods and drugs with enhanced efficacy. The findings offer a scientific foundation for further exploration of natural polyphenols in pharmaceutical and food additive applications
Methodology
The study utilized multispectral methods, including fluorescence, UV-vis, and circular dichroism (CD), along with dynamic light scattering (DLS), to investigate the binding mechanisms and interactions between galangin (Gal)/baicalein (Bai) and HB.
Both Gal and Bai induce static quenching of HB fluorescence, leading to conformational changes characterized by a decrease in α-helix content and an increase in β-sheet, β-turn, and random coil structures. Bai, with its three adjacent hydroxyl groups on the A-ring, exhibits a stronger binding affinity to HB and greater influence on its secondary structure compared to Gal.
The introduction of NaTDC significantly enhances the binding constants of both Gal-HB and Bai-HB systems. This enhancement also translates to improved antioxidant, antibacterial, solubility, and cytotoxic properties of the flavonoid-HB complexes. The presence of NaTDC stabilizes the interactions, leading to potential applications in developing HB-based delivery systems for natural small molecules.

Role of Sodium Taurodeoxycholate in the Encapsulation of Doxorubicin in TPGS Micelles

Sarolia J, et al. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2021, 622, 126693.

Sodium taurodeoxycholate (NaTDC) plays a crucial role in modulating the encapsulation and release of doxorubicin (DOX) in D-α-tocopherol polyethylene glycol 1000 succinate (TPGS) micelles. By inducing electrostatic charges, NaTDC effectively drives DOX into the apolar core, enhancing drug stability and offering a controlled release mechanism. This method, leveraging a biocompatible additive like NaTDC, presents a promising approach for drug delivery applications, particularly for ionizable drugs like DOX.
At low NaTDC concentrations (0.05-0.5 mM), NaTDC induced micelle contraction. As concentration increased (up to 2 mM), NaTDC and TPGS formed mixed micelles (8-11 nm) and larger swollen aggregates (200-300 nm), without altering the micelles' shape or the optical properties of the solution.
Initially, NaTDC engaged with the core-forming segment of TPGS. Beyond 1.0 mM concentration, NaTDC migrated to the micelle shell, imparting electrostatic charges that significantly influenced the micelle's aggregation and the effective charge of the system. This charge facilitated the migration of positively charged DOX from the hydrophilic shell to the apolar core, enhancing the stability of DOX within the micelles.
The encapsulated DOX remained stable over 50 days and across temperature variations (25-40 °C), demonstrating the effectiveness of NaTDC in maintaining drug stability.

Sodium Taurodeoxycholate in the Determination of L-Carnitine via Fluorescence Detection

Isaguirre AC, et al. Microchemical Journal, 2016, 129, 268-273.

The study successfully demonstrated a novel and efficient method for determining L-Carnitine (L-CAR) in dietary supplements using fluorescence detection with Sodium taurodeoxycholate (NaTDC)-enhanced on-line coacervation. NaTDC played a crucial role in improving the isolation and detection of L-CAR, leading to highly sensitive and accurate results. This methodology offers a cost-effective, high-throughput alternative to traditional techniques, making it valuable for routine analysis of L-CAR in various products.
The study developed an analytical method that combines on-line coacervation with fluorescence detection to determine L-CAR levels in various dietary supplements. The process involves several key steps:
Stock Solutions: L-CAR stock solution (6.2 × 10-4 mol L-1) and NaTDC solution (0.020 mol L-1) were prepared in ultrapure water.
Derivatization: L-CAR was mixed with a carbonate buffer and FMOC, then reacted at 50°C for 60 minutes. The reaction was halted with an acetate buffer.
Sample Preparation: Dietary supplement samples were diluted and homogenized before undergoing the derivatization procedure. The resulting solution was mixed with NaTDC, HCl, and ultrapure water to prepare it for analysis.
On-line Extraction and Fluorescence Detection: The coacervate containing the L-CAR-FMOC derivative was analyzed using a flow injection system with a packed mini-column connected to a spectrofluorimeter. The fluorescence signal, proportional to L-CAR concentration, was recorded as the peak area.
The developed methodology provided a detection limit of 2.4 × 10-8 mol L-1 and a quantification limit of 7.30 × 10-8 mol L-1, with recoveries ranging from 82% to 103%. These results demonstrate the method's sensitivity and accuracy.
Enhanced Isolation and Detection: The use of NaTDC in the on-line coacervation process significantly improved the isolation of L-CAR from complex matrices, enabling accurate fluorescence detection. The coacervate system effectively retained the L-CAR-FMOC derivative, allowing for precise quantification.

Sodium Taurodeoxycholate in Enhancing Intranasal Delivery of Galantamine Hydrobromide

Elhabak M, et al. International Journal of Pharmaceutics, 2023, 632, 122588.

The combination of sodium taurodeoxycholate (NaTDC) and polyacrylic acid (PAA) in a nanosized formulation significantly enhances the intranasal delivery of galantamine hydrobromide (GAL), offering a promising approach for non-invasive drug administration targeting the brain. NaTDC played a crucial role as a permeability enhancer, improving drug bioavailability and therapeutic efficacy. The formulation exhibited favorable characteristics, such as optimal particle size, uniform distribution, and high yield, making it a viable candidate for future clinical applications in Alzheimer's treatment.
The study utilized a mixed factorial experimental design to optimize the formulation parameters, including particle size, polydispersity index (PDI), spray rate, drying efficiency, and yield.
The optimized formulation F6 demonstrated a particle size of 185.55 nm with a low PDI, indicating uniform particle distribution. The formulation's spray rate and drying efficiency were also optimized, ensuring efficient production and consistent quality.
The formulation, which included NaTDC, significantly improved the intranasal delivery of GAL to the brain. This was evidenced by increased brain uptake and penetration of the fluorescent dye-labeled nanoparticles, indicating that NaTDC effectively enhanced the permeability of the drug across the nasal mucosa.
The study also evaluated the efficacy of the optimized formulation in a lipopolysaccharide (LPS)-induced Alzheimer's disease model in mice. The results showed that the formulation led to downregulation of pro-inflammatory markers NF-κβ, IL-1β, and GFAP, and upregulation of the anti-inflammatory marker TGF-β, suggesting a potential therapeutic benefit in reducing Alzheimer's disease-related inflammation.

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