CAS 83-44-3 Deoxycholic Acid - Vaccine Lab / Alfa Chemistry

Deoxycholic Acid for the Synthesis of a Novel Amphiphilic Chitosan Derivative (DA-NTMC)

Enhancing oral delivery and anticancer efficacy of 7-ethyl-10-hydroxycamptothecin through self-assembled micelles of deoxycholic acid grafted N'-nonyl-trimethyl chitosan Huang J, et al. Colloids and Surfaces B: Biointerfaces, 2024, 234, 113736.

Deoxycholic acid can be used to synthesize a chitosan derivative, namely N-deoxycholic acid grafted N'-nonyltrimethyl chitosan (DA-NTMC). It is synthesized by grafting nonyl and deoxycholic acid (DA) onto N, N, N-trimethyl chitosan (TMC). DA-NTMC can self-assemble into micelles in an aqueous environment while encapsulating SN38 in its core.
DA-NTMC
To synthesize nonyl-trimethyl chitosan (NTMC), 300 mg of trimethyl chitosan (TMC) was dissolved in 10 mL of methanol. The solution was stirred at 1000 rpm for 12 hours with the addition of 1.8 mL of nonylaldehyde. After this period, 114 mg of sodium borohydride was added, and the reaction continued for another 24 hours. The resulting precipitate was collected by centrifugation, dried in an oven at 40°C, and yielded NTMC.
For the synthesis of deoxycholic acid-modified NTMC (DA-NTMC), 39.2 mg of deoxycholic acid, 38.4 mg of EDCI, and 11.5 mg of NHS were dissolved in 10 mL of methanol and stirred magnetically at 600 rpm for 2 hours. Subsequently, 48.3 mg of NTMC was added to the mixture, which was left to stir overnight. The precipitate was isolated by high-speed centrifugation, dialyzed in deionized water, and freeze-dried to obtain DA-NTMC.
SN38-Loaded Micelles (SN38/DA-NTMC-M)
To prepare SN38-loaded micelles, 8 mg of SN38 was dissolved in 200 μL of DMSO. This solution was gradually added to a 10 mL aqueous dispersion of 50 mg DA-NTMC while stirring at 800 rpm at room temperature. The mixture was then ultrasonicated in an ice water bath for 6 minutes (with cycles of 3 seconds on and 2 seconds off at 455 W). Finally, the solution was dialyzed in deionized water for 24 hours, resulting in the formation of SN38-loaded micelles.

Deoxycholic Acid in the Treatment of Lumbar Epidural Lipomatosis

Minimally invasive treatment of lumbar epidural lipomatosis with local administration of deoxycholic acid McCandless MG, et al. Medical Hypotheses, 2024, 182, 111246.

Lumbar epidural lipomatosis (LEL) is a rare neurological condition characterized by excessive adipose tissue accumulation in the spinal canal, which can compress nerve roots or the spinal cord, often requiring surgical decompression. Deoxycholic acid injections could offer a minimally invasive treatment option for LEL, with the potential to reduce adipose tissue volume in the spinal canal and alleviate symptoms, providing an alternative to traditional surgical approaches.
Mechanism of Action: Deoxycholic acid, traditionally used for submental fat reduction, works by disrupting adipocyte cell membranes. It introduces hydroxyl groups into the lipid bilayer, causing cell lysis and the release of intracellular contents. This breakdown of adipose tissue triggers an inflammatory response, where macrophages are recruited to engulf the cellular debris and lipids, promoting tissue remodeling. As inflammation subsides, normal tissue architecture is restored, and the lipids are cleared through the lymphatic system and liver, ultimately reducing the volume of adipose tissue in the treated area.
Proposed Application in LEL: Given DCA's ability to reduce adipose tissue, it is hypothesized that its injection into the epidural space could decrease the adipose tissue burden in LEL, thereby decompressing the nerve roots and spinal cord. This approach may provide a viable alternative to surgical decompression, potentially reducing procedural risks, recovery times, and healthcare costs.
Clinical Trial Proposal: A phase 1 clinical trial is proposed to evaluate the safety of DCA injections in patients with LEL. The trial aims to assess whether DCA can effectively reduce epidural fat and improve symptoms associated with nerve root or spinal cord compression in LEL.

Preparation of Deoxycholic Acid-Chalcone Conjugates as Anticancer Agents

Design, synthesis, characterization and anticancer activity evaluation of deoxycholic acid-chalcone conjugates Patel S, et al. Bioorganic Chemistry, 2022, 127, 106036.

Deoxycholic acid can react with chalcone to form deoxycholic acid-chalcone conjugates. These hybrid molecules combine the biological activities of deoxycholic acid and chalcone and are designed to enhance their cytotoxic effects on cancer cells, especially on the human lung cancer cell line A549 and cervical cancer cell line SiHa.
The synthesis of deoxycholic acid-chalcone conjugates is as follows.
The deoxycholic acid-chalcone conjugates were synthesized using the mixed anhydride method. Ethyl chloroformate was added dropwise to a cooled solution of deoxycholic acid and triethylamine in 1,4-dioxane. After 20 minutes, 4-aminochalcone derivative and triethylamine were added to the reaction mixture as a DMF solution. The reaction mixture was stirred until the reaction was complete. After completion, the crude product was purified using silica gel chromatography using ethyl acetate and hexane as eluents to obtain deoxycholic acid-chalcone conjugates. All reactions were performed under nitrogen atmosphere.

Deoxycholic Acid as Carrier to Prepare Ketoconazole-loaded Micelle (KET-M) by Thin Film Hydration Method

Effect of deoxycholic acid-modified MPEG-oligo-chitosan micelles on the delivery, anti-biofilm activity and ROS induction of ketoconazole against C. albicans Wang M, et al. Journal of Drug Delivery Science and Technology, 2023, 87, 104884.

Deoxycholic acid (DXC) can be used to modify MPEG-oligo-chitosan (MPEG-oligo-CS) to create the amphiphilic polymer MPEG-CS-DXC. This polymer serves as a carrier for ketoconazole (KET)-loaded micelles (KET-M), which are prepared using the thin film hydration method. KET-M has been shown to induce greater reactive oxygen species production and exhibit superior anti-biofilm activity compared to free KET.
The synthesis of the amphiphilic polymer MPEG-CS-(DXC)₂ is as follows:
MPEG (2000 mg, 1.0 mmol) was combined with triethylamine (111 mg, 1.1 mmol) and reacted with p-nitrophenyl chloroformate (167.0 mg, 1.0 mmol) in dichloromethane at room temperature for 24 hours. After most of the solvent was evaporated, the residue was precipitated with ether to yield activated MPEG. Oligo-CS (1000 mg, 1.0 mmol) was then reacted with activated MPEG (2165 mg, 1 mmol) and triethylamine (202.0 mg, 2.0 mmol) in dimethyl sulfoxide (DMSO) at 50°C for 24 hours. The resulting mixture was dialyzed against distilled water and freeze-dried to produce MPEG-oligo-CS. Next, DXC (700.0 mg, 2.0 mmol) was activated using EDC (342.1 mg, 2.2 mmol) and NHS (253 mg, 2.2 mmol) in DMSO at room temperature for 5 hours. MPEG-oligo-CS (3 g, 1 mmol) was then added to the activated DXC mixture, and stirring was continued for 24 hours. The final product, MPEG-CS-(DXC)₂, was obtained by dialysis against water and subsequent freeze-drying.

Deoxycholic Acid for the Preparation of Novel Oral Nanocomplexes (LW-CS-DA/OA)

The novel nanocomplexes containing deoxycholic acid-grafted chitosan and oleanolic acid displays the hepatoprotective effect against CCl4-induced liver injury in vivo Xin C, et al. International Journal of Biological Macromolecules, 2021, 185, 338-349.

Deoxycholic acid (DA) can be used to modify low molecular weight chitosan (LW-CS) to produce LW-CS-DA, which can be combined with oleanolic acid (OA) to create a novel oral nanocomplex, LW-CS-DA/OA. This core-shell nanocomplex, with controlled release properties, enhances the protective effects of OA against CCl4-induced liver injury by restoring biochemical and tissue functions and reducing oxidative stress and inflammatory responses.
The synthesis of LW-CS-DA involves the following steps:
3 g of LW-CS is dissolved in 75 mL of 1% hydrochloric acid solution, adjusting the final pH to approximately 6.2. Separately, 0.9 g of DA, 0.5 g of NHS, and 0.3 g of EDC.HCl are dissolved in 90 mL of DMSO, stirred for 30 minutes, and then mixed with the LW-CS solution. The reaction is allowed to proceed at room temperature for 24 hours. The pH is then adjusted to 8 using 1 mol/L NaOH, followed by centrifugation at 8000 g for 5 minutes. The resulting precipitate is collected, washed three times with water and ethanol, respectively, and freeze-dried.
The synthesis of the LW-CS-DA/OA nanocomplex involves:
Dissolving 20 mg of LW-CS-DA and 20 mg of OA separately in 10 mL of DMSO. The LW-CS-DA solution is then premixed with the OA solution, stirred for 15 minutes, and dialyzed against deionized water for 24 hours using a membrane with a molecular weight cut-off (MWCO) of 1000 Da. After dialysis, the mixture is subjected to ultrafiltration (100 kDa, 5000 g, 20 min) to remove residual free OA, yielding the self-assembled LW-CS-DA/OA nanocomplex.

Catalog Number	ACM83443-2
CAS	83-44-3
Structure
Synonyms	Choleic acid
IUPAC Name	(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]pentanoic acid
Molecular Weight	392.58
Molecular Formula	C24H40O4
Canonical SMILES	CC(CCC(=O)O)C1CCC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)O)C
InChI	InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1
InChI Key	KXGVEGMKQFWNSR-LLQZFEROSA-N
Boiling Point	437.26 °C
Melting Point	171-174 °C(lit.)
Flash Point	9 °C
Purity	98%
Density	0.9985 g/cm³
Solubility	Soluble in water
Appearance	White to off-white solid
Storage	Room temperature
Complexity	605
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	10
EC Number	201-478-5
Exact Mass	392.29265975
Heavy Atom Count	28
Hydrogen Bond Acceptor Count	4
Hydrogen Bond Donor Count	3
Isomeric SMILES	C[C@H](CCC(=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
MDL Number	MFCD00003673
Monoisotopic Mass	392.29265975
Physical State	Solid
Rotatable Bond Count	4
Shipping	Ambient temperature
Storage Conditions	Room temperature
Topological Polar Surface Area	77.8 Å²