Synthesis of Cholic Acid Oligomer–Taurine Conjugates: A Study of Their Aggregation and Cholesterol Solubilization

Satyanarayana, Tirumalasetty; Maitra, Uday; Savyasachi, Aramballi J.

doi:10.1002/ejoc.201200312

Cited by 6 publications

(8 citation statements)

References 56 publications

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“…Bile acids are cholesterol-derived naturally occurring amphiphilic molecules, which are essential for digestion and absorption of fats and fat-soluble vitamins in the small intestine to adjust cholesterol levels in the body. 1 Bile acid derivatives have been used for cholesterol gallstone dissolution, 2 treating primary biliary cirrhosis, 3 antiviral and antifungal properties, gene therapy, radiopharmaceuticals, etc. 4 Supramolecular gels from salts of bile acid derivatives have immense application potential in biomedical and materials science.…”

Section: Introductionmentioning

confidence: 99%

Synthesis via RAFT polymerization of thermo- and pH-responsive random copolymers containing cholic acid moieties and their self-assembly in water

Pal

Roy

2014

Polym. Chem.

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Here we report the design and synthesis of polymers containing cholic acid pendant groups, a major bile acid synthesized in the liver from cholesterol. Random copolymers derived from 2-(methacryloyloxy)ethyl cholate (MAECA) with polyethylene glycol methyl ether methacrylate (PEGMA) and N,Ndimethylaminoethyl methacrylate (DMAEMA) have been synthesized by reversible additionfragmentation chain transfer (RAFT) polymerization. Compositions of co-monomers in the copolymers were determined by 1 H NMR spectroscopy, which were further used to determine reactivity ratios of the monomers using the extended Kelen-Tüdös method at high conversions. Copolymers from MAECA with PEGMA (P(MAECA-co-PEGMA)) series displayed lower critical solution temperatures (LCSTs) up to 23% MAECA content in the copolymer, which was studied by UV-visible spectroscopy. Both thermo-and pHresponsiveness were observed for the P(MAECA-co-DMAEMA) copolymers with an MAECA unit in the copolymer up to 11.8%. The critical aggregation concentration (CAC) of water soluble copolymers was determined by fluorescence spectroscopy. Self-assembly of random copolymers was investigated by 1 H NMR spectroscopy, dynamic light scattering (DLS), atomic force microscopy (AFM) and scanning electron microscopy (SEM), which indicated micellar structures in water from cholic acid based random copolymers. The polymeric aggregates were further explored for their drug encapsulation capabilities in aqueous medium using nile red as a hydrophobic model compound.

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Section: Introductionmentioning

confidence: 99%

Synthesis via RAFT polymerization of thermo- and pH-responsive random copolymers containing cholic acid moieties and their self-assembly in water

Pal

Roy

2014

Polym. Chem.

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“…The crumbling of the liposomal membrane leads to the destabilization and leakage of the membrane (Figure ). In this work, we suggest that the certain impact of the polymeric charge along with the synergy of the cholate presence helped to effectively control the membrane permeation potency. Our cholate-conjugated polymers authenticated its signature as efficient membrane disrupting nanoarchitectures, thereby opening a wide avenue for various biomedical future outlooks.…”

Section: Resultsmentioning

confidence: 85%

“…Bile acids are naturally occurring amphipathic end products of cholesterol and play a critical role in altering the lipid levels in the body by cholesterol gallstone dissolution . Bile acid derivatives have immense applications in biomedical sciences, including biliary cirrhosis therapy, gene transfection, and as antiviral, antibacterial, and antifungal agents .…”

Section: Introductionmentioning

confidence: 99%

Controlling the Membrane Perturbation by Tuning Charge Variable Cholate-Based Macromolecules

Sahoo

Hazra

Tarafdar

et al. 2022

ACS Appl. Polym. Mater.

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Access to the interior of the cell by destabilizing the natural barrier of the cell membrane is fundamental to drug and therapeutic delivery. Taking the unique facial amphiphilicity advantage of cholic acid to facilitate switching over impermeable cellular membranes, we report the synthesis of three different series of charge variable (anionic, cationic, and neutral) amphiphilic copolymers with various cholate contents and their membrane destabilization behavior. The synthesized cholate-containing amphiphilic copolymers self-organized into 80−100 nm sized nanoaggregates in aqueous media, while cholate moieties resided in the core of the self-assembled nanoparticles, as confirmed by 1 H NMR spectroscopy. The cholate-containing polymeric micelles proficiently destabilized the liposomes at pH 5.0 and pH 7.4. Interestingly, the cholate-appended neutral polymer exhibited up to 15fold enhancement in the membrane destabilization efficiency in comparison with respective cholate-based anionic or cationic polymers. Mechanistic studies using fluorescence, dynamic light scattering, and transmission electron microscopy established that the polymer−membrane interaction, subsequent reorganization, and insertion of cholate into the bilayer play a crucial role. Model drug (Nile red) encapsulation and release studies suggested the therapeutic potential of the cholate-conjugated polymeric nanoclusters.

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“…They produce mixed micelles using alimentary fats and lipophilic endogenous composites, and undergoes enterohepatic circulation via portal veins. 21 Bile acids were also reported to be useful in clinical therapy when applied in recommended doses. This is associated with several important biological applications like biliary cirrhosis therapy, 22 and antiviral and antifungal remedies.…”

Section: Introductionmentioning

confidence: 99%

Cholate-conjugated cationic polymers for regulation of actin dynamics

et al. 2022

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Synthesis of Cholic Acid Oligomer–Taurine Conjugates: A Study of Their Aggregation and Cholesterol Solubilization

Cited by 6 publications

References 56 publications

Synthesis via RAFT polymerization of thermo- and pH-responsive random copolymers containing cholic acid moieties and their self-assembly in water

Synthesis via RAFT polymerization of thermo- and pH-responsive random copolymers containing cholic acid moieties and their self-assembly in water

Controlling the Membrane Perturbation by Tuning Charge Variable Cholate-Based Macromolecules

Cholate-conjugated cationic polymers for regulation of actin dynamics

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