Precipitation and 13C-NMR relaxation enhancement measurements of the interactions of bile acids with synthetic cationic bile acid derivatives, and with spin labelled fatty acids

Reid, David G.; Gajjar, Kaushika; Robinson, Simon P.; Hickey, Deirdre M. B.; Benson, G. Martin; Haynes, Claire; Leeson, Paul D.; Whittaker, Caroline

doi:10.1016/0009-3084(91)90037-c

Cited by 3 publications

(1 citation statement)

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“…Over the last few decades, researchers have worked on the synthesis and studies of cationic bile acid derivatives owing to their wide range of applications as cancerostatic, cholesterol dissolution agents, gallstone dissolution enhancers, and DNA transfection agents. − Moreover, these derivatives were found to be potent antibacterial agents in biomedical applications. , Many reports are available on the synthesis of cationic bile salts through ether, ester, and amide linkages in both facial and side chain of the bile acids and the level of difficulty varies widely in these syntheses. − In most of the cases, bile salts has been synthesized with a cationic group at the side chain by introducing a bis (amine) through amide conjugation chemistry and converting the second amine to a quaternary ammonium salt. , On the other hand, Maitra and co-workers has reported cationic bile salts without amide linkage at the side chain and studied their aggregation and gelation behavior . Recently, Galantini and co-workers has reported the self-assembly of a tryptophan and phenylalanine substituted bile acids …”

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confidence: 99%

Hierarchical Self-Assembly of Bile-Acid-Derived Dicationic Amphiphiles and Their Toxicity Assessment on Microbial and Mammalian Systems

Muthukumarasamyvel

Raju

Chandirasekar

et al. 2016

ACS Appl. Mater. Interfaces

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A thiol-yne click chemistry approach was adopted for the first time to prepare highly water-soluble bile acid derived dicationic amphiphiles. The synthesized amphiphiles dicationic cysteamine conjugated cholic acid (DCaC), dicationic cysteamine conjugated deoxycholic acid (DCaDC), and dicationic cysteamine conjugated lithocholic acid (DCaLC) exhibited hierarchically self-assembled microstructures at various concentrations in an aqueous medium. Interestingly at below critical micellar concentration (CMC) the amphiphiles showed distinct fractal patterns such as fractal grass, microdendrites and fern leaf like fractals for DCaC, DCaDC and DCaLC respectively. The fractal dimension (Df) analysis indicated that the formation of fractal like aggregates is a diffusion limited aggregation (DLA) process. The preliminary aggregation studies such as determination of CMC, fluorescence quenching, wettability and contact angle measurements were elaborately investigated. The morphology of the aggregates were analyzed by SEM and OPM techniques. Further, we demonstrated the antimicrobial and hemolytic activity for the cationic amphiphiles. DCaC had potent antimicrobial activity and showed no toxicity on human RBCs indicating that DCaC could be used in biomedical applications, in addition to their industrial and laboratory applications such as detergency, surface cleaning, and disinfection agent.

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Section: Introductionmentioning

confidence: 99%

Hierarchical Self-Assembly of Bile-Acid-Derived Dicationic Amphiphiles and Their Toxicity Assessment on Microbial and Mammalian Systems

Muthukumarasamyvel

Raju

Chandirasekar

et al. 2016

ACS Appl. Mater. Interfaces

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Use of novel cationic bile salts in cholesterol crystallization and solubilization in vitro

Bhat

Leikin-Gobbi

Konikoff

et al. 2006

Biochimica et Biophysica Acta (BBA) - General Subjects

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Self-Assembly of Bile Steroid Analogues: Molecules, Fibers, and Networks

et al. 2009

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Structural and rheological features of a series of molecular hydrogels formed by synthetic bile salt analogues have been scrutinized. Among seven gelators, two are neutral compounds, while the others are cationic systems among which one is a tripodal steroid derivative. Despite the fact that the chemical structures are closely related, the variety of physical characteristics is extremely large in the structures of the connected fibers (either plain cylinders or ribbons), in the dynamical modes for stress relaxation of the associated SAFINs, in the scaling laws of the shear elasticity (typical of either cellular solids or fractal floc-like assemblies), in the micron-scale texture and the distribution of ordered domains (spherulites, crystallites) embedded in a random mesh, in the type of nodal zones (either crystalline-like, fiber entanglements, or bundles), in the evolution of the distribution and morphology of fibers and nodes, and in the sensitivity to added salt. SANS appears to be a suitable technique to infer all geometrical parameters defining the fibers, their interaction modes, and the volume fraction of nodes in a SAFIN. The tripodal system is particularly singular in the series and exhibits viscosity overshoots at the startup of shear flows, an "umbrella-like" molecular packing mode involving three molecules per cross section of fiber, and scattering correlation peaks revealing the ordering and overlap of 1d self-assembled polyelectrolyte species.

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Precipitation and 13C-NMR relaxation enhancement measurements of the interactions of bile acids with synthetic cationic bile acid derivatives, and with spin labelled fatty acids

Cited by 3 publications

References 16 publications

Hierarchical Self-Assembly of Bile-Acid-Derived Dicationic Amphiphiles and Their Toxicity Assessment on Microbial and Mammalian Systems

Hierarchical Self-Assembly of Bile-Acid-Derived Dicationic Amphiphiles and Their Toxicity Assessment on Microbial and Mammalian Systems

Use of novel cationic bile salts in cholesterol crystallization and solubilization in vitro

Self-Assembly of Bile Steroid Analogues: Molecules, Fibers, and Networks

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