Use of Bile Acids in Pharmacological and Supramolecular Applications

Virtanen, Elina; Kolehmainen, Erkki

doi:10.1002/chin.200445285

Cited by 23 publications

(31 citation statements)

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“…1 H-NMR spectral characterization of 5-16 was based on our results on bile acids and their derivatives [1], as well as on cholic acid-porphyrin conjugates 1-4 reported before [15]. As in the case of cholic acid derivatives 1-4 [15], the C18 and 19 angular methyls of the steroidal moieties in 5-16 are strongly shielded, due to the anisotropic ring current effect of the BAP porphyrin core.…”

Section: Thementioning

confidence: 87%

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Synthesis, Characterization, and Saccharide Binding Studies of Bile Acid − Porphyrin Conjugates

et al. 2007

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Synthesis and characterization of bile acid-porphyrin conjugates (BAPs) are reported. Binding of saccharides with BAPs in aqueous methanol was studied by monitoring changes in the visible absorption spectral of the porphyrin-moieties. Although these studies clearly showed absorbance changes, suggesting quite high if non-selective binding, the mass spectral studies do not unambiguously support these results.

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Section: Thementioning

confidence: 87%

“…Bile acids possess a large number of applications in pharmaceutical and supramolecular chemistry, as recently reviewed [1]. For example, bile acids are potential carriers for liver specific drugs and they can be used as cholesterol level lowering agents [2].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Saccharide Binding Studies of Bile Acid − Porphyrin Conjugates

et al. 2007

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“…Taminen and Kolekmainen [44] have recently reviewed the potential of bile acids as building blocks for the formation of supramolecular structures, which have been shown to possess molecular recognition properties. As an example bile acid-porphyrin conjugates are investigated with respect to their saccharide binding capacities [45][46][47]. Other applications are described, especially in the field of protein biochemistry in order to use bile salts for the isolation of membrane bound proteins or other structures [23,41,48,49].…”

Section: Compartment Concentrationmentioning

confidence: 99%

Membranolytic Activity of Bile Salts: Influence of Biological Membrane Properties and Composition

et al. 2007

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Abstract:The two main steps of the membranolytic activity of detergents: 1) the partitioning of detergent molecules in the membrane and 2) the solubilisation of the membrane are systematically investigated. The interactions of two bile salt molecules, sodium cholate (NaC) and sodium deoxycholate (NaDC) with biological phospholipid model membranes are considered. The membranolytic activity is analysed as a function of the hydrophobicity of the bile salt, ionic strength, temperature, membrane phase properties, membrane surface charge and composition of the acyl chains of the lipids. The results are derived from calorimetric measurements (ITC, isothermal titration calorimetry). A thermodynamic model is described, taking into consideration electrostatic interactions, which is used for the calculation of the partition coefficient as well as to derive the complete thermodynamic parameters describing the interaction of detergents with biological membranes (change in enthalpy, change in free energy, change in entropy etc). The solubilisation properties are described in a so-called vesicle-to-micelle phase transition diagram. The obtained results are supplemented and confirmed by data obtained from other biophysical techniques (DSC differential scanning calorimetry, DLS dynamic light scattering, SANS small angle neutron scattering).

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“…[2][3][4] This easily available and low-cost chemical, thanks to its intrinsic biodegradability, biocompatibility and renewability combined with the easy modifiability of the hydroxyl and carboxyl groups and the stability of steroid skeleton, was chosen by many researchers to design and synthesize new cholic acid-containing oligomeric or polymeric materials. [5,6] Various types of such polymers were produced in the last two decades: in several of these, the CAs were part of the main chain, [7][8][9][10] while in others, the CAs were connected as pendants [11][12][13] or, more recently, as the core of star-shaped polymers.…”

Section: Introductionmentioning

confidence: 99%

Novel tri- and tetrafunctional cholic acid-based initiators for the synthesis of star-shaped poly(L-lactide)s

Donvito

Fantin

Fogagnolo

et al. 2016

Designed Monomers and Polymers

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In this investigation, two novel multifunctional initiators for ring-opening polymerization were synthesized in three steps starting from cholic acid. Thus, cholic acid (1a) and its methyl ester (1b) were quantitatively transformed, via solvent-free reaction with succinic anhydride, to the corresponding 3, 7, 12-tri-hemisuccinate derivatives (3a-b). The polyacidic compounds (3a-b) were treated with thionyl chloride affording the corresponding acyl chlorides 4a-b which, in turn, were reacted with ethylene glycol to give the derivatives 2a-b having three and four primary alcohol end groups. These compounds, fully characterized by 1 H, 13C NMR and mass spectrometry, have been assessed as initiators in the ring-opening polymerization of L-lactide using stannous octanoate as catalyst. The resulting three-and four-armed star-shaped poly(L-lactide)s, which were characterized by 1 H NMR, SEC, DSC and TGA analysis, were amorphous, and their glass transition temperatures ranged from 13.7 to 36.5 °C. Additionally, some cholic acid-based star-shaped polylactic structures recently published have been critically reconsidered showing that these molecules, described as star polymers, were actually linear polymers.

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Use of Bile Acids in Pharmacological and Supramolecular Applications

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 23 publications

References 1 publication

Synthesis, Characterization, and Saccharide Binding Studies of Bile Acid − Porphyrin Conjugates

Synthesis, Characterization, and Saccharide Binding Studies of Bile Acid − Porphyrin Conjugates

Membranolytic Activity of Bile Salts: Influence of Biological Membrane Properties and Composition

Novel tri- and tetrafunctional cholic acid-based initiators for the synthesis of star-shaped poly(L-lactide)s

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