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Special Issue "Bile Acids"

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products".

Deadline for manuscript submissions: closed (30 August 2007)

Special Issue Editor

Guest Editor
Prof. Dr. Erkki Kolehmainen (Website)

Department of Chemistry, University of Jyväskylä, P. O. Box 35, FI-40014, Jyväskylä, Finland
Phone: +358 40 805 3695
Fax: +358 14 260 2501
Interests: structural chemistry; bile acid chemistry

Special Issue Information

Bile acids - steroid acids found predominantly in the bile of mammals. Bile acids in supramolecular and nanochemistry, Conjugation, supramolecular chemistry, nanochemistry, glycine-conjugated bile acids, biliary lipids, etc. Oxidation of cholesterol.

Leading Papers

Jari Tamminen* and Erkki Kolehmainen
Department of Chemistry, University of Jyväskylä, P. O. Box 35, FIN-40351, Jyväskylä, Finland Tel.: + 358 14 2602659, Fax: +358 14 2602501 , E-mail: jatata@cc.jyu.fi
Review: Bile Acids as Building Blocks of Supramolecular Hosts
Molecules 2001, 6, 21-46 (PDF format, 280 K)
Times Cited: 33 (up to end 2006)

Submission

All papers should be submitted to molecules@mdpi.com with copy to the guest editor. To be published continuously until the deadline and papers will be listed together at the special websites.
Submitted papers should not have been previously published nor be currently under consideration for publication elsewhere. All papers are refereed through a peer review process. A guide for authors, sample copies and other relevant information for submitting papers are available on the Instructions for Authors page. Molecules is an international peer-reviewed monthly journal published by MDPI.
Please visit the Instructions for Authors page before submitting a paper. Open Access publication fees are 800 CHF per paper. English correction fees (250 CHF) will be added in certain cases (1050 CHF per paper for those papers that require extensive additional formatting and/or English corrections.).

Keywords

Bile salts, Bile acids, Cholic acid, Chenodeoxycholic acid, Glycocholic acid, Taurocholic acid, Deoxycholic acid.

Published Papers (9 papers)

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Research

Jump to: Review

Open AccessArticle Membranolytic Activity of Bile Salts: Influence of Biological Membrane Properties and Composition
Molecules 2007, 12(10), 2292-2326; doi:10.3390/12102292
Received: 9 September 2007 / Revised: 15 October 2007 / Accepted: 15 October 2007 / Published: 23 October 2007
Cited by 51 | PDF Full-text (1277 KB) | HTML Full-text | XML Full-text
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 [...] Read more.
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). Full article
(This article belongs to the Special Issue Bile Acids)
Open AccessArticle Hydrogels as Reaction Vessels: Acenaphthylene Dimerization in Hydrogels Derived from Bile Acid Analogues
Molecules 2007, 12(9), 2181-2189; doi:10.3390/12092181
Received: 8 August 2007 / Accepted: 17 September 2007 / Published: 18 September 2007
Cited by 14 | PDF Full-text (118 KB) | HTML Full-text | XML Full-text
Abstract
Many chemical reactions which are otherwise clean often lead to the formation of multiple products. Such products may be formed due to a lack of chemo-, regio- and/or stereoselectivity. For such reactions to be useful, one should be able to control them [...] Read more.
Many chemical reactions which are otherwise clean often lead to the formation of multiple products. Such products may be formed due to a lack of chemo-, regio- and/or stereoselectivity. For such reactions to be useful, one should be able to control them to yield a single desired product. Of the many approaches used in this context, the use of reaction media with features different from those of isotropic solutions has been very effective. Surfactant micelles have been shown to control the product selectivity in photochemical reactions, but the dynamic nature of the micelles probably results in differential effects on reaction selectivity. In this article we provide the results on photodimerization reactions performed in bile salt gels. Full article
(This article belongs to the Special Issue Bile Acids)
Open AccessArticle Structural, Thermoanalytical and Molecular Modeling Studies on N-(3-hydroxypropyl) 3α,12α-Dihydroxy-5β-cholan-24-amide and Its Monohydrates
Molecules 2007, 12(9), 2161-2178; doi:10.3390/12092161
Received: 17 August 2007 / Revised: 9 September 2007 / Accepted: 12 September 2007 / Published: 12 September 2007
Cited by 8 | PDF Full-text (366 KB) | HTML Full-text | XML Full-text
Abstract
The synthetic method for preparing N-(3-hydroxypropyl) 3α,12α-dihydroxy-5β- cholan-24-amide can lead to formation of at least three different crystal forms – an anhydrous compound and two monohydrates. The structural and thermal properties of these forms have been characterized by 13C-CP/MAS-NMR and IR spectroscopy, [...] Read more.
The synthetic method for preparing N-(3-hydroxypropyl) 3α,12α-dihydroxy-5β- cholan-24-amide can lead to formation of at least three different crystal forms – an anhydrous compound and two monohydrates. The structural and thermal properties of these forms have been characterized by 13C-CP/MAS-NMR and IR spectroscopy, thermo- gravimetry, differential scanning calorimetry and by powder and single crystal x-ray crystallography. In addition, theoretical 13C-NMR chemical shift calculations were also performed for the anhydrous compound and for the first monohydrate, starting from single crystal structures and the structures of these species have now been verified. The first monohydrate, C27H47NO4 · H2O, crystallizes in orthorhombic space group P212121 with cell parameters: a = 7.1148(2), b = 18.1775(5), c = 20.1813(6), Z = 4. Full article
(This article belongs to the Special Issue Bile Acids)
Open AccessArticle Synthesis of Novel Steroid-Peptoid Hybrid Macrocycles by Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs)
Molecules 2007, 12(8), 1890-1899; doi:10.3390/12081890
Received: 24 May 2007 / Accepted: 15 August 2006 / Published: 17 August 2007
Cited by 24 | PDF Full-text (127 KB) | HTML Full-text | XML Full-text
Abstract
Two new groups of cholane-peptoid hybrid macrocycles were produced by implementing novel combinations of the MiB methodology. Steroid-based hybrid macrolactams including heterocycle and aryl moieties were obtained by utilizing cholanic dicarboxylic acids and diamines in a bidirectional double Ugi-Four-Component (Ugi-4CR) based macrocyclization [...] Read more.
Two new groups of cholane-peptoid hybrid macrocycles were produced by implementing novel combinations of the MiB methodology. Steroid-based hybrid macrolactams including heterocycle and aryl moieties were obtained by utilizing cholanic dicarboxylic acids and diamines in a bidirectional double Ugi-Four-Component (Ugi-4CR) based macrocyclization protocol. Alternatively, N-substituted cyclocholamides were produced from a cholanic pseudo-amino acid by an Ugi-4CR-based cyclooligomerization approach. Both types of macrocycles are steroid-peptoid hybrid macrocycles containing exocyclic peptidic chains. These novel frameworks are a result of the use of bile acids bifunctionalized with carboxylic and amino functionalities as bifunctional building blocks of the Ugi-MiB approach. Full article
(This article belongs to the Special Issue Bile Acids)
Open AccessArticle Synthesis, Characterization, and Saccharide Binding Studies of Bile Acid − Porphyrin Conjugates
Molecules 2007, 12(1), 13-24; doi:10.3390/12010013
Received: 17 November 2006 / Revised: 2 January 2007 / Accepted: 4 January 2007 / Published: 5 January 2007
Cited by 12 | PDF Full-text (550 KB) | HTML Full-text | XML Full-text
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Bile Acids)

Review

Jump to: Research

Open AccessReview Bile Acid Scaffolds in Supramolecular Chemistry: The Interplay of Design and Synthesis
Molecules 2007, 12(9), 2106-2122; doi:10.3390/12082106
Received: 7 July 2007 / Accepted: 8 August 2007 / Published: 29 August 2007
Cited by 57 | PDF Full-text (129 KB) | HTML Full-text | XML Full-text
Abstract
Since early work in the 1980s, the bile acids have become well established as building blocks for supramolecular chemistry. The author’s laboratory has specialised in converting cholic acid, the archetypal bile acid, into macrocyclic and acyclic receptors for anions and carbohydrates. This [...] Read more.
Since early work in the 1980s, the bile acids have become well established as building blocks for supramolecular chemistry. The author’s laboratory has specialised in converting cholic acid, the archetypal bile acid, into macrocyclic and acyclic receptors for anions and carbohydrates. This review highlights the synthetic aspects of this work, especially the use of modern synthetic methodology to perform less obvious structural transformations. Full article
(This article belongs to the Special Issue Bile Acids)
Open AccessReview Supramolecular Chirality in Crystalline Assemblies of Bile Acids and Their Derivatives; Three-Axial, Tilt, Helical, and Bundle Chirality
Molecules 2007, 12(8), 1973-2000; doi:10.3390/12081973
Received: 30 June 2007 / Revised: 20 August 2007 / Accepted: 20 August 2007 / Published: 22 August 2007
Cited by 27 | PDF Full-text (1189 KB) | HTML Full-text | XML Full-text
Abstract
Steroidal bile acids and their derivatives exhibit characteristic inclusion behaviors in the crystalline state. Their crystals present varied assemblies due to asymmetric molecular structures, which relate to supramolecular properties through cooperative weak interactions. An overview indicates that the steroidal assemblies lie in [...] Read more.
Steroidal bile acids and their derivatives exhibit characteristic inclusion behaviors in the crystalline state. Their crystals present varied assemblies due to asymmetric molecular structures, which relate to supramolecular properties through cooperative weak interactions. An overview indicates that the steroidal assemblies lie in an intermediate position among various molecules and have hierarchical structures such as primary, secondary, tertiary, and host-guest assemblies like proteins. Such an interpretation brought about the idea that the assemblies with dimensionality present supramolecular chirality such as three-axial, tilt, helical, bundle, and complementary chirality. This concept of the supramolecular chirality enables us to understand formation of chiral crystals starting from the molecular chirality of the steroidal molecules. Full article
(This article belongs to the Special Issue Bile Acids)
Open AccessReview Exploitation of Bile Acid Transport Systems in Prodrug Design
Molecules 2007, 12(8), 1859-1889; doi:10.3390/12081859
Received: 6 June 2007 / Revised: 13 August 2007 / Accepted: 14 August 2007 / Published: 16 August 2007
Cited by 62 | PDF Full-text (168 KB) | HTML Full-text | XML Full-text
Abstract
The enterohepatic circulation of bile acids is one of the most efficient recycling routes in the human body. It is a complex process involving numerous transport proteins, which serve to transport bile acids from the small intestine into portal circulation, from the [...] Read more.
The enterohepatic circulation of bile acids is one of the most efficient recycling routes in the human body. It is a complex process involving numerous transport proteins, which serve to transport bile acids from the small intestine into portal circulation, from the portal circulation into the hepatocyte, from the hepatocyte into the bile, and from the gall bladder to the small intestine. The tremendous transport capacity and organ specificity of enterohepatic circulation combined with versatile derivatization possibilities, rigid steroidal backbone, enantiomeric purity, availability, and low cost have made bile acids attractive tools in designing pharmacological hybrid molecules and prodrugs with the view of improving intestinal absorption, increasing the metabolic stability of pharmaceuticals, specifically targeting drugs to organs involved in enterohepatic circulation, as well as sustaining therapeutically reasonable systemic concentrations of active agents. This article briefly describes bile acid transport proteins involved in enterohepatic circulation, summarizes the key factors affecting on the transport by these proteins, and reviews the use of bile acids and their derivatives in designing prodrugs capable of exploiting the bile acid transport system. Full article
(This article belongs to the Special Issue Bile Acids)
Open AccessReview Supra-molecular Association and Polymorphic Behaviour In Systems Containing Bile Acid Salts
Molecules 2007, 12(8), 1731-1754; doi:10.3390/12081731
Received: 9 May 2007 / Revised: 12 July 2007 / Accepted: 12 July 2007 / Published: 7 August 2007
Cited by 43 | PDF Full-text (467 KB) | HTML Full-text | XML Full-text
Abstract
A wide number of supra-molecular association modes are observed in mixtures containing water and bile salts, BS, (with, eventually, other components). Molecular or micellar solutions transform into hydrated solids, fibres, lyotropic liquid crystals and/or gels by raising the concentration, the temperature, adding [...] Read more.
A wide number of supra-molecular association modes are observed in mixtures containing water and bile salts, BS, (with, eventually, other components). Molecular or micellar solutions transform into hydrated solids, fibres, lyotropic liquid crystals and/or gels by raising the concentration, the temperature, adding electrolytes, surfactants, lipids and proteins. Amorphous or ordered phases may be formed accordingly. The forces responsible for this very rich polymorphism presumably arise from the unusual combination of electrostatic, hydrophobic and hydrogen-bond contributions to the system stability, with subsequent control of the supra-molecular organisation modes. The stabilising effect due to hydrogen bonds does not occur in almost all surfactants or lipids and is peculiar to bile acids and salts. Some supra-molecular organisation modes, supposed to be related to malfunctions and dis-metabolic diseases in vivo, are briefly reported and discussed. Full article
(This article belongs to the Special Issue Bile Acids)

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