Synthesis and Alkaline Metal Ion Binding Ability of New Steroid Dimers Derived from Cholic and Lithocholic Acids

Joachimiak, Roman; Paryzek, Z.

doi:10.1023/b:jiph.0000031125.76093.f0

Cited by 13 publications

(5 citation statements)

References 18 publications

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“…Davis has briefly reviewed his work in this area, directed toward the construction of enzyme mimics [16]. The study on dimerization and oligomerization of the cholic acid skeleton as an architectural building block was particularly intensive [17][18][19]. Various methods of synthesis of steroid dimers with linear [20] or cyclic [21] structures, e.g., Sonogashira coupling, Yamaguchi esterification, Wurtz reaction, ring closing metathesis, etc., were employed [22].…”

Section: Introductionmentioning

confidence: 99%

Montmorillonite Catalyzed Synthesis of Novel Steroid Dimers

Tomkiel,

Majewski,

Siergiejczyk

et al. 2023

Molecules

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The reactions of sterols (androst-5-en-3β-ol-17-one, diosgenin, and cholesterol) and their tosylates with hydroquinone aimed at the synthesis of O,O-1,4-phenylene-linked steroid dimers were studied. The reaction course strongly depended on the conditions used. The study has shown that the major reaction products are the elimination products and unusual steroid dimers resulting from the nucleophilic attack of the hydroquinone C2 carbon atom on the steroid C3 position, followed by an intramolecular addition to the C5–C6 double bond. A different reaction course was observed when montmorillonite K10 was used as a catalyst. The reaction of androst-5-en-3β-ol-17-one under the promotion of this catalyst afforded the O,O-1,4-phenylene-linked steroid dimer in addition to the disteroidal ether. The formation of the latter compound was suppressed by using 3-tosylate as a substrate instead of the free sterol. The reactions of androst-5-en-3β-ol-17-one tosylate and cholesteryl tosylate with hydroquinone catalyzed by montmorillonite K10 carried out under optimized conditions afforded the desired dimers in 31% and 67% yield, respectively.

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Section: Introductionmentioning

confidence: 99%

Montmorillonite Catalyzed Synthesis of Novel Steroid Dimers

Tomkiel,

Majewski,

Siergiejczyk

et al. 2023

Molecules

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“…Mostly, the design and the synthesis of artificial receptors (AR´s) capable of recognising specific substrates, have been taken up [8] in order to improve their stability, transport and bioavailability. Bile acid-based compounds, namely cholic and lithocholic acids, are readily available chiral building blocks for designing novel supramolecular hosts for molecular recognition [9][10][11][12][13]. The design and synthesis of entities displaying a tailored molecular recognition profile (AR´s) are accomplished not only by gathering the various required chemical elements, but also by achieving a precise relative spatial disposition of these moieties and a suitable three-dimensional shape of the overall assembly.…”

Section: Introductionmentioning

confidence: 99%

Lithocholic Acid Derivative as a Model for Artificial Receptors: A Raman Study

Roleira¹,

Silva²,

Carvalho³

et al. 2010

LDDD

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Two lithocholic acid (LCA) derivatives-mono-and diesters (newly synthetised)-are studied for their main conformational preferences, by Raman spectroscopy coupled to theoretical (DFT) methods. Raman bands characteristic of each compound were assigned, allowing an accurate and rapid identification of this kind of systems. The conformational preferences of the LCA diester were related with its ability to function as a model for artificial receptors, displaying a tailored structural profile.

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“…After the synthesis in 1977 by McKenna et al of the first bis-steroid containing two cholic acid molecules, other dimers [tail-to-tail (bolaform), head-to-head (gemini), , and head-to-tail , ], oligomers (lineal polymers, , molecular baskets, , molecular umbrellas, , molecular clefts, and dendrimers, , ), and cyclic oligomers − have also been reported. Concerning dimers, most of the published papers refer to their synthesis , or biological effects, − but their aggregation behavior is not generally reported. The only exhaustive study of the aggregation of a bile salt dimer refers to a new gemini surfactant derived from 3α,12α-dihydroxy-5β-cholan-24-amine and ethylenediaminetetraacetic acid (EDTA) .…”

Section: Introductionmentioning

confidence: 99%

Aggregation Behavior of Tetracarboxylic Surfactants Derived from Cholic and Deoxycholic Acids and Ethylenediaminetetraacetic Acid

et al. 2009

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The reaction of 3beta-aminoderivatives of cholic and deoxycholic acids (steroid residues) with dimethyl ester of ethylenediaminetetraacetic acid (bridge) leads to the formation of dimers carrying four carboxylic organic functions, two of them located on the side chain of each steroid residue and the other two on the bridge. As tetrasodium salts, these new compounds behave as surfactants and have been characterized by surface tension, fluorescence intensity of pyrene (as a probe), and static and dynamic light scattering measurements. Thermodynamic parameters for micellization were obtained from the dependence of the critical micelle concentration (cmc) with temperature. For both surfactants, the fraction of bound counterions is close to 0.5. The aggregation behavior is similar to one of their bile salt residues [i.e., sodium cholate (NaC) and sodium deoxycholate (NaDC)] and can be summarized as follows: (i) molecular areas at the interface for the new surfactants are fairly close to twice the value for a single molecule in a monolayer of natural bile salts; (ii) the environment where pyrene is solubilized is very apolar, as in natural bile salt aggregates; (iii) Gibbs free energies (per steroid residue) for micellization are not far from published values for NaC and NaDC, and the differences can be understood on the basis of less hydrophobicity of the new surfactants due to the charges in the bridge; and (iv) as for NaC and NaDC, aggregates have rather low aggregation numbers (which depend on the amount of added inert salt, NaCl). A structure based on the disklike model accepted for small bile salt aggregates is proposed.

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Synthesis and Alkaline Metal Ion Binding Ability of New Steroid Dimers Derived from Cholic and Lithocholic Acids

Cited by 13 publications

References 18 publications

Montmorillonite Catalyzed Synthesis of Novel Steroid Dimers

Montmorillonite Catalyzed Synthesis of Novel Steroid Dimers

Lithocholic Acid Derivative as a Model for Artificial Receptors: A Raman Study

Aggregation Behavior of Tetracarboxylic Surfactants Derived from Cholic and Deoxycholic Acids and Ethylenediaminetetraacetic Acid

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