Bile acid alkylamide derivatives as low molecular weight organogelators: Systematic gelation studies and qualitative structural analysis of the systems

Löfman, Miika; Koivukorpi, Juha; Noponen, Virpi; Salo, Hannu; Sievänen, Elina

doi:10.1016/j.jcis.2011.04.112

Cited by 55 publications

(49 citation statements)

References 91 publications

(175 reference statements)

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“…The translucent, gelating material which formed first was penetrated by spherulitic microfibers after 10 minutes of cooling at room temperature. The other systems conformed to the established gelation tendencies [32,37].…”

Section: Interface-controlled Fiber Growth In Three Dimensionssupporting

confidence: 65%

“…This secondary nucleation [40] is a common occurrence in crystalline gelator systems [18,30]. At the end of the fiber network formation, the end result was morphologically the same as seen before [32,37]. Some aggregate and fibrils formed on solvent evaporation, in addition to the common fiber formation process.…”

Section: Gelator 1 In Chlorobenzenementioning

confidence: 93%

“…The gelators N-(2-aminoethyl)-3α-hydroxy-5β-cholan-24-amide [32][33][34][35][36][37] 1 and N-(4-aminobutyl)-3α-hydroxy-5β-cholan-24-amide [32] 2 were synthesized, purified, and characterized as described previously. The used solvents included chlorobenzene (Acros Organics, 99+%), bromobenzene (Acros Organics, 99%), iodobenzene (Fluka, > 99% puriss.…”

Section: Methodsmentioning

confidence: 99%

“…There are earlier observations of similar residual colloidal aggregate [32,37], which could not be characterized spectroscopically [37]. A c c e p t e d M a n u s c r i p t 9…”

Section: Page 10 Of 32mentioning

confidence: 97%

See 3 more Smart Citations

Insights into localized manipulation of organogel-related microcrystalline spherulite formation

Löfman

Lahtinen

Pettersson

et al. 2015

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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Section: Interface-controlled Fiber Growth In Three Dimensionssupporting

confidence: 65%

Section: Gelator 1 In Chlorobenzenementioning

confidence: 93%

Section: Methodsmentioning

confidence: 99%

“…There are earlier observations of similar residual colloidal aggregate [32,37], which could not be characterized spectroscopically [37]. A c c e p t e d M a n u s c r i p t 9…”

Section: Page 10 Of 32mentioning

confidence: 97%

See 2 more Smart Citations

Insights into localized manipulation of organogel-related microcrystalline spherulite formation

Löfman

Lahtinen

Pettersson

et al. 2015

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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“…7 Another structural feature distinguishing BSs from conventional amphiphiles is their application as low-molecular-weight gelators. 18,51 Aggregates formed at low concentration were attributed to hydrophobic interaction between steroidal domains, whereas aggregates formed by further increase in concentration were reported to exhibit hydrogen bonding between hydroxyl and carboxyl groups of various dimeric BS units. 52 BSs exhibit intriguing phase behavior in mixtures with other amphiphiles, as mainly exemplified in BS-PL mixtures commonly utilized in solubilizing hydrophobic actives.…”

Section: Peculiar Structure and Self-assembled Topologiesmentioning

confidence: 99%

Multifaceted applications of bile salts in pharmacy: an emphasis on nanomedicine

Elnaggar¹

2015

IJN

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The human body has long provided pharmaceutical science with biomaterials of interesting applications. Bile salts (BSs) are biomaterials reminiscent of traditional surfactants with peculiar structure and self-assembled topologies. In the pharmaceutical field, BSs were employed on the basis of two different concepts. The first concept exploited BSs’ metabolic and homeostatic functions in disease modulation, whereas the second one utilized BSs’ potential to modify drug-delivery characteristics, which recently involved nanotechnology. This review is the first to gather major pharmaceutical applications of BSs from endogenous organotropism up to integration into nanomedicine, with a greater focus on the latter domain. Endogenous applications highlighted the role of BS in modulating hypercholesterolemia and cancer therapy in view of enterohepatic circulation. In addition, recent BS-integrated nanomedicines have been surveyed, chiefly size-tunable cholate nanoparticles, BS-lecithin mixed micelles, bilosomes, probilosomes, and surface-engineered bilosomes. A greater emphasis has been laid on nanosystems for vaccine and cancer therapy. The comparative advantages of BS-integrated nanomedicines over conventional nanocarriers have been noted. Paradoxical effects, current pitfalls, future perspectives, and opinions have also been outlined.

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Systematic Modulation of the Supramolecular Gelation Properties of Bile Acid Alkyl Amides

Kuosmanen

Puttreddy

Sievänen

2018

Chemistry A European J

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The self‐assembly properties of nine low‐molecular‐weight gelators (LMWGs) based on bile acid alkyl amides were studied in detail. Based on the results, the number of hydroxyl groups attached to the steroidal backbone plays a major role in the gelation, although the nature of the aliphatic side chain also modulates the gelation abilities. Of the 50 gel systems studied, 35 are based on lithocholic acid and 15 on cholic acid derivatives. The deoxycholic acid derivatives did not form any gels. The gelation occurred primarily in aromatic solvents and the gels manifested typical fibrous or spherical morphologies. The 13C cross‐polarized magic angle spinning (CPMAS) NMR spectra measured on the crystalline materials and the corresponding wet organogels were analogous, suggesting that the chemical environments, that is, the intermolecular interactions found in the two materials were similar. The single‐crystal X‐ray structures of all nine bile‐acid amide derivatives studied revealed very similar molecular conformations in the solid state and gave insights into the possible intermolecular interactions in the gel state.

show abstract

Bile acid alkylamide derivatives as low molecular weight organogelators: Systematic gelation studies and qualitative structural analysis of the systems

Cited by 55 publications

References 91 publications

Insights into localized manipulation of organogel-related microcrystalline spherulite formation

Insights into localized manipulation of organogel-related microcrystalline spherulite formation

Multifaceted applications of bile salts in pharmacy: an emphasis on nanomedicine

Systematic Modulation of the Supramolecular Gelation Properties of Bile Acid Alkyl Amides

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