A tryptophan-substituted cholic acid: Expanding the family of labelled biomolecules

Travaglini, Leana; Gubitosi, Marta; Gregorio, Maria Chiara di; D’Annibale, Andrea; Meijide, Francisco; Giustini, Mauro; Sennato, Simona; Obiols‐Rabasa, Marc; Schillén, Karin; Pavel, Nicolae Viorel; Galantini, Luciano

doi:10.1016/j.colsurfa.2015.03.033

Cited by 10 publications

(5 citation statements)

References 65 publications

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“…Again, the substitution in C-3 was considered in light of the remarkable effect it has on the self-assembly of the BSDs. In particular, we reported on C derivatives bearing phenylalanine in α ( 6 ) and β ( 7 ) orientations on C , and tryptophan on both DC ( 8 ) and C acids ( 9 ) with the β configuration. These amphoteric compounds were investigated in both acidic and alkaline aqueous solutions.…”

Section: Functionalized Bs Derivativesmentioning

confidence: 99%

Bile Salts: Natural Surfactants and Precursors of a Broad Family of Complex Amphiphiles

et al. 2018

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Bile salts (BSs) are naturally occurring rigid surfactants with a steroidal skeleton and specific self-assembly and interface behaviors. Using bile salts as precursors, derivatives can be synthesized to obtain molecules with specific functionalities and amphiphilic structure. Modifications on single molecules are normally performed by substituting the least-hindered hydroxyl group on carbon C-3 of the steroidal A ring or at the end of the lateral chain. This leads to monosteroidal rigid building blocks that are often able to self-organize into 1D structures such as tubules, twisted ribbons, and fibrils with helical supramolecular packing. Tubular aggregates are of particular interest, and they are characterized by cross-section inner diameters spanning a wide range of values (3−500 nm). They can form through appealing pH-or temperature-responsive aggregation and in mixtures of bile salt derivatives to provide mixed tubules with tunable charge and size. Other derivatives can be prepared by covalently linking two or more bile salt molecules to provide complex systems such as oligomers, dendrimers, and polymeric materials. The unconventional amphiphilic molecular structure imparts specific features to BSs and derivatives that can be exploited in the formulation of capsules, drug carriers, dispersants, and templates for the synthesis of nanomaterials.

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Section: Functionalized Bs Derivativesmentioning

confidence: 99%

Bile Salts: Natural Surfactants and Precursors of a Broad Family of Complex Amphiphiles

et al. 2018

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“…Due to the steroid rigidity and the peculiar distribution of hydrophobic and hydrophilic domains, these molecules are particularly attractive for the bottom up construction of complex nanostructures. They often self-assemble in tubes or fibers and behave as low molecular weight gelators [15][16][17][18][19][20][21][22][23][24][25][26]. The tubes have cross section diameters spanning a wide range of values (3-450 nm) [9,19,[27][28][29][30][31][32][33][34] and sometimes they form through appealing pH [35,36] or temperature responsive aggregations [37].…”

Section: Introductionmentioning

confidence: 99%

Wormlike reverse micelles in lecithin/bile salt/water mixtures in oil

Cautela

Giustini

Pavel

et al. 2017

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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Knowing the ability of water and bile salts to promote the reverse wormlike micelle growth in lecithin/water or lecithin/bile salt mixtures in oil, this work was aimed at elucidating the association properties of the three\ud solutes lecithin, water and the bile salt (BS) sodium deoxycholate in cyclohexane. By systematically changing the fraction of the two additives (i.e.: water and BS) we could identify a region at low additive/lecithin molar ratios\ud where stable wormlike micelle dispersions were formed. Small angle X-ray scattering and oscillatory rheology measurements demonstrated that the ability of bile salt and water to transform the originally spherical lecithin\ud reverse micelles into wormlike micelles and thereby impart to the sample viscoelastic properties is preserved in the three-solute mixture. The results suggest that reverse micelle including both bile salt and water are formed in\ud this system. Reasonably the two primers interact with the same region of the lecithin headgroups and are complementary in altering the packing parameter of the amphiphile to values suitable for the formation of\ud cylindrical aggregate

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“…Typically, fibers or ribbons are formed together with more complex tubular nano- and micro-aggregates with diameters ranging from a few nanometers to half a micron. Tubules are reported to form in aqueous systems of C-3 substituted BA with various residues such as aromatic organic groups [ 6 , 182 , 183 , 184 , 185 , 186 , 187 , 188 ] or amino acids [ 189 , 190 , 191 , 192 ], and sugars [ 193 , 194 ], often via stimuli-responsive self-assembly, triggered by pH [ 182 , 183 ] or temperature [ 184 , 195 ]. Interesting systems of tubules with tunable charge or diameter have been implemented by mixtures of cationic and anionic derivatives [ 196 , 197 ] or precursor and derivative [ 198 ].…”

Section: Self-assembly Of Natural and Chemically Modified Basmentioning

confidence: 99%

“…Keeping the same substituent, the ability to form tubules was reported to be lost for aminoacid substituted derivatives obtained from more hydrophilic BA precursors [ 191 , 192 ], whereas for organic aromatic substituent, tubules with remarkably different sizes were observed to form by BA differing for number, positions and orientations of the hydroxyl groups [ 184 , 185 , 186 , 195 ]. Spectroscopies, such as circular dichroism, show that the substituents are strongly involved in intermolecular interactions in the aggregates thereby demonstrating their relevance in the self-assembly of the derivatives.…”

Section: Self-assembly Of Natural and Chemically Modified Basmentioning

confidence: 99%

Physiology and Physical Chemistry of Bile Acids

Gregorio

Cautela

Galantini

2021

IJMS

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Bile acids (BAs) are facial amphiphiles synthesized in the body of all vertebrates. They undergo the enterohepatic circulation: they are produced in the liver, stored in the gallbladder, released in the intestine, taken into the bloodstream and lastly re-absorbed in the liver. During this pathway, BAs are modified in their molecular structure by the action of enzymes and bacteria. Such transformations allow them to acquire the chemical–physical properties needed for fulling several activities including metabolic regulation, antimicrobial functions and solubilization of lipids in digestion. The versatility of BAs in the physiological functions has inspired their use in many bio-applications, making them important tools for active molecule delivery, metabolic disease treatments and emulsification processes in food and drug industries. Moreover, moving over the borders of the biological field, BAs have been largely investigated as building blocks for the construction of supramolecular aggregates having peculiar structural, mechanical, chemical and optical properties. The review starts with a biological analysis of the BAs functions before progressively switching to a general overview of BAs in pharmacology and medicine applications. Lastly the focus moves to the BAs use in material science.

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A tryptophan-substituted cholic acid: Expanding the family of labelled biomolecules

Cited by 10 publications

References 65 publications

Bile Salts: Natural Surfactants and Precursors of a Broad Family of Complex Amphiphiles

Bile Salts: Natural Surfactants and Precursors of a Broad Family of Complex Amphiphiles

Wormlike reverse micelles in lecithin/bile salt/water mixtures in oil

Physiology and Physical Chemistry of Bile Acids

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