Multi stimuli response of a single surfactant presenting a rich self-assembly behavior

Gregorio, Maria Chiara di; Varenik, Maxim; Gubitosi, Marta; Travaglini, Leana; Pavel, Nicolae Viorel; Jover, Aida; Meijide, Francisco; Regev, Oren; Galantini, Luciano

doi:10.1039/c5ra01394a

Cited by 29 publications

(26 citation statements)

References 64 publications

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“…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]. Mixed tubes with tunable composition and related features such as charge [38] and sizes [39] can sometimes be prepared.…”

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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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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“…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%

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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“…Molecules that arrange into tubules are often observed. In some cases, tubules can present stimuli-responsive features as well as tunable size or charge [35][36][37][38][39][40][41][42]. A plentitude of low molecular weight gelators formed by BA derivatives have been also investigated [30,[43][44][45][46].…”

Section: U N C O R R E C T E D P R O O Fmentioning

confidence: 99%

Twisted nanoribbons from a RGD-bearing cholic acid derivative

Travaglini

Giordano

D’Annibale

et al. 2017

Colloids and Surfaces B: Biointerfaces

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In light of the biomedical interest for self-assembling amphiphiles bearing the tripeptide Arg-Gly-Gly (RGD), a cholic acid derivative was synthesized by introducing an aromatic moiety on the steroidal skeleton and the RGD sequence on the carboxylic function of its chain 17-24, thus forming a peptide amphiphile with the unconventional rigid amphiphilic structure of bile salts. In aqueous solution, the compound self-assembled into long twisted ribbons characterized by a very low degree of polydispersity in terms of width (≈25nm), thickness (≈4.5nm) and pitch (≈145nm). It was proposed that in the ribbon the molecules are arranged in a bilayer structure with the aromatic moieties in the interior, strongly involved in the intermolecular interaction, whereas the RGD residues are located at the bilayer-water interface. The nanostructure is significantly different from those generally provided by RGD-containing amphiphiles with the conventional peptide-tail structure, for which fibers with a circular cross-section were observed, and successfully tested as scaffolds for tissue regeneration. From previous work on the use of this kind of nanostructures, it is known that features like morphology, rigidity, epitope spacing and periodicity are important factors that dramatically affect cell adhesion and signaling. Within this context, the reported results demonstrate that bile salt-based peptide surfactants are promising building blocks in the preparation of non-trivial RGD-decorated nanoaggregates with well-defined morphologies and epitope distributions.

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Multi stimuli response of a single surfactant presenting a rich self-assembly behavior

Cited by 29 publications

References 64 publications

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

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

Physiology and Physical Chemistry of Bile Acids

Twisted nanoribbons from a RGD-bearing cholic acid derivative

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