C-12 vs C-3 substituted bile salts: An example of the effects of substituent position and orientation on the self-assembly of steroid surfactant isomers

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C-12 vs C-3 substituted bile salts : An example of the effects of substituent position and orientation on the self-assembly of steroid surfactant isomers. / Cautela, Jacopo; Severoni, Emilia; Redondo-Gómez, Carlos; di Gregorio, Maria Chiara; Del Giudice, Alessandra; Sennato, Simona; Angelini, Roberta; D'Abramo, Marco; Schillén, Karin; Galantini, Luciano.

In: Colloids and Surfaces B: Biointerfaces, Vol. 185, 110556, 2020.

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Cautela, Jacopo ; Severoni, Emilia ; Redondo-Gómez, Carlos ; di Gregorio, Maria Chiara ; Del Giudice, Alessandra ; Sennato, Simona ; Angelini, Roberta ; D'Abramo, Marco ; Schillén, Karin ; Galantini, Luciano. / C-12 vs C-3 substituted bile salts : An example of the effects of substituent position and orientation on the self-assembly of steroid surfactant isomers. In: Colloids and Surfaces B: Biointerfaces. 2020 ; Vol. 185.

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TY - JOUR

T1 - C-12 vs C-3 substituted bile salts

T2 - An example of the effects of substituent position and orientation on the self-assembly of steroid surfactant isomers

AU - Cautela, Jacopo

AU - Severoni, Emilia

AU - Redondo-Gómez, Carlos

AU - di Gregorio, Maria Chiara

AU - Del Giudice, Alessandra

AU - Sennato, Simona

AU - Angelini, Roberta

AU - D'Abramo, Marco

AU - Schillén, Karin

AU - Galantini, Luciano

PY - 2020

Y1 - 2020

N2 - Biomolecule derivatives are transversally used in nanotechnology. Deciphering their aggregation behavior is a crucial issue for the rational design of functional materials. To this end, it is necessary to build libraries of selectively functionalized analogues and infer general rules. In this work we enrich the highly applicative oriented collection of steroid derivatives, by reporting a rare example of C-12 selectively modified bile salt. While nature often exploits such position to encode functions, it is unusual and not trivial to prepare similar analogues in the laboratory. The introduction of a tert-butyl phenyl residue at C-12 provided a molecule with a self-assembly that remarkably switched from rigid pole-like structures to twisted ribbons at a biologically relevant critical temperature (∼25 °C). The system was characterized by microscopy and spectroscopy techniques and compared with the C-3 functionalized analogue. The twisted ribbons generate samples with a gel texture and a viscoelastic response. The parallel analysis of the two systems suggested that the observed thermoresponsive self-assemblies occur at similar critical temperatures and are probably dictated by the nature of the substituent, but involve aggregates with different structures depending on position and orientation of the substituent. This study highlights the self-assembly properties of two appealing thermoresponsive systems. Moreover, it adds fundamental insights hereto missing in the investigations of the relation between self-assembly and structure of synthetic steroids, which are valuable for the rational design of steroidal amphiphiles.

AB - Biomolecule derivatives are transversally used in nanotechnology. Deciphering their aggregation behavior is a crucial issue for the rational design of functional materials. To this end, it is necessary to build libraries of selectively functionalized analogues and infer general rules. In this work we enrich the highly applicative oriented collection of steroid derivatives, by reporting a rare example of C-12 selectively modified bile salt. While nature often exploits such position to encode functions, it is unusual and not trivial to prepare similar analogues in the laboratory. The introduction of a tert-butyl phenyl residue at C-12 provided a molecule with a self-assembly that remarkably switched from rigid pole-like structures to twisted ribbons at a biologically relevant critical temperature (∼25 °C). The system was characterized by microscopy and spectroscopy techniques and compared with the C-3 functionalized analogue. The twisted ribbons generate samples with a gel texture and a viscoelastic response. The parallel analysis of the two systems suggested that the observed thermoresponsive self-assemblies occur at similar critical temperatures and are probably dictated by the nature of the substituent, but involve aggregates with different structures depending on position and orientation of the substituent. This study highlights the self-assembly properties of two appealing thermoresponsive systems. Moreover, it adds fundamental insights hereto missing in the investigations of the relation between self-assembly and structure of synthetic steroids, which are valuable for the rational design of steroidal amphiphiles.

KW - Bile acid

KW - Hydrogel

KW - Steroid derivatives

KW - Thermoresponsive self-assembly

U2 - 10.1016/j.colsurfb.2019.110556

DO - 10.1016/j.colsurfb.2019.110556

M3 - Article

VL - 185

JO - Colloids and Surfaces. B, Biointerfaces

JF - Colloids and Surfaces. B, Biointerfaces

SN - 1873-4367

M1 - 110556

ER -