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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 LU and Galantini, Luciano (2020) In Colloids and Surfaces B: Biointerfaces 185.
Abstract

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... (More)

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.

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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Bile acid, Hydrogel, Steroid derivatives, Thermoresponsive self-assembly
in
Colloids and Surfaces B: Biointerfaces
volume
185
article number
110556
publisher
Elsevier
external identifiers
  • scopus:85074417041
ISSN
0927-7765
DOI
10.1016/j.colsurfb.2019.110556
language
English
LU publication?
yes
id
8e876198-93d8-46ff-8e67-70e085287ac7
date added to LUP
2019-11-15 13:29:26
date last changed
2020-01-13 02:31:39
@article{8e876198-93d8-46ff-8e67-70e085287ac7,
  abstract     = {<p>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.</p>},
  author       = {Cautela, Jacopo and Severoni, Emilia and Redondo-Gómez, Carlos and di Gregorio, Maria Chiara and Del Giudice, Alessandra and Sennato, Simona and Angelini, Roberta and D'Abramo, Marco and Schillén, Karin and Galantini, Luciano},
  issn         = {0927-7765},
  language     = {eng},
  publisher    = {Elsevier},
  series       = {Colloids and Surfaces B: Biointerfaces},
  title        = {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},
  url          = {http://dx.doi.org/10.1016/j.colsurfb.2019.110556},
  doi          = {10.1016/j.colsurfb.2019.110556},
  volume       = {185},
  year         = {2020},
}