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

Travaglini, Leana; Gubitosi, Marta; di Gregorio, Maria Chiara; D'Annibale, Andrea; Meijide, Francisco; Giustini, Mauro; Sennato, Simona; Obiols-Rabasa, Marc LU ; Schillén, Karin LU and Pavel, Nicolae Viorel, et al. (2015) In Colloids and Surfaces A: Physicochemical and Engineering Aspects 483(Online 31 March 2015). p.142-149
Abstract
The synthesis of a novel cholic acid derivative bearing in the C-3 position a residue of tryptophan linked through an amide bond is herein described. Acidic or basic conditions are needed for the solubilization of the derivative in water. In alkaline solutions the molecule shows a self-association similar to the one of its natural precursor leading to the formation of ellipsoidal micelles which does not involve significant Trp–Trp interactions. On the contrary, in acidic conditions strong interactions between the tryptophan moieties occur, leading to the formation of a gel at low temperature. These interactions are broken upon heating and small micelles similar to those observed at high pH are formed. In both cases, fluorescence spectra... (More)
The synthesis of a novel cholic acid derivative bearing in the C-3 position a residue of tryptophan linked through an amide bond is herein described. Acidic or basic conditions are needed for the solubilization of the derivative in water. In alkaline solutions the molecule shows a self-association similar to the one of its natural precursor leading to the formation of ellipsoidal micelles which does not involve significant Trp–Trp interactions. On the contrary, in acidic conditions strong interactions between the tryptophan moieties occur, leading to the formation of a gel at low temperature. These interactions are broken upon heating and small micelles similar to those observed at high pH are formed. In both cases, fluorescence spectra suggest a polar environment for the amino acid fluorophore not remarkably affected by the self-assembly. (Less)
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publication status
published
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in
Colloids and Surfaces A: Physicochemical and Engineering Aspects
volume
483
issue
Online 31 March 2015
pages
142 - 149
publisher
Elsevier
external identifiers
  • wos:000362146200019
  • scopus:84941743096
ISSN
0927-7757
DOI
10.1016/j.colsurfa.2015.03.033
language
English
LU publication?
yes
id
7aa7c3c1-ab33-4b81-a6dc-6de6eb350e1b (old id 5276499)
date added to LUP
2015-06-23 17:47:20
date last changed
2017-10-01 03:09:21
@article{7aa7c3c1-ab33-4b81-a6dc-6de6eb350e1b,
  abstract     = {The synthesis of a novel cholic acid derivative bearing in the C-3 position a residue of tryptophan linked through an amide bond is herein described. Acidic or basic conditions are needed for the solubilization of the derivative in water. In alkaline solutions the molecule shows a self-association similar to the one of its natural precursor leading to the formation of ellipsoidal micelles which does not involve significant Trp–Trp interactions. On the contrary, in acidic conditions strong interactions between the tryptophan moieties occur, leading to the formation of a gel at low temperature. These interactions are broken upon heating and small micelles similar to those observed at high pH are formed. In both cases, fluorescence spectra suggest a polar environment for the amino acid fluorophore not remarkably affected by the self-assembly.},
  author       = {Travaglini, Leana and Gubitosi, Marta and di Gregorio, Maria Chiara and D'Annibale, Andrea and Meijide, Francisco and Giustini, Mauro and Sennato, Simona and Obiols-Rabasa, Marc and Schillén, Karin and Pavel, Nicolae Viorel and Galantini, Luciano},
  issn         = {0927-7757},
  language     = {eng},
  number       = {Online 31 March 2015},
  pages        = {142--149},
  publisher    = {Elsevier},
  series       = {Colloids and Surfaces A: Physicochemical and Engineering Aspects},
  title        = {A tryptophan-substituted cholic acid : expanding the family of labelled biomolecules},
  url          = {http://dx.doi.org/10.1016/j.colsurfa.2015.03.033},
  volume       = {483},
  year         = {2015},
}