A tryptophan-substituted cholic acid : expanding the family of labelled biomolecules
(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)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/5276499
- author
- organization
- publishing date
- 2015
- type
- Contribution to journal
- publication status
- published
- subject
- 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
- 2016-04-01 10:10:35
- date last changed
- 2022-02-02 07:07:46
@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}}, doi = {{10.1016/j.colsurfa.2015.03.033}}, volume = {{483}}, year = {{2015}}, }