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On the self-assembly of a tryptophan labeled deoxycholic acid

Travaglini, Leana; Gubitosi, Marta; Chiara di Gregorio, Maria; Pavel, Nicolae Viorel; D'Annibale, Andrea; Giustini, Mauro; Tellini, Victor Hugo Soto; Vázquez Tato, José; Obiols-Rabasa, Marc LU and Bayati, Solmaz LU , et al. (2014) In Physical Chemistry Chemical Physics 16(36). p.19492-19504
Abstract
Self-assembly of peptides and bile acids has been widely investigated because of their biological role and their potential as a tool for the preparation of nanostructured biomaterials. We herein report both the synthesis and the self-association behavior of a compound that combines the aggregation properties of bile acid- and amino acid-based molecules. The derivative has been prepared by introducing a L-tryptophan residue into the C-3 position of the deoxycholic acid skeleton and resulted in an amphoteric fluorescent labeled bile acid that shows a pH-dependent self-assembly. Under alkaline conditions it assembles into 28 nm diameter tubules, thus showing a completely different behavior compared to the precursor bile acid, which forms... (More)
Self-assembly of peptides and bile acids has been widely investigated because of their biological role and their potential as a tool for the preparation of nanostructured biomaterials. We herein report both the synthesis and the self-association behavior of a compound that combines the aggregation properties of bile acid- and amino acid-based molecules. The derivative has been prepared by introducing a L-tryptophan residue into the C-3 position of the deoxycholic acid skeleton and resulted in an amphoteric fluorescent labeled bile acid that shows a pH-dependent self-assembly. Under alkaline conditions it assembles into 28 nm diameter tubules, thus showing a completely different behavior compared to the precursor bile acid, which forms micelles under similar conditions. Upon heating the tubules break and turn into micelles, leading to an increase in the exposure to water of the tryptophan residue. On the other hand, in acidic solutions it aggregates into elongated micelles that further self-assemble forming a gel network, when an electrolyte is added. (Less)
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Physical Chemistry Chemical Physics
volume
16
issue
36
pages
19492 - 19504
publisher
Royal Society of Chemistry
external identifiers
  • wos:000341299500050
  • scopus:84906569199
ISSN
1463-9084
DOI
10.1039/C4CP02371D
language
English
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yes
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c6f9582e-a12e-463e-a2e3-88732aa6c502 (old id 4611335)
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http://pubs.rsc.org/en/content/articlehtml/2014/cp/c4cp02371d
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2014-09-22 12:32:26
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2017-10-08 04:02:40
@article{c6f9582e-a12e-463e-a2e3-88732aa6c502,
  abstract     = {Self-assembly of peptides and bile acids has been widely investigated because of their biological role and their potential as a tool for the preparation of nanostructured biomaterials. We herein report both the synthesis and the self-association behavior of a compound that combines the aggregation properties of bile acid- and amino acid-based molecules. The derivative has been prepared by introducing a L-tryptophan residue into the C-3 position of the deoxycholic acid skeleton and resulted in an amphoteric fluorescent labeled bile acid that shows a pH-dependent self-assembly. Under alkaline conditions it assembles into 28 nm diameter tubules, thus showing a completely different behavior compared to the precursor bile acid, which forms micelles under similar conditions. Upon heating the tubules break and turn into micelles, leading to an increase in the exposure to water of the tryptophan residue. On the other hand, in acidic solutions it aggregates into elongated micelles that further self-assemble forming a gel network, when an electrolyte is added.},
  author       = {Travaglini, Leana and Gubitosi, Marta and Chiara di Gregorio, Maria and Pavel, Nicolae Viorel and D'Annibale, Andrea and Giustini, Mauro and Tellini, Victor Hugo Soto and Vázquez Tato, José and Obiols-Rabasa, Marc and Bayati, Solmaz and Galantini, Luciano},
  issn         = {1463-9084},
  language     = {eng},
  number       = {36},
  pages        = {19492--19504},
  publisher    = {Royal Society of Chemistry},
  series       = {Physical Chemistry Chemical Physics},
  title        = {On the self-assembly of a tryptophan labeled deoxycholic acid},
  url          = {http://dx.doi.org/10.1039/C4CP02371D},
  volume       = {16},
  year         = {2014},
}