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Between Peptides and Bile Acids: Self-Assembly of Phenylalanine Substituted Cholic Acids

Travaglini, Leana ; D'Annibale, Andrea ; di Gregorio, Maria Chiara ; Schillén, Karin LU orcid ; Olsson, Ulf LU ; Sennato, Simona ; Pavel, Nicolae V. and Galantini, Luciano (2013) In The Journal of Physical Chemistry Part B 117(31). p.9248-9257
Abstract
Biocompatible molecules that undergo self-assembly are of high importance in biological and medical applications of nanoscience. Peptides and bile acids are among the most investigated due to their ability to self-organize into many different, often stimuli-sensitive, supramolecular structures. With the aim of preparing molecules mixing the aggregation properties of bile acid and amino acid-based molecules, we report on the synthesis and self-association behavior of two diastereomers obtained by substituting a hydroxyl group of cholic acid with a L-phenylalanine residue. The obtained molecules are amphoteric, and we demonstrate that they show a pH-dependent self-assembly. Both molecules aggregate in globular micelles at high pH, whereas... (More)
Biocompatible molecules that undergo self-assembly are of high importance in biological and medical applications of nanoscience. Peptides and bile acids are among the most investigated due to their ability to self-organize into many different, often stimuli-sensitive, supramolecular structures. With the aim of preparing molecules mixing the aggregation properties of bile acid and amino acid-based molecules, we report on the synthesis and self-association behavior of two diastereomers obtained by substituting a hydroxyl group of cholic acid with a L-phenylalanine residue. The obtained molecules are amphoteric, and we demonstrate that they show a pH-dependent self-assembly. Both molecules aggregate in globular micelles at high pH, whereas they form tubular superstructures under acid conditions. Unusual narrow nanotubes with outer and inner cross-section diameters of about 6 and 3 um are formed by the derivatives. The diasteroisomer with alpha orientation of the substituent forms in addition a wider tubule (17 nm cross-section diameter). The ability to pack in supramolecular tubules is explained in terms of a wedge-shaped bola-form structure of the derivatives. Parallel or antiparallel face-to-face dimers are hypothesized as fundamental building blocks for the formation of the narrow and wide nanotubes, respectively. (Less)
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author
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
The Journal of Physical Chemistry Part B
volume
117
issue
31
pages
9248 - 9257
publisher
The American Chemical Society (ACS)
external identifiers
  • wos:000323082200013
  • scopus:84881434851
  • pmid:23844889
ISSN
1520-5207
DOI
10.1021/jp405342v
language
English
LU publication?
yes
id
abe60f39-572c-4f59-8424-f750b85c55b7 (old id 4062473)
date added to LUP
2016-04-01 13:07:46
date last changed
2022-03-29 05:45:17
@article{abe60f39-572c-4f59-8424-f750b85c55b7,
  abstract     = {{Biocompatible molecules that undergo self-assembly are of high importance in biological and medical applications of nanoscience. Peptides and bile acids are among the most investigated due to their ability to self-organize into many different, often stimuli-sensitive, supramolecular structures. With the aim of preparing molecules mixing the aggregation properties of bile acid and amino acid-based molecules, we report on the synthesis and self-association behavior of two diastereomers obtained by substituting a hydroxyl group of cholic acid with a L-phenylalanine residue. The obtained molecules are amphoteric, and we demonstrate that they show a pH-dependent self-assembly. Both molecules aggregate in globular micelles at high pH, whereas they form tubular superstructures under acid conditions. Unusual narrow nanotubes with outer and inner cross-section diameters of about 6 and 3 um are formed by the derivatives. The diasteroisomer with alpha orientation of the substituent forms in addition a wider tubule (17 nm cross-section diameter). The ability to pack in supramolecular tubules is explained in terms of a wedge-shaped bola-form structure of the derivatives. Parallel or antiparallel face-to-face dimers are hypothesized as fundamental building blocks for the formation of the narrow and wide nanotubes, respectively.}},
  author       = {{Travaglini, Leana and D'Annibale, Andrea and di Gregorio, Maria Chiara and Schillén, Karin and Olsson, Ulf and Sennato, Simona and Pavel, Nicolae V. and Galantini, Luciano}},
  issn         = {{1520-5207}},
  language     = {{eng}},
  number       = {{31}},
  pages        = {{9248--9257}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{The Journal of Physical Chemistry Part B}},
  title        = {{Between Peptides and Bile Acids: Self-Assembly of Phenylalanine Substituted Cholic Acids}},
  url          = {{http://dx.doi.org/10.1021/jp405342v}},
  doi          = {{10.1021/jp405342v}},
  volume       = {{117}},
  year         = {{2013}},
}