Between Peptides and Bile Acids: Self-Assembly of Phenylalanine Substituted Cholic Acids
(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)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/4062473
- author
- Travaglini, Leana ; D'Annibale, Andrea ; di Gregorio, Maria Chiara ; Schillén, Karin LU ; Olsson, Ulf LU ; Sennato, Simona ; Pavel, Nicolae V. and Galantini, Luciano
- organization
- publishing date
- 2013
- 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}}, }