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Title: Supramolecular Assembly of Peptide Amphiphiles

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [3]
  1. Simpson Querrey Institute for BioNanotechnology, Northwestern University, Chicago, Illinois 60611, United States
  2. Simpson Querrey Institute for BioNanotechnology, Northwestern University, Chicago, Illinois 60611, United States, Department of Chemistry, Northwestern University, Evanston, Illinois 60208, United States
  3. Simpson Querrey Institute for BioNanotechnology, Northwestern University, Chicago, Illinois 60611, United States, Department of Chemistry, Northwestern University, Evanston, Illinois 60208, United States, Department of Materials Science and Engineering, Northwestern University, Evanston, Illinois 60208, United States, Department of Medicine, Northwestern University, Chicago, Illinois 60611, United States, Department of Biomedical Engineering, Northwestern University, Evanston, Illinois 60208, United States
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1380069
Grant/Contract Number:
FG02-00ER45810; SC0000989
Resource Type:
Journal Article: Published Article
Journal Name:
Accounts of Chemical Research
Additional Journal Information:
Journal Volume: 50; Journal Issue: 10; Related Information: CHORUS Timestamp: 2017-10-17 04:05:22; Journal ID: ISSN 0001-4842
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English

Citation Formats

Hendricks, Mark P., Sato, Kohei, Palmer, Liam C., and Stupp, Samuel I.. Supramolecular Assembly of Peptide Amphiphiles. United States: N. p., 2017. Web. doi:10.1021/acs.accounts.7b00297.
Hendricks, Mark P., Sato, Kohei, Palmer, Liam C., & Stupp, Samuel I.. Supramolecular Assembly of Peptide Amphiphiles. United States. doi:10.1021/acs.accounts.7b00297.
Hendricks, Mark P., Sato, Kohei, Palmer, Liam C., and Stupp, Samuel I.. 2017. "Supramolecular Assembly of Peptide Amphiphiles". United States. doi:10.1021/acs.accounts.7b00297.
@article{osti_1380069,
title = {Supramolecular Assembly of Peptide Amphiphiles},
author = {Hendricks, Mark P. and Sato, Kohei and Palmer, Liam C. and Stupp, Samuel I.},
abstractNote = {},
doi = {10.1021/acs.accounts.7b00297},
journal = {Accounts of Chemical Research},
number = 10,
volume = 50,
place = {United States},
year = 2017,
month = 9
}

Journal Article:
Free Publicly Available Full Text
This content will become publicly available on September 6, 2018
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  • Co-assembly of binary systems driven by specific non-covalent interactions can greatly expand the structural and functional space of supramolecular nanostructures. We report here on the self-assembly of peptide amphiphiles and fatty acids driven primarily by anion-π interactions. The peptide sequences investigated were functionalized with a perfluorinated phenylalanine residue to promote anion-π interactions with carboxylate headgroups in fatty acids. These interactions were verified here by NMR and circular dichroism experiments as well as investigated using atomistic simulations. Positioning the aromatic units close to the N-terminus of the peptide backbone near the hydrophobic core of cylindrical nanofibers leads to strong anion-π interactionsmore » between both components. With a low content of dodecanoic acid in this position, the cylindrical morphology is preserved. However, as the aromatic units are moved along the peptide backbone away from the hydrophobic core, the interactions with dodecanoic acid transform the cylindrical supramolecular morphology into ribbon-like structures. Increasing the ratio of dodecanoic acid to PA leads to either the formation of large vesicles in the binary systems where the anion-π interactions are strong, or a heterogeneous mixture of assemblies when the peptide amphiphiles associate weakly with dodecanoic acid. Our findings reveal how co-assembly involving designed specific interactions can drastically change supramolecular morphology and even cross from nano to micro scales.« less
  • This feature article presents an overview of a study of several different aromatic-functionalized amphiphiles-fatty acid and phospholipid derivatives. These amphiphiles form organized assemblies when the fatty acids are spread as monolayers at the air-water interface or when the phospholipids are dispersed in aqueous solutions. For a wide range of aromatic chromophores--trans-stilbene derivatives and a series of vinylogues (1,4-diphenyl-1,3-butadiene and 1,6-diphenyl-1,3,5-hexatriene), diphenylacetylenes, and azobenzenes such as phenyl, biphenyl, and terphenyl derivatives and modified stilbenes (styryl thiophenes and styryl naphthalenes)--assembly formation is accompanied by formation of aggregates of the aromatic groups. Results of experimental studies and simulations indicate that in many casesmore » the aromatics form a small, stable unit aggregate characterized by strong noncovalent edge-to-face interactions among adjacent aromatics. Although the unit aggregates exhibit characteristic spectral shifts and strong induced circular dichroism indicating a chiral pinwheel aggregate structure, they may be packed together in pure films or dispersions to form an extended glide or herringbone structure. Although the pinwheel unit aggregate and the extended glide or herringbone structure. Although the pinwheel unit aggregate and the extended glide structure is favored for the majority of aromatics studied, for certain aromatics (styrenes, styrylthiophenes, and {alpha}-styrylnaphthalenes) a translation layer, characterized by face-to-face noncovalent interactions, is preferred. The glide or herringbone aggregates are readily distinguished from the translation aggregates by different spectral signatures and different photochemical and photophysical behavior. Factors controlling the type of aggregate and hence extended structure formed from different aromatic functionalized aromatics include shape and steric factors and strength of the competing noncovalent edge-face and face-face interactions.« less