Programmable Assembly of Peptide Amphiphile via Noncovalent-to-Covalent Bond Conversion

Sato, Kohei; Ji, Wei; Palmer, Liam C.; Weber, Benjamin; Barz, Matthias; Stupp, Samuel I.

doi:10.1021/jacs.7b03878

Title: Programmable Assembly of Peptide Amphiphile via Noncovalent-to-Covalent Bond Conversion

Journal Article · Thu Jun 22 00:00:00 EDT 2017 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.7b03878· OSTI ID:1374762

; Ji, Wei ^[1];

; Weber, Benjamin ^[2]; Barz, Matthias ^[2];

Prometheus, Division of Skeletal Tissue Engineering, and ∥Skeletal Biology and Engineering Research Center, Department of Development and Regeneration, KU Leuven, Leuven 3000, Belgium
Institut für Organische Chemie, Johannes Gutenberg-Universtität Mainz, Mainz 55099, Germany

Controlling the number of monomers in a supramolecular polymer has been a great challenge in programmable self-assembly of organic molecules. One approach has been to make use of frustrated growth of the supramolecular assembly by tuning the balance of attractive and repulsive intermolecular forces. We report here on the use of covalent bond formation among monomers, compensating for intermolecular electrostatic repulsion, as a mechanism to control the length of a supramolecular nanofiber formed by self-assembly of peptide amphiphiles. Circular dichroism spectroscopy in combination with dynamic light scattering, size-exclusion chromatography, and transmittance electron microscope analyses revealed that hydrogen bonds between peptides were reinforced by covalent bond formation, enabling the fiber elongation. To examine these materials for their potential biomedical applications, cytotoxicity of nanofibers against C2C12 premyoblast cells was tested. We demonstrated that cell viability increased with an increase in fiber length, presumably because of the suppressed disruption of cell membranes by the fiber end-caps.

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Research Organization:: Northwestern Univ., Evanston, IL (United States); Energy Frontier Research Centers (EFRC) (United States). Center for Bio-Inspired Energy Science (CBES)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0000989

OSTI ID:: 1374762

Alternate ID(s):: OSTI ID: 1426435; OSTI ID: 1507998; OSTI ID: 1821870; OSTI ID: 1846802

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Vol. 139 Journal Issue: 26; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 56 works

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Title: Programmable Assembly of Peptide Amphiphile via Noncovalent-to-Covalent Bond Conversion

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