Self-Assembly, Hydrogelation, and Nanotube Formation by Cation-Modified Phenylalanine Derivatives

Langmuir : the ACS Journal of Surfaces and Colloids
Annada RajbhandaryBradley L Nilsson

Abstract

Fluorenylmethoxycarbonyl-protected phenylalanine (Fmoc-Phe) derivatives are a privileged class of molecule that spontaneously self-assemble into hydrogel fibril networks. Fmoc-Phe-derived hydrogels are typically formed by dilution of the hydrogelator from an organic cosolvent into water, by dissolution of the hydrogelator under basic aqueous conditions followed by adjustment of the pH with acid, or by other external triggering forces, including sonication and heating. These conditions complicate biological applications of these hydrogels. Herein, we report C-terminal cation-modified Fmoc-Phe derivatives that are positively charged across a broad range of pH values and that can self-assemble and form hydrogel networks spontaneously without the need to adjust pH or to use an organic cosolvent. In addition, these cationic Fmoc-Phe derivatives are found to self-assemble into novel sheet-based nanotube structures at higher concentrations. These nanotube structures are unique to C-terminal cationic Fmoc-Phe derivatives; the parent Fmoc-Phe carboxylic acids form only fibril or worm-like micelle structures. Nanotube formation by the cationic Fmoc-Phe molecules is dependent on positive charge at the C-terminus, since at basic pH where t...Continue Reading

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Citations

Apr 27, 2018·Chemical Society Reviews·Danielle M Raymond, Bradley L Nilsson
Jan 28, 2020·Soft Matter·Sanjoy MondalArun K Nandi
Sep 17, 2020·Advanced Healthcare Materials·Ying CaiPengcheng Zhang
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Mar 14, 2019·ACS Applied Materials & Interfaces·Chloé Guilbaud-ChéreauCécilia Ménard-Moyon
Apr 4, 2019·ACS Applied Bio Materials·Danielle M RaymondBradley L Nilsson
Mar 28, 2019·Langmuir : the ACS Journal of Surfaces and Colloids·Rashmi JainSangita Roy
Jun 27, 2018·Langmuir : the ACS Journal of Surfaces and Colloids·Yuki OharaShin-Ichi Yusa

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