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Supramolecular self-assembly of fluorescent peptide amphiphiles for accurate and reversible pH measurement

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Abstract

We report the synthesis and self-assembly of fluorescent peptide amphiphiles (NBD-PA) composed of a fluorescent NBD probe and a peptide derivative VVAADD with a C12-alkyl-chain as the linker (NBD-C12-VVAADD). The self-assembly of NBD-PA formed beta-sheet structures at neutral pH in aqueous solution, contributed to an ∼10-fold increase in the fluorescence and quantum yield of NBD molecules, and conferred a supramolecular hydrogel with excellent viscoelastic properties, while gel-to-sol transition of NBD-PA occurred rapidly when the pH value was adjusted to strongly alkaline (e.g. pH 11). Through the pH-responsive self-assembly behavior, we further explored the relationship between fluorescence of NBD-PA and pH values. Interestingly, the fluorescence of the NBD-PA system exhibited an excellent sigmoidal function relationship (R2 = 0.9999) with the alkaline pH values, which enabled accurate pH measurement regardless of salt types and ionic strength of solvents. Furthermore, the fluorescence of NBD-PA was fully reversible upon cycles of pH shifts, with the chemical structure of NBD-PA well-maintained throughout the process. These features of NBD-PA would facilitate the design of in situ pH detection systems as well as pH-responsive actuators for various applications in future.

Graphical abstract: Supramolecular self-assembly of fluorescent peptide amphiphiles for accurate and reversible pH measurement

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Publication details

The article was received on 30 Nov 2018, accepted on 02 Jan 2019 and first published on 03 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB02983K
Citation: Org. Biomol. Chem., 2019, Advance Article
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    Supramolecular self-assembly of fluorescent peptide amphiphiles for accurate and reversible pH measurement

    L. Mei, S. He, L. Zhang, K. Xu and W. Zhong, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB02983K

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