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Tuning the Solubility of Self-Assembled Fluorescent Aromatic Cages Using Functionalized Amino Acid Building Blocks

We previously reported novel fluorescent aromatic cages that are self-produced using a set of orthogonal dynamic covalent reactions, operating simultaneously in one-pot, to assemble up to 10 components through 12 reactions into a single cage-type structure. We now introduce N-functionalized amino ac...

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Autores principales: Konopka, Marcin, Cecot, Piotr, Ulrich, Sébastien, Stefankiewicz, Artur R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6647868/
https://www.ncbi.nlm.nih.gov/pubmed/31380348
http://dx.doi.org/10.3389/fchem.2019.00503
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author Konopka, Marcin
Cecot, Piotr
Ulrich, Sébastien
Stefankiewicz, Artur R.
author_facet Konopka, Marcin
Cecot, Piotr
Ulrich, Sébastien
Stefankiewicz, Artur R.
author_sort Konopka, Marcin
collection PubMed
description We previously reported novel fluorescent aromatic cages that are self-produced using a set of orthogonal dynamic covalent reactions, operating simultaneously in one-pot, to assemble up to 10 components through 12 reactions into a single cage-type structure. We now introduce N-functionalized amino acids as new building blocks that enable tuning the solubility and analysis of the resulting cages. A convenient divergent synthetic approach was developed to tether different side chains on the N-terminal of a cysteine-derived building block. Our studies show that this chemical functionalization does not prevent the subsequent self-assembly and effective formation of desired cages. While the originally described cages required 94% DMSO, the new ones bearing hydrophobic side chains were found soluble in organic solvents (up to 75% CHCl(3)), and those grafted with hydrophilic side chains were soluble in water (up to 75% H(2)O). Fluorescence studies confirmed that despite cage functionalization the aggregation-induced emission properties of those architectures are retained. Thus, this work significantly expands the range of solvents in which these self-assembled cage compounds can be generated, which in turn should enable new applications, possibly as fluorescent sensors.
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spelling pubmed-66478682019-08-02 Tuning the Solubility of Self-Assembled Fluorescent Aromatic Cages Using Functionalized Amino Acid Building Blocks Konopka, Marcin Cecot, Piotr Ulrich, Sébastien Stefankiewicz, Artur R. Front Chem Chemistry We previously reported novel fluorescent aromatic cages that are self-produced using a set of orthogonal dynamic covalent reactions, operating simultaneously in one-pot, to assemble up to 10 components through 12 reactions into a single cage-type structure. We now introduce N-functionalized amino acids as new building blocks that enable tuning the solubility and analysis of the resulting cages. A convenient divergent synthetic approach was developed to tether different side chains on the N-terminal of a cysteine-derived building block. Our studies show that this chemical functionalization does not prevent the subsequent self-assembly and effective formation of desired cages. While the originally described cages required 94% DMSO, the new ones bearing hydrophobic side chains were found soluble in organic solvents (up to 75% CHCl(3)), and those grafted with hydrophilic side chains were soluble in water (up to 75% H(2)O). Fluorescence studies confirmed that despite cage functionalization the aggregation-induced emission properties of those architectures are retained. Thus, this work significantly expands the range of solvents in which these self-assembled cage compounds can be generated, which in turn should enable new applications, possibly as fluorescent sensors. Frontiers Media S.A. 2019-07-16 /pmc/articles/PMC6647868/ /pubmed/31380348 http://dx.doi.org/10.3389/fchem.2019.00503 Text en Copyright © 2019 Konopka, Cecot, Ulrich and Stefankiewicz. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Konopka, Marcin
Cecot, Piotr
Ulrich, Sébastien
Stefankiewicz, Artur R.
Tuning the Solubility of Self-Assembled Fluorescent Aromatic Cages Using Functionalized Amino Acid Building Blocks
title Tuning the Solubility of Self-Assembled Fluorescent Aromatic Cages Using Functionalized Amino Acid Building Blocks
title_full Tuning the Solubility of Self-Assembled Fluorescent Aromatic Cages Using Functionalized Amino Acid Building Blocks
title_fullStr Tuning the Solubility of Self-Assembled Fluorescent Aromatic Cages Using Functionalized Amino Acid Building Blocks
title_full_unstemmed Tuning the Solubility of Self-Assembled Fluorescent Aromatic Cages Using Functionalized Amino Acid Building Blocks
title_short Tuning the Solubility of Self-Assembled Fluorescent Aromatic Cages Using Functionalized Amino Acid Building Blocks
title_sort tuning the solubility of self-assembled fluorescent aromatic cages using functionalized amino acid building blocks
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6647868/
https://www.ncbi.nlm.nih.gov/pubmed/31380348
http://dx.doi.org/10.3389/fchem.2019.00503
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