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Open AccessArticle

A Candidate for Multitopic Probes for Ligand Discovery in Dynamic Combinatorial Chemistry

1
Graduate School of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
2
Graduate School of Chemical Sciences and Technology, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
3
Department of Chemistry, Faculty of Science Division II, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
*
Author to whom correspondence should be addressed.
Academic Editors: Alexander Dömling and Shabnam Shaabani
Molecules 2019, 24(11), 2166; https://doi.org/10.3390/molecules24112166
Received: 7 May 2019 / Revised: 30 May 2019 / Accepted: 7 June 2019 / Published: 8 June 2019
(This article belongs to the Special Issue Macrocycles in Drug Discovery)
Multifunctionalized materials are expected to be versatile probes to find specific interactions between a ligand and a target biomaterial. Thus, efficient methods to prepare possible combinations of the functionalities is desired. The concept of dynamic combinatorial chemistry (DCC) is ideal for the generation of any possible combination, as well as screening for target biomaterials. Here, we propose a new molecular design of multitopic probes for ligand discovery in DCC. We synthesized a new Gable Porphyrin, GP1, having prop-2-yne groups as a scaffold to introduce various functional groups. GP1 is a bis(imidazolylporphyrinatozinc) compound connected through a 1,3-phenylene moiety, and it gives macrocycles spontaneously and quantitatively by strong imidazole-to-zinc complementary coordination. Some different types of functional groups were introduced into GP1 in high yields. Formation of heterogeneous macrocycles composed of GP1 derivatives having different types of substituents was accomplished under equilibrium conditions. These results promise that enormous numbers of macrocycles having various functional groups can be provided when the kinds of GP components increase. These features are desirable for DCC, and the present system using GP1 is a potential candidate to provide a dynamic combinatorial library of multitopic probes to discover specific interactions between a ligand and a biomaterial. View Full-Text
Keywords: dynamic combinatorial chemistry (DCC); dynamic combinatorial library (DCL); supramolecular macrocycle; zinc porphyrin; multifunctionalized material; complementary coordination; copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC); gel permeation chromatography (GPC); amphiphilic dynamic combinatorial chemistry (DCC); dynamic combinatorial library (DCL); supramolecular macrocycle; zinc porphyrin; multifunctionalized material; complementary coordination; copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC); gel permeation chromatography (GPC); amphiphilic
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Yoneyama, K.; Suzuki, R.; Kuramochi, Y.; Satake, A. A Candidate for Multitopic Probes for Ligand Discovery in Dynamic Combinatorial Chemistry. Molecules 2019, 24, 2166.

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