A candidate for multitopic probes for ligand discovery in dynamic combinatorial chemistry

Keiko Yoneyama, Rina Suzuki, Yusuke Kuramochi, Akiharu Satake

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Article number2166
JournalMolecules
Volume24
Issue number11
DOIs
Publication statusPublished - 8 Jun 2019

Fingerprint

Biocompatible Materials
chemistry
Functional groups
Ligands
ligands
probes
Porphyrins
Zinc
imidazoles
Scaffolds
porphyrins
Screening
screening
zinc
interactions
Derivatives

Keywords

  • Amphiphilic
  • Complementary coordination
  • Copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC)
  • Dynamic combinatorial chemistry (DCC)
  • Dynamic combinatorial library (DCL)
  • Gel permeation chromatography (GPC)
  • Multifunctionalized material
  • Supramolecular macrocycle
  • Zinc porphyrin

Cite this

@article{4f16552d47e644978a38b4f7e3ee4a4a,
title = "A candidate for multitopic probes for ligand discovery in dynamic combinatorial chemistry",
abstract = "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.",
keywords = "Amphiphilic, Complementary coordination, Copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC), Dynamic combinatorial chemistry (DCC), Dynamic combinatorial library (DCL), Gel permeation chromatography (GPC), Multifunctionalized material, Supramolecular macrocycle, Zinc porphyrin",
author = "Keiko Yoneyama and Rina Suzuki and Yusuke Kuramochi and Akiharu Satake",
year = "2019",
month = "6",
day = "8",
doi = "10.3390/molecules24112166",
language = "English",
volume = "24",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "11",

}

A candidate for multitopic probes for ligand discovery in dynamic combinatorial chemistry. / Yoneyama, Keiko; Suzuki, Rina; Kuramochi, Yusuke; Satake, Akiharu.

In: Molecules, Vol. 24, No. 11, 2166, 08.06.2019.

Research output: Contribution to journalArticle

TY - JOUR

T1 - A candidate for multitopic probes for ligand discovery in dynamic combinatorial chemistry

AU - Yoneyama, Keiko

AU - Suzuki, Rina

AU - Kuramochi, Yusuke

AU - Satake, Akiharu

PY - 2019/6/8

Y1 - 2019/6/8

N2 - 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.

AB - 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.

KW - Amphiphilic

KW - Complementary coordination

KW - Copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC)

KW - Dynamic combinatorial chemistry (DCC)

KW - Dynamic combinatorial library (DCL)

KW - Gel permeation chromatography (GPC)

KW - Multifunctionalized material

KW - Supramolecular macrocycle

KW - Zinc porphyrin

UR - http://www.scopus.com/inward/record.url?scp=85067346858&partnerID=8YFLogxK

U2 - 10.3390/molecules24112166

DO - 10.3390/molecules24112166

M3 - Article

C2 - 31181809

AN - SCOPUS:85067346858

VL - 24

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 11

M1 - 2166

ER -