Natural and Synthetic Oligoarylamides: Privileged Structures for Medical Applications

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OriginalspracheEnglisch
Seiten (von - bis)7321-7339
Seitenumfang19
FachzeitschriftChemistry - a European journal
Jahrgang27
Ausgabenummer26
Frühes Online-Datum22 Jan. 2021
PublikationsstatusVeröffentlicht - 6 Mai 2021

Abstract

The term “privileged structure” refers to a single molecular substructure or scaffold that can serve as a starting point for high-affinity ligands for more than one receptor type. In this report, a hitherto overlooked group of privileged substructures is addressed, namely aromatic oligoamides, for which there are natural models in the form of cystobactamids, albicidin, distamycin A, netropsin, and others. The aromatic and heteroaromatic core, together with a flexible selection of substituents, form conformationally well-defined scaffolds capable of specifically binding to conformationally well-defined regions of biomacromolecules such as helices in proteins or DNA often by acting as helices mimics themselves. As such, these aromatic oligoamides have already been employed to inhibit protein–protein and nucleic acid–protein interactions. This article is the first to bring together the scattered knowledge about aromatic oligoamides in connection with biomedical applications.

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Natural and Synthetic Oligoarylamides: Privileged Structures for Medical Applications. / Seedorf, Tim; Kirschning, Andreas; Solga, Danny.
in: Chemistry - a European journal, Jahrgang 27, Nr. 26, 06.05.2021, S. 7321-7339.

Publikation: Beitrag in FachzeitschriftÜbersichtsarbeitForschungPeer-Review

Seedorf T, Kirschning A, Solga D. Natural and Synthetic Oligoarylamides: Privileged Structures for Medical Applications. Chemistry - a European journal. 2021 Mai 6;27(26):7321-7339. Epub 2021 Jan 22. doi: 10.1002/chem.202005086
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abstract = "The term “privileged structure” refers to a single molecular substructure or scaffold that can serve as a starting point for high-affinity ligands for more than one receptor type. In this report, a hitherto overlooked group of privileged substructures is addressed, namely aromatic oligoamides, for which there are natural models in the form of cystobactamids, albicidin, distamycin A, netropsin, and others. The aromatic and heteroaromatic core, together with a flexible selection of substituents, form conformationally well-defined scaffolds capable of specifically binding to conformationally well-defined regions of biomacromolecules such as helices in proteins or DNA often by acting as helices mimics themselves. As such, these aromatic oligoamides have already been employed to inhibit protein–protein and nucleic acid–protein interactions. This article is the first to bring together the scattered knowledge about aromatic oligoamides in connection with biomedical applications.",
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T2 - Privileged Structures for Medical Applications

AU - Seedorf, Tim

AU - Kirschning, Andreas

AU - Solga, Danny

N1 - Funding Information: We are indebted to the BMBF (OpCyBac; grant number 16GW0219K) for funding our research on the cystobactamids. Open access funding enabled and organized by Projekt DEAL.

PY - 2021/5/6

Y1 - 2021/5/6

N2 - The term “privileged structure” refers to a single molecular substructure or scaffold that can serve as a starting point for high-affinity ligands for more than one receptor type. In this report, a hitherto overlooked group of privileged substructures is addressed, namely aromatic oligoamides, for which there are natural models in the form of cystobactamids, albicidin, distamycin A, netropsin, and others. The aromatic and heteroaromatic core, together with a flexible selection of substituents, form conformationally well-defined scaffolds capable of specifically binding to conformationally well-defined regions of biomacromolecules such as helices in proteins or DNA often by acting as helices mimics themselves. As such, these aromatic oligoamides have already been employed to inhibit protein–protein and nucleic acid–protein interactions. This article is the first to bring together the scattered knowledge about aromatic oligoamides in connection with biomedical applications.

AB - The term “privileged structure” refers to a single molecular substructure or scaffold that can serve as a starting point for high-affinity ligands for more than one receptor type. In this report, a hitherto overlooked group of privileged substructures is addressed, namely aromatic oligoamides, for which there are natural models in the form of cystobactamids, albicidin, distamycin A, netropsin, and others. The aromatic and heteroaromatic core, together with a flexible selection of substituents, form conformationally well-defined scaffolds capable of specifically binding to conformationally well-defined regions of biomacromolecules such as helices in proteins or DNA often by acting as helices mimics themselves. As such, these aromatic oligoamides have already been employed to inhibit protein–protein and nucleic acid–protein interactions. This article is the first to bring together the scattered knowledge about aromatic oligoamides in connection with biomedical applications.

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KW - cystobactamids

KW - DNA-binding

KW - dystamycin

KW - foldamers

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