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The Relation Between Position and Chemical Composition of Bis-Indole Substituents Determines Their Interactions With G-Quadruplex DNA
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.ORCID iD: 0000-0001-6347-2169
Umeå University, Faculty of Medicine, Department of Medical Biochemistry and Biophysics.ORCID iD: 0000-0001-6871-7663
Umeå University, Faculty of Science and Technology, Department of Chemistry.ORCID iD: 0000-0002-7268-9519
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2020 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 26, no 43, p. 9561-9572Article in journal (Refereed) Published
Abstract [en]

G‐quadruplex (G4) DNA structures are linked to fundamental biological processes and human diseases, which has triggered the development of compounds that affect these DNA structures. However, more knowledge is needed about how small molecules interact with G4 DNA structures. This study describes the development of a new class of bis‐indoles (3,3‐diindolyl‐methyl derivatives) and detailed studies of how they interact with G4 DNA using orthogonal assays, biophysical techniques, and computational studies. This revealed compounds that strongly bind and stabilize G4 DNA structures, and detailed binding interactions which e.g. show that charge variance can play a key role in G4 DNA binding. Furthermore, the structure‐activity relationships generated opened the possibilities to replace or introduce new substituents on the core structure, which is of key importance to optimize compound properties or introduce probes to further expand the possibilities of these compounds as tailored research tools to study G4 biology.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2020. Vol. 26, no 43, p. 9561-9572
National Category
Chemical Engineering Medical Biotechnology (with a focus on Cell Biology (including Stem Cell Biology), Molecular Biology, Microbiology, Biochemistry or Biopharmacy)
Identifiers
URN: urn:nbn:se:umu:diva-171213DOI: 10.1002/chem.202000579ISI: 000544966200001PubMedID: 32187406Scopus ID: 2-s2.0-85087461969OAI: oai:DiVA.org:umu-171213DiVA, id: diva2:1432994
Funder
The Kempe Foundations, SMK-1632Swedish Research Council, VR-MH 2018-2651Swedish Research Council, 2017-05235Knut and Alice Wallenberg Foundation, KAW2015-0189Swedish Cancer Society, CAN2019/126Available from: 2020-05-28 Created: 2020-05-28 Last updated: 2023-03-24Bibliographically approved

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Prasad, BagineniDas, Rabindra NathJamroskovic, JanKumar, RajendraHedenström, MattiasSabouri, NasimChorell, Erik

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Prasad, BagineniDas, Rabindra NathJamroskovic, JanKumar, RajendraHedenström, MattiasSabouri, NasimChorell, Erik
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Department of ChemistryDepartment of Medical Biochemistry and Biophysics
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Chemistry - A European Journal
Chemical EngineeringMedical Biotechnology (with a focus on Cell Biology (including Stem Cell Biology), Molecular Biology, Microbiology, Biochemistry or Biopharmacy)

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