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DNA Binding To Guide the Development of Tetrahydroindeno[1,2-b]pyrido[4,3,2-de]quinoline Derivatives as Cytotoxic Agents

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    DNA Binding To Guide the Development of Tetrahydroindeno[1,2-b]pyrido[4,3,2-de]quinoline Derivatives as Cytotoxic Agents
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    Institut de Chimie Pharmaceutique Albert Lespagnol, EA 2692, Université de Lille 2, Rue du Professeur Laguesse, BP 83, 59006 Lille, France, Biospectroscopy and Physical Chemistry Unit, University of Liege, Sart-Tilman, 4000 Liege, Belgium, and INSERM U-524 and Laboratoire de Pharmacologie Antitumorale du Centre Oscar Lambret, IRCL, Place de Verdun, 59045 Lille, France
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2004, 47, 14, 3665–3673
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    https://doi.org/10.1021/jm0400193
    Published June 3, 2004
    Copyright © 2004 American Chemical Society
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    Abstract

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    The tetrahydroindeno[1,2-b]pyrido[4,3,2-de]quinoline chromophore was initially designed as a DNA intercalating unit because of its planar structure. Unexpectedly, one molecule (15d) bearing two N-methylpiperazine chains on both sides of this condensed pentacyclic skeleton fits into the minor groove of DNA and preferentially recognizes AT-rich sequences. The monosubstituted compound 16d was identified as a potent cytotoxic DNA intercalator, whereas the disubstituted analogue 15d represents a new structural motif for the development of DNA sequence-reading small molecules.

    Copyright © 2004 American Chemical Society

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    §

     Université de Lille 2.

    †

     Present address:  Department of Chemistry, Georgia State University, Atlanta, GA 30303-3083.

    ‡

     INSERM U-524 and Laboratoire de Pharmacologie Antitumorale du Centre Oscar Lambret.

    #

     University of Liege.

    ⊥

     Present address:  Département de Cancérologie Expérimentale, Centre de Recherche Pierre Fabre, Avenue Jean Moulin, 81106 Castres, France.

    *

     To whom correspondence should be addressed. Phone: +33-3-2096-4374. Fax:  +33-3-2096-4906. E-mail:  henicha@ pharma.univ-lille2.fr.

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    Elemental analyses for compounds 9i, 14a−d,g−k, 15d,j,k, and 16a−d,g,h,j,k. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cited By

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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2004, 47, 14, 3665–3673
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jm0400193
    Published June 3, 2004
    Copyright © 2004 American Chemical Society
    Request reuse permissions

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