Synthesis, crystal structure and effect of indeno[1,2-b]indole derivatives on prostate cancer in vitro. Potential effect against MMP-9

Gricela Lobo, Melina Monasterios, Juan Rodrigues, Neira Gamboa, Mario V. Capparelli, Javier Martínez-Cuevas, Michael Lein, Klaus Jung, Claudia Abramjuk, Jaime Charris

    Research output: Contribution to journalArticleResearchpeer-review

    27 Citations (Scopus)

    Abstract

    © 2015 Elsevier Masson SAS. All rights reserved. A highly regiospecific synthesis of a series of indenoindoles is reported, together with X-ray studies and their activity against human prostate cancer cells PC-3 and LNCaP in vitro. The most effective compound 7,7-dimethyl-5-[(3,4-dichlorophenyl)]-(4bRS,9bRS)-dihydroxy-4b,5,6,7,8,9bhexahydro-indeno[1,2-b]indole-9,10-dione 7q reduced the viability in both cell lines in a time and dose-dependent manner. Inhibitory effects were also observed on the adhesion, migration, and invasion of the prostate cancer cells as well as on clonogenic possibly by inhibition of MMP-9 activity. Molecular docking of 7q and 6k into MMP-9 human active site was also performed to determine the probable binding mode.
    Original languageEnglish
    Pages (from-to)281-295
    JournalEuropean Journal of Medicinal Chemistry
    Volume96
    DOIs
    Publication statusPublished - 26 May 2015

    Keywords

    • Cancer
    • Crystal
    • Indeno
    • MMP-9
    • Prostate
    • Regiospecif

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