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Issue 4, 2016
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Identification of bisindolylmethane–hydrazone hybrids as novel inhibitors of β-glucuronidase, DFT, and in silico SAR intimations

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Abstract

The present study involves the synthesis of bisindolylmethane–hydrazone hybrids, 1–30, in a three-step reaction sequence, followed by evaluation against β-glucuronidase enzyme. The IC50 values for the potent compounds were in the range from 0.10 to 83.50 μM. Compound, a trihydroxy analog was found to be the most potent derivative, having an IC50 value of 0.10 ± 0.001 μM. Molecular docking revealed that the active compounds could fit perfectly into the binding groove of β-D-glucuronidase. The presence of hydroxyl groups on the aromatic side chain proved to be the single most important factor that contributed toward the inhibitory potential of these compounds. On the other hand, the imino group of the hydrazone linkage displayed interactions with the side chain carboxyl oxygen (Oε2) of Asp207. The high inhibitory potential of these compounds could be associated with these strong hydrogen bonds. Structures of all the synthesized compounds were confirmed using modern spectroscopic methods.

Graphical abstract: Identification of bisindolylmethane–hydrazone hybrids as novel inhibitors of β-glucuronidase, DFT, and in silico SAR intimations

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Publication details

The article was received on 22 Sep 2015, accepted on 07 Dec 2015 and first published on 15 Dec 2015


Article type: Paper
DOI: 10.1039/C5RA19513F
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RSC Adv., 2016,6, 3276-3289

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    Identification of bisindolylmethane–hydrazone hybrids as novel inhibitors of β-glucuronidase, DFT, and in silico SAR intimations

    M. Taha, N. H. Ismail, S. Imran, E. H. Anouar, M. Ali, W. Jamil, N. Uddin and S. M. Kashif, RSC Adv., 2016, 6, 3276
    DOI: 10.1039/C5RA19513F

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