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Spiropyrrolidine-3, 3´-oxindole as potent anti-breast cancer compounds: Their design, synthesis, biological evaluation and cellular target identification
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Spiropyrrolidine-3, 3´-oxindole as potent anti-breast cancer compounds: Their design, synthesis, biological evaluation and cellular target identification
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Spiropyrrolidine-3, 3´-oxindole as potent anti-breast cancer compounds: Their design, synthesis, biological evaluation and cellular target identification
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Journal Article
Spiropyrrolidine-3, 3´-oxindole as potent anti-breast cancer compounds: Their design, synthesis, biological evaluation and cellular target identification
2016
Overview
The spiro[pyrrolidine-3, 3´-oxindole] moiety is present as a core in number of alkaloids with substantial biological activities. Here in we report design and synthesis of a library of compounds bearing spiro[pyrrolidine-3, 3´-oxindole] motifs that demonstrated exceptional inhibitory activity against the proliferation of MCF-7 breast cancer cells. The synthesis involved a one pot Pictet Spengler-Oxidative ring contraction of tryptamine to the desired scaffolds and occurred in 1:1 THF and water with catalytic trifluoroacetic acid and stoichiometric N-bromosuccinimide as an oxidant. Phenotypic profiling indicated that these molecules induce apoptotic cell death in MCF-7 cells. Target deconvolution with most potent compound
5l
from the library, using chemical proteomics indicated histone deacetylase 2 (HDAC2) and prohibitin 2 as the potential cellular binding partners. Molecular docking of
5l
with HDAC2 provided insights pertinent to putative binding interactions.
Publisher
Nature Publishing Group UK,Nature Publishing Group
Subject
/ Animals
/ Antineoplastic Agents - chemical synthesis
/ Antineoplastic Agents - chemistry
/ Antineoplastic Agents - pharmacology
/ Breast Neoplasms - metabolism
/ Breast Neoplasms - pathology
/ Cell Proliferation - drug effects
/ Female
/ Humanities and Social Sciences
/ Humans
/ Molecular Dynamics Simulation
/ Science
/ Spiro Compounds - chemical synthesis
