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Synthesis, Molecular Characterization, and Biological Activity of Novel Synthetic Derivatives of Chromen-4-one in Human Cancer Cells

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Department of Chemistry, University of Pune, Pune 411007, India, Department of Pathology, Barbara Ann Karmanos Cancer Institute, Wayne State University School of Medicine, 9374 Scott Hall, 540 East Canfield Avenue, Detroit, Michigan 48201, Vlife Science Technologies Pvt Ltd., 1 Akshay Residency, Plot No. 50 Anand Park, Aundh Pune 411007, India, and Institute for Inorganic Chemistry, University of Karlsruhe, D-76128 Karlsruhe, Germany
Cite this: J. Med. Chem. 2006, 49, 13, 3800–3808
Publication Date (Web):June 3, 2006
https://doi.org/10.1021/jm051068y
Copyright © 2006 American Chemical Society
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Abstract

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The synthesis and characterization of Schiff base derivatives of 3-formylchromone 36 (FPA-120 to FPA-123), the minimal biologically active structural motif of soy isoflavone, genistein, and their copper(II) complexes 710 (FPA-124 to FPA-127) are reported here. These copper complexes possess distorted square-planar geometries capable of stabilizing Cu2+/Cu+ redox forms. The molecular modeling study revealed that the key interaction of the metal complexes was with amino acids in the pleckstrin homology (PH) and the kinase domain of the PKB (Akt) protein. Copper complex 7 significantly forms stronger charge interactions in the kinase domain than genistein, leading to better stabilization in the active pocket. In vitro evaluation of copper complexes against hormone-independent and metastatic breast (BT20), prostate (PC-3), and K-ras mutant (COLO 357) and K-ras wild-type (BxPC-3) pancreatic cancer cells revealed that 7 was the most potent compound which exhibited PKB (Akt protein) inhibitory activities and caused NF-κB inactivation in a well-established orthotopic pancreatic tumor model using COLO 357 cells. An inverse relationship was observed between IC50 values of the anti-proliferative activities and the Cu2+/Cu+ redox couple for these compounds, which may provide a rapid screen for evaluating the efficacy of active metallodrugs affecting redox-senstitive transcription factors such as NF-κB and its upstream target, the PKB (Akt) pathway, in multiple cancers.

 University of Pune.

 V.A. and F.A. have contributed equally to this work.

§

 Wayne State University.

 Vlife Science Technologies Pvt Ltd.

 University of Karlsruhe.

*

 To whom correspondence should be addressed at the Department of Pathology, Karmanos Cancer Institute, Wayne State University School of Medicine, 715 Hudson Webber Cancer Research Center, 110 E. Warren, Detroit, MI 48201. Phone:  313-576-8327. Fax:  313-576-8389. E-mail:  [email protected]

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Full experimental information for Schiff base isoflavone derivatives 36 and the metal complexes 710, analytical characterization, and biological experimental assays. This material is available free of charge via the Internet at http://pubs.acs.org.

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