Synthesis, Evaluation for Cytotoxicity and Molecular Docking Studies of Benzo[c ]furan-Chalcones for Potential to Inhibit Tubulin Polymerization and/or EGFR-Tyrosine Kinase Phosphorylation

International Journal of Molecular Sciences
Malose J MphahleleSibusiso T Malindisa

Abstract

A series of 2-arylbenzo[c]furan-chalcone hybrids 3a⁻y have been synthesized and evaluated for antiproliferative effects against the human breast cancer (MCF-7) cell line and for its potential to induce apoptosis and also to inhibit tubulin polymerization and/or epidermal growth factor receptor-tyrosine kinase (EGFR-TK) phosphorylation. Most of these compounds exhibited moderate to significant antigrowth effects in vitro against the MCF-7 cell line when compared to the reference standard actinomycin D. The capabilities of the most cytotoxic benzofuran-chalcone hybrids 3b and 3i, to induce apoptosis, have been evaluated by Annexin V-Cy3 SYTOX staining and caspase-3 activation. The experimental and molecular docking results suggest that the title compounds have the potential to exhibit inhibitory effects against tubulin polymerization and epidermal growth factor receptor tyrosine kinase (EGFR-TK) phosphorylation. The modeled structures of representative compounds displayed hydrophobic interactions as well as hydrogen and/or halogen bonding with the protein residues. These interactions are probably responsible for the observed increased binding affinity for the two receptors and their significant antigrowth effect against the MCF-7...Continue Reading

References

May 23, 1998·The Journal of Biological Chemistry·R U JänickeA G Porter
Apr 13, 2000·International Journal of Cancer. Journal International Du Cancer·J KleeffM Korc
Jan 5, 2002·Biochimica Et Biophysica Acta·E B YangP Mack
Aug 28, 2002·The Journal of Biological Chemistry·Jennifer StamosCharles Eigenbrot
Mar 26, 2003·Cell Death and Differentiation·U FischerK Schulze-Osthoff
Jul 23, 2003·Current Medicinal Chemistry·Nguyen-Hai Nam
Jan 17, 2008·Chemical Society Reviews·Sophie PurserVéronique Gouverneur
Apr 10, 2008·Journal of Medicinal Chemistry·Domenico AlloattiClaudio Pisano
Oct 11, 2008·Cell Death and Differentiation·G KroemerUNKNOWN Nomenclature Committee on Cell Death 2009
Apr 7, 2009·Bioorganic & Medicinal Chemistry Letters·Shadia A GalalHoda I El-Diwani
Jul 27, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kiattawee ChoowongkomonJumras Limtrakul
Jul 28, 2011·Medicinal Research Reviews·Rafael LeónJosé Marco-Contelles
May 29, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Suvitha SyamSyam Mohan
Jul 21, 2012·Pharmaceutical Research·Yan LuDuane D Miller
Dec 12, 2012·Protein Science : a Publication of the Protein Society·Matthew R ScholfieldP Shing Ho
Aug 2, 2013·Bioorganic & Medicinal Chemistry·Marion ThéveninJoëlle Dubois
Oct 12, 2013·CA: a Cancer Journal for Clinicians·Carol DeSantisAhmedin Jemal
Aug 20, 2014·European Journal of Medicinal Chemistry·Parvesh SinghVipan Kumar
Dec 9, 2014·European Journal of Medicinal Chemistry·Hena Khanam, Shamsuzzaman
Jan 23, 2016·Medicinal Chemistry·Bo Zhou, Chengguo Xing
Jun 20, 2016·European Journal of Medicinal Chemistry·Hassan Mirzaei, Saeed Emami
May 11, 2017·Chemical Reviews·Chunlin ZhuangZhenyuan Miao
Aug 2, 2017·European Journal of Medicinal Chemistry·Nagaraju KerruVipan Kumar

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Citations

Jun 20, 2020·Chemical Biology & Drug Design·Malikotsi A QhobosheaneRichard M Beteck
Jul 3, 2021·Biomolecules·Yang OuyangQi Wu
Aug 28, 2021·European Journal of Medicinal Chemistry·Osama M SoltanMohamed Abdel-Aziz

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Methods Mentioned

BETA
nuclear magnetic resonance
X-ray
Assay
enzyme-linked immunosorbent assay

Software Mentioned

OriginPro
Discovery Studio
CDOCKER

Related Concepts

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Apoptosis

Apoptosis is a specific process that leads to programmed cell death through the activation of an evolutionary conserved intracellular pathway leading to pathognomic cellular changes distinct from cellular necrosis