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Synthesis, Molecular Docking, and DFT Calculation of a Half-Strapped BODIPY as Potential EGFR Inhibitor**

Lookup NU author(s): Rua Alnoman, Dr Julian Knight


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© 2020 Wiley-VCH GmbHThe identification of drug candidates inhibiting specific cellular functions in cancer cell progression is reflected as a key in cancer treatment. The overexpression of epidermal growth factor receptor, EGFR is witnessed in a huge number of cancers. Hence targeting the EGFR and its downstream signaling cascades are considered as a coherent approach in cancer therapy. Keeping this in view, we have synthesized six 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene/boron-dipyrromethene (BODIPY) compounds, 1–6. Absorption, distribution, metabolism and excretion (ADME) and Lipinski's drug likeness of compounds 1–6 was predicted revealing that they exhibited promising physicochemical properties for oral bioavailability. Molecular docking results revealed that compound 6 displayed highest lipophilicity, hence strongest binding to the protein (ΔG=−8.78 kcal/mol) as compared to compounds 4 and 5. The density functional calculations have been investigated to validate the evidence about the reactivity of the compounds as inhibitors. These results were illustrated in terms of the chemical reactivity descriptors and the molecular electrostatic potential (MEP). Compound 6 showed the highest lying HOMO (highest occupied molecular orbital), the smallest energy gap between the FMOs (Frontier molecular orbitals) and the lowest basicity index, all of these parameters could affect the binding affinity, to different extents, to impact the degree of the binding of compound 6 with the active protein sites.

Publication metadata

Author(s): Parveen S, Alnoman RB, Hagar M, Ahmed HA, Knight JG

Publication type: Article

Publication status: Published

Journal: ChemistrySelect

Year: 2020

Volume: 5

Issue: 42

Pages: 13163-13173

Online publication date: 17/11/2020

Acceptance date: 27/10/2020

ISSN (electronic): 2365-6549

Publisher: Wiley-Blackwell


DOI: 10.1002/slct.202003621


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