Heterobimetallic propargyl gold complexes with π-bound copper or silver with enhanced anticancer activity.

JOHNSON, Alice, MARZO, Isabel and GIMENO, M Concepción (2020). Heterobimetallic propargyl gold complexes with π-bound copper or silver with enhanced anticancer activity. Dalton Transactions, 49 (33), 11736-11742.

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Official URL: https://pubs.rsc.org/en/content/articlelanding/202...
Open Access URL: https://pubs.rsc.org/en/content/articlepdf/2020/dt... (Published version)
Link to published version:: https://doi.org/10.1039/d0dt02113j
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    Abstract

    Several propargyl functionalised substrates with different heteroatoms (N, O or S) have been used for the preparation of propargyl gold(i) phosphine complexes. The complexes were prepared in high yields either by reaction of the substrate with [Au(acac)PPh3] or by reaction of [AuCl(PPh3)] with potassium hydroxide and the substrate in methanol. Several of the complexes have been characterised by X-ray diffraction showing the presence of secondary bonds such as π-stacking and aurophilic interactions. The reaction of the propargyl gold(i) phosphine complexes with [Cu(NO3)(PPh3)2] or [Ag(OTf)(PPh3)2] afforded heterobimetallic complexes with π-coordination of {Cu(PPh3)2} or {Ag(PPh3)2} to the alkyne bond. When the substituent of the propargyl unit contained more strongly coordinating pyridine moieties, [(PyCH2)2NCH2C[triple bond, length as m-dash]CAuPPh3], coordination of the heterometal to the pyridine units occurred, displacing the phosphine groups and giving rise to a dimeric structure. The antiproliferative activity of the complexes against cisplatin resistant lung cancer cell line A549 was determined by MTT assay. The mononuclear gold complexes showed excellent activities with IC50 values < 14 μM. Coordination of copper of silver to the alkynyl fragment resulted in a significant increase in activity suggesting a synergistic effect between the two metal centres.

    Item Type: Article
    Uncontrolled Keywords: A549 Cells; Antineoplastic Agents; Apoptosis; Cell Proliferation; Cisplatin; Coordination Complexes; Copper; Crystallography, X-Ray; Drug Resistance, Neoplasm; Gold; Humans; Ligands; Molecular Structure; Phosphines; Pyridines; Silver; Structure-Activity Relationship; X-Ray Diffraction; Humans; Cisplatin; Copper; Gold; Silver; Phosphines; Pyridines; Antineoplastic Agents; Ligands; X-Ray Diffraction; Crystallography, X-Ray; Apoptosis; Cell Proliferation; Molecular Structure; Structure-Activity Relationship; Drug Resistance, Neoplasm; Coordination Complexes; A549 Cells; 0302 Inorganic Chemistry; 0307 Theoretical and Computational Chemistry; 0399 Other Chemical Sciences; Inorganic & Nuclear Chemistry
    Identification Number: https://doi.org/10.1039/d0dt02113j
    Page Range: 11736-11742
    SWORD Depositor: Symplectic Elements
    Depositing User: Symplectic Elements
    Date Deposited: 13 May 2022 11:21
    Last Modified: 13 May 2022 11:21
    URI: http://shura.shu.ac.uk/id/eprint/29937

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