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Synthesis and antitumor activity of novel alkynyl (phosphine) digold(I) complexes

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Abstract

A series of 1,4-disubstituted digold–alkynyl complexes, [(PPh3)Au]2(μ-C≡C–Ar–CH≡C)], in which the 1,4-diethenylbenzene bridge contains two alkyl or oligo(ethylene glycol)methylether side chains at different positions (2,5- and 2,3-positions), have been synthesized and structurally characterized by spectroscopic techniques. The structure of [(AuPPh3)2{µ-C≡C–C6H2(OC6H13)2-2,5-C≡C}] (2c) has been established by X-ray crystallography. Their antitumor activities in vitro were investigated by MTT assay against four tumor cell lines. Compared to alkyl-functionalized complexes, the oligo(ethylene glycol)methylether-functionalized complexes showed significant antitumor activity, which may be attributed to the improvement of the hydrophilicity of the complex to achieve the appropriate lipophilicity. In particular, complex [(AuPPh3)2{µ-C≡C–C6H2(OCH2CH2OCH2CH2OCH3)2-2,3-C≡C}] (2j) displayed high activity against the A549 cell line and low cytotoxicity toward normal cell lines. Notably, further investigations are required if complex 2j is to undergo trials as a new potential antitumor agent.

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Acknowledgements

The authors acknowledge financial support from Natural Science Foundation of Yunnan Province (No. 202001AT070068).

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming, 650500, People’s Republic of China

    Qiu Mei Chen, Yi Chen & Xiang Hua Wu

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  1. Qiu Mei Chen
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  2. Yi Chen
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  3. Xiang Hua Wu
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Correspondence to Xiang Hua Wu.

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Appendix

Appendix

CCDC 1,019,402 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

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Chen, Q.M., Chen, Y. & Wu, X.H. Synthesis and antitumor activity of novel alkynyl (phosphine) digold(I) complexes. Transit Met Chem 46, 495–501 (2021). https://doi.org/10.1007/s11243-021-00467-3

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