Synthesis of heterobimetallic gold(I) ferrocenyl-substituted 1,2,3-triazol-5-ylidene complexes as potential anticancer agents

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dc.contributor.author Aucamp, Danielle
dc.contributor.author Kumar, Sreedhar V.
dc.contributor.author Liles, David C.
dc.contributor.author Fernandes, Manuel A.
dc.contributor.author Harmse, Leonie
dc.contributor.author Bezuidenhout, Daniela I.
dc.date.accessioned 2018-12-10T12:18:48Z
dc.date.issued 2018-09
dc.description.abstract 1,2,3-Triazol-5-ylidene (trz) complexes of gold(I) containing a ferrocenyl substituent on the C4-position of the trz ring were synthesized to yield the neutral heterobimetallic gold(I) trz chlorido (2), gold(I) trz phenyl (3), and the cationic gold(I) trz triphenylphospine (5) complexes. In order to compare the effect of silver(I) as central metal vs. gold(I), [Ag(trz)2]+ (4) was also prepared, while variation of the C4-1,2,3-triazol-5-ylidene substituent from a ferrocenyl to a phenyl group was done to prepare the monometallic analogue of 5, namely the cationic Au(I) trz triphenylphosphine complex 6. The complexes were characterised with spectroscopic and electrochemical methods, and the single crystal X-ray structures of 2–6 were determined. NMR stability studies of 5 as a representative example of the series of complexes were performed to confirm the stability of the complexes in the solvent dimethylsulfoxide and in aqueous solution. The anti-cancer potential of 5 was evaluated against the lung cancer cell lines A549 and H1975, and the human embryonic kidney cell line (HEK-293) was used as a non-cancer model. IC50 values of 0.89, 0.23 and 5.43 μM, respectively, were obtained for A549, H1975 and HEK-293, respectively, indicating the activity and selectivity of 5 for cancer cells. Fluorescence microscopy experiments as a preliminary mode-of-action study evidenced an apoptotic cell death mechanism rather than necrotic cell death. en_ZA
dc.description.department Chemistry en_ZA
dc.description.embargo 2019-09-25
dc.description.librarian hj2018 en_ZA
dc.description.sponsorship DA, MAF and DIB acknowledge the National Research Foundation, South Africa (NRF 105529; NRF 111705, NRF 100119, respectively), and Sasol Technology R&D Pty. Ltd (South Africa) for financial support. SVK thanks WITS URC for a postdoctoral fellowship. LH gratefully acknowledges the financial support of the McGill Bequest to the Pharmacology Division. en_ZA
dc.description.uri http://www.rsc.org/journals-books-databases/about-journals/dalton-transactions en_ZA
dc.identifier.citation Aucamp, D., Kumar, S.V., Liles, D.C. et al. 2018, 'Synthesis of heterobimetallic gold(I) ferrocenyl-substituted 1,2,3-triazol-5-ylidene complexes as potential anticancer agents', Dalton Transactions, vol. 47, no. 45, pp. 16072-16081. en_ZA
dc.identifier.issn 1477-9226 (print)
dc.identifier.issn 1364-5447 (online)
dc.identifier.other 10.1039/C8DT03116A
dc.identifier.uri http://hdl.handle.net/2263/68077
dc.language.iso en en_ZA
dc.publisher Royal Society of Chemistry en_ZA
dc.rights © The Royal Society of Chemistry 2018 en_ZA
dc.subject Gold(I) en_ZA
dc.subject C4-position en_ZA
dc.subject Anticancer agents en_ZA
dc.subject Heterobimetallic gold(I) en_ZA
dc.subject Ferrocenyl-substituted 1,2,3-triazol-5-ylidene complexes en_ZA
dc.title Synthesis of heterobimetallic gold(I) ferrocenyl-substituted 1,2,3-triazol-5-ylidene complexes as potential anticancer agents en_ZA
dc.type Postprint Article en_ZA


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