Carbene-metal complexes as anticancer and antibacterial drug candidates

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Title: Carbene-metal complexes as anticancer and antibacterial drug candidates
Authors: Hackenberg, Frauke Marie
Advisor: Tacke, Matthias
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Date: 2013
Online since: 2015-08-12T08:54:28Z
Abstract: Within this project, novel silver(I)-, ruthenium(II)- and gold(I)-NHC complexes have been synthesised by the formation of appropriately substituted (benz)imidazolium and 4,5-diaryl-imidazolium halides followed by either metallation with silver acetate, or metallation with silver oxide followed by transmetallation with dichloro ruthenium (<italic>p</italic>-cymene) dimer or dimethylsulfido gold chloride. The three obtained NHC-gold(I) chlorides were further functionalised by reacting them with silver acetate or 2,3,4,6-tetra-<italic>O</italic>-benzyl-1-thio-&#946;-D-glucopyranose to give NHC-gold(I) acetates or NHC-gold(I) thioglucopyranoses, respectively.All complexes were characterised by NMR (<super>1</super>H and <super>13</super>C), IR, microanalysis and MS. Melting points were determined for all complexes with the exception of (benz)imidazol-2-ylidene silver(I) acetates. The <italic>in vitro</italic> antibacterial activity against bacterial strains of <italic>E. coli</italic> and <italic>MRSA</italic> of all NHC-Ag(I)OAc complexes has been investigated utilizing the Kirby-Bauer disk diffusion method. <italic>In vitro</italic> MTT-based cytotoxicity assays against the human renal cancer cell line Caki-1 were carried out on all complexes and additionally against the human breast cancer cell line MCF-7 on all 4,5-diaryl-NHC silver(I) acetate as well as on all Ru(II)-NHC and Au(I)-NHC complexes. Lowest IC<sub>50</sub> values down to 0.51 (± 0.07) &#956;M against Caki-1 and 1.4 (± 0.1) &#956;M against MCF-7 have been found for the most promising NHC-silver(I) acetate complex 1,3-di(<italic>p</italic>-methylbenzyl)-4,5-di(<italic>p</italic>-methylphenyl)imidazol-2-ylidene silver(I) acetate, which is currently under further investigation. Moreover, after identifying Ag(I)-NHC lead structures and subsequently transmetallating them to their ruthenium- and gold-derivatives, four promising Ru(II)-NHC and Au(I)-NHC derivatives have been discovered.
Type of material: Doctoral Thesis
Publisher: University College Dublin. School of Chemistry and Chemical Biology
Qualification Name: Ph.D.
Copyright (published version): 2013 the author
Keywords: AntibacterialCytotoxicityGoldN-heterocyclic carbenesSilverTransition metals
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Language: en
Status of Item: Peer reviewed
Appears in Collections:Chemistry Theses

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