Naphthalimide gold(i) phosphine complexes as anticancer metallodrugs

Bagowski, Christoph P.; You, Ya; Scheffler, Heike; Vlecken, Danielle H.; Schmitz, Daan J.; Ott, Ingo

doi:10.1039/b912378d

Cited by 89 publications

(73 citation statements)

References 43 publications

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“…Development of gold(I) phosphine complexes bearing a thionaphthalimide ligand such as 56 was found to be an important design strategy to enhance the antiproliferative activity of gold(I)-complexes. 79 Compound 56 was shown to display significant growth inhibitory effects in MCF-7 breast cancer and HT-29 colon carcinoma cells. The presence of a thionaphthalimide ligand also increased the cellular uptake and accumulation of gold in the nuclei of tumour cells compared to the naphthalimide free analogue.…”

Section: 8-naphthalimide-oligonucleotide/peptide Nucleotide Conjugatesmentioning

confidence: 99%

Recent advances in the development of 1,8-naphthalimide based DNA targeting binders, anticancer and fluorescent cellular imaging agents

et al. 2013

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The development of functional 1,8-naphthalimide derivatives as DNA targeting, anticancer and cellular imaging agents is a fast growing area and has resulted in several such derivatives entering into clinical trials.This review gives an overview of the many discoveries and the progression of the use of 1,8-naphthalimides as such agents and their applications to date; focusing mainly on mono-, bis-naphthalimide based structures, and their various derivatives (e.g. amines, polyamine conjugates, heterocyclic, oligonucleotide and peptide based, and those based on metal complexes). Their cytotoxicity, mode of action and cell-selectivity are discussed and compared. The rich photophysical properties of the naphthalimides (which are highly dependent on the nature and the substitution pattern of the aryl ring) make them prime candidates as probes as the changes in spectroscopic properties such as absorption, dichroism, and fluorescence can all be used to monitor their binding to biomolecules. This also makes them useful species for monitoring their uptake and location within cells without the use of co-staining. The photochemical properties of the compounds have also been exploited, for example, for photocleavage of nucleic acids and for the destruction of tumour cells.

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Section: 8-naphthalimide-oligonucleotide/peptide Nucleotide Conjugatesmentioning

confidence: 99%

Recent advances in the development of 1,8-naphthalimide based DNA targeting binders, anticancer and fluorescent cellular imaging agents

et al. 2013

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“…1) and its thiosugar analogue (GoPIsugar) led to cytotoxic activities in the low micromolar range against glioblastoma or breast cancer cells in vitro [19,20]. Ott et al combined Et 3 P-Au(I) with an anticancer agent that acts through DNA intercalation [21,22]. The resulting Au-Naphth-1 compound ( Fig.…”

Section: Introductionmentioning

confidence: 95%

Gold(I) NHC-based homo- and heterobimetallic complexes: synthesis, characterization and evaluation as potential anticancer agents

et al. 2015

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While N-heterocyclic carbenes (NHC) are ubiquitous ligands in catalysis for organic or industrial syntheses, their potential to form transition metal complexes for medicinal applications has still to be exploited. Within this frame, we synthesized new homo- and heterobimetallic complexes based on the Au(I)-NHC scaffold. The compounds were synthesized via a microwave-assisted method developed in our laboratories using Au(I)-NHC complexes carrying a pentafluorophenol ester moiety and another Au(I) phosphane complex or a bipyridine ligand bearing a pendant amine function. Thus, we developed two different methods to prepare homo- and heterobimetallic complexes (Au(I)/Au(I) or Au(I)/Cu(II), Au(I)/Ru(II), respectively). All the compounds were fully characterized by several spectroscopic techniques including far infrared, and were tested for their antiproliferative effects in a series of human cancer cells. They showed moderate anticancer properties. Their toxic effects were also studied ex vivo using the precision-cut tissue slices (PCTS) technique and initial results concerning their reactivity with the seleno-enzyme thioredoxin reductase were obtained.

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“…These are generally derivatives of the thiol containing amino acid cysteine (Cys), and are subsequently used in solid phase peptide synthesis as a means of incorporating the gold(I) phosphine into the peptide sequence [5]. This approach has been successfully employed; however, these synthetic procedures can potentially be time consuming, restricted by the harsh chemical synthesis conditions required and ultimately would be limited to peptide sequences that can readily be synthesized.…”

Section: Introductionmentioning

confidence: 99%

“…It has been recognized that this offers an opportunity to incorporate a bioactive ligand in its place [3][4][5][6][7]. One attractive class of bioactive and biocompatible ligands are peptides, which offer targeting and therapeutic opportunities, e.g.…”

Section: Introductionmentioning

confidence: 99%