The synthesis, spectroscopic characterization and anticancer activity of new mono and binuclear phosphanegold(<scp>i</scp>) dithiocarbamate complexes

Altaf, Muhammad; Monim-ul-Mehboob, Muhammad; Isab, Anvarhusein A.; Dhuna, Vikram; Bhatia, Gaurav; Dhuna, Kshitija; Altuwaijri, Saleh

doi:10.1039/c4nj00747f

Cited by 44 publications

(27 citation statements)

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“…[21][22][23][24] The roles of sulfur and Ph 2 Sn groups as bridging ligands have been widely explored to construct polynuclear sulfur-rich metal complexes. [26][27][28][29][30][31] The unique redox property of the sulfur atom makes it a key residue for enzyme catalysis, protein folding and redox signaling, which are important processes required for cellular energy metabolism, motility and subsistence of cellular systems. Recently, a good number of reports emphasizing the ability of metal dithiocarbamate complexes as potential anticancer agents have been published.…”

Section: Introductionmentioning

confidence: 99%

Binuclear diphenyltin(IV)dithiocarbamate complexes bearing functionalized linkers: Synthesis, spectral characterization, DFT and in vitro anticancer activity

Pillai

Patel

Buch

et al. 2018

Applied Organom Chemis

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A new series of diphenyltin(IV)dithiocarbamate complexes of the type [(Ph2Sn)2‐μ2‐bis{(κ2S,S‐S2CN(R)CH2CONHC6H4)2SO2}] {R = Cy (1), iPr (2), nBu (3)} and [(Ph2Sn)2‐μ2‐bis{(κ2S,S‐S2CN(R)CH2CONH)2C6H4}] {R = Cy (4), iPr (5)} has been efficiently synthesized and characterized by the relevant spectroscopic (1H, 13C, 1H DOSY, 119Sn NMR, ESI MS, UV–visible absorption, IR) and thermogravimetric methods. Density functional theory level calculations have been carried out to reinforce the experimental data. Compounds have been screened for their in vitro anticancer ability against a malignant human tumor HepG2 (hepatoma) cell line by MTT assay. Remarkably, the anticancer activities of binuclear organotin(IV)dithiocarbamate complexes 1–5 are evidently boosted as high as 22‐fold in 1 (3.32 ± 0.14 μM), 44‐fold in 2 (1.77 ± 0.11 μM), 37‐fold in 3 (2.02 ± 0.47 μM), 8 fold in 4 (8.72 ± 0.19 μM) and 29‐fold in 5 (2.60 ± 0.67 μM), compared with the reference drug cisplatin (75.67 ± 0.51 μM). Morphological proofs like shrinking of cells specifies the induction of apoptosis as part of the mechanism of action of these compounds, which is further reinforced by the individual staining of the cells by acridine orange/ethidium bromide.

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Section: Introductionmentioning

confidence: 99%

Binuclear diphenyltin(IV)dithiocarbamate complexes bearing functionalized linkers: Synthesis, spectral characterization, DFT and in vitro anticancer activity

Pillai

Patel

Buch

et al. 2018

Applied Organom Chemis

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“…Prominent amongst these are gold dithiocarbamates, including phosphane gold(I) dithiocarbamates. The exploration of the potential anti-cancer activity of phosphane gold(I) dithiocarbamates dates back over a decade [12] and studies on related compounds continue [13][14][15]. Recently, phosphanegold(I) dithiocarbamates, functionalised with ethylhydroxy groups, proved to be very effective against breast cancer MCF-7R cell lines and to induce cell death (apoptosis or necrosis) via both extrinsic and intrinsic pathways [16].…”

Section: Introductionmentioning

confidence: 99%

Bis(phosphane)copper(I) and silver(I) dithiocarbamates: crystallography and anti-microbial assay

Jamaludin

Halim

Khoo

et al. 2016

Zeitschrift Für Kristallographie - Crystalline Materials

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Keywords: Copper(I) / silver(I) / dithiocarbamate / crystal structure analysis / X-ray diffraction Abstract.The crystal and molecular structures of (Ph3P)2M[S2CN(Me)CH2CH2OH], M = Cu, isolated as a 1:1 dichloromethane solvate (1.CH2Cl2), and M = Ag (4) show the central metal atom to be coordinated by a symmetrically (1.CH2Cl2) and asymmetrically chelating (4) dithiocarbamate ligand. The distorted tetrahedral geometries are completed by two PPh3 ligands. The presence of hydroxyl-O-H … S(dithiocarbamate) hydrogen bonds leads to centrosymmetric dimeric aggregates in each crystal structure. In the molecular packing of 1.CH2Cl2, channels comprising 1 are formed via aryl-C-H … O interactions with the solvent molecules associated with the walls of the channels via methylene-C-H … S, π(aryl) interactions. For 4, the dimeric aggregates are connected via a network of aryl-C-H … π(aryl) interactions. Preliminary screening for antimicrobial activity was conducted. The compounds were only potent against Gram-positive bacteria. Some further selectivity in activity was noted. Most notably, all compounds were active against methicillin resistant Staphylococcus aureus.

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“…Series of 1a – c , which have no gold in their structures, as well as [ClAu(µ‐dppm)AuCl] exhibited low potency in inhibiting cell proliferation and significantly lower in vitro cytotoxicities against the studied cancer cell lines, compared to series of 2a – c . The improvement of the IC 50 values of the heterometallic complexes suggests a cooperative effect of both metal fragments.…”

Section: Resultsmentioning

confidence: 99%

Heterobimetallic Pt^II‐Au^I Complexes Comprising Unsymmetrical 1,1‐Bis(diphenylphosphanyl)methane Bridges: Synthesis, Photophysical, and Cytotoxic Studies

et al. 2019

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In the present work, a series of aryl‐cycloplatinated(II) complexes with general formula [Pt(C^N)(Ar)(κ1‐dppm)], 1, [C^N = 7,8‐benzoquinolinyl (bzq) or 2‐phenylpyridinyl (ppy); Ar = C6F5 or p‐MeC6H4, dppm = 1,1‐bis(diphenylphosphanyl)methane] was employed in the reaction with AuCl(SMe2) in order to generate heterobimetallic PtII‐AuI complexes, [Pt(C^N)(Ar)(µ‐dppm)Au(Cl)], 2, featuring a dppm bridge between the metal centers. The expectation was to induce metallophilic character into the excited state and to reduce non‐radiative deactivation pathways of the dangling auxiliary κ1‐dppm ligand through molecular motions, to improve the photophysical properties. After characterization of the new complexes by means of NMR spectroscopy and X‐ray crystallography technique, the photophysical properties of all the complexes were investigated by UV/Vis and photoluminescence spectroscopy. Both of the monometallic complexes and heterobimetallic products have shown to be luminescent in different states and temperature conditions. However, by addition of AuI, the impact on the photophysics of the heterobimetallic products in relation to the precursors with dangling dppm is minimal, a finding which can be attributed to the absence of a PtII‐AuI bond in these compounds. Indeed, the character of the excited states of the monomer PtII complexes and their corresponding bimetallic PtII‐AuI ones are similar, as confirmed by density functional theory (DFT) and time resolved DFT (TD‐DFT) calculations. The cytotoxic activities of the compounds along with that of [ClAu(µ‐dppm)AuCl] were evaluated against human breast cancer (MCF‐7), human lung cancer (A549), human ovarian cancer (SKOV3) and non‐tumorigenic epithelial breast (MCF‐10A) cell lines. The highest activity was found for the heterometallic Pt‐Au species, suggesting a cooperative effect of both metallic fragments. The most cytotoxic compound, i.e. [Pt(bzq)(p‐MeC6H4)(µ‐dppm)Au(Cl)], 2b, effectively causes cell death in MCF‐7 cancer cell line by inducing apoptosis. Fluorescence microscopy experiments for 2a were performed.

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The synthesis, spectroscopic characterization and anticancer activity of new mono and binuclear phosphanegold(i) dithiocarbamate complexes

Abstract: Four new gold(i) complexes were synthesized and characterized. The structure of [t-Bu3PAuS2CN(C7H7)2] was determined by X-ray diffraction.

Cited by 44 publications

References 53 publications

Binuclear diphenyltin(IV)dithiocarbamate complexes bearing functionalized linkers: Synthesis, spectral characterization, DFT and in vitro anticancer activity

Binuclear diphenyltin(IV)dithiocarbamate complexes bearing functionalized linkers: Synthesis, spectral characterization, DFT and in vitro anticancer activity

Bis(phosphane)copper(I) and silver(I) dithiocarbamates: crystallography and anti-microbial assay

Heterobimetallic Pt^II‐Au^I Complexes Comprising Unsymmetrical 1,1‐Bis(diphenylphosphanyl)methane Bridges: Synthesis, Photophysical, and Cytotoxic Studies

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The synthesis, spectroscopic characterization and anticancer activity of new mono and binuclear phosphanegold(i) dithiocarbamate complexes

Abstract: Four new gold(i) complexes were synthesized and characterized. The structure of [t-Bu3PAuS2CN(C7H7)2] was determined by X-ray diffraction.

Cited by 44 publications

References 53 publications

Binuclear diphenyltin(IV)dithiocarbamate complexes bearing functionalized linkers: Synthesis, spectral characterization, DFT and in vitro anticancer activity

Binuclear diphenyltin(IV)dithiocarbamate complexes bearing functionalized linkers: Synthesis, spectral characterization, DFT and in vitro anticancer activity

Bis(phosphane)copper(I) and silver(I) dithiocarbamates: crystallography and anti-microbial assay

Heterobimetallic PtII‐AuI Complexes Comprising Unsymmetrical 1,1‐Bis(diphenylphosphanyl)methane Bridges: Synthesis, Photophysical, and Cytotoxic Studies

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Heterobimetallic Pt^II‐Au^I Complexes Comprising Unsymmetrical 1,1‐Bis(diphenylphosphanyl)methane Bridges: Synthesis, Photophysical, and Cytotoxic Studies