Anticancer activity, DNA-binding and DNA-denaturing aptitude of palladium(II) dithiocarbamates

Amir, Muhammad Kashif; Khan, Shahan Zeb; Hayat, Faisal; Hassan, Abbas; Butler, Ian S.; Rehman, Zia ur

doi:10.1016/j.ica.2016.06.036

Cited by 65 publications

(30 citation statements)

References 44 publications

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“…[5] Thus, the limitations of platinum chemotherapeutic metallopharmaceuticals lead to development towards non-platinum chemotherapeutics aiming to increase the proficiency of such medications. [9][10][11] For instance, the initial biocidal properties of triorganotin compounds like tripropyltin, triphenyltin and tributyltin were studied by Van der Kerk and Luijten [12] during 1954, and these compounds were further known to battle the parasite that roots for schistosomiasis in human beings. [9][10][11] For instance, the initial biocidal properties of triorganotin compounds like tripropyltin, triphenyltin and tributyltin were studied by Van der Kerk and Luijten [12] during 1954, and these compounds were further known to battle the parasite that roots for schistosomiasis in human beings.…”

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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“…Non-classical (noncovalent) DNA binding modes such as intercalation or groove-binding play a vital role in the pursuit of more efficient and more target-specific drugs displaying fewer side effects [7]. In the field of bioinorganic chemistry, the DNA-binding of platinum [8], ruthenium [9,10], copper [11,12], palladium [13], and gold [14] complexes has been extensively studied due to the array of readily available ligands for coordination, together with the different geometries, coordination numbers, redox potentials, kinetic and thermodynamic characteristics of the resultant complexes. Ligands such as the π-delocalized planar polypyridyls (e.g., diphenylphenazine) have afforded moderate-to-strong DNA-intercalating complexes [15,16].…”

Section: Introductionmentioning

confidence: 99%

DNA-Binding and Anticancer Activity of Binuclear Gold(I) Alkynyl Complexes with a Phenanthrenyl Bridging Ligand

et al. 2020

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3,6-Diethynyl-9,10-diethoxyphenanthrene (4) was synthesized from phenanthrene and employed in the synthesis of the binuclear gold(I) alkynyl complexes (R3P)Au(C≡C–3-[C14H6-9,10-diethoxy]-6–C≡C)Au(PR3) (R = Ph (5a), Cy (5b)). The diyne 4 and complexes 5a and 5b were characterized by NMR spectroscopy, mass spectrometry, and elemental analysis. UV-Vis spectroscopy studies of the metal complexes and precursor diyne show strong π → π* transitions in the near UV region that red shift by ca. 50 nm upon coordination at the gold centers. The emission spectrum of 4 shows an intense fluorescence band centered at 420 nm which red shifts, slightly upon coordination of 4 to gold. Binding studies of 4, 5a, and 5b against calf thymus DNA were carried out, revealing that 4, 5a, and 5b have ≥40% stronger binding affinities than the commonly used intercalating agent ethidium bromide. The molecular docking scores of 4, 5a, and 5b with B-DNA suggest a similar trend in behavior to that observed in the DNA-binding study. Unlike the ligand 4, promising anticancer properties for 5a and 5b were observed against several cell lines; the DNA binding capability of the precursor alkyne was maintained, and its anticancer efficacy enhanced by the gold centers. Such phenanthrenyl complexes could be promising candidates in certain biological applications because the two components (phenanthrenyl bridge and metal centers) can be altered independently to improve the targeting of the complex, as well as the biological and physicochemical properties.

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“…Different metal complexes of dithiocarbamates with promising anticancer activities have been studied [ 13 , 14 , 15 ]. The mechanism of action of the studied metal dithiocarbamate complexes is similar to that of cisplatin , as they strongly and irreversibly bind to DNA [ 16 , 17 , 18 ]. They also show a better activity on cisplatin-resistant cancer cell lines [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structures and Anticancer Studies of Morpholinyldithiocarbamato Cu(II) and Zn(II) Complexes

et al. 2020

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Cu(II) and Zn(II) morpholinyldithiocarbamato complexes, formulated as [Cu(MphDTC)2] and [Zn(μ-MphDTC)2(MphDTC)2], where MphDTC is morpholinyldithiocarbamate were synthesized and characterized by elemental analysis, spectroscopic techniques and single-crystal X-ray crystallography. The molecular structure of the Cu(II) complex revealed a mononuclear compound in which the Cu(II) ion was bonded to two morpholinyl dithiocarbamate ligands to form a four-coordinate distorted square planar geometry. The molecular structure of the Zn(II) complex was revealed to be dinuclear, and each metal ion was bonded to two morpholinyl dithiocarbamate bidentate anions, one acting as chelating ligand, the other as a bridge between the two Zn(II) ions. The anticancer activity of the morpholinyldithiocarbamate ligand, Cu(II) and Zn(II) complexes were evaluated against renal (TK10), melanoma (UACC62) and breast (MCF7) cancer cells by a Sulforhodamine B (SRB) assay. Morpholinyldithiocarbamate was more active than the standard drug parthenolide against renal and breast cancer cell lines, and [Zn(μ-MphDTC)2(MphDTC)2] was the most active complex against breast cancer. The copper(II) complex had a comparable activity with the standard against renal and breast cancer cell lines but showed an enhanced potency against melanoma when compared to parthenolide.

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Anticancer activity, DNA-binding and DNA-denaturing aptitude of palladium(II) dithiocarbamates

Cited by 65 publications

References 44 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

DNA-Binding and Anticancer Activity of Binuclear Gold(I) Alkynyl Complexes with a Phenanthrenyl Bridging Ligand

Synthesis, Crystal Structures and Anticancer Studies of Morpholinyldithiocarbamato Cu(II) and Zn(II) Complexes

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