Synthesis and structural characterization of copper(I) complexes bearing N-methyl-1,3,5-triaza-7-phosphaadamantane (mPTA)

Porchia, Marina; Benetollo, Franco; Refosco, Fiorenzo; Tisato, Francesco; Marzano, Cristina; Gandin, Valentina

doi:10.1016/j.jinorgbio.2009.09.005

Cited by 60 publications

(34 citation statements)

References 42 publications

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“…These compounds have shown cytotoxic activity against a wide panel of human tumour cell lines belonging to a variety of tumour types, including cisplatin and multidrug resistant phenotypes [13][14][15][16]. These results support the view that phosphino copper(I) complexes adopt mechanisms of action different from the DNA damage induced by cisplatin.…”

Section: Introductionsupporting

confidence: 65%

“…Looking for less toxic copper compounds, we have recently prepared a series of more hydrophilic copper(I) derivatives including the water soluble tris(hydroxymethyl) phosphine (thp) and 1,3,5-triaza-7-phosphaadamantane (PTA) phosphine ligands, either alone [13,14] or in combination with hydrophilic scorpionates [15,16]. These compounds have shown cytotoxic activity against a wide panel of human tumour cell lines belonging to a variety of tumour types, including cisplatin and multidrug resistant phenotypes [13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxicity in human cancer cells and mitochondrial dysfunction induced by a series of new copper(I) complexes containing tris(2-cyanoethyl)phosphines

Zanella

Gandin

Porchia³

et al. 2010

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Over the last few years a lot of research has been done to develop novel metal-based anti-cancer drugs, with the aim of improving clinical effectiveness, reducing general toxicity, and broadening the spectrum of activity. The search for novel metal-based antitumour drugs other than Pt agents includes the investigation of the cytotoxic activity of copper(I/II) compounds. Among these copper agents, particular attention has been recently devoted to hydrophilic copper(I) species bearing phosphines because of their noteworthy stability in aqueous media together with their remarkable in vitro cytotoxic activity. In this study we report on the synthesis, characterization and cytotoxic assays of a series of Cu(I) complexes with tris(2-cyanoethyl)phosphine (PCN) and bis(2-cyanoethyl)phenylphosphine (PCNPh). They were prepared by reaction of [Cu(CH(3)CN)(4)](+) or CuX(2) precursors with the pertinent phosphine in acetone or acetonitrile solutions producing compounds of the following formulation: [Cu(PCN)(2)](+) 2, [Cu(CH(3)CN)(PCN)](+) 3, [Cu(X)(PCN)] (X = Cl, 4; Br, 5), and [Cu(PCNPh)(2)](+) 6. The new copper(I) complexes were tested for their cytotoxic properties against a panel of several human tumour cell lines. Cellular copper uptake rate was correlated with cell growth inhibition in 2008 human ovarian cancer cells. Moreover, copper(I)-PCN complexes were evaluated for their ability to alter the most relevant mitochondrial pathophysiological parameters such as respiration, coupling, ATP-synthetase activity and membrane potential in isolated mitochondria. These data were correlated with changes in mitochondrial membrane potential and production of reactive oxygen species (ROS) in drug-treated 2008 cells.

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Section: Introductionsupporting

confidence: 65%

Section: Introductionmentioning

confidence: 99%

Cytotoxicity in human cancer cells and mitochondrial dysfunction induced by a series of new copper(I) complexes containing tris(2-cyanoethyl)phosphines

Zanella

Gandin

Porchia³

et al. 2010

Invest New Drugs

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“…Thp was prepared in accordance with the literature methods [47,48]. The copper complexes [Cu(thp) 4 ]PF 6 1 [38] and [Cu(PTA) 4 ]PF 6 4 have been prepared as previously reported [45]. Ph 3 PAuCl was synthesized from tetrachloroauric acid and a double molar amount of PPh 3 in ethyl alcohol as previously reported [49,50] (2) To an acetonitrile solution (40 mL) of AgPF 6 (0.253 g, 1.0 mmol), tris(hydroxymethyl)phosphine, thp, (0.521 g, 4.2 mmol) was added at room temperature.…”

Section: Synthesismentioning

confidence: 99%

“…The coordination ability of such an anion is negligible, thus preventing its direct coordination to the metal, which is common for other anions as, for example, iodide [45]. In addition, PF 6 ensures good aqueous solubility of the metal salts and displays a typical septet in the 31 P NMR spectrum, allowing characterization of charged complexes in deuterated solvents (see Experimental Section).…”

Section: Synthesis and Characterization Of The Complexesmentioning

confidence: 99%

“…[Cu(PTA) 4 ] + 4 [41][42][43][44][45] was found to be roughly 1.5-fold more powerful than cisplatin towards human non-small cell lung carcinoma cells [45], and to be equally cytotoxic in both the cisplatinsensitive and -resistant sublines of human ovarian and cervical squamous carcinoma cells ruling out the occurrence of crossresistance phenomena. Taken together, these results again confirm a mechanism of action for water soluble copper(I) complexes different from the covalent binding to DNA shown by platinum based drugs, thus suggesting a reduced genotoxic potential for this class of copper (I) complexes.…”

Section: Introductionmentioning

confidence: 99%

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In vitro antitumour activity of water soluble Cu(I), Ag(I) and Au(I) complexes supported by hydrophilic alkyl phosphine ligands

Santini

Pellei

Papini

et al. 2011

Journal of Inorganic Biochemistry

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Complexes of Copper(I) Thiocyanate with Monodentate Phosphine and Pyridine Ligands and the P(,N)‐Donor Diphenyl(2‐pyridyl)phosphine

et al. 2014

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Copper(I) thiocyanate derivatives were prepared by the reaction of CuNCS with pyridine (py) and tertiary monophosphine ligands [PR3 in general; in detail: PPh3, triphenylphosphine, P(4‐FPh)3, tris(4‐fluorophenyl)phosphine)], as well as the potentially bidentate ligand diphenyl(2‐pyridyl)phosphine (PPh2py). Mechanochemical methods were used in some cases to investigate stoichieometries that were not easily accessible by conventional solution syntheses. Three forms of the resulting adducts of CuNCS/PR3/py‐base (1:3–n:n) stoichiometry―all containing four‐coordinate copper(I) atoms and monodentate N‐thiocyanate groups―were confirmed crystallographically. Mononuclear arrays are defined for [(PPh2py)3–n(py)nCuNCS], n = 0, 1, 2, the monodentate thiocyanate being N‐coordinated in all; two polymorphs are observed for the n = 2 complex, both crystallizing in monoclinic P21 (Z = 2) cells with similar cell dimensions, but with aromatic components eclipsed about the Cu–P bond in the PPh3 complex, and staggered in the PPh2py complex. Bridging thiocyanate groups are found in the 1:1:1 CuNCS/PPh2py/2‐methylpyridine (mpy) and P(4‐FPh)3/mpy complexes, wherein centrosymmetric dimers with eight‐membered central rings are obtained: [(R3P)(mpy)Cu(NCS)2Cu(PR3)(mpy)], as is also the case in the parent 1:2 CuNCS/PPh2py adduct [(pyPh2P)2Cu(NCS)2Cu(PPh2py)2]. For the 1:1:1 CuNCS/P(4‐FPh)3/py and PPh3/Brmpy (Brmpy = 3‐bromo‐4‐methylpyridine) adducts, and, likely, CuNCS/PPh2py/py (1:1:1), single‐stranded polymers of the form [···Cu(NCS)(PR3)(py‐base)(Cu)···](∞|∞) with linearly bridging NCS ligands were obtained. Some derivatives, representative of all forms, display medium to strong green to blue luminescence when excited with radiation at 365 nm. The 31P CPMAS NMR spectroscopic data clearly differentiate the inequivalent phosphorus positions within each system, showing a wide range of 1J(31P,63/65Cu) values ranging from 965 Hz for [Cu(NCS)(PPh2py)3] to 1540 Hz for dimeric [(4‐FPh)3P(mpy)Cu(NCS)2Cu(P(4‐FPh)3)(mpy)], reflecting the large variations in the Cu–P bond length.

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Synthesis and structural characterization of copper(I) complexes bearing N-methyl-1,3,5-triaza-7-phosphaadamantane (mPTA)

Cited by 60 publications

References 42 publications

Cytotoxicity in human cancer cells and mitochondrial dysfunction induced by a series of new copper(I) complexes containing tris(2-cyanoethyl)phosphines

Cytotoxicity in human cancer cells and mitochondrial dysfunction induced by a series of new copper(I) complexes containing tris(2-cyanoethyl)phosphines

In vitro antitumour activity of water soluble Cu(I), Ag(I) and Au(I) complexes supported by hydrophilic alkyl phosphine ligands

Complexes of Copper(I) Thiocyanate with Monodentate Phosphine and Pyridine Ligands and the P(,N)‐Donor Diphenyl(2‐pyridyl)phosphine

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