Synthesis and Crystal Structures of Bromo(1,10-phenanthroline-N,N′)tris(2-cyanoethyl)phosphinocopper(I) and Bromo(2,2′-bipyridine-N,N′)tris(2-cyanoethyl)phosphinocopper(I)

Al-Fayez, Sahar; Abdel‐Rahman, Laila H.; Shemsi, Ahsan M.; Seddigi, Zaki S.; Fettouhi, Mohammed

doi:10.1007/s10870-007-9198-5

Cited by 6 publications

(5 citation statements)

References 12 publications

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“…A search in the CCDC database shows that other chemically related mononuclear Cu(I) complexes in which the metal has an N 2 PX donor set (with the N 2 atoms belonging to a cyclic imine) are only about 20 (see Supporting Information and references therein) and that only three complexes including PCN have been structurally characterized so far. , In the series of [CuX(phen)(PCN)] complexes (X = Cl, Br, or I), the change of the halide has little effect on other bonds involving copper. Considering all the complexes grouped in Table S1, Supporting Information, the mean Cu–N distance in chloride, bromide, and iodide complexes is, respectively, 2.095, 2.092, and 2.081 Å, whereas some dependence from the pertinent halide is observed for Cu–P distances, the mean values being 2.180, 2.190, and 2.201 Å for chloride, bromide and iodide, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…[CuCl(PCN)] ( 1 ) and [CuBr(PCN)] ( 2 ) were prepared according to the literature . Copper complexes 3 – 10 were synthesized with a method similar to that reported by Al-Fayez et al, here detailed for [CuCl(phen)(PCN)], 5 . In a two-necked round-bottom flask equipped with a condenser, under stirring, an equimolar amount of copper(I) chloride (99 mg; 1 mmol), PCN (193 mg; 1 mmol), and phen (198 mg; 1 mmol) was dissolved in degassed dimethylformamide (20 mL) at room temperature under a nitrogen atmosphere.…”

Section: Methodsmentioning

confidence: 99%

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Novel Mixed-Ligand Copper(I) Complexes: Role of Diimine Ligands on Cytotoxicity and Genotoxicity

Gandin

Porchia²,

Tisato³

et al. 2013

J. Med. Chem.

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Novel tetrahedral copper(I) mixed-ligand complexes of the type [Cu(X)(N(∩)N)(PCN)], 3-10, where X = Cl or Br, N(∩)N = 2,2'-bipyridine (bipy), 1,10-phenanthroline (phen), 5,6-dimethyl-1,10-phenanthroline (dmp), and dipyrido-[3,2-d:2',3'-f]-quinoxaline (dpq), and PCN = tris-(2-cyanoethyl)phosphine, have been synthetized and characterized by NMR, ESI-MS, and X-ray diffraction on two representative examples, [CuCl(phen)(PCN)]·DMF (5·DMF) and [CuBr(dpq)(PCN)]·2DMF (10·2DMF). Cu(I) complexes were evaluated for their in vitro antitumor properties against a panel of human cancer cell lines, including cisplatin- and multidrug-resistant sublines. The most effective complex, [CuCl(dpq)(PCN)] (9), exhibited nanomolar cytotoxicity toward both sensitive and resistant cancer cells, but it significantly inhibited the growth of cultured normal cells. In vitro DNA assays and single cell gel electrophoresis revealed that 9 induced DNA fragmentation resulting in cell apoptosis. In parallel, fluorescence in situ hybridization (FISH) micronucleus assay attested high levels of genotoxicity following treatment of peripheral blood lymphocytes with complex 9, suggesting that the potential risk posed by diimine metal complexes should be carefully reconsidered.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Novel Mixed-Ligand Copper(I) Complexes: Role of Diimine Ligands on Cytotoxicity and Genotoxicity

Gandin

Porchia²,

Tisato³

et al. 2013

J. Med. Chem.

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“…For related structures and their applications, see: Dehghanpour et al (2006Dehghanpour et al ( , 2008; Saha et al (2010Saha et al ( , 2011a; Habibi et al (2007); Morshedi et al (2009); Al-Fayez et al (2007); Kickelbick et al (2003); Massa et al (2009); Chen et al (2012); Roy et al (2011). For standard bond lengths, see: Allen et al (1987).…”

Section: Related Literaturementioning

confidence: 99%

“…Although reports of copper(I) complexes are numerous, limited work has been done on mixed ligand copper(I) complexes of the type [Cu(Schiff base)PX] (X= Cl, Br, I) (Dehghanpour et al, 2006;Saha et al, 2010Saha et al, , 2011aSaha et al, , 2011bHabibi et al, 2007;Morshedi et al, 2009;Al-Fayez et al, 2007;Kickelbick et al, 2003). This study is a part of our ongoing efforts to synthesize and characterize copper(I) complexes with bidentate Schiff base ligands.…”

Section: Crystal Datamentioning

confidence: 99%

[4-Bromo-N-(pyridin-2-ylmethylidene)aniline-κ²N,N′]iodido(triphenylphosphane-κP)copper(I)

et al. 2012

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Key indicators: single-crystal X-ray study; T = 120 K; mean (C-C) = 0.007 Å; R factor = 0.038; wR factor = 0.110; data-to-parameter ratio = 18.1.In the title compound, [CuI(C 12 H 9 BrN 2 )(C 18 H 15 P)], the Cu I ion is bonded to one I atom, one triphenylphosphane P atom and two N atoms of the diimine ligand in a distorted tetrahedral geometry. The Schiff base acts as a chelating ligand and coordinates to the Cu I atom via two N atoms. In the diimine ligand, the dihedral angle between the pyridine and bromophenyl rings is 19.2 (2) . In the crystal, molecules are connected by -stacking interactions between inversionrelated pyridine rings [centroid-centroid distance = 3.404 (3) Å ]. Related literature

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“…Coordination chemistry of PCN with groups 9 and 10 transition metals (mainly second and third row elements) has been widely explored [22][23][24][25], while few reports have been reported with group 11 metals. Examples include crystallographically characterized homoleptic [Ag(PCN) 2 ] + [26] and [Au(PCN) 2 ] + [27] together with few heteroleptic derivatives including copper complexes such as [CuBr (PCN)] [22] and [CuX(PCN)(N ∩ N)] [28] where X = Br, Cl and N ∩ N = o-phenantroline or bipyridine.…”

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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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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Synthesis and Crystal Structures of Bromo(1,10-phenanthroline-N,N′)tris(2-cyanoethyl)phosphinocopper(I) and Bromo(2,2′-bipyridine-N,N′)tris(2-cyanoethyl)phosphinocopper(I)

Cited by 6 publications

References 12 publications

Novel Mixed-Ligand Copper(I) Complexes: Role of Diimine Ligands on Cytotoxicity and Genotoxicity

Novel Mixed-Ligand Copper(I) Complexes: Role of Diimine Ligands on Cytotoxicity and Genotoxicity

[4-Bromo-N-(pyridin-2-ylmethylidene)aniline-κ²N,N′]iodido(triphenylphosphane-κP)copper(I)

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

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Synthesis and Crystal Structures of Bromo(1,10-phenanthroline-N,N′)tris(2-cyanoethyl)phosphinocopper(I) and Bromo(2,2′-bipyridine-N,N′)tris(2-cyanoethyl)phosphinocopper(I)

Cited by 6 publications

References 12 publications

Novel Mixed-Ligand Copper(I) Complexes: Role of Diimine Ligands on Cytotoxicity and Genotoxicity

Novel Mixed-Ligand Copper(I) Complexes: Role of Diimine Ligands on Cytotoxicity and Genotoxicity

[4-Bromo-N-(pyridin-2-ylmethylidene)aniline-κ2N,N′]iodido(triphenylphosphane-κP)copper(I)

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

Contact Info

Product

Resources

About

[4-Bromo-N-(pyridin-2-ylmethylidene)aniline-κ²N,N′]iodido(triphenylphosphane-κP)copper(I)