1:2 Adducts of copper (I) halides with 1,2-bis(di-2-pyridylphosphino)ethane: solid state and solution structural studies and antitumour activity

R.J. Bowen, Maribel Navarro, Anne-Marie Shearwood, P.C. Healy, Brian Skelton, Aleksandra Filipovska, Susan Berners-Price

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Abstract

The 1 : 2 adducts of copper(I) halides with 1,2-bis(2-pyridylphosphino)ethane (d2pype) have been synthesized and solution properties characterized by variable temperature 1H, 31P and 65Cu NMR spectroscopy. Single-crystal structure determinations for the chloride, bromide and iodide complexes show these to crystallize from acetonitrile in the triclinic space group P as isostructural centrosymmetric dimers [(d2pype)Cu(μ-d2pype)2Cu(d2pype)]X2·(solvent) with a 12.6, b 12.7, c15.3 Å, α 84, β 67, γ 84°. In contrast to the analogous AuCl:2(d2pype) and AgNO3:2(d2pype) adducts, in solution these CuX:2(d2pype) adducts (where X = Cl, Br and I) exist almost exclusively as bis-chelated monomeric [Cu(d2pype)2]X; evidence for an equilibrium between monomeric and dimeric forms is detected only for the CuCl adduct in methanol. Cytotoxicity studies in two human breast cancer lines and two matched liver progenitor cell lines indicate that [Cu(d2pype)2]Cl is non selectively toxic to both non-tumourigenic and tumourigenic cells. However, the analogous Au(I) compound [Au(d2pype)2]Cl, is toxic to highly tumourigenic cells and more selective in its toxicity to tumourigenic cells compared to non-tumourigenic cells. The significance of these results to the further development of selective, mitochondria-targeted, Au(I) antitumour complexes is discussed.
Original languageEnglish
Pages (from-to)10861-10870
JournalDalton Transactions
Volume2009
Issue number48
DOIs
Publication statusPublished - 2009

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Ethane
Poisons
Copper
Mitochondria
Iodides
Cytotoxicity
Bromides
Dimers
Liver
Nuclear magnetic resonance spectroscopy
Methanol
Toxicity
Chlorides
Crystal structure
Cells
Single crystals
Temperature
acetonitrile

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@article{98aebf69062349d9b66d1a6e8399afa2,
title = "1:2 Adducts of copper (I) halides with 1,2-bis(di-2-pyridylphosphino)ethane: solid state and solution structural studies and antitumour activity",
abstract = "The 1 : 2 adducts of copper(I) halides with 1,2-bis(2-pyridylphosphino)ethane (d2pype) have been synthesized and solution properties characterized by variable temperature 1H, 31P and 65Cu NMR spectroscopy. Single-crystal structure determinations for the chloride, bromide and iodide complexes show these to crystallize from acetonitrile in the triclinic space group P as isostructural centrosymmetric dimers [(d2pype)Cu(μ-d2pype)2Cu(d2pype)]X2·(solvent) with a 12.6, b 12.7, c15.3 {\AA}, α 84, β 67, γ 84°. In contrast to the analogous AuCl:2(d2pype) and AgNO3:2(d2pype) adducts, in solution these CuX:2(d2pype) adducts (where X = Cl, Br and I) exist almost exclusively as bis-chelated monomeric [Cu(d2pype)2]X; evidence for an equilibrium between monomeric and dimeric forms is detected only for the CuCl adduct in methanol. Cytotoxicity studies in two human breast cancer lines and two matched liver progenitor cell lines indicate that [Cu(d2pype)2]Cl is non selectively toxic to both non-tumourigenic and tumourigenic cells. However, the analogous Au(I) compound [Au(d2pype)2]Cl, is toxic to highly tumourigenic cells and more selective in its toxicity to tumourigenic cells compared to non-tumourigenic cells. The significance of these results to the further development of selective, mitochondria-targeted, Au(I) antitumour complexes is discussed.",
author = "R.J. Bowen and Maribel Navarro and Anne-Marie Shearwood and P.C. Healy and Brian Skelton and Aleksandra Filipovska and Susan Berners-Price",
year = "2009",
doi = "10.1039/b912281h",
language = "English",
volume = "2009",
pages = "10861--10870",
journal = "Dalton Transactions: the international journal for inorganic, organometallic and bioinorganic chemistry",
issn = "1477-9226",
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number = "48",

}

1:2 Adducts of copper (I) halides with 1,2-bis(di-2-pyridylphosphino)ethane: solid state and solution structural studies and antitumour activity. / Bowen, R.J.; Navarro, Maribel; Shearwood, Anne-Marie; Healy, P.C.; Skelton, Brian; Filipovska, Aleksandra; Berners-Price, Susan.

In: Dalton Transactions, Vol. 2009, No. 48, 2009, p. 10861-10870.

Research output: Contribution to journalArticle

TY - JOUR

T1 - 1:2 Adducts of copper (I) halides with 1,2-bis(di-2-pyridylphosphino)ethane: solid state and solution structural studies and antitumour activity

AU - Bowen, R.J.

AU - Navarro, Maribel

AU - Shearwood, Anne-Marie

AU - Healy, P.C.

AU - Skelton, Brian

AU - Filipovska, Aleksandra

AU - Berners-Price, Susan

PY - 2009

Y1 - 2009

N2 - The 1 : 2 adducts of copper(I) halides with 1,2-bis(2-pyridylphosphino)ethane (d2pype) have been synthesized and solution properties characterized by variable temperature 1H, 31P and 65Cu NMR spectroscopy. Single-crystal structure determinations for the chloride, bromide and iodide complexes show these to crystallize from acetonitrile in the triclinic space group P as isostructural centrosymmetric dimers [(d2pype)Cu(μ-d2pype)2Cu(d2pype)]X2·(solvent) with a 12.6, b 12.7, c15.3 Å, α 84, β 67, γ 84°. In contrast to the analogous AuCl:2(d2pype) and AgNO3:2(d2pype) adducts, in solution these CuX:2(d2pype) adducts (where X = Cl, Br and I) exist almost exclusively as bis-chelated monomeric [Cu(d2pype)2]X; evidence for an equilibrium between monomeric and dimeric forms is detected only for the CuCl adduct in methanol. Cytotoxicity studies in two human breast cancer lines and two matched liver progenitor cell lines indicate that [Cu(d2pype)2]Cl is non selectively toxic to both non-tumourigenic and tumourigenic cells. However, the analogous Au(I) compound [Au(d2pype)2]Cl, is toxic to highly tumourigenic cells and more selective in its toxicity to tumourigenic cells compared to non-tumourigenic cells. The significance of these results to the further development of selective, mitochondria-targeted, Au(I) antitumour complexes is discussed.

AB - The 1 : 2 adducts of copper(I) halides with 1,2-bis(2-pyridylphosphino)ethane (d2pype) have been synthesized and solution properties characterized by variable temperature 1H, 31P and 65Cu NMR spectroscopy. Single-crystal structure determinations for the chloride, bromide and iodide complexes show these to crystallize from acetonitrile in the triclinic space group P as isostructural centrosymmetric dimers [(d2pype)Cu(μ-d2pype)2Cu(d2pype)]X2·(solvent) with a 12.6, b 12.7, c15.3 Å, α 84, β 67, γ 84°. In contrast to the analogous AuCl:2(d2pype) and AgNO3:2(d2pype) adducts, in solution these CuX:2(d2pype) adducts (where X = Cl, Br and I) exist almost exclusively as bis-chelated monomeric [Cu(d2pype)2]X; evidence for an equilibrium between monomeric and dimeric forms is detected only for the CuCl adduct in methanol. Cytotoxicity studies in two human breast cancer lines and two matched liver progenitor cell lines indicate that [Cu(d2pype)2]Cl is non selectively toxic to both non-tumourigenic and tumourigenic cells. However, the analogous Au(I) compound [Au(d2pype)2]Cl, is toxic to highly tumourigenic cells and more selective in its toxicity to tumourigenic cells compared to non-tumourigenic cells. The significance of these results to the further development of selective, mitochondria-targeted, Au(I) antitumour complexes is discussed.

U2 - 10.1039/b912281h

DO - 10.1039/b912281h

M3 - Article

VL - 2009

SP - 10861

EP - 10870

JO - Dalton Transactions: the international journal for inorganic, organometallic and bioinorganic chemistry

JF - Dalton Transactions: the international journal for inorganic, organometallic and bioinorganic chemistry

SN - 1477-9226

IS - 48

ER -