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Issue 29, 2014
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Dinuclear CuI complexes of pyridyl-diazadiphosphetidines and aminobis(phosphonite) ligands: synthesis, structural studies and antiproliferative activity towards human cervical, colon carcinoma and breast cancer cells

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Abstract

The copper(I) complexes containing phosphorus donor ligands such as diazadiphosphetidine, cis-{(o-OCH2C5H4N)P(μ-NtBu)}2 (1) and aminobis(phosphonite), C6H5N{P(OC6H3(OMe-o)(C3H5-p))2}2 (2, PNP), have been synthesized. Treatment of 1 with copper iodide afforded the 1D coordination polymer [{Cu(μ-I)}2{(o-OCH2C5H4N)P(μ-NtBu)}2]n (3). Treatment of 3 with 2,2′-bipyridine (bpy) and 1,10-phenanthroline (phen) produced mixed-ligand complexes [(L)2Cu2{(o-OCH2C5H4N)P(μ-NtBu)}2][I]2 (4 L = bpy; 5 L = phen) in good yields. The reaction of 2 with copper iodide yielded a rare tetranuclear copper complex [(CuI)2C6H5N(PR2)2]2 (6), which on subsequent treatment with various pyridyl ligands produced binuclear complexes [{Cu(μ-I)(py)}2(μ-PNP)] (7), [Cu2(μ-I)(bpy)2(μ-PNP)]I (8), [Cu2(μ-I)I(bpy)(μ-PNP)] (9), [Cu2(phen)(bpy)(μ-PNP)](OTf)2 (10), [Cu2(μ-I)I(phen)(μ-PNP)] (11) and [Cu2(μ-I)(phen)2(μ-PNP)]I (12), in an almost quantitative yield. The new copper(I) complexes (4, 5 and 7–12) were tested for anti-cancer activity against three human tumor cell lines. Compounds 5, 10 and 12 showed in vitro antitumor activity 5–7 fold higher than cisplatin, the most used anticancer drug. These three most potent compounds (5, 10 and 12) were chosen for detailed study to understand their mechanism of action. The copper(I) compounds studied in the present investigation were found to inhibit tumor cell growth by arresting cells at the S-phase of the cell cycle. The characteristic nuclear morphology of treated cells showed signs of DNA damage. The experimental evidence clearly indicated that these compounds initiated apoptosis, which is mediated through the p53 pathway.

Graphical abstract: Dinuclear CuI complexes of pyridyl-diazadiphosphetidines and aminobis(phosphonite) ligands: synthesis, structural studies and antiproliferative activity towards human cervical, colon carcinoma and breast cancer cells

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Publication details

The article was received on 19 Mar 2014, accepted on 19 May 2014 and first published on 20 May 2014


Article type: Paper
DOI: 10.1039/C4DT00832D
Citation: Dalton Trans., 2014,43, 11339-11351
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    Dinuclear CuI complexes of pyridyl-diazadiphosphetidines and aminobis(phosphonite) ligands: synthesis, structural studies and antiproliferative activity towards human cervical, colon carcinoma and breast cancer cells

    A. Rashid, G. S. Ananthnag, S. Naik, J. T. Mague, D. Panda and M. S. Balakrishna, Dalton Trans., 2014, 43, 11339
    DOI: 10.1039/C4DT00832D

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