Issue 17, 2008

Large-bite bis(phosphite) ligand containing mesocyclic thioether moieties: synthesis, reactivity, group 11 (CuI, AuI) metal complexes and anticancer activity studies on a human cervical cancer (HeLa) cell line

Abstract

The large-bite bis(phosphite) ligand [{(–OC10H6(µ-S)C10H6O–)P{µ-(–OC10H6(µ-S)C10H6O–)}P(–OC10H6(µ-S)C10H6O–)}] (P⁁P) (2) was obtained by the reaction of PCl3 and thiobis(2,2′-naphthol) (1). The stoichiometric reactions of 2 with elemental sulfur and selenium afforded the corresponding chalcogenide derivatives [(E)P⁁P(E)] (3, E = S; 4, E = Se) in good yield. Treatment of two equivalents of [ClAu(SMe2)] with 2 afforded a dinuclear complex [ClAu(P⁁P)AuCl] (5), whereas the 1 : 1 reaction with CuI yielded the [(P⁁P)CuI] (6) complex. The copper(I) complex 6 on treatment with various pyridyl derivatives, produced mixed-ligand complexes [(P⁁P)CuI(NC5H5)] (7), [(P⁁P)Cu(2,2′-bpy)]I (8), [(P⁁P)Cu(1,10-phen)]I (9) and {[(P⁁P)Cu(4,4′-bpy)]I} (10). The compounds 25 were tested for their cytotoxic activity on the human cervical cancer (HeLa) cell line. Compounds 2 and 3 were found to inhibit proliferation of HeLa cells significantly. These agents also induced apoptotic cell death in cancer cells. Evidence presented in this study indicated that the compounds 2 and 3 activate the tumor suppressor protein p53 in the colon adenocarcinoma (HCT-116) cell line.

Graphical abstract: Large-bite bis(phosphite) ligand containing mesocyclic thioether moieties: synthesis, reactivity, group 11 (CuI, AuI) metal complexes and anticancer activity studies on a human cervical cancer (HeLa) cell line

Supplementary files

Article information

Article type
Paper
Submitted
02 Jan 2008
Accepted
25 Feb 2008
First published
18 Mar 2008

Dalton Trans., 2008, 2285-2292

Large-bite bis(phosphite) ligand containing mesocyclic thioether moieties: synthesis, reactivity, group 11 (CuI, AuI) metal complexes and anticancer activity studies on a human cervical cancer (HeLa) cell line

D. Suresh, M. S. Balakrishna, K. Rathinasamy, D. Panda and J. T. Mague, Dalton Trans., 2008, 2285 DOI: 10.1039/B719904J

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