Large-bite bis(phosphite) ligand containing mesocyclic thioether moieties: synthesis, reactivity, group 11 (Cu(I), Au(I)) metal complexes and anticancer activity studies on a human cervical cancer (HeLa) cell line.
The large-bite bis(phosphite) ligand [{(-OC(10)H(6)(mu-S)C(10)H(6)O-)P{mu-(-OC(10)H(6)(mu-S)C(10)H(6)O-)}P(-OC(10)H(6)(mu-S)C(10)H(6)O-)}] (Pinsertion markP) () was obtained by the reaction of PCl(3) and thiobis(2,2'-naphthol) (). The stoichiometric reactions of with elemental sulfur and selenium afforded the corresponding chalcogenide derivatives [(E)Pinsertion markP(E)] (, E = S; , E = Se) in good yield. Treatment of two equivalents of [ClAu(SMe(2))] with afforded a dinuclear complex [ClAu(Pinsertion markP)AuCl] (), whereas the 1 : 1 reaction with CuI yielded the [(Pinsertion markP)CuI] () complex. The copper(i) complex on treatment with various pyridyl derivatives, produced mixed-ligand complexes [(Pinsertion markP)CuI(NC(5)H(5))] (), [(Pinsertion markP)Cu(2,2'-bpy)]I (), [(Pinsertion markP)Cu(1,10-phen)]I () and {[(Pinsertion markP)Cu(4,4'-bpy)]I}(infinity) (). The compounds were tested for their cytotoxic activity on the human cervical cancer (HeLa) cell line. Compounds and 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 and activate the tumor suppressor protein p53 in the colon adenocarcinoma (HCT-116) cell line.
Suresh
D
D
Phosphorus Laboratory, Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400 076, India.
Balakrishna
Maravanji S
MS
Rathinasamy
Krishnan
K
Panda
Dulal
D
Mague
Joel T
JT
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects; D003300:Copper / Q000737:chemistry; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D005260:Female; D017612:Gold Compounds / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D008024:Ligands; D015394:Molecular Structure; D050607:Organogold Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017905:Phosphites / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013440:Sulfides / Q000494:pharmacology; D016159:Tumor Suppressor Protein p53 / Q000378:metabolism*
D000970:Antineoplastic Agents; D017612:Gold Compounds; D008024:Ligands; D050607:Organogold Compounds; D009942:Organometallic Compounds; D017905:Phosphites; D013440:Sulfides; D016159:Tumor Suppressor Protein p53; D003300:Copper