Copper(I) halide complexes of 5-carbethoxy-2-thiouracil: synthesis, structure and in vitro cytotoxicity.
5-Carbethoxy-2-thiouracil (eitotH2) reacts with copper(I) halides CuX (X = Cl, Br, I) to give dinuclear complexes of the formula [CuX(eitotH2)2]2 while mononuclear mixed-ligand complexes of the formula [CuX(PPh3)2(eitotH2)] result when the reactions are performed in the presence of two equivalents of triphenylphosphine (PPh3). The molecular structures of representative compounds from each of the above types of complexes, namely [CuI(eitotH2)2]2, [CuCl(PPh3)2(eitotH2)] and [CuBr(PPh3)2(eitotH2)] have been established by single-crystal X-ray diffraction. The new copper(I) complexes were evaluated for in vitro antitumor properties against two tumor cell lines, A549 (human pulmonary carcinoma cell line) and HeLa (human epithelial carcinoma cell line) and one normal immortalized cell line MRC5 (human fetal lung fibroblast). The mixed-ligand complexes possessing triphenylphosphine were found to be highly cytotoxic in contrast to the phosphine-free ones which inhibited cell proliferation only in relatively high concentrations.
Aristotle University of Thessaloniki, Faculty of Chemistry, Inorganic Chemistry Laboratory, P.O. Box 135, GR-541 24 Thessaloniki, Greece.
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Papazoglou
School of Pharmacy and Life Sciences, Riverside East, Robert Gordon University, Garthdee Road, Aberdeen AB10 7GJ, Scotland, UK.
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Cox
Aristotle University of Thessaloniki, Faculty of Chemistry, Inorganic Chemistry Laboratory, P.O. Box 135, GR-541 24 Thessaloniki, Greece.
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Hatzidimitriou
Laboratory of Biochemistry, Department of Chemistry, Aristotle University of Thessaloniki, GR-541 24 Thessaloniki, Greece.
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Kokotidou
Laboratory of Biochemistry, Department of Chemistry, Aristotle University of Thessaloniki, GR-541 24 Thessaloniki, Greece. Electronic address: tcholi@chem.auth.gr.
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Choli-Papadopoulou
Aristotle University of Thessaloniki, Faculty of Chemistry, Inorganic Chemistry Laboratory, P.O. Box 135, GR-541 24 Thessaloniki, Greece. Electronic address: aslanidi@chem.auth.gr.
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Aslanidis
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001965:Bromides / Q000737:chemistry*; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D002712:Chlorides / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D007454:Iodides / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013889:Thiouracil / Q000031:analogs & derivatives* / Q000737:chemistry
C000593735:5-carbethoxy-2-thiouracil; D000970:Antineoplastic Agents; D001965:Bromides; D002712:Chlorides; D007454:Iodides; D009942:Organometallic Compounds; D013889:Thiouracil; D003300:Copper
5-Carbethoxy-2-thiouracil; Copper(I); Cytotoxicity; Triphenylphosphine