Synthesis, Characterization and Antiproliferative Activity of Transition Metal Complexes with 3-(4,5-Diphenyl-1,3-oxazol-2-yl)propanoic Acid (Oxaprozin)
Abstract
A series of novel Mn(II), Co(II), Ni(II), Cu(II) and Zn(II) complexes with oxaprozin (Hoxa), a nonsteroidal anti-inflammatory drug, has been synthesized. The drug and complexes have been characterized by elemental and thermogravimetric (TG) analysis, Fourier transform (FT)-IR, H-1-NMR, C-13-NMR, UV-Vis spectroscopy and magnetic susceptibility measurements. The (pseudo)octahedral geometry has been proposed for all complexes based on electronic spectra and magnetic moments. With exception of the Cu(II) complex, where bridging bidentate mode of COO groups has been found, FT-IR spectra confirmed chelately coordinated COO groups in the other complexes. The general formula of the complexes is [M(H2O)(2)(oxa)(2)]center dot xH(2)O, with x=2 for M=Mn, Co and Ni and x=1.5 for Zn. The binuclear Cu(II) complex, [Cu-2(H2O)(2)(OH)(oxa)(3)]center dot 2H(2)O, has strong Cu-Cu interactions of antiferromagnetic type. The complexes and Hoxa did not exhibit the cytotoxic effect to peritoneal macrophages. ...For the first time these complexes have been tested for their in vitro antiproliferative activity against human colon and breast cancer cell lines, HCT-116 and MDA-231, respectively. For all investigated compounds significant antiproliferative effects have been observed. Ni(II) complex has been shown to be a promising antiproliferative agent exerting excellent activity against HCT-116 even in nanomolar concentrations.
Keywords:
oxaprozin / transition metal complex / antiferromagnetic interaction / cytotoxic effect / antiproliferative activitySource:
Chemical and Pharmaceutical Bulletin, 2012, 60, 7, 865-869Funding / projects:
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
- Zero- to Three-Dimensional Nanostructures for Application in Electronics and Renewable Energy Sources: Synthesis, Characterization and Processing (RS-45007)
DOI: 10.1248/cpb.c12-00185
ISSN: 0009-2363
PubMed:
WoS: 000305868800009
Scopus: 2-s2.0-84863546411
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Božić, Bojan AU - Rogan, Jelena AU - Poleti, Dejan AU - Trišović, Nemanja AU - Božić, Biljana AU - Ušćumlić, Gordana PY - 2012 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1970 AB - A series of novel Mn(II), Co(II), Ni(II), Cu(II) and Zn(II) complexes with oxaprozin (Hoxa), a nonsteroidal anti-inflammatory drug, has been synthesized. The drug and complexes have been characterized by elemental and thermogravimetric (TG) analysis, Fourier transform (FT)-IR, H-1-NMR, C-13-NMR, UV-Vis spectroscopy and magnetic susceptibility measurements. The (pseudo)octahedral geometry has been proposed for all complexes based on electronic spectra and magnetic moments. With exception of the Cu(II) complex, where bridging bidentate mode of COO groups has been found, FT-IR spectra confirmed chelately coordinated COO groups in the other complexes. The general formula of the complexes is [M(H2O)(2)(oxa)(2)]center dot xH(2)O, with x=2 for M=Mn, Co and Ni and x=1.5 for Zn. The binuclear Cu(II) complex, [Cu-2(H2O)(2)(OH)(oxa)(3)]center dot 2H(2)O, has strong Cu-Cu interactions of antiferromagnetic type. The complexes and Hoxa did not exhibit the cytotoxic effect to peritoneal macrophages. For the first time these complexes have been tested for their in vitro antiproliferative activity against human colon and breast cancer cell lines, HCT-116 and MDA-231, respectively. For all investigated compounds significant antiproliferative effects have been observed. Ni(II) complex has been shown to be a promising antiproliferative agent exerting excellent activity against HCT-116 even in nanomolar concentrations. T2 - Chemical and Pharmaceutical Bulletin T1 - Synthesis, Characterization and Antiproliferative Activity of Transition Metal Complexes with 3-(4,5-Diphenyl-1,3-oxazol-2-yl)propanoic Acid (Oxaprozin) EP - 869 IS - 7 SP - 865 VL - 60 DO - 10.1248/cpb.c12-00185 ER -
@article{ author = "Božić, Bojan and Rogan, Jelena and Poleti, Dejan and Trišović, Nemanja and Božić, Biljana and Ušćumlić, Gordana", year = "2012", abstract = "A series of novel Mn(II), Co(II), Ni(II), Cu(II) and Zn(II) complexes with oxaprozin (Hoxa), a nonsteroidal anti-inflammatory drug, has been synthesized. The drug and complexes have been characterized by elemental and thermogravimetric (TG) analysis, Fourier transform (FT)-IR, H-1-NMR, C-13-NMR, UV-Vis spectroscopy and magnetic susceptibility measurements. The (pseudo)octahedral geometry has been proposed for all complexes based on electronic spectra and magnetic moments. With exception of the Cu(II) complex, where bridging bidentate mode of COO groups has been found, FT-IR spectra confirmed chelately coordinated COO groups in the other complexes. The general formula of the complexes is [M(H2O)(2)(oxa)(2)]center dot xH(2)O, with x=2 for M=Mn, Co and Ni and x=1.5 for Zn. The binuclear Cu(II) complex, [Cu-2(H2O)(2)(OH)(oxa)(3)]center dot 2H(2)O, has strong Cu-Cu interactions of antiferromagnetic type. The complexes and Hoxa did not exhibit the cytotoxic effect to peritoneal macrophages. For the first time these complexes have been tested for their in vitro antiproliferative activity against human colon and breast cancer cell lines, HCT-116 and MDA-231, respectively. For all investigated compounds significant antiproliferative effects have been observed. Ni(II) complex has been shown to be a promising antiproliferative agent exerting excellent activity against HCT-116 even in nanomolar concentrations.", journal = "Chemical and Pharmaceutical Bulletin", title = "Synthesis, Characterization and Antiproliferative Activity of Transition Metal Complexes with 3-(4,5-Diphenyl-1,3-oxazol-2-yl)propanoic Acid (Oxaprozin)", pages = "869-865", number = "7", volume = "60", doi = "10.1248/cpb.c12-00185" }
Božić, B., Rogan, J., Poleti, D., Trišović, N., Božić, B.,& Ušćumlić, G.. (2012). Synthesis, Characterization and Antiproliferative Activity of Transition Metal Complexes with 3-(4,5-Diphenyl-1,3-oxazol-2-yl)propanoic Acid (Oxaprozin). in Chemical and Pharmaceutical Bulletin, 60(7), 865-869. https://doi.org/10.1248/cpb.c12-00185
Božić B, Rogan J, Poleti D, Trišović N, Božić B, Ušćumlić G. Synthesis, Characterization and Antiproliferative Activity of Transition Metal Complexes with 3-(4,5-Diphenyl-1,3-oxazol-2-yl)propanoic Acid (Oxaprozin). in Chemical and Pharmaceutical Bulletin. 2012;60(7):865-869. doi:10.1248/cpb.c12-00185 .
Božić, Bojan, Rogan, Jelena, Poleti, Dejan, Trišović, Nemanja, Božić, Biljana, Ušćumlić, Gordana, "Synthesis, Characterization and Antiproliferative Activity of Transition Metal Complexes with 3-(4,5-Diphenyl-1,3-oxazol-2-yl)propanoic Acid (Oxaprozin)" in Chemical and Pharmaceutical Bulletin, 60, no. 7 (2012):865-869, https://doi.org/10.1248/cpb.c12-00185 . .