Mononuclear metal complexes with piroxicam: synthesis, structure and biological activity.
Piroxicam (=Hpir) is a non-steroidal anti-inflammatory and an anti-arthritic drug. VO(2+), Mn(2+), Fe(3+), MoO(2)(2+) and UO(2)(2+) complexes with deprotonated piroxicam have been prepared and characterized with the use of infrared, UV-Vis, nuclear magnetic resonance and electron paramagnetic resonance spectroscopies. The experimental data suggest that piroxicam acts as a deprotonated bidentate ligand in all complexes and is coordinated to the metal ion through the pyridine nitrogen and the amide oxygen. Molecular mechanics calculations in the gas state have been performed in order to propose a model for the Fe(3+), VO(2+) and MoO(2)(2+) complexes. Potential anticancer cytostatic and cytotoxic effects of piroxicam complexes with VO(2+), Mn(2+) and MoO(2)(2+) on human promyelocytic leukemia HL-60 cells have been investigated. Among all complexes, only VO(pir)(2)(H(2)O) clearly induces apoptosis after 24-h incubation, whereas piroxicam induces apoptosis after 57-h incubation.
Christofis
Petros
P
Institute of Physical Chemistry, NCSR Demokritos, 15310 Aghia Paraskevi Attikis, GR15310 Athens, Greece.
Katsarou
Maria
M
Papakyriakou
Athanasios
A
Sanakis
Yiannis
Y
Katsaros
Nikos
N
Psomas
George
G
D017209:Apoptosis / Q000187:drug effects; D002247:Carbon Isotopes; D004563:Electrochemistry; D004578:Electron Spin Resonance Spectroscopy; D018922:HL-60 Cells; D006801:Humans; D006859:Hydrogen; D007501:Iron / Q000737:chemistry / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008670:Metals / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D010894:Piroxicam / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014639:Vanadium / Q000737:chemistry / Q000378:metabolism
D002247:Carbon Isotopes; D008670:Metals; D014639:Vanadium; D010894:Piroxicam; D006859:Hydrogen; D007501:Iron