TY - JOUR
T1 - Synthesis, spectroscopy (IR, multinuclear NMR, ESI-MS), diffraction, density functional study and in vitro antiproliferative activity of pyrazole-beta-diketone dihalotin(IV) compounds on 5 melanoma cell lines
AU - Pettinari, Claudio
AU - Caruso, Francesco
AU - Zaffaroni, Nadia
AU - Villa, Raffaella
AU - Marchetti, Fabio
AU - Pettinari, Riccardo
AU - Phillips, Christine
AU - Tanski, Joseph
AU - Rossi, Miriam
PY - 2006/1
Y1 - 2006/1
N2 - Novel 4-acylpyrazolon-5-ato-dihalotin(IV) complexes, [Q2SnX 2], (X = F, Cl, Br or I); HQ = HQCHPh2 (1,2-dihydro-3-methyl-1-phenyl-4-(2,2-diphenylacetyl)pyrazol-5-one), HQ Bn (1,2-dihydro-3-methyl-1-phenyl-4-(2-phenylacetyl)pyrazol-5-one) or HQCF3,py (4-(2,2,2-trifluoroacetyl)-1,2-dihydro-3-methyl-1-(pyridin- 2-yl)pyrazol-5-one) have been synthesized and characterized by spectroscopic (IR, 1H, 13C, 19F and 119Sn NMR, electrospray ionisation mass spectrometry (ESI-MS)), analytical and structural methods (X-ray and density functional theory). 119Sn chemical shifts depend on the nature of the halides bonded to tin. Isomer conversion, detected in solution by NMR spectroscopy, is related to the acyl moiety bulkiness while the cis(Cl)-cis(acyl)-trans(pyrazolonato) scheme is found in the solid state. The in vitro antiproliferative tests of three derivatives on three human melanoma cell lines (JR8, SK-MEL-5, MEL501) and two melanoma cell clones (2/21 and 2/60) show dose-dependent decrease of cell proliferation in all cell lines. The activity correlates with the nature of the substituent on position 1 of pyrazole, decreasing in the order pyridyl > Ph ≫ methyl. The activity for (QCF3,py)2SnCl2 on the SK-MEL-5 cell line is IC50 = 50 μM.
AB - Novel 4-acylpyrazolon-5-ato-dihalotin(IV) complexes, [Q2SnX 2], (X = F, Cl, Br or I); HQ = HQCHPh2 (1,2-dihydro-3-methyl-1-phenyl-4-(2,2-diphenylacetyl)pyrazol-5-one), HQ Bn (1,2-dihydro-3-methyl-1-phenyl-4-(2-phenylacetyl)pyrazol-5-one) or HQCF3,py (4-(2,2,2-trifluoroacetyl)-1,2-dihydro-3-methyl-1-(pyridin- 2-yl)pyrazol-5-one) have been synthesized and characterized by spectroscopic (IR, 1H, 13C, 19F and 119Sn NMR, electrospray ionisation mass spectrometry (ESI-MS)), analytical and structural methods (X-ray and density functional theory). 119Sn chemical shifts depend on the nature of the halides bonded to tin. Isomer conversion, detected in solution by NMR spectroscopy, is related to the acyl moiety bulkiness while the cis(Cl)-cis(acyl)-trans(pyrazolonato) scheme is found in the solid state. The in vitro antiproliferative tests of three derivatives on three human melanoma cell lines (JR8, SK-MEL-5, MEL501) and two melanoma cell clones (2/21 and 2/60) show dose-dependent decrease of cell proliferation in all cell lines. The activity correlates with the nature of the substituent on position 1 of pyrazole, decreasing in the order pyridyl > Ph ≫ methyl. The activity for (QCF3,py)2SnCl2 on the SK-MEL-5 cell line is IC50 = 50 μM.
KW - β-Diketone
KW - Crystal
KW - Melanoma
KW - NMR
KW - Tin
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U2 - 10.1016/j.jinorgbio.2005.10.002
DO - 10.1016/j.jinorgbio.2005.10.002
M3 - Article
C2 - 16313961
AN - SCOPUS:29344463046
VL - 100
SP - 58
EP - 69
JO - Journal of Inorganic Biochemistry
JF - Journal of Inorganic Biochemistry
SN - 0162-0134
IS - 1
ER -