Synthesis and characterization of complexes of p-isopropyl benzaldehyde and methyl 2-pyridyl ketone thiosemicarbazones with Zn(II) and Cd(II) metallic centers. Cytotoxic activity and induction of apoptosis in Pam-ras cells (original) (raw)

The reaction of [ReOCl 3 (PPh 3 ) 2 ] with N, N-bis(2-mercaptoethyl)benzylamine and 4bromobenzenethiol allowed for the isolation of [ReO{η 3 -(SCH 2 CH 2 ) 2 N(CH 2 C 6 H 5 )}-(η 1 -C 6 H 4 Br-4-S)] (1). The reaction of [ReOCl 3 (PPh 3 ) 2 ] with [(HSCH 2 CH 2 ) 2 N(CH 2 C 5 H 4 N)] and the appropriate thiol in chloroform treated with triethylamine has led to the isolation of a series of neutral rhenium complexes of the type [ReO{η 3 -(SCH 2 CH 2 ) 2 N(CH 2 C 5 H 4 N)}(η 1 -C 6 H 4 X-4-S)] (X = Br (2), Cl (3), F (4), and OCH 3 (5)) and [ReO{η 3 -(SCH 2 CH 2 ) 2 N(CH 2 C 5 H 4 N)}(η 1 -C 6 H 4 OCH 3 -4-CH 2 S)] (6). Likewise, under similar reaction conditions, the use of the related tridentate ligand, [(HSCH 2 CH 2 ) 2 N(CH 2 CH 2 C 5 H 4 N)], has led to the isolation of a series of rhenium complexes of the type [ReO{η 3 -(SCH 2 CH 2 ) 2 N(CH 2 CH 2 C 5 H 4 N)}(η 1 -C 6 H 4 X-4-S)] (X=Br , Cl (8), OCH 3 (9)), as well as [ReO{η 3 -(SCH 2 CH 2 ) 2 N(CH 2 CH 2 C 5 H 4 N)}(η 1 -C 6 H 4 Cl-4-CH 2 S)]·0.5CH 3 (CH 2 ) 4 CH 3 (10). These compounds are extensions of the '3+1' approach to the synthesis of materials with the {MO} 3+ core (M=Tc and Re), which have applications in nuclear medicine. The ligands chosen allow systematic exploration of the consequences of para-substitution on the monodentate thiolate ligand [S] and of derivatization of the substituent R on the tridentate aminodithiol ligand [SNS] of the type (HSCH 2 CH 2 ) 2 NR. Such modifications can influence lipophilicity, charge, size and molecular weight of the complex and consequently the biodistribution.