A new set of penta-coordinated copper(II) hydrazone complexes containing solvated methanol were synthesized by reacting the hydrazone ligands, 2-acetylpyridine benzoyl hydrazone (HL1) and 2-acetylpyridine thiophene-2-carboxylic acid hydrazone (HL2), with [CuCl2(DMSO)2] and characterized by different spectral methods. Single crystal X-ray diffraction studies of the complexes revealed that both of them, [CuCl(L1)(MeOH)] (1) and [CuCl(L2)(MeOH)] (2), have square pyramidal geometry around the cupric ion, in which the hydrazone is coordinated through NNO atoms along with a molecule of methanol in the apical position. Interaction of the ligands HL1 and HL2 along with the corresponding copper complexes 1 and 2 with calf thymus DNA (CT-DNA) has been estimated by absorption and emission titration methods which revealed that the compounds interacted with CT-DNA through intercalation. Binding of the compounds, i.e., free ligands and complexes (1) and (2) with bovine serum albumin (BSA) protein investigated using UV-visible, fluorescence and synchronous fluorescence spectroscopic methods indicated that there occurred strong binding of copper complexes to BSA over the ligands. Further, the cytotoxicity of the compounds examined in vitro on a panel of cancerous cell lines such as a human cervical cancer cell line (HeLa), a pancreatic cancer cell line (PANC-1), an Ehrlich ascites cancer cell line (EAC) and Dalton's lymphoma ascitic cancer cells (DLA) and a normal mouse embryonic fibroblasts cell line (NIH3) demonstrated that the complexes 1 and 2 possessed superior cytotoxicity than that of well-known commercial anticancer drug cisplatin to the tumor cells but are less toxic to the normal cell line and have emerged as potential candidates for further studies.
Synthesis, spectral, electrochemical and single crystal X-ray diffraction data of a new series of DMSO containing bivalent ruthenium hydrazone complexes are presented. XRD data of two of the new complexes revealed an octahedral coordination around the ruthenium ion satisfied by NOS2Cl2 atoms. Electrochemical studies showed the metal centred, quasi-reversible, one-electron redox behaviour of the new complexes. The binding of these complexes with biomolecules such as calf thymus DNA (CT-DNA) and bovine serum albumin (BSA) protein investigated by different spectrophotometric methods revealed an intercalative mode of interaction. The in vitro cytotoxicity of these complexes evaluated by the MTT assay on a panel of cancer and normal cell lines indicated that the above complexes are more toxic to cancer cells with a few micromolar concentrations as the IC50 value, but are significantly less toxic to normal cell lines. The observed variations in the binding interactions and cytotoxicity of the complexes were attributed to the nature of the hydrazide moiety of the hydrazones that influences their biological activities.
A new set of ruthenium(II) hydrazone complexes [Ru(H)(CO)(PPh3)2(L)] (1) and [RuCl2(DMSO)2(HL)] (2), with triphenyl phosphine or DMSO as co-ligands was synthesized by reacting benzoyl pyridine furoic acid hydrazone (HL) with [Ru(H)(Cl)(CO)(PPh3)3] and [RuCl2(DMSO)4]. The single crystal X-ray data of complexes 1 and 2 revealed an octahedral geometry around the ruthenium ion in which the hydrazone is coordinated through ON and NN atoms in complexes 1 and 2 respectively. The interaction of the compounds with calf thymus DNA (CT-DNA) has been estimated by absorption and emission titration methods which indicated that the ligand and the complexes interacted with CT-DNA through intercalation. In addition, the DNA cleavage ability of these newly synthesized ruthenium complexes assessed by an agarose gel electrophoresis method demonstrated that complex 2 has a higher DNA cleavage activity than that of complex 1. The binding properties of the free ligand and its complexes with bovine serum albumin (BSA) protein have been investigated using UV-visible, fluorescence and synchronous fluorescence spectroscopic methods which indicated the stronger binding nature of the ruthenium complexes to BSA than the free hydrazone ligand. Furthermore, the cytotoxicity of the compounds examined in vitro on a human cervical cancer cell line (HeLa) and a normal mouse embryonic fibroblasts cell line (NIH 3T3) revealed that complex 2 exhibited a superior cytotoxicity than complex 1 to the cancer cells but was less toxic to the normal mouse embryonic fibroblasts under identical conditions.
Neutralization of 4-[(2,2,3,3-tetrafluoropropoxy)methyl]pyridine with hydrohalo acids HX (X = Cl and Br) yielded the pyridinium salts 4-[(2,2,3,3-tetrafluoropropoxy)methyl]pyridinium chloride, CHFNO·Cl, (1), and 4-[(2,2,3,3-tetrafluoropropoxy)methyl]pyridinium bromide, CHFNO·Br, (2), both carrying a fluorous side chain at the para position of the pyridinium ring. Single-crystal X-ray diffraction techniques revealed that (1) and (2) are isomorphous. The halide anions accept four hydrogen bonds from N-H, ortho-C-H and CF-H groups. Two cations and two anions form a centrosymmetric dimeric building block, utilizing complimentary N-H...X...H-Csp connections. These dimers are further crosslinked, utilizing another complimentary Csp-H...X...H-Csp connection. The pyridinium rings are π-stacked, forming columns running parallel to the a axis that make angles of ca 44-45° with the normal to the pyridinium plane. There are also supramolecular C-H...F-C interactions, namely bifurcated C-H...F and bifurcated C-F...H interactions; additionally, one type II C-F...F-C halogen bond has been observed.
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