ABSTRACT
Cisplatin and other metal-based drugs often display side effects and tumor resistance after prolonged use. Because rhenium-based anticancer complexes are often less toxic, a novel series of organorhenium complexes were synthesized of the types: XRe(CO)3Z (X = α-diimines and Z = p-toluenesulfonate, 1-naphthalenesulfonate, 2-naphthalenesulfonate, picolinate, nicotinate, aspirinate, naproxenate, flufenamate, ibuprofenate, mefenamate, tolfenamate, N-acetyl-tryptophanate), and their biological properties were examined. Specifically, in hormone-dependent MCF-7 and hormone-independent triple-negative MDA-MB-231 breast cancer cells, the p-toluenesulfonato, 1-naphthalenesulfonato, 2-naphthalenesulfonato, picolinato, nicotinato, acetylsalicylato, flufenamato, ibuprofenato, mefenamato, and N-acetyl-tryptophanato complexes were found to be far more potent than conventional drug cisplatin. DNA-binding studies were performed in each case via UV-Vis titrations, cyclic voltammetry, gel electrophoresis, and viscosity, which suggest DNA partial intercalation interaction, and the structure-activity relationship studies suggest that the anticancer activities increase with the increasing lipophilicities of the compounds, roughly consistent with their DNA-binding activities.
Subject(s)
Antineoplastic Agents , Coordination Complexes , Organometallic Compounds , Rhenium , Triple Negative Breast Neoplasms/drug therapy , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Coordination Complexes/chemistry , Coordination Complexes/pharmacology , Female , Humans , MCF-7 Cells , Organometallic Compounds/chemistry , Organometallic Compounds/pharmacology , Rhenium/chemistry , Rhenium/pharmacology , Triple Negative Breast Neoplasms/metabolism , Triple Negative Breast Neoplasms/pathologyABSTRACT
In the title compound, C12H10N2O4, the furan-2-ylmethyl group is disordered over two sets of sites, with refined occupancies of 0.858â (3) and 0.143â (3). In the major component of disorder, the dihedral angle between the furan and benzene rings is 63.1â (2)° and for the minor component this value is 67.9â (6)°. The planes of the nitro group and the attached benzene ring form a dihedral angle of 4.34â (17)°. In the crystal, inversion-related mol-ecules are linked by two pairs of weak C-Hâ¯O inter-actions, one involving the nitro group and the other involving the O-H group as an acceptor. As a result of these associations, ribbons are formed along [120]. A strong intra-molecular O-Hâ¯N hydrogen bond is observed.
