New Water-Soluble Copper(II) Complexes with Morpholine-Thiosemicarbazone Hybrids: Insights into the Anticancer and Antibacterial Mode of Action

Six morpholine-(iso)thiosemicarbazone hybrids HL1-HL6 and their Cu(II) complexes with good-to-moderate solubility and stability in water were synthesized and characterized. Cu(II) complexes [Cu(L1-6)Cl] (1-6) formed weak dimeric associates in the solid state, which did not remain intact in solution as evidenced by ESI-MS. The lead proligands and Cu(II) complexes displayed higher antiproliferative activity in cancer cells than triapine. In addition, complexes 2-5 were found to specifically inhibit the growth of Gram-positive bacteria Staphylococcus aureus with MIC50 values at 2-5 μg/mL. Insights into the processes controlling intracellular accumulation and mechanism of action were investigated for 2 and 5, including the role of ribonucleotide reductase (RNR) inhibition, endoplasmic reticulum stress induction, and regulation of other cancer signaling pathways. Their ability to moderately inhibit R2 RNR protein in the presence of dithiothreitol is likely related to Fe chelating properties of the proligands liberated upon reduction

2-[(Pyridin-2-yl)amino]pyridinium 2,4,6-trinitrophenolate

In the cation of the title salt, C10H10N3+·C6H2N3O7−, the pyridine and pyridinium rings are linked by an intramolecular N—H...N hydrogen bond and are approximately coplanar, with a dihedral angle between their planes of 4.24 (6)°. In the crystal, the cations and anions are linked through N—H...O hydrogen bonds, forming supramolecular chains propagating along the c-axis direction. π–π stacking is observed between neighbouring chains, the centroid–centroid distances being 3.7638 (11) (between pyridinium rings) and 3.5331 (11) Å (between benzene rings)

Crystal structure of 2-{[(E)-(4-anilinophenyl)iminiumyl]methyl}-5-(diethylamino)phenolate

The title compound, C23H25N3O, crystallized with one single molecule in the asymmetric unit and is present in the zwitterionic form. There is an intramolecular N—H...O hydrogen bond in the molecule with the phenol ring being inclined to the central benzene ring by 20.67 (14)°. The terminal aminophenyl ring forms a dihedral angle of 54.21 (14)° with the central benzene ring. The two outer aromatic rings are inclined to one another by 74.54 (14)°. In the crystal, the molecules are connected by N—H...O hydrogen bonds, with adjacent molecules related by a 21 screw axis, generating –A–B–A–B– zigzag chains extending along [010]. The chains are linked via C—H...π and π–π interactions [with a centroid–centroid distance of 3.444 (3) Å] between the benzene ring and the imino group of symmetry-related molecules, forming slabs lying parallel to (100)

Crystal structure of bis(μ-N-hydroxypicolinamidato)bis[bis(N-hydroxypicolinamide)sodium]

The title compound, [Na2(C6H5N2O2)2(C6H6N2O2)4], is a centrosymmetric coordination dimer based on the sodium(I) salt of N-hydroxypicolinamide. The molecule has an {Na2O6(μ-O)2} core with two bridging carbonyl O atoms and two hydroxamate O atoms of two mono-deprotonated residues of N-hydroxypicolinamide, while two neutral N-hydroxypicolinamide molecules are coordinated in a monodentate manner to each sodium ion via the carbonyl O atoms [the Na—O distances range from 2.3044 (2) to 2.3716 (2) Å]. The pentacoordinated sodium ion exhibits a distorted trigonal–pyramidal coordination polyhedron. In the crystal, the coordination dimers are linked into chains along the c axis via N—H...O and N—H...N hydrogen bonds; the chains are linked into a two-dimensional framework parallel to (100) via weak C—H...O and π–π stacking interactions