Synthesis, crystal structure and in vitro anticancer studies of two bis(8-quinolinolato-N,O)-platinum(II) complexes

Abstract

Two bis(8-quinolinolato-N,O)-platinum(II) complexes, C18H12N2O2Pt (1) and C20H16N2O2Pt (2), were synthesized and characterized by FT-IR, elementary analysis and X-ray single crystal diffraction. Complex 1 crystallizes in monoclinic, space group P21/c with a = 9.3413(7), b = 10.3893(9), c = 14.8495(12) Å, β = 100.574(7)°, V = 1416.7(2) Å3. Complex 2 crystallizes in monoclinic, space group P21/n with a = 9.5115(11), b = 15.5692(18), c = 16.720(2) Å, β = 94.544(2)°, V = 2468.3(5) Å3. Intermolecular C-H···O hydrogen bonding interactions, as well as Pt···Pt and π-π stacking interactions, help to stabilize the crystal structures. The preliminary in vitro anticancer activity of complexes 1 and 2 and the corresponding ligands (L1 and L2) were investigated using human cervical (Hela) and hepatocellular carcinoma (Hep-G2) cancer cell lines. The platinum(II) complexes can greatly inhibit the cell proliferation and show stronger cytotoxic activities against the tested cancer cell lines than both ligands.

Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of Some Fe(III) Complexes Bearing Unsymmetrical Salen-Type Ligands Derived from 2-Hydroxynaphthaldehyde and Substituted Salicylaldehydes

“…e developments in transition metal complexes have gained considerable attention about various structures and potential applications in catalysis, analysis, advanced materials science, and biochemistry especially [1][2][3][4][5][6][7][8][9]. Besides the meaningful efficiency of platinum complexes as anticancer agents [10][11][12], recent bioinorganic chemists have focused on the design and preparation of new transition metal complexes with Schiff base ligands [13][14][15]. Schiff bases with donors (N, O, etc.)…”

“…Z)-1-(((2-((E)-(2-Hydroxybenzylidene) amino) phenyl) amino) methylene) naphthalen-2 (1H)-one (H 2 L1): yellow powder, 91%; HP-TOF-MS (m/z): 367.1430 [M + H] + (Cal. 367.4199); IR (KBr, cm −1 ): 3060 (], C-H), 2678 (], O-H), 1611 (], C�N), 1571 (], C�C), 1483, 1353, 1315 and 1278 (], C-N), 1188 and 1153 (], C-O); 837, 744 (δ, C-H), 481; 1 H-NMR (DMSO-d 6 , 500 MHz, δ (ppm), J (Hz)): δ 15.63 (d, J � 7.0, 1H, NH), 11.93 (s, 1H, OH), 9.60 (d, J � 7.0, 1H, HC−N), 8.99 (s, 1H, HC � N), 8.43 (d, J � 8.5, 1H, Naph), 7.99 (d, J � 8.5, 1H, Naph), 7.91 (d, J � 7.5, 1H, Sal), 7.86 (d, J � 9.5, 1H, Naph), 7.73 (d, J � 6.5, 1H, Ph), 7.51 (t, J � 7.0, 1H, Naph), 7.44 (m, 3H, 1H-Naph, 2H-Sal), 7.36 (t, J � 7.5, 1H, Ph), 7.31 (t, J � 7.0, 1H, Ph), 7.00 (m, 2H, 1H-Ph, 1H-Sal), 6.90 (d, J � 9.5, 1H, Naph); 13 C-NMR (DMSO-d 6 , 125 MHz, δ (ppm)): δ 174.31 (1C, C�O), 162.98 (1C, C�N), 159.70 (1C, C-O), 152.68 (1C, HC−NH), 141.26 (1C, N−C Ar ), 137.69 (1C, HN−C Ar ), 136.60 (1C, Naph), 133.63 (1C, Naph), 133.47 (1C, Sal), 131.80 (1C, Sal), 128.99 (1C, Naph), 128.14 (1C, Naph), 127.71 (1C, Naph), 126.95 (1C, Naph), 126.31 (1C, Ph), 123.57 (1C, Naph), 123.41 (1C, Ph), 120.21 (1C, Ph), 120.11 (1C, Naph), 119.54 (1C, Naph), 119.32 (1C, Sal), 118.26 (1C, Sal), 116.62 (1C, Sal), 108.51 (1C, Ph); UV-Vis (MeOH, 3 × 10 −5 M, λ/nm, ε/cm −1 M −1 ): 233 (42,000), 266(22,333), 320 (17,000), 348(16,333), 450(12,333), 472(11,333). (Z)-1-(((2-((E)-(5-Fluoro-2-hydroxybenzylidene) amino) phenyl) amino) methylene) naphthalen-2 (1H)-one (H 2 L2): yellow powder, 93%; HP-TOF-MS (m/z): 385.1379 [M + H] + (Cal.…”