Cyclometalated platinum(II) complexes bearing natural arylolefin and quinolines ligands: Synthesis, characterizations, and in vitro cytotoxicity. (1st December 2022)

• Record Type: Journal Article
• Authors: Van Thong, Pham; Van Meervelt, Luc; Chi, Nguyen Thi Thanh
• Is Part Of: Polyhedron. Volume 228(2022)
• Publication Date: 2022-12-01
• Subjects: Platinacyclic complex -- Eugenol derivatives -- Quinoline derivatives -- π…π stacking interaction -- Cytotoxicity; Chemistry, Inorganic -- Periodicals; Chimie inorganique -- Périodiques; Organometaalverbindingen; Anorganische chemie; 546.05
• DOI: 10.1016/j.poly.2022.116180
• Languages: English
• ISSNs: 0277-5387

Abstract

Graphical abstract: Interaction of [Pt( µ -Cl)(arylolefin)]2 with either quinoline (Q) or four derivatives ( N, O H) afforded 2 –10. The N atom of Q and ( N, O ) are at the cis position with respect to the allyl group in all the complexes. The cytotoxicity of 4 against Lu and 5 against KB cell lines are approximately 6 and 4 times lower than cisplatin, respectively. Abstract: Nine new cyclometalated platinum(II) complexes of the formula [PtCl(arylolefin)(Q)] (2, 3 ) and [Pt(arylolefin)( N, O )] (4 –10 ) (arylolefinH: eugenoxyacetic acid, isopropyl eugenoxyacetate; Q: quinoline; ( N, O H): quinolin-8-ol, 2-methylquinolin-8-ol, 5, 7-dichloroquinloin-8-ol and quinoline-2-carboxylic acid] were synthesized and fully characterized by EA, ESI mass spectrometry, IR and NMR spectroscopy and single-crystal X-ray diffraction for 3, 7 and 10 . The results show that the arylolefin binds with Pt II via the C5 atom of the phenyl ring and the CC allyl in all the synthesized complexes. Quinoline coordinates with Pt II via its N atom in 2, 3, while deprotonated ( N, O H) coordinates with Pt II via both the N and O atoms in 4 –10 . The N atom of Q and ( N, O ) in all complexes are at the cis position with respect to the allyl group of the arylolefin. The XRD confirms the square-planar coordination of Pt II and trans position of the arylolefin and quinoline ligands. The results of in vitro cytotoxicity tests against human cancer cell lines KB and Lu of 2, 4 –8 indicate that 4 and 5 exhibit the highest activities against Lu and KB cell lines with the IC50 values of 7.1 and 4.1 µM, respectively, which are approximately 6 and 4 times lower than cisplatin.