Syntheses, structures, in vitro cytostatic activity and antifungal activity evaluation of four diorganotin( iv ) complexes based on norfloxacin and levofloxacin

• Published in: New journal of chemistry 2022-02, Vol.46 (9), p.4314-4324
• Main Authors: Guo, Qiang, Zhang, Ru-Fen, Hua, Xue-Wen, Li, Qian-Li, Du, Xiu-Mei, Ru, Jing, Ma, Chun-Lin
• Format: Article
• Language: English
• Subjects: Cell death; Chains; Chemical analysis; Chemical synthesis; Colon; Coordination compounds; Crystal structure; Fungi; Fungicides; Infrared analysis; Ligands; Monomers; NMR; Norfloxacin; Nuclear magnetic resonance; Single crystals
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/D1NJ05742A

Four organotin( iv ) complexes, [(Me 2 Sn) 4 O 2 (C 16 H 17 FN 3 O 3 ) 4 ] (1), [Ph 2 Sn(C 16 H 17 FN 3 O 3 ) 2 ] (2), [(Me 2 Sn) 4 O 2 (C 18 H 19 FN 3 O 4 ) 4 ] (3), and [Ph 2 Sn(C 18 H 19 FN 3 O 4 ) 2 ] (4), have been synthesized via the reaction of R 2 SnO (R = Me, and Ph) with the corresponding ligands [HL 1 = C 16 H 18 FN 3 O 3 , norfloxacin; and HL 2 = C 18 H 20 FN 3 O 4 , levofloxacin]. The four complexes were characterized via elemental analysis, FT-IR, NMR ( 1 H, 13 C and 119 Sn), as well as through single crystal X-ray diffraction analysis. Crystal structure results disclosed that complexes 1 and 3 represent tetranuclear tin monomers, which exist as a ladder-like structure containing a tetraorganodistannoxane unit and four deprotonated ligands. Complexes 2 and 4 represented mononuclear tin monomers. Further C–H⋯F non-covalent intermolecular contacts form 1D chain structures for complex 1. The C–H⋯N and N–H⋯O intermolecular contacts construct 2D planar supramolecular structures for complex 2. The C–H⋯O intermolecular contacts form 2D planar supramolecular structures and 1D chain structures for complexes 3 and 4, respectively. Furthermore, complexes 1–4 were evaluated for their in vitro cytostatic activity against the human cervical carcinoma (HeLa) cell line, the human hepatocellular carcinoma (HepG-2) cell line and normal human colon cells (NCM460). The results indicated that complexes 2 and 4 displayed a high in vitro cytostatic activity. Meanwhile, four phytopathogenic fungi were used in antifungal activity screening for complexes 2 and 4. The study confirmed that complexes 2 and 4 exhibited good antifungal activity. Furthermore, morphological and ultrastructural studies were carried out on the fungi affected by complex 2, and the results indicated that complex 2 may act on the vacuoles of cells and ultimately lead to cell death.