Citation: Jingjing QING, Fan HE, Zhihui LIU, Shuaipeng HOU, Ya LIU, Yifan JIANG, Mengting TAN, Lifang HE, Fuxing ZHANG, Xiaoming ZHU. Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin[J]. Chinese Journal of Inorganic Chemistry, ;2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003 shu

Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin

Hunan Provincial Key Laboratory of Functional Metal-Organic Compounds, Key Laboratory of Organometallic New Materials, College of Hunan Province, Hunan Engineering Research Center for Monitoring and Treatment of Heavy Metals Pollution in the Upper Reaches of Xiangjiang River, Department of Chemistry and Material Science, Hengyang Normal University, Hengyang, Hunan 421008, China

Corresponding author: Fuxing ZHANG, zfx8056@163.com
Received Date: 3 January 2024
Revised Date: 1 February 2024

Figures(5)

Two dimethylglyoxime organotin compounds, bis(tri(2-methyl-2-phenylpropyl)tin) dimethylglyoxime complex (C₆H₅C(CH₃)₂CH₂)₃Sn(ON=C(CH₃)C(CH₃) =NO)Sn(CH₂C(CH₃)₂C₆H₅)₃ (1) and di(benzyl)tin oxide, chlorine, butanedione oxime multinuclear complex [μ₃-O-((C₆H₅CH₂)₂Sn)₂(ON=C(CH₃)C(CH₃)=NOH)(O)Cl]₂ (2), were synthesized. The compounds were characterized by elemental analysis, IR spectroscopy, NMR (¹H, ¹³C, and ¹¹⁹Sn), thermogravimetric analysis, and single-crystal X-ray diffraction, and quantum chemical ab initio calculation was performed for their structure and in vitro anticancer activity were studied for the compounds. The results showed that complex 1 is a central symmetric molecule with double tin nuclei bridged by the ligand dimethylglyoxime, and the tin atoms are distorted tetrahedral configurations with four coordination. Complex 2 is a central symmetric polycyclic polymerization structure of tetratin nuclei bridged by oxygen atoms and dimethylglyoxime, and the tin atoms are five-coordinated distorted triangular bipyramidal configuration and six-coordinated distorted octahedral configuration, respectively. In addition, the complexes have stronger inhibitory activity on human liver cancer cells(HUH7), human lung cancer cells (A549), human epidermal cancer cells (A431), human colon cancer cells (HCT-116), and breast cancer cells (MDA-MB-231).
1. [1]
  Vieira F T, Lima G M, Maia J R S, Speziali N L, Ardisson J D, Rodrigues L, Junior A C, Romero O B. Synthesis, characterization and biocidal activity of new organotin complexes of 2-(3-oxocyclohex-1-enyl)benzoic acid[J]. Eur. J. Med. Chem., 2010,45(3):883-889. doi: 10.1016/j.ejmech.2009.11.026
2. [2]
  Xiao X, Liang J W, Xie J Y, Liu X, Zhu D S, Dong Y. Organotin(Ⅳ) carboxylates based on 2-(1, 3-dioxo-1H-benzo[J]. J. Mol. Struct., 2017,1146:233-241. doi: 10.1016/j.molstruc.2017.05.141
3. [3]
  Yusof E N M, Latif M A M, Tahir , M I M, Sakoff J A, Veerakumarasivam A, Page A J, Tiekink E R T, Ravoof T B S A. Homoleptic tin(Ⅳ) compounds containing tridentate ONS dithiocarbazate Schiff bases: synthesis, X-ray crystallography, DFT and cytotoxicity studies[J]. J. Mol. Struct., 2020,1205127635. doi: 10.1016/j.molstruc.2019.127635
4. [4]
  Somesan A A, Vieriu S M, Crăciun A, Silvestru C, Chiroi P, Nutu A, Jurj A, Lajos R, Berindan-Neagoe I, Varga R A. C, O-chelated organotin(Ⅳ) derivatives as potential anticancer agents: Synthesis, characterization, and cytotoxic activity[J]. Appl. Organomet. Chem., 2022,36(3)6540. doi: 10.1002/aoc.6540
5. [5]
  Dahmani M, Harit T, Et-touhami A, Yahyi A, Eddike D, Tillardc M, Benabbes R. Two novel macrocyclic organotin(Ⅳ) carboxylates based on bipyrazoledicarboxylic acid derivatives: Syntheses, crystal structures and antifungal activities[J]. J. Organomet. Chem., 2021,948121913. doi: 10.1016/j.jorganchem.2021.121913
6. [6]
  LIU X, ZHANG F X, HE L F, LI D W, ZENG W H, JIANG S Y, HE X, SHENG L B, ZHU X M. Synthesis, structure and antitumor activity of two tris(o-bromobenzyl)tin carboxylates[J]. Chinese J. Inorg. Chem., 2022,38(1):46-52.
7. [7]
  ZHOU Y L, ZHANG F X, ZHU X M, TIAN J, XU S N, ZHAO B J, CHEN J J, LI F F, DENG X. Synthesis, structure and anticancer activity of two organotin heterocyclic carboxylates[J]. Chinese J. Inorg. Chem., 2022,38(8):1533-1540.
8. [8]
  Attanzio A, D'Agostino S, Busà R, Frazzitta A, Rubino S, Girasolo M A, Sabatino P, Tesoriere L. Cytotoxic activity of organotin(Ⅳ) derivatives with triazolopyrimidine containing exocyclic oxygen atoms[J]. Molecules, 2020,25(4)859. doi: 10.3390/molecules25040859
9. [9]
  Kumari R, Banerjee S, Roy P, Nath M. Organotin(Ⅳ) complexes of NSAID, ibuprofen, X-ray structure of Ph₃Sn(IBF), binding and cleavage interaction with DNA and in vitro cytotoxic studies of several organotin complexes of drugs[J]. Appl. Organomet. Chem., 2020,34(1)e5283. doi: 10.1002/aoc.5283
10. [10]
  Liu J, Lin Y C, Liu M, Wang S Q, Li Y X, Liu X C, Tian L J. Synthesis, structural characterization and cytotoxic activity of triorganotin 5-(salicylideneamino)salicylates[J]. Appl. Organomet. Chem., 2019,33(3)e4715. doi: 10.1002/aoc.4715
11. [11]
  Shu S, Zhang F X, Tang R H, Yan S Y, Zhu X M, Sheng L B, Kuang D Z, Feng Y L, Yu J X, Jiang W J. Syntheses, structures and antitumor activities of tri(o-bromobenzyl)tin diethyldithiocarbamate and tri(m‑fluorobenzyl)tin pyrrolidine dithiocarbamate[J]. Chin. J. Struct. Chem., 2020,39(3):459-466.
12. [12]
  KUANG D Z, YU J X, FENG Y L, ZHU X M, JIANG W J, ZHANG F X. Syntheses, structures and in vitro antitumor activity of bis(tricyclohexyltin) pyridinedicarboxylate with macrocyclic supramolecular structure[J]. Chinese J. Inorg. Chem., 2018,34(6):1035-1042.
13. [13]
  Paul A, Khan R A, Shaik G M, Shaik J P, Rai A K, Guedes da Silva M F C, Pombeiro A J L. Anthracene appended organotin(Ⅳ) compounds: Synthesis, structure elucidation and their cytotoxicity against A549 and RBL cancer cell lines[J]. Appl. Organomet. Chem., 2023,37(3)e7232.
14. [14]
  Gul R, Muhammad N, Sirajuddin M, Noor A, Tumanov N, Wouters J, Chafik A, Solak K, Mavi A, Shujah S, Ali S, Khan G S, Qayyum S. Design, physicochemical confirmation, single crystal structures as well as exploration of antibacterial and anticancer potential of organotin(Ⅳ) carboxylates[J]. J. Mol. Struct., 2024,1300137306. doi: 10.1016/j.molstruc.2023.137306
15. [15]
  Shi H L, Ma J W, Li Q L, Du X M, Meng Z X, Ru J, Ma C L. Four organotin(Ⅳ) complexes derived from 2, 6-difluoro-3-(propylsulfona-mido)benzoic acid: Synthesis, structure, in vitro cytostatic activity and antifungal activity evaluation[J]. Inorg. Chim. Acta, 2023,551121485. doi: 10.1016/j.ica.2023.121485
16. [16]
  DENG X, ZHANG F X, QING J J, YANG G, HE F, HE L F, LIU Z H, HOU S P. Synthesis, structure and anticancer activity of two benzohydroxamic acid organotin complexes[J]. Chinese J. Inorg. Chem., 2023,39(11):2086-2090.
17. [17]
  Lakadamyali F, Reisner E. Photocatalytic H₂ evolution from neutral water with a molecular cobalt catalyst on a dye-sensitized TiO₂ nanoparticle[J]. Chem. Commun., 2011,47(6):1695-1697. doi: 10.1039/c0cc04658b
18. [18]
  Mercier F A G, Meddour A, Gielen M, Biesemans M, Willem R, Tiekink E R T. Crystal structures of μ₂-fluoro- and μ₂-salicylaldoximato‑bridged μ₃‑oxo‑tris(dimethyltin(Ⅳ)) bis(salicylaldoximate)[J]. Organometallics, 1998,17(26):5933-5936. doi: 10.1021/om980609x
19. [19]
  Sharma V, Sharma R K, Bohra R, Ratnani R, Jain V K, Drake J E. Synthesis, spectroscopic and structural aspects of some tetraorganodistannoxanes with internally functionalized oxime: Crystal and molecular structures of[{R₂Sn(ONC(Me)py)}₂O]₂ (R=Buⁿ and Et) and 2-NC₅H₄C(Me)NOH[J]. J. Organomet. Chem., 2002,651(1/2):98-104.
20. [20]
  Zhang F X, Kuang D Z, Li X J, Liang F, Feng Y L, Zhu X M, Yu J X, Jiang W J. Synthesis, structures and vitro anticancer activity of μ₂-O-and μ₂-dimethylglyoximato-bridged μ₃-O-tris[di(m-fluorobenzyl)tin] bis(dimethylglyoximate)[J]. Chin. J. Struct. Chem., 2016,35(10):1510-1516.
21. [21]
  ZHANG F X, KUANG D Z, WANG J Q, F ENG Y L, CHEN Z M, ZENG R Y. Synthesis and crystal structure of the tri(o-methylbenzyl)tin chloride and the bis(p-methylbenzyl)tin dichloride[J]. Chinese J. Inorg. Chem., 2006,22(7):1246-1250. doi: 10.3321/j.issn:1001-4861.2006.07.016
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