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
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
3. [3]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
4. [4]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
5. [5]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
6. [6]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
7. [7]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
8. [8]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
9. [9]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
10. [10]
  Yongzhi LI , Han ZHANG , Gangding WANG , Yanwei SUI , Lei HOU , Yaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307
11. [11]
  Jinfeng Chu , Lan Jin , Yu-Fei Song . Exploration and Practice of Flipped Classroom in Inorganic Chemistry Experiment: a Case Study on the Preparation of Inorganic Crystalline Compounds. University Chemistry, 2024, 39(2): 248-254. doi: 10.3866/PKU.DXHX202308016
12. [12]
  Yan Liu , Yuexiang Zhu , Luhua Lai . Introduction to Blended and Small-Class Teaching in Structural Chemistry: Exploring the Structure and Properties of Crystals. University Chemistry, 2024, 39(3): 1-4. doi: 10.3866/PKU.DXHX202306084
13. [13]
  Weina Wang , Fengyi Liu , Wenliang Wang . “Extracting Commonality, Delving into Typicals, Deriving Individuality”: Constructing a Knowledge Graph of Crystal Structures. University Chemistry, 2024, 39(3): 36-42. doi: 10.3866/PKU.DXHX202308029
14. [14]
  Junqiao Zhuo , Xinchen Huang , Qi Wang . Symbol Representation of the Packing-Filling Model of the Crystal Structure and Its Application. University Chemistry, 2024, 39(3): 70-77. doi: 10.3866/PKU.DXHX202311100
15. [15]
  Wenyan Dan , Weijie Li , Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060
16. [16]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
17. [17]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
18. [18]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
19. [19]
  Yuyao Wang , Zhitao Cao , Zeyu Du , Xinxin Cao , Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-. doi: 10.3866/PKU.WHXB202406014
20. [20]
  Hongwei Ma , Hui Li . Three Methods for Structure Determination from Powder Diffraction Data. University Chemistry, 2024, 39(3): 94-102. doi: 10.3866/PKU.DXHX202310035

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(718)
HTML views(108)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142