Citation: Xin DENG, Fu-Xing ZHANG, Jing-Jing QING, Ge YANG, Fan HE, Li-Fang HE, Zhi-Hui LIU, Shuai-Peng HOU. Synthesis, structure, and anticancer activity of two benzohydroxamic acid organotin complexes[J]. Chinese Journal of Inorganic Chemistry, ;2023, 39(11): 2083-2090. doi: 10.11862/CJIC.2023.182 shu

Synthesis, structure, and anticancer activity of two benzohydroxamic acid organotin complexes

Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Key Laboratory of Organometallic New Materials, University 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: Fu-Xing ZHANG, zfx8056@163.com
Received Date: 23 May 2023
Revised Date: 27 September 2023

Figures(5)

Two benzohydroxamic acid organotin complexes[(o-Cl-C₆H₄CH₂)₂Sn(C₆H₅CONO)₂] (1) and[(o-CH₃-C₆H₄CH₂)₂Sn(C₆H₅CONO) (C₆H₅COO)] (2) were synthesized by solvothermal method using methanol as a solvent. Complexes 1 and 2 were characterized by elemental analysis, IR, ¹H NMR, thermogravimetric analysis, single-crystal X-ray diffraction, etc. The study on the complexes has been performed with quantum chemistry calculation and in vitro anticancer activity. The results show that the two complexes are monotin nuclear structures; complexes 1 and 2 are the six-coordinated distorted octahedron configuration and seven-coordinated distorted triangular bipyramid configuration, respectively. Complex 1 showed stronger inhibitory activity on human cervical cancer cells (HeLa), hepatoma cells (HuH-7), and lung adenocarcinoma cells (H1975) than cisplatin, while complex 2 showed much weaker inhibitory activity.
1. [1]
  ZHENG R S, SU K X, ZHANG S W, ZENG H M, ZOU X N, CHEN R, GU X Y, WEI W Q, HE J. Report of cancer epidemiology in China, 2015[J]. Chinese Journal of Oncology, 2019,41(1):19-28.
2. [2]
  Zaki M, Hairat S, Aazam E S. Scope of organometallic compounds based on transition metal-arene systems as anticancer agents: Starting from the classical paradigm to targeting multiple strategies[J]. RSC Adv., 2019,9(6):3239-3278. doi: 10.1039/C8RA07926A
3. [3]
  Kenny R G, Marmion C J. Toward multi-targeted platinum and ruthenium drugs-A new paradigm in cancer drug treatment regimens[J]. Chem. Rev., 2019,119(2):1058-1137. doi: 10.1021/acs.chemrev.8b00271
4. [4]
  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
5. [5]
  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[de]-isoquinolin-2(3H)-yl)acetic acid: Syntheses, crystal structures, luminescent properties and antitumor activities[J]. J. Mol. Struct., 2017,1146:233-241. doi: 10.1016/j.molstruc.2017.05.141
6. [6]
  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., 2020,1205:127635-127643. doi: 10.1016/j.molstruc.2019.127635
7. [7]
  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)e6540. doi: 10.1002/aoc.6540
8. [8]
  Dahmani M, Harit T, Et-touhami A, Yahyi A, Eddike D, Tillard 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
9. [9]
  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.
10. [10]
  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 complexes[J]. Chinese J. Inorg. Chem., 2022,38(8):1533-1540.
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  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.
15. [15]
  Shang X M, Cui J R, Wu J H, Pombeiro A J L, Li Q S. Polynuclear diorganotin (Ⅳ) complexes with arylhydroxamates: Syntheses, structures and in vitro cytotoxic activities[J]. Inorg. Biochem., 2008,102(4):901-909. doi: 10.1016/j.jinorgbio.2007.12.010
16. [16]
  Zhao X J, Zhang Q F, Li D C, Dou J M, Wang D Q. Syntheses, structural characterizations and properties of 12-MC-4 organotin(Ⅳ) metal-lacrowns: [12-MC_{RSn(Ⅳ)N(shi)}-4] and[12-MC_{RSn(Ⅳ)N(Clshi})-4] (R=Et, Bu, Ph; H₃shi=salicylhydroxamic acid; H₃Clshi=5-chlorosalicylhy-droxamic acid)[J]. J. Organomet. Chem., 2010,695(18):2134-2141. doi: 10.1016/j.jorganchem.2010.05.027
17. [17]
  Shang X M, Li Q S, Wu J Z. Synthesis and crystal structure of a mixed-ligand compound di-n-butyl(4-chlorobenzoxy)(4-chlorobenzo-hydroxamato)tin(Ⅳ)[J]. J. Organomet. Chem., 2005,690(17):3997-4000. doi: 10.1016/j.jorganchem.2005.05.043
18. [18]
  Shang X M, Wu J Z, Li Q S. New coordination modes of substituted benzohydroxamic acid with dialkyltin(Ⅳ): Structural diversity through ligand isomerization[J]. Eur. J. Inorg. Chem., 2006(20):4143-4150.
19. [19]
  Shang X M, Ding N, Xiang G Y. Novel di-n-butyltin(Ⅳ) derivatives: Synthesis, high levels of cytotoxicity in tumor cells and the induction of apoptosis in KB cancer cells[J]. Eur. J. Med. Chem., 2012,48:305-312. doi: 10.1016/j.ejmech.2011.12.032
20. [20]
  Zhao X J, Li D C, Zhang Q F, Wang D Q, Dou J M. The novel example of organotin (Ⅳ) metallacrowns: Syntheses, characterizations and crystal structures of[12-MC_{[RSn(Ⅳ)] N(shi)}-4] complexes (R=Et, Bu, Ph; shi=salicylhydroxamic acid)[J]. Inorg. Chem. Commun., 2010,13(3):346-349. doi: 10.1016/j.inoche.2009.12.018
21. [21]
  ZHANG F X, KUANG D Z, LI X J, FENG Y L, WANG J Q, YU J X, JIANG W J, ZHU X M. Synthesis, structures and properties of the tris(o-methylbenzyl)tin thiosalicylate and di(m-fluorobenzyl)tin thiosalicylate[J]. Chinese Journal of Applied Chemistry, 2017,34(2):163-171.
22. [22]
  ZHANG F X, DENG X, YANG Z H, ZHANG X, FU K X, SHENG L B, ZHU X M, JIANG W J, YU J X. Synthesis, structure and anticancer activity of organotin 9-fluorenone-4-carboxylates[J]. Chinese J. Inorg. Chem., 2023,39(7):1287-1294.
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