Citation: Yu-Lin ZHOU, Fu-Xing ZHANG, Xiao-Ming ZHU, Jie TIAN, Sai-Nan XU, Bin-Jie ZHAO, Jing-Jiao CHEN, Fang-Fang LI, Xin DENG. Synthesis, Structure, and Anticancer Activity of Two Organotin Heterocyclic Carboxylates Complexes[J]. Chinese Journal of Inorganic Chemistry, ;2022, 38(8): 1533-1540. doi: 10.11862/CJIC.2022.161 shu

Synthesis, Structure, and Anticancer Activity of Two Organotin Heterocyclic Carboxylates Complexes

Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Key Laboratory of Organometallic New Materials of 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: 12 February 2022
Revised Date: 26 April 2022

Figures(6)

Two organotin heterocyclic carboxylate complexes di(o - bromobenzyl)tin bis(2-pyridinecarboxylate) (1) and tri(2-methyl-2-phenyl propyl)tin 3-indole butyrate (2) have been synthesized by a solvothermal method using methanol as solvent. The complexes were characterized by elemental analysis, IR spectroscopy, NMR (¹H, ¹³C, and ¹¹⁹Sn), X-ray diffraction, and thermogravimetric analysis. The crystal structures of the complexes were determined by X-ray single-crystal diffraction. The results show that the complexes have a single tin core structure, and the tin atoms are six-coordinate distorted octahedron configuration and four-coordinate distorted tetrahedron configuration respectively. The stabilities, orbital energies, and composition characteristics of some frontier molecular orbitals of 1 and 2 have been carefully investigated with quantum chemistry calculation. In addition, the in vitro antitumor activities suggest that 1 and 2 had higher activities than cisplatinum against human hepatoma 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]
  Su H Q, Zhang R F, Guo Q, Wang J, Li Q L, Du X M, Ru J, Zhang Q F, Ma C L. Five Organotin Complexes Derived from Hydroxycinnamic Acid Ligands: Synthesis, Structure, In Vitro Cytostatic Activity and Binding Interaction with BSA[J]. J. Mol. Struct., 2022,1247131290. doi: 10.1016/j.molstruc.2021.131290
2. [2]
  Ruan B F, Tian Y P, Zhou H P, Wu J Y, Hu R T, Zhu C H, Yang J X, Zhu H L. Synthesis, Characterization and In Vitro Antitumor Activity of Three Organotin(Ⅳ) Complexes with Carbazole Ligand[J]. Inorg. Chim. Acta, 2011,365(1):302-308. doi: 10.1016/j.ica.2010.09.024
3. [3]
  FENG Y L, KUANG D Z, ZHANG F X, YU J X, JIANG W J, ZHU X M. Two Di-n-butyltin Carboxylates with a Sn₄O₄ Ladder-like Framework: Microwave Solvothermal Syntheses, Structures and In Vitro Antitumor Activities[J]. Chinese J. Inorg. Chem., 2017,33(5):830-836.
4. [4]
  Airapetyan D V, Petrosyan V S, Gruener S V, Zaitsev K V, Arkhipov D E, Korlyukov A A. Disproportionation Reactions within the Series of Coordinated Monoorganostannanes[J]. J. Organomet. Chem., 2013,747:241-248. doi: 10.1016/j.jorganchem.2013.07.005
5. [5]
  Iqbal M, Ali S, Muhammad N, Parvez M, Langer P, Villinger A. Synthesis, Characterization, Crystal Structures and Electrochemical Studies of Organotin(Ⅳ) Carboxylates[J]. J. Organomet. Chem., 2013,723:214-223. doi: 10.1016/j.jorganchem.2012.10.006
6. [6]
  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.
7. [7]
  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., 2010,45:883-889. doi: 10.1016/j.ejmech.2009.11.026
8. [8]
  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
9. [9]
  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
10. [10]
  He T F, Zhang F X, Yao S F, Zhu X M, Sheng L B, Kuang D Z, Feng Y L, Yu J X, Jiang W J. Synthesis, Structure and Biological Activities of a Novel Anionic Organotin (Ⅳ) Complex {[(p-ClC₆H₄CH₂)Sn(H₂O) (Cl)₂OCOCH(O)CH(O)CO₂Sn(H₂O) (Cl)₂(p-ClC₆H₄CH₂)] ·2(HNEt₃)}[J]. Chin. J. Struct. Chem., 2018,37(12):1899-1906.
11. [11]
  Zhang F X, Wu J Q, Kuang D Z, Yu J X, Jiang W J, Zhu X M. Synthesis, Crystal Structure and Properties of a Triphenyltin Schiff Complex with Salicylidene-2-aminophenol[J]. Chin. J. Struct. Chem., 2018,37(2):270-276.
12. [12]
  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):859-875. doi: 10.3390/molecules25040859
13. [13]
  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.
14. [14]
  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
15. [15]
  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.
16. [16]
  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.
17. [17]
  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.
18. [18]
  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
19. [19]
  ZHANG F X, KUANG D Z, WANG J Q, FENG Y L, CHEN Z M. Synthesis and Crystal Structure of the Di(o-fluorobenzyl)tin Bis(2-picolinate) and the Tri(o-fluorobenzyl)tin 4-Picolinate[J]. Chinese J. Inorg. Chem., 2006,22(1):7-12. doi: 10.3321/j.issn:1001-4861.2006.01.002
20. [20]
  ZHANG F X, KUANG D Z, WANG J Q, FENG Y L, CHEN Z M, ZENG R Y. Study on Synthesis and Crystal Structure and Quantum Chemistry of the Dibenzyltin Bis(2-quininate)[J]. Chinese J. Inorg. Chem., 2006,22(7):1321-1326. doi: 10.3321/j.issn:1001-4861.2006.07.031
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