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

  • 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).
  • 加载中
    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

  • 加载中
    1. [1]

      Haitang WANGYanni LINGXiaqing MAYuxin CHENRui ZHANGKeyi WANGYing ZHANGWenmin WANG . Construction, crystal structures, and biological activities of two Ln3 complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188

    2. [2]

      Jingjing QINGFan HEZhihui LIUShuaipeng HOUYa LIUYifan JIANGMengting TANLifang HEFuxing ZHANGXiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003

    3. [3]

      Xin MAYa SUNNa SUNQian KANGJiajia ZHANGRuitao ZHUXiaoli 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

    4. [4]

      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

    5. [5]

      Xiaoling LUOPintian ZOUXiaoyan WANGZheng LIUXiangfei KONGQun TANGSheng 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

    6. [6]

      Yingchun ZHANGYiwei SHIRuijie YANGXin WANGZhiguo SONGMin 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]

      Xinting XIONGZhiqiang XIONGPanlei XIAOXuliang NIEXiuying SONGXiuguang 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

    8. [8]

      Jia Zhou . Constructing Potential Energy Surface of Water Molecule by Quantum Chemistry and Machine Learning: Introduction to a Comprehensive Computational Chemistry Experiment. University Chemistry, 2024, 39(3): 351-358. doi: 10.3866/PKU.DXHX202309060

    9. [9]

      Dongju Zhang Rongxiu Zhu . Construction of Ideological and Political Education in Quantum Chemistry Course: Several Teaching Cases to Reveal the Universal Connection of Things. University Chemistry, 2024, 39(7): 272-277. doi: 10.3866/PKU.DXHX202311032

    10. [10]

      Guoxian Zhu Jing Chen Rongkai Pan . Enhancing the Teaching Quality of Atomic Structure: Insights and Strategies. University Chemistry, 2024, 39(3): 376-383. doi: 10.3866/PKU.DXHX202305027

    11. [11]

      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

    12. [12]

      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

    13. [13]

      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

    14. [14]

      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

    15. [15]

      Xiaowei TANGShiquan XIAOJingwen SUNYu ZHUXiaoting CHENHaiyan 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

    16. [16]

      Zhaoyang WANGChun YANGYaoyao SongNa HANXiaomeng LIUQinglun 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 ZHANGDongdong YANGNing LIYuanyu YANGQi 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]

      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

    19. [19]

      Meirong HANXiaoyang WEISisi FENGYuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu2+. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150

    20. [20]

      Lu LIUHuijie WANGHaitong WANGYing LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489

Metrics
  • PDF Downloads(2)
  • Abstract views(511)
  • HTML views(54)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return