Citation: Le CHEN, Xin DENG, Yu-Xing TAN, Fu-Xing ZHANG, Dai-Zhi KUANG, Wu-Jiu JIANG. Synthesis, Anti⁃tumor Activity, and Interaction with DNA of Two Substituted Benzyltin Complexes[J]. Chinese Journal of Inorganic Chemistry, ;2022, 38(6): 1081-1089. doi: 10.11862/CJIC.2022.124 shu

Synthesis, Anti⁃tumor Activity, and Interaction with DNA of Two Substituted Benzyltin Complexes

Figures(10)

  • Two organotin complexes (C1, C2) were synthesized by di(2, 4-dichlorobenzyl)tin dichloride reacting with p-methyl benzoyl hydrazide or p-tert-butyl benzoyl hydrazide, and sodium pyruvate. The structure of the complexes were characterized through elemental analysis, IR, 1H NMR, 13C NMR, 119Sn NMR, HRMS, and X-ray single crystal diffraction. The thermal stability of complexes C1 and C2 were analyzed, and the antitumor activities of the complexes were evaluated by MTT against three cell lines (human lung cancer cells NCI-H460, human liver cancer cells HepG2, and human breast cancer cells MCF7). It was found that complex C1 showed a good inhibitory effect on NCI-H460, HepG2, and MCF7. The interaction of the complexes with DNA was investigated using UV-Vis spectroscopy, fluorescence spectroscopy, and viscosity measurement. It is found that the complexes can bind to DNA through an intercalation mode. CCDC: 2124763, C1; 2124764, C2.
  • 加载中
    1. [1]

      Zhou S Y, Zou H Y, Chen G Y, Huang G L. Synthesis and Biological Activities of Chemical Drugs for the Treatment of Rheumatoid Arthritis[J]. Top. Curr. Chem., 2019,377(5)28. doi: 10.1007/s41061-019-0252-5

    2. [2]

      Kazakov A S, Lepakhin V K, Bukatina T M, Snegireva I I, Zatolochina K É. Efficacies and Chemical Structures of Modern Drugs for Hepatitis C Virus Treatment[J]. Pharm. Chem. J., 2018,52(6):497-500. doi: 10.1007/s11094-018-1847-9

    3. [3]

      Zhang M, Saint-Germain C, He G, Sun R W Y. Drug Delivery Systems for Anti-cancer Active Complexes of Some Coinage Metals[J]. Curr. Med. Chem., 2018,25(4):493-505. doi: 10.2174/0929867324666170511152441

    4. [4]

      Damia G, Broggini M. Platinum Resistance in Ovarian Cancer: Role of DNA Repair[J]. Cancers, 2019,11(1)119. doi: 10.3390/cancers11010119

    5. [5]

      Pages B J, Garbutcheon-Singh K B, Aldrich-Wright J R. Platinum Intercalators of DNA as Anticancer Agents[J]. Eur. J. Inorg. Chem., 2017,2017(12):1613-1624. doi: 10.1002/ejic.201601204

    6. [6]

      Brabec V, Hrabina O, Kasparkova J. Cytotoxic Platinum Coordination Compounds. DNA Binding Agents[J]. Coord. Chem. Rev., 2017,351:2-31. doi: 10.1016/j.ccr.2017.04.013

    7. [7]

      Tüzün B. Investigation of Pyrazoly Derivatives Schiff Base Ligands and Their Metal Complexes Used as Anti-cancer Drug[J]. Spectrochim. Acta A, 2020,227117663. doi: 10.1016/j.saa.2019.117663

    8. [8]

      Ott I, Gust R. Non Platinum Metal Complexes as Anti-cancer Drugs[J]. Arch. Pharm., 2007,340(3):117-126. doi: 10.1002/ardp.200600151

    9. [9]

      Annuar S N S, Kamaludin N F, Awang N, Chan K M. Cellular Basis of Organotin(Ⅳ) Derivatives as Anticancer Metallodrugs: A Review[J]. Front. Chem., 2021,9(522)657599.

    10. [10]

      Shah S A S, Ashfaq M, Waseem A, Ahmed M M, Najam T, Shaheen S, Rivera G. Synthesis and Biological Activities of Organotin(Ⅳ) Complexes as Antitumoral and Antimicrobial Agents. A Review[J]. Mini-Rev. Med. Chem., 2015,15(5):406-426. doi: 10.2174/138955751505150408142958

    11. [11]

      Snoeij N J, Penninks A H, Seinen W. Biological Activity of Organotin Compounds—An Overview[J]. Environ. Res., 1987,44(2):335-353. doi: 10.1016/S0013-9351(87)80242-6

    12. [12]

      Jiang W J, Fan S J, Zhou Q, Zhang F X, Kuang D Z, Tan Y X. Diversity of Complexes Based on p-Nitrobenzoylhydrazide, Benzoylformic Acid and Diorganotin Halides or Oxides Self-Assemble: Cytotoxicity, the Induction of Apoptosis in Cancer Cells and DNA-Binding Properties[J]. Bioorg. Chem., 2020,94103402. doi: 10.1016/j.bioorg.2019.103402

    13. [13]

      Devi J, Pachwania S. Recent Advancements in DNA Interaction Studies of Organotin(Ⅳ) Complexes[J]. Inorg. Chem. Commun., 2018,91:44-62. doi: 10.1016/j.inoche.2018.03.012

    14. [14]

      Piro V, Di Simone F, Madonia G, Silvestri A, Giuliani A M, Ruisi G, Barbieri R. The Interaction of Organotins with Native DNA[J]. Appl. Organomet. Chem., 1992,6(6):537-542. doi: 10.1002/aoc.590060611

    15. [15]

      Poletto J, da Silva M J V, Jacomini A P, Bidóia D L, Volpato H, Nakamura C V, Rosa F A. Antiparasitic Activities of Novel Pyrimidine N-Acylhydrazone Hybrids[J]. Drug Dev. Res., 2021,82(2):230-240. doi: 10.1002/ddr.21745

    16. [16]

      Zhao Z X, Cheng L P, Li M, Pang W, Wu F H. Discovery of Novel Acylhydrazone Neuraminidase Inhibitors[J]. Eur. J. Med. Chem., 2019,173:305-313. doi: 10.1016/j.ejmech.2019.04.006

    17. [17]

      Chen L W, Xie J L, Song H J, Liu Y X, Gu Y C, Wang L Z, Wang Q M. Design, Synthesis, and Biological Activities of Spirooxindoles Containing Acylhydrazone Fragment Derivatives Based on the Biosynthesis of Alkaloids Derived from Tryptophan[J]. J. Agric. Food. Chem., 2016,64(34):6508-6516. doi: 10.1021/acs.jafc.6b02683

    18. [18]

      Sisido K, Takeda Y, Kinugawa Z. Direct Synthesis of Organotin Compounds. Ⅰ. Di- and Tribenzyltin Chlorides[J]. J. Am. Chem. Soc., 1961,83(3):538-541. doi: 10.1021/ja01464a008

    19. [19]

      Tan C P, Liu J, Chen L M, Shi S, Ji L N. Synthesis, Structural Characteristics, DNA Binding Properties and Cytotoxicity Studies of a Series of Ru(Ⅲ) Complexes[J]. J. Inorg. Biochem., 2008,102(8):1644-1653. doi: 10.1016/j.jinorgbio.2008.03.005

    20. [20]

      HUANG M L, LUO G G, LIN J Q. Synthesis, Crystal Structure and Fluorescence Properties of Cadmium Complexes of Pyridine-2-formaldehyde Hydrazone[J]. Chinese J. Inorg. Chem., 2021,37(2):251-258.  

    21. [21]

      FAN S J, XU J X, HU Z C, CUI Y, TAN Y X, JIANG W J. Syntheses, Antitumor Activity and DNA Interaction of p-Chlorine-Benzyltin Complexes Based on Acylhydrazone Ligand[J]. Chinese J. Inorg. Chem., 2021,37(4):684-692.  

    22. [22]

      El-bendary M M, Etaiw S E H. Structure and Applications of Organotin Complex Based on Trimethyltin Cation and Quinaldic Acid[J]. Appl. Organomet. Chem., 2018,32(3)e4152. doi: 10.1002/aoc.4152

    23. [23]

      Tan Y X, Zhang Z J, Liu Y, Yu J X, Zhu X M, Kuang D Z, Jiang W J. Synthesis, Crystal Structure and Biological Activity of the Schiff Base Organotin(Ⅳ) Complexes Based on Salicylaldehyde-o-aminophenol[J]. J. Mol. Struct., 2017,1149:874-881. doi: 10.1016/j.molstruc.2017.08.058

    24. [24]

      Tan Y X, Zhang Z J, Feng Y L, Yu J X, Zhu X M, Zhang F X, Kuang D Z, Jiang W J. Syntheses, Crystal Structures and Biological Activity of the 1D Chain Benzyltin Complexes Based on 2-Oxo-propionic Acid Benzoyl Hydrazone[J]. J. Inorg. Organomet. Polym Mater., 2017,27(1):342-352. doi: 10.1007/s10904-016-0477-5

    25. [25]

      Wang M, Yu F, Jiang W J, Tan Y X, Zhang F X, Kuang D Z. Syntheses, Crystal Structures and Biological Activity of the Diorganotin 2-(2-(4-Methoxybenzoyl)hydrazono)-3-phenylpropanoic Carboxylate Complexes[J]. Chin. J. Struct. Chem., 2020,39(11):56-63.

    26. [26]

      Li Y X, Yu H T, Zeng H T, Liu M Q, Kuang D Z, Tan Y X, Jiang W J. Syntheses, Crystal Structures and Biological Activities of the 2-Oxo-3-phenylpropionic Acid Arylformylhydrazone Dibenzyltin Complexes[J]. Chin. J. Struct. Chem., 2019,38(11):124-132.

    27. [27]

      Nath M, Mridula , Kumari R. Microwave-Assisted Synthesis of Mixed Ligands Organotin(Ⅳ) Complexes of 1, 10-Phenanthroline and l-Proline: Physicochemical Characterization, DFT Calculations, Chemotherapeutic Potential Validation by In Vitro DNA Binding and Nuclease Activity[J]. J. Photochem. Photobiol. B, 2017,174:182-194. doi: 10.1016/j.jphotobiol.2017.07.017

    28. [28]

      Arjmand F, Yousuf I. Synthesis, Characterization and In Vitro DNA Binding of Chromone Schiff Base Organotin(Ⅳ) Complexes[J]. J. Organomet. Chem., 2013,743:55-62. doi: 10.1016/j.jorganchem.2013.06.018

    29. [29]

      Noureen S, Sirajuddin M, Ali S, Shaheen F, Tahir M N. Synthesis, Structural Elucidation and DNA Binding Study of Fluorine Substituted Organotin(Ⅳ) Dithiocarbamates[J]. Polyhedron, 2015,102:750-758. doi: 10.1016/j.poly.2015.10.056

    30. [30]

      Tariq M, Ali S, Shah N A, Muhammad N, Tahir M N, Khalid N. Catalytic, Biological and DNA Interaction Studies of 3-(4-Cyanophenyl)-2-methylacrylate Organotin(Ⅳ) Carboxylates Derivatives: Synthesis, Spectroscopic Characterization and X-ray Structures[J]. Inorg. Chim. Acta, 2013,405:444-454. doi: 10.1016/j.ica.2013.06.036

    31. [31]

      Alsaedi S, Babgi B A, Abdellattif M H, Arshad M N, Emwas A H M, Jaremko M, Humphrey M G, Asiri A M, Hussien M A. DNA-Binding and Cytotoxicity of Copper Complexes(Ⅰ) Containing Functionalized Dipyridylphenazine Ligands[J]. Pharmaceutics, 2021,13(5)764. doi: 10.3390/pharmaceutics13050764

  • 加载中
    1. [1]

      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

    2. [2]

      Ping Song Nan Zhang Jie Wang Rui Yan Zhiqiang Wang Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087

    3. [3]

      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

    4. [4]

      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

    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]

      Jiaming Xu Yu Xiang Weisheng Lin Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093

    7. [7]

      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

    8. [8]

      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

    9. [9]

      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

    10. [10]

      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

    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]

      Tianyun Chen Ruilin Xiao Xinsheng Gu Yunyi Shao Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017

    16. [16]

      Liang TANGJingfei NIKang XIAOXiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139

    17. [17]

      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

    18. [18]

      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

    19. [19]

      Aiai WANGLu ZHAOYunfeng BAIFeng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225

    20. [20]

      Feng Sha Xinyan Wu Ping Hu Wenqing Zhang Xiaoyang Luan Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082

Metrics
  • PDF Downloads(0)
  • Abstract views(599)
  • HTML views(86)

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