Citation: 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[J]. Chinese Journal of Inorganic Chemistry, ;2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278 shu

Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand

Figures(4)

  • To study the synthesis and antitumor activities of the transition metal complexes incorporating a novel naphthol-aldehyde Schiff base ligand, three transition metal complexes [Cu(L)2(DMF)2] (1), [Ni(L)2(DMF)2] (2), and [Zn(L)2] (3) were synthesized using a Schiff base of N-[(2-hydroxy-1-naphthalenyl)methylene]-[(1H-indol-3-yl)ethyl] imine (HL) by liquid diffusion method. The complexes 1-3 were characterized by IR analysis, elemental analysis, and single-crystal X-ray diffraction. Moreover, their antitumor activities in vitro were screened through three human cancer cell lines (MGC-803, A549, MDA-MB-231) by the MTT assay. It revealed that complexes 1-3 showed high antitumor activities. Complex 1 showed much higher antitumor activities than complexes 2 and 3, and even than cisplatin. Among them, complex 1 had the highest inhibitory effects on tumor cells with its IC50 value (half-inhibitory concentration) being (4.8±0.2) μmol·L-1 against MGC-803 cells. These demonstrated a potential anti-cancer candidate for complex 1, which induced MGC-803 cancer cells' late apoptosis by flow cytometry. Subsequently, the cell scraper experiment showed that the killing effect of MGC-803 cells was enhanced with the increase in the concentration of complex 1.
  • 加载中
    1. [1]

      Rosenberg B, Vancamp L, Trosko J E, Mansour V H. Platinum compounds: A new class of potent antitumour agents[J]. Nature, 1969,222(5191):385-386. doi: 10.1038/222385a0

    2. [2]

      Adhikari S, Nath P, Das A, Datta A, Baildya N, Duttaroy A K, Pathak S. A review on metal complexes and its anti-cancer activities: Recent updates from in vivo studies[J]. Biomed. Pharmacother., 2024,171116211. doi: 10.1016/j.biopha.2024.116211

    3. [3]

      Zhao S, Yang Z B, Jiang G Z, Huang S, Bian M L, Lu Y L, Liu W K. An overview of anticancer platinum N-heterocyclic carbene complexes[J]. Coord. Chem. Rev., 2021,449214217. doi: 10.1016/j.ccr.2021.214217

    4. [4]

      Wang W T, Wang P C, Liao X L, Yang B, Gao C Z, Yang J. A series of planar phosphorescent cyclometalated platinum(Ⅱ) complexes as new anticancer theranostic agents that induce oncosis[J]. J. Med. Chem., 2023,66(18):13103-13115. doi: 10.1021/acs.jmedchem.3c01126

    5. [5]

      Gillem J, Giuffrida M, Krick E. Efficacy and toxicity of carboplatin and cytarabine chemotherapy for dogs with relapsed or refractory lymphoma (2000-2013)[J]. Vet. Comp. Oncol., 2017,15:400-410. doi: 10.1111/vco.12176

    6. [6]

      Argyriou A A, Polychronopoulos P, Iconomou G, Chroni E, Kalofonos H P. A review on oxaliplatin-induced peripheral nerve damage[J]. Cancer Treat. Rev., 2008,34:368-377. doi: 10.1016/j.ctrv.2008.01.003

    7. [7]

      Liang J X, Zhong H J, Yang G J, Vellaisamy K, Ma D L, Leung C H. Recent development of transition metal complexes with in vivo antitumor activity[J]. J. Inorg. Biochem., 2017,177:276-286. doi: 10.1016/j.jinorgbio.2017.06.002

    8. [8]

      Pellei M, Del G J, Caviglia M, Gandin V, Marzano C, Karade D V, Noonikara P A, Dias H V R, Santini C. Synthesis and investigations of the antitumor effects of first-row transition metal(Ⅱ) complexes supported by two fluorinated and non-fluorinated β-diketonates[J]. Int. J. Mol. Sci., 2024,25(4)2038. doi: 10.3390/ijms25042038

    9. [9]

      Qi F, Yuan H, Chen Y C, Peng X X, Wu Y P, He W J, Guo Z J. Type Ⅰ photoreaction and photoinduced ferroptosis by a Ru(Ⅱ) complex to overcome tumor hypoxia in photodynamic therapy[J]. CCS Chem., 2023,5(7):1583-1591. doi: 10.31635/ccschem.022.202202074

    10. [10]

      Li S M, Yuan H, Chen Y C, Guo Z J. Metal complexes induced ferroptosis for anticancer therapy[J]. Fundamental Res., 2023,3(4):525-528. doi: 10.1016/j.fmre.2022.10.001

    11. [11]

      Gong J Y, Wei P F, Liu J K, Chen Y C, Zhao Z, Zhao W J, Xie H L, Ma C, Lam J W Y, Wo ng, K S, Li Y, Tang B Z. Polarity-triggered anti-Kasha system for high-contrast cell imaging and classification[J]. Aggregate, 2023,4(2)e265. doi: 10.1002/agt2.265

    12. [12]

      Kolhe N H, Jadhav S S. Synthesis, characterization and biological activity of mixed ligands complexes of quinolin-8-ol and substituted chromones with MnⅡ, Co(Ⅱ), Ni(Ⅱ) and Cu(Ⅱ) metal ions[J]. Res. Chem. Intermed., 2019,45:973-996. doi: 10.1007/s11164-018-3656-x

    13. [13]

      Das M, Mukherjee S, Koley B, Choudhuri I, Bhattacharyya N, Roy P, Samanta B C, Barai M, Maity T. Developing novel zinc(Ⅱ) and copper(Ⅱ) Schiff base complexes: Combined experimental and theoretical investigation on their DNA/protein binding efficacy and anticancer activity[J]. New J. Chem., 2020,44:18347-18361. doi: 10.1039/D0NJ03844J

    14. [14]

      Ghassemzadeh M, Moghadam M E, Saeidifar M, Jahangiri S, Yarahmadi A, Aghapoor K, Mohsenzadeh F, Neumüller B. Novel nickel(Ⅱ) complex bearing acenaphthenequinone based thiosemicarbazone bis-Schiff base: Synthesis, characterization, linkage isomers, antitumor activity, DFT, and DNA docking simulation[J]. J. Mol. Struct., 2024,1313138716. doi: 10.1016/j.molstruc.2024.138716

    15. [15]

      Eichhorn G L, Shin Y A. Interaction of metal ions with polynucleotides and related compounds Ⅻ: The relative effect of various metal ions on DNA helicity[J]. J. Am. Chem. Soc., 1968,90:7323-7328. doi: 10.1021/ja01028a024

    16. [16]

      Maheswari P U, Roy S, Dulk H D, Barends S, Wezel G V, Kozlevčar B, Gamez P, Reedijk J. The square-planar cytotoxic[Cu(pyrimol)Cl] complex acts as an efficient DNA cleaver without reductant[J]. J. Am. Chem. Soc., 2006,128:710-711. doi: 10.1021/ja056970+

    17. [17]

      Kumar R, Singh A A, Kumar U, Jain P, Sharma A K, Kant C, Faizi , M S H. Recent advances in synthesis of heterocyclic Schiff base transition metal complexes and their antimicrobial activities especially antibacterial and antifungal[J]. J. Mol. Struct., 2023,1294136346. doi: 10.1016/j.molstruc.2023.136346

    18. [18]

      Liu C, Liu X C, Ge X X, Wang Q H, Zhang L, Shang W J, Zhang Y, Yuan X A, Tian L J, Liu Z, You J M. Fluorescent iridium(Ⅲ) coumarin-salicylaldehyde Schiff base compounds as lysosome-targeted antitumor agents[J]. Dalton Trans., 2020,49:5988-5998. doi: 10.1039/D0DT00627K

    19. [19]

      Shi S Z, Yu S, Quan L X, Mansoor M, Chen Z L, Hu H C, Liu D C, Liang Y N, Liang F P. Synthesis and antitumor activities of transition metal complexes of a bis-Schiff base of 2-hydroxy-1-naphthalenecarboxaldehyde[J]. J. Inorg. Biochem., 2020,210111173. doi: 10.1016/j.jinorgbio.2020.111173

    20. [20]

      Scalese G, Mosquillo M F, Rostan S, Castiglioni J, Alho I, Perez L, Correia I, Marques F, Pessoa J C, Gambino D. Heteroleptic oxidovanadium􀃯 complexes of 2-hydroxynaphtylaldimine and polypyridyl ligands against Trypanosoma cruzi and prostate cancer cells[J]. J. Inorg. Biochem., 2017,175:154-166. doi: 10.1016/j.jinorgbio.2017.07.014

    21. [21]

      Zhang Z Y, Bi C F, Fan Y H, Zhang N, Deshmukh R, Yan X C, Lv X W, Zhang P F, Zhang X, Dou Q P. L-Ornithine Schiff base-copper and -cadmium complexes as new proteasome inhibitors and apoptosis inducers in human cancer cells[J]. J. Biol. Inorg. Chem., 2015,20:109-121. doi: 10.1007/s00775-014-1219-1

    22. [22]

      WANG H, CUI G W, CAO W, LIU S X, LIU Y, GU X X. Synthesis, characterization and fluorescence properties of copper complexes of naphthalene-phenolic Schiff base[J]. Journal of Hangzhou Normal University (Natural Science Edition), 2022,21(2):119-123.

    23. [23]

      Mahmoud N H, Elsayed G H, Aboelnaga A, Fahim A M. Spectroscopic studies, DFT calculations, cytotoxicity activity, and docking stimulation of novel metal complexes of Schiff base ligand of isonicotino hydrazide derivative[J]. Appl. Organomet. Chem., 2022,36(7)e6697. doi: 10.1002/aoc.6697

  • 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]

      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

    3. [3]

      Changqing MIAOFengjiao CHENWenyu LIShujie WEIYuqing YAOKeyi WANGNi WANGXiaoyan XINMing 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]

      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

    5. [5]

      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

    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]

      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

    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]

      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

    10. [10]

      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

    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]

      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

    16. [16]

      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

    17. [17]

      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

    18. [18]

      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

    19. [19]

      Geyang Song Dong Xue Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030

    20. [20]

      Yanyang Li Zongpei Zhang Kai Li Shuangquan Zang . Ideological and Political Design for the Comprehensive Experiment of the Synthesis and Aggregation-Induced Emission (AIE) Performance Study of Salicylaldehyde Schiff-Base. University Chemistry, 2024, 39(2): 105-109. doi: 10.3866/PKU.DXHX202307020

Metrics
  • PDF Downloads(1)
  • Abstract views(54)
  • HTML views(9)

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