Citation:
SHI Peng-Fei, JIANG Qin, DUAN Hai-Chao, TIAN Yu-Peng. Synthesis, Crystal Structure and Antitumor Ability of a Fluorescent Organotin Compound[J]. Chinese Journal of Inorganic Chemistry,
;2014, 30(5): 984-992.
doi:
10.11862/CJIC.2014.158
-
A Schiff base derivate from isonicotinohydrazide and p-N,N-di(2-hydroxyethyl)amino benzaldehyde, together with its organotin complex, have been synthesized and characterized by 1H NMR spectroscopy, elemental analyses and X-ray crystallography. The planar Schiff base compound coordinated to the tin center in a bidentate mode, with the trans-C=N-conformation changed to be cis in the complex. The crystal data of the complex and the large red shift in the fluorescence spectra demonstrated an extension of the π-conjunction due to the coordination. In vitro cytotoxicity data showed that both compounds were more cytotoxic than cisplatin against A-549, MCF-7 and Hela tumor cell lines. The interactions of both compounds with CT-DNA were preliminarily studied by UV-Vis and fluorescence spectroscopy, which suggested that the organotin complex likely induces the distortion of DNA double helix through covalent bonding, while the hydrogen bonds and the large planar structure of the molecule hindered the Schiff base compound from intercalating into the DNA double helix.
-
-
-
[1]
[1] Gajda T, Jancsó A. Met. Ions Life Sci., 2010, 7:111-151
-
[2]
[2] Nath M, Saini P K. Dalton Trans., 2011, 40:7077-7121
-
[3]
[3] Alama A, Tasso B, Novelli F, et al. Drug. Disc. Tod., 2009, 14:500-508
-
[4]
[4] Hadjikakou S K, Hadjiliadis N. Coord. Chem. Rev., 2009, 253:235-249
-
[5]
[5] Sadimenko A P. Adv. Heterocycl. Chem., 2012, 107:133-218
-
[6]
[6] Agarwal R K, Prasad S, Singh U. Int. J. Chem., 2012, 1:264-280
-
[7]
[7] Sreenivasulu B. Supramol. Chem., 2012, 3:826-862
-
[8]
[8] Anand P, Patil V M, Sharma V K, et al. Int. J. Drug Des. Disc., 2012, 3:851-868
-
[9]
[9] Becker E M, Lovejoy D B, Greer J M, et al. J. Pharmacol., 2003, 138:819-830
-
[10]
[10] Bernhardt P V, Caldwell L M, Chaston T B, et al. J. Biol. Inorg. Chem., 2003, 8:866-880
-
[11]
[11] Bernhardt P V, Mattsson J, Richardson D R. Inorg. Chem., 2006, 45:752-760
-
[12]
[12] Bernhardt P V, Wilson G J, Sharpe P C, et al. J. Biol. Inorg. Chem., 2008, 13:107-119
-
[13]
[13] Jeena Pearl A, Abbs F, Reji T F. J. Chem. Pharmac. Res., 2013, 5:115-122
-
[14]
[14] Tabassum S, Amir A, Arjmand F, et al. Eur. J. Med. Chem., 2013, 60:216-232
-
[15]
[15] Sheeja L K L P, Christudhas M, Isac S R C. J. Chem. Pharmac. Res., 2012, 4:4762-4769
-
[16]
[16] Sathiyaraj S, Butcher R J, Jayabalakrishnan C. J. Coord. Chem., 2013, 66:580-591
-
[17]
[17] Yin H D, Liu H, Hong M. J. Organomet. Chem., 2012, 713: 11-19
-
[18]
[18] Rehman W, Baloch M K, Badshah A. Eur. J. Med. Chem., 2008, 43:2380-2385
-
[19]
[19] Hong M, Yin H D, Zhang X Y, et al. J. Organomet. Chem., 2013, 724:23-31
-
[20]
[20] Mun L S, Hapipah M A, Shin S K, et al. Appl. Organomet. Chem., 2012, 26:310-319
-
[21]
[21] Sedaghat T, Naseh M, Khavasi H R, et al. Polyhedron, 2012, 33:435-440
-
[22]
[22] Rehman W, Badshah A, Khan S, et al. Eur. J. Med. Chem., 2009, 44:3981-3985
-
[23]
[23] Ni W X, Li M, Zhan S Z, et al. Inorg. Chem., 2009, 48:1433-1441
-
[24]
[24] Lemmerer A. CrystEngComm, 2012, 14:2465-2478
-
[25]
[25] APEX2 Software Suite (SMART, SAINT, SADABS, etc.), Bruker AXS Inc., Madison, Wisconsin, USA.
-
[26]
[26] Sheldrick G M. SHELXL 2008, Program for the Refinement of Crystal Structure, University of Göttingen, Germany, 2008.
-
[27]
[27] Zhang J Y, Wang X Y, Tu C, et al. J. Med. Chem., 2003, 46: 3502-3507
-
[28]
[28] Elhamzaoui H, Jousseaume B, Toupance T, et al. Chem. Commun., 2006:1304-1306
-
[29]
[29] Švec P, Černošková E, Padělková Z, et al. J. Organomet. Chem., 2010, 695:2475-2485
-
[30]
[30] Li S H, Chen F R, Zhou Y F, et al. Chem. Commun., 2009: 4179-4181
-
[31]
[31] Niu Y F, Han F F, Zhang Q, et al. Angew. Chem. Int. Ed., 2013, 52:1-6
-
[32]
[32] Ni W X, Li M, Zhou X P, et al. Chem. Commun., 2007:3479-3481
-
[33]
[33] Przhonska O V, Webster S, Padilha L A, et al. Fluorescence, 2010, 8:105-148
-
[34]
[34] Hancock R D. Chem. Soc. Rev., 2013, 42:1500-1524
-
[35]
[35] Liu Z P, He W J, Guo Z J. Chem. Soc. Rev., 2013, 42:1568-1600
-
[36]
[36] Terenzi A, Tomasello L, Spinello A, et al. J. Inorg. Biochem., 2012, 117:103-110
-
[37]
[37] Chen X, Gao F, Yang W Y, et al. Chem. Biodivers, 2013, 10:367-384
-
[38]
[38] Kumar C V, Barton J K, Turro N J. J. Am. Chem. Soc., 1985, 107:5518-5523
-
[1]
-
-
-
[1]
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. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
-
[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]
Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming 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]
Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng 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
-
[5]
Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli 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
-
[6]
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
-
[7]
Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two LnⅢ3 complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
-
[8]
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
-
[9]
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
-
[10]
Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming 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
-
[11]
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
-
[12]
Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang 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
-
[13]
Yongzhi LI , Han ZHANG , Gangding WANG , Yanwei SUI , Lei HOU , Yaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307
-
[14]
Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min 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
-
[15]
Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan 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]
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
-
[17]
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
-
[18]
Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
-
[19]
Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun 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
-
[20]
Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi 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
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(417)
- HTML views(35)