Citation: Si-Jia YI, Xia HE, Shu-Qi GU, Zhe-Yu DENG, Jia-Hong LI, Jiang-Xi YU, Fu-Xing ZHANG, Xiao-Ming ZHU. Microwave solvothermal syntheses, crystal structures, and in vitro antitumor activity of three organotin 2, 2′-biphenyl dicarboxylate[J]. Chinese Journal of Inorganic Chemistry, ;2023, 39(5): 874-882. doi: 10.11862/CJIC.2023.050 shu

Microwave solvothermal syntheses, crystal structures, and in vitro antitumor activity of three organotin 2, 2′-biphenyl dicarboxylate

Hunan Engineering Research Center for Monitoring and Treatment of Heavy Metals Pollution in the Upper Reaches of Xiangjiang River, Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Key Laboratory of Organometallic New Materials, College of Hunan Province, College of Chemistry and Material Science, Hengyang Normal University, Hengyang, Hunan 421008, China

Corresponding author: Xiao-Ming ZHU, zxmhunhy@163.com
Received Date: 24 November 2022
Revised Date: 24 March 2023

Figures(5)

Three organotin 2, 2′-biphenyl dicarboxylates, namely [((PhC(Me)₂CH₂)₃Sn)₂(DPA)] (1), [(Cy)₃Sn(DPA)]_n (2), and [(n-Bu)₂Sn(DPA)]_n (3), have been prepared by the microwave-assisted solvothermal reaction of 2, 2′-biphenyl dicarboxylic acid (H₂DPA) with bis(tri(2-methyl-2-phenyl)propyl)tin oxide, tricyclohexyltin hydroxide, and dibutyltin oxide, respectively. Complexes 1-3 have been characterized by IR, NMR, elemental analysis, and thermogravimetry, and the crystal structures have been determined by X-ray diffraction. The crystals of 1-3 belong to the monoclinic system. Due to the influence of alkyl group steric, the steric resistance of the group for PhC(Me)₂CH₂ (1) > Cy (2) > n-Bu (3), the coordination number of tin atoms of complexes 1-3 increases successively, and the coordination number of tin atoms are 4, 5, and 6, respectively. Complex 1 has a binuclear structure, and complexes 2 and 3 are 1D chain structures. The antitumor activity shows that complexes 1-3 have higher activities than cisplatin in Human lung cancer cells (NCI-H460), human breast adenocarcinoma cells (MCF-7), and human liver cancer cells (HepG2) line in vitro.
- organotin 2, 2′-biphenyldicarboxylate,
- microwave solvothermal synthesis,
- crystal structure,
- in vitro antitumor activity
1. [1]
  Sharps M C, Frederick R T, Javitz M L, Herman G S, Johnson D W, Hutchison J E. Organotin carboxylate reagents for nanopatterning: Chemical transformations during direct-write electron beam processes[J]. Chem. Mater., 2019,31(13):4840-4850. doi: 10.1021/acs.chemmater.9b01440
2. [2]
  Sirajuddin M, Tariq M, Ali S. Organotin(Ⅳ) carboxylates as an effective catalyst for the conversion of corn oil into biodiesel[J]. J. Organomet. Chem., 2015,779:30-38. doi: 10.1016/j.jorganchem.2014.12.019
3. [3]
  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
4. [4]
  Amir M K, Khan S, Rehman Z, Shah A, Butler I S. Anticancer activity of organotin(Ⅳ) carboxylates[J]. Inorg. Chim. Acta, 2014,423:14-25. doi: 10.1016/j.ica.2014.07.053
5. [5]
  Sharma S, Agnihotri N, Kumar K, Sihag S, Randhawa V, Kaur R, Singh R, Kaur V. Glutamine conjugated organotin(Ⅳ) Schiff base compounds: Synthesis, structure, and anticancer properties[J]. Appl. Organomet. Chem., 2022,36(2):6521-6540.
6. [6]
  Tariq M, Khan R, Hussain A, Batool A, Rasool F, Yar M, Ayub K, Sirajuddin M, Ullah F, Ali S, Akhtar A, Kausar S, Altaf A A. Synthesis, characterization, antimicrobial, cytotoxic, DNA-interaction, molecular docking and DFT studies of novel di- and tri-organotin(Ⅳ) carboxylates using 3-(3-nitrophenyl)2-methylpropenoic acid[J]. J. Coord. Chem., 2021,74(14):2407-2426. doi: 10.1080/00958972.2021.1964019
7. [7]
  KUANG D Z, ZHU X M, FENG Y L, ZHANG F X, YU J X, JIANG W J, TAN Y X, ZHANG Z J. Syntheses, crystal structures and biological activities of bis(tricyclohexyltin)dicarboxylates with macrocyclic building 2D network[J]. Chinese J. Inorg. Chem., 2015,31(10):2044-2050. doi: 10.11862/CJIC.2015.268
8. [8]
  Su H Q, Zhang R F, Gao 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
9. [9]
  Chen X, Wang H, Wang J J, Zhao L, Li C B, Liu C L. Synthesis, structures, spectroscopies and properties studies of two organotin(Ⅳ) carboxylates with 1, 4-naphthalenedicarboxylic acid[J]. J. Mol. Struct., 2022,1250131738. doi: 10.1016/j.molstruc.2021.131738
10. [10]
  He L, Gao Y J, Xiao Y H, Chen E X, Luo M B, Li Z H, Lin Q P. Imparting superhydrophobicity to porphyrinic coordination frameworks using organotin[J]. CCS Chem., 2022,4(7):2286-2293. doi: 10.31635/ccschem.021.202101378
11. [11]
  Yin H D, Hong M, Yang M L, Cui J C. Cyclotrimeric and weakly-bridged cyclotetrameric organotin(Ⅳ) compounds assembled from 5-hydroxyisophthalic acid: Synthesis and structural characterization[J]. J. Mol. Struct., 2010,984(1/2/3):383-388.
12. [12]
  Cantón-Diaz A, Muñoz-Floresa B M, Berrones-Reyes J, Moggio I, Arias E, Turlakov G, Santillán R, Jiménez-Pérez V M. Organotin compounds bearing C₃-symmetric Schiff base: Microwave-assisted multicomponent synthesis and their photophysical properties[J]. J. Organomet. Chem., 2021,954-955122111. doi: 10.1016/j.jorganchem.2021.122111
13. [13]
  López-Espejel M, Gómez-Treviño A, Muñoz-Flores B M, Treto-Suarez M A, Schott E, Páez-Hernández D, Zarate X, Jiménez-Pérez V M. Organotin Schiff bases as halofluorochromic dyes: Green synthesis, chemio-photophysical characterization, DFT, and their fluorescent bioimaging in vitro[J]. J. Mater. Chem. B, 2021,9(37):7698-7712. doi: 10.1039/D1TB01405F
14. [14]
  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. doi: 10.11862/CJIC.2017.107
15. [15]
  YANG C L, FENG Y L, ZHANG F X, YU J X, JIANG W J, KUANG D Z, YANG N F. Microwave-solvent thermal syntheses, crystal structures and herbicidal activity of bis(3, 5-di-t-butylsalicylaldehyde) carbohydrazide dibutyltin complexes[J]. Chinese J. Inorg. Chem., 2017,33(8):1397-1402. doi: 10.11862/CJIC.2017.175
16. [16]
  JIANG W J, KUANG D Z, FENG Y L, YU J X, ZHANG F X, ZHU X M. Microwave-assisted synthesis, characterization and fluorescence properties of the salicylaldehyde-o-aminophenol Schiff base with appended donor functionality and their n-butyltin(Ⅳ) complexes[J]. Chin. J. Org. Chem., 2014,34(11):2288-2295.
17. [17]
  Liu X J, Zhang Y H, Chang Z, Li A L, Tian D, Yao Z Q, Jia Y Y, Bu X H. A water-stable metal-organic framework with a double-helical structure for fluorescent sensing[J]. Inorg. Chem., 2016,55(15):7326-7328. doi: 10.1021/acs.inorgchem.6b00935
18. [18]
  Song Y, Fan R Q, Fan J Z, Xing K, Du X, Wang P, Yang Y L. Highly sensitive and selective fluorescent probe for Hg²⁺ in Ag(Ⅰ)/Cu(Ⅱ) 3D supramolecular architecture based on noncovalent interactions[J]. Dalton Trans., 2016,45(41):16422-16432. doi: 10.1039/C6DT02694J
19. [19]
  Zhang B J, Wang C J, Qiu G M, Huang S, Zhou X L, Weng J, Wang Y Y. Polycarboxylate anions effect on the structures of a series of transition metal-based coordination polymers: Syntheses, crystal structures and bioactivities[J]. Inorg. Chim. Acta, 2013,397:48-59. doi: 10.1016/j.ica.2012.11.018
20. [20]
  WANG C C, SONG Y X, WANG Y L, WANG P. Syntheses, crystal structure and optical property of two bis-ligand silver(Ⅰ) complexes containing diphenic acid and bidentate N-donor ligands[J]. Chinese J. Inorg. Chem., 2011,27(2):361-366.
21. [21]
  Li N Y, Jiang Z D, Wang Y J, Liu L L, Liu D. Crystallographic visualization of a guest-induced solar-driven cycloaddition reaction based on a recyclable nonporous coordination polymer[J]. Inorg. Chem., 2021,60(22):17173-17177. doi: 10.1021/acs.inorgchem.1c02477
22. [22]
  Thirumurugan A, Pati S K, Green M A, Natarajan S. Observation of tancoite-like chains in a one-dimensional metal-organic polymer[J]. J. Mater. Chem., 2003,13(12):2937-2941. doi: 10.1039/B310778G
23. [23]
  Wang R H, Hong M C, Luo J H, Cao R, Weng J B. Synthesis and crystal structures of the first two novel dicarboxylate organotin polymers constructed from dimeric tetraorganodistannoxane units[J]. Eur. J. Inorg. Chem., 2002(8):2082-2085.
24. [24]
  WENG S F. Fourier translation infrared spectroscopy analysis. 2nd ed. Beijing: Chemical Industry Press, 2005: 305-306
25. [25]
  ZHU X M, KUANG D Z, FENG Y L, ZHANG F X, YU J X, JIANG W J, ZHANG Z J. Syntheses, crystal structures, thermal stability and biological activities of two bis[tri(2-methyl-2-phenyl)propyltin] dicarboxylates (CH₂)_n[CO₂Sn(CH₂CMe₂Ph₃)₂(n=5, 6)[J]. Chinese J. Inorg. Chem., 2015,31(7):1373-1379. doi: 10.11862/CJIC.2015.181
26. [26]
  Ma C L, Sun J S, Zhang R F, Wang D Q. Self-assembled diorganotin(Ⅳ) moieties with 2, 3, 4, 5-tetrafluorobenzoic acid: Syntheses, characterizations and crystal structures[J]. Inorg. Chim. Acta, 2006,359(13):4179-4190.
27. [27]
  Chandrasekhar V, Thirumoorthi R, Metre R K, Mahanti B. Steric control in the reactions of 3-pyrazolecarboxylic acid with diorganotin dichlorides[J]. J. Organomet. Chem., 2011,696(2):600-606.
28. [28]
  Molloy K C, Purcell T G, Quill K. Organotin biocides: 1. The structure of triphenyltin acetate[J]. J. Organomet. Chem., 1984,267(3):237-247.
29. [29]
  Forrester A R, Garden S J, Howie R A, Wardell J L. Structural study of 3-oxypropyltin compounds[J]. J. Chem. Soc. Dalton. Trans., 1992(17):2615-2621.
1. [1]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
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]
  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
15. [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. [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. [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. [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. [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. [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

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(674)
HTML views(101)

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