Citation: Ya-Wen REN, Hang-Na HU, Jun ZHANG, Xin-Jing ZHUANG, Dong-Ping LI, Yong-Xiu LI. Characterization and DNA Interaction of Lanthanide Complexes Based on Thiourea Ligand[J]. Chinese Journal of Structural Chemistry, ;2021, 40(1): 47-54. doi: 10.14102/j.cnki.0254–5861.2011–2760 shu

Characterization and DNA Interaction of Lanthanide Complexes Based on Thiourea Ligand

a.
Department of Chemistry, Nanchang University, Nanchang 330031, China
b.
Key Laboratory of Functional Molecule Design and Interface Process, Anhui Jianzhu University, Hefei 230022, China

Corresponding author: Dong-Ping LI, nculdp@126.com
Received Date: 8 February 2020
Accepted Date: 1 April 2020

Fund Project: the National Natural Science Foundation of China 21101090the National Natural Science Foundation of China 21561021

Figures(3)

Three isostructural lanthanide complexes, namely [Ln(L)₃·CH₃OH] (Ln = Tb(1), Dy(2), Ho(3), HL = N-(pyridin-2-ylcarbamothioyl)benzamide), were successfully synthesized and characterized by IR, UV, elemental analysis, single-crystal X-ray diffraction and DNA-biding analysis. X-ray single-crystal diffractions show that the family of lanthanide complexes crystallizes in monoclinic C2/c space group. Each lanthanide atom is coordinated with three carbonyl-O atoms, three pyridyl-N atoms and three imine-N atoms from three distinct L^–1 ligands, forming a distorted tricapped trigonal prism. The binding properties of complexes with ct-DNA were studied by simulating the physiological environment of human body. The results suggest that compounds could bind with ct-DNA through interaction under a spontaneous process.
- lanthanide complex,
- crystal structure,
- DNA-binding activity
1. [1]
  Nandhini, R.; Krishnamoorthy, B. S.; Venkatachalam, G. Binuclear half-sandwich ruthenium(II) Schiff base complexes: synthesis, characterization, DFT study and catalytic activity for the reduction of nitroarenes. J. Organomet. Chem. 2019, 903, 120984–120992. doi: 10.1016/j.jorganchem.2019.120984
2. [2]
  Rogolino, D.; Cavazzoni, A.; Gatti, A.; Tegoni, M.; Pelosi, G.; Verdolino, V.; Fumarola, C.; Cretella, D.; Petronini, P. G.; Carcelli, M. Anti-proliferative effects of copper(II) complexes with hydroxyquinoline-thiosemicarbazone ligands. Eur. J. Med. Chem. 2017, 128, 140–153. doi: 10.1016/j.ejmech.2017.01.031
3. [3]
  (a) Bisceglie, F.; Musiari, A.; Pinelli, S.; Alinovi, R.; Menozzi, I.; Polverini, E.; Tarasconi, P.; Tavone, M.; Pelosi, G. Quinoline-2-carboxaldehyde thiosemicarbazones and their Cu(II) and Ni(II) complexes as topoisomerase IIa inhibitors. J. Inorg. Biochem. 2015, 152, 10–19. (b) Li, W.; Liu, Y.; Li, C. H.; Yang, Y. Q. Crystal structure, electrochemical and fluorescent properties of a new copper(II) coordination polymer with 2, 3-pyridinedi-carboxylic acid. Chin. J. Struct. Chem. 2019, 38, 1940–1946.
4. [4]
  Garcia-Tojal, J.; Gil-Garcia, R.; Fouz, V. I.; Madariag, G.; Lezama, L.; Galletero, M. S.; Borras, J.; Nollmann, F. I.; Garcia-Giron, C.; Alcarz, R.; Cavia-Saiz, M.; Muniz, P.; Palacios, O.; Sarriper, K. G.; Rojo, T. Revisiting the thiosemicarbazone copper(II) reaction with glutathione. Activity against colorectal carcinoma cell lines. J. Inorg. Biochem. 2018, 180, 69–79. doi: 10.1016/j.jinorgbio.2017.12.005
5. [5]
  Li, X.; Zhang, D. D. ; Liu, Z. H.; Xu, Y.; Wang, D. F. Synthesis, characterization of a ternary Cu(II) Schiff base complex with degradation activity of organophosphorus pesticides. Inorg. Chim. Acta 2018, 471, 280–289. doi: 10.1016/j.ica.2017.11.024
6. [6]
  Chai, L. Q.; Tang, L. J.; Chen, L. C.; Huang, J. J. Structural, spectral, electrochemical and DFT studies of two mononuclear manganese(II) and zinc(II) complexes. Polyhedron 2017, 122, 228–240. doi: 10.1016/j.poly.2016.11.032
7. [7]
  Sivaraman, G.; Iniya, M.; Anand, T.; Kotla, N. G.; Sunnapu, O.; Singaravadivel, S.; Gulyani, A.; Chellappa, D. Chemically diverse small molecule fluorescent chemosensors for copper ion. Coordin. Chem. Rev. 2018, 357, 50–104. doi: 10.1016/j.ccr.2017.11.020
8. [8]
  Unluer, D.; Kamiloglu, A. A.; Direkel, S.; Bektas, E.; Kantekin, H.; Sancak, K. Synthesis and characterization of metallophthalocyanine with morpholine containing Schiff base and determination of their antimicrobial and antioxidant activities. J. Organomet. Chem. 2019, 900, 120936–120938. doi: 10.1016/j.jorganchem.2019.120936
9. [9]
  Nematidil, N.; Sadeghi, M.; Nezami, S.; Sadeghi, H. Synthesis and characterization of Schiff-base based chitosan-g-glutaraldehyde/NaMMTNPs-APTES for removal Pb²⁺ and Hg²⁺ ions. Carbohyd. Polym. 2019, 222, 114971–114978. doi: 10.1016/j.carbpol.2019.114971
10. [10]
  Aligholivand, M.; Shaghaghi, Z.; Bikas, R.; Kozakiewicz, A. Electrocatalytic water oxidation by a Ni(II) salophen-type complex. Rsc. Advances 2019, 9, 40424–40436. doi: 10.1039/C9RA08585H
11. [11]
  Sabolova, D.; Kristian, P.; Kozurkova, M. Proflavine/acriflavine derivatives with versatile biological activities. J. Appl. Toxicol. 2020, 40, 64–71. doi: 10.1002/jat.3818
12. [12]
  Gandhaveeti, R.; Konakanchi, R.; Jyothi, P.; Bhuvanesh, N. S. P.; Anandaram, S. Unusual coordination mode of aroyl/acyl thiourea ligands and their pi-arene ruthenium(II) piano-stool complexes: synthesis, molecular geometry, theoretical studies and biological applications. Appl. Organomet. Chem. 2019, 33, 1–13.
13. [13]
  Lomzik, M.; Mazuryk, O.; Rutkowska-Zbik, D.; Stochel, G.; Gros, P. C.; Brindell, M. New ruthenium compounds bearing semicarbazone 2-formylopyridine moiety: playing with auxiliary ligands for tuning the mechanism of biological activity. J. Inorg. Biochem. 2017, 175, 80–91. doi: 10.1016/j.jinorgbio.2017.07.006
14. [14]
  (a) Enoyer, D.; Masaldan, S.; Fontaine, S. L.; Cater, M. A. Targeting copper in cancer therapy: 'Copper That Cancer'. Metallomics 2015, 7, 1459–1476. (b) Muhammad, D.; Rabia, A. B.; Muhammad, N. T.; Muhammad, A.; Syeda, T. H. UV assisted preliminary DNA binding studies and single-crystal X-ray structure of 4-{(4-nitrophenyl-sulfonamido)methyl}cyclohexane-carboxylic acid. Chin. J. Struct. Chem. 2017, 36, 745–750.
15. [15]
  (a) Santini, C.; Pellei, M.; Gandin, V.; Porchia, M.; Tisato, F.; Marzano, C. Advances in copper complexes as anticancer agents. Chem. Rev. 2014, 114, 815–862. (b) Li, Q. X.; Wang, W. L.; Meng, X. G. A novel copper(II) complex of asymmetrically N-functionalized 1, 4, 7-triazacyclononane ligand: syntheses, structure, electrochemical property and biological activities. Chin. J. Struct. Chem. 2018, 37, 878–886.
16. [16]
  Sumrra, S. H.; Hanif, M.; Chohan, Z. H.; Akram, M. S.; Akhtar, J.; Al-Shehri, S. M. Metal based drugs: design, synthesis and in-vitro antimicrobial screening of Co(II), Ni(II), Cu(II) and Zn(II) complexes with some new carboxamide derived compounds: crystal structures of N-[ethyl(propan-2-yl)carbamothioyl]thiophene-2-carboxamide and its copper(II) complex. J. Enzym. Inhib. Med. Ch. 2016, 31, 590–598. doi: 10.3109/14756366.2015.1050011
17. [17]
  Homzova, K.; Gyoryova, K.; Hudecova, D.; Koman, M.; Melnik, M.; Kovarova, J. Synthesis, thermal, spectral, and biological properties of zinc(II) 4-aminobenzoate complexes. J. Therm. Anal. Calorim. 2017, 129, 1065–1082. doi: 10.1007/s10973-017-6184-9
18. [18]
  Krajnikova, A.; Gyoryova, K.; Kovarova, J.; Hudecova, D.; Hubackova, J.; El-Dien, F. N.; Koman, M. Thermoanalytical, spectral and biological study of 4-bromobenzoatozinc(II) complexes containing bioactive organic ligands. J. Therm. Anal. Calorim. 2012, 110, 177–185. doi: 10.1007/s10973-012-2299-1
19. [19]
  Hirano, S.; Suzuki, K. T. Exposure, metabolism, and toxicity of rare earths and related compounds. Environ. Health. Persp. 1996, 104, 85–95.
20. [20]
  Song, Y. M.; Xu, J. P.; Ding, L.; Hou, Q.; Liu, J. W.; Zhu, Z. L. Syntheses, characterization and biological activities of rare earth metal complexes with curcumin and 1, 10-phenanthroline-5, 6-dione, J. Inorg. Biochem. 2009, 103, 396–400. doi: 10.1016/j.jinorgbio.2008.12.001
21. [21]
  Rogolino, D.; Cavazzoni, A.; Gatti, A.; Tegoni, M.; Pelosi, G.; Verdolino, V.; Fumarola, C.; Cretella, D.; Petronini, P. G.; Carcelli, M. Anti-proliferative effects of copper(II) complexes with hydroxyquinoline-thiosemicarbazone ligands. Eur. J. Med. Chem. 2017, 128, 140–153. doi: 10.1016/j.ejmech.2017.01.031
22. [22]
  Garcia-Tojal, J.; Gil-Garcia, R.; Fouz, V. I.; Madariag, G.; Lezama, L.; Galletero, M. S.; Borras, J.; Nollmann, F. I.; Garcia-Giron, C.; Alcarz, R.; Cavia-Saiz, M.; Muniz, P.; Palacios, O.; Sarriper, K. G.; Rojo, T. Revisiting the thiosemicarbazone copper(II) reaction with glutathione. Activity against colorectal carcinoma cell lines. J. Inorg. Biochem. 2018, 180, 69–79. doi: 10.1016/j.jinorgbio.2017.12.005
23. [23]
  Li, H.; Wang, X.; Huang, D. X.; Chen, G. Y. Recent advances of lanthanide-doped upconversion nanoparticles for biological applications. Nanotechnology 2020, 31, 7–37.
24. [24]
  (a) Wang, L.; Nagesha, D. K.; Selvarasah, S.; Dokmeci, M. R.; Carrier, R. L. Toxicity of CdSe nanoparticles in caco-2 cell cultures. J. Nanobiotech 2008, 6, 11. (b) Wang, J. K.; Li, B.; Wu, H. P.; Tian, X. Y.; Ma, X. X. Synthesis, crystal structure and DNA-binding property of a Mn(II) complex based on 5-(trifluoromethyl)pyridine-2-carboxylic acid. Chin. J. Struct. Chem. 2019, 38, 1349–1355.
25. [25]
  (a) Shiri, F.; Rahimi-Nasrabadi, M.; Ahmadi, F.; Ehrlich, H. Multispectroscopic and molecular modeling studies on the interaction of copper-ibuprofenate complex with bovine serum albumin (BSA). Spectrochim. Acta A 2018, 203, 510–521. (b) Liu, Y. Z.; Gao, H. Y.; Yi, X. G.; Li, D. P.; Li, Y. X. Crystal structures and DNA binding properties of 2-naphthoxyacetic acid Cu(II) complexes. Chin. J. Struct. Chem. 2019, 38, 1362–1369.
26. [26]
  Kalaiarasi, G.; Jain, R.; Puschman, H.; Poorna, C. S.; Preethi, K.; Prabhakaran, R. New binuclear Ni(II) metallates containing ONS chelators: synthesis, characterisation, DNA binding, DNA cleavage, protein binding, antioxidant activity, antimicrobial and in vitro cytotoxicity. New J. Chem. 2017, 41, 2543–2560. doi: 10.1039/C6NJ03516G
27. [27]
  Gatti, A.; Habtemariam, A.; Romero-Canelon, I.; Song, J. I.; Heer, B.; Clarkson, G. J.; Rogolino, D.; Sadler, P. J.; Carcelli, M. Half-sandwich arene ruthenium(II) and osmium(II) thiosemicarbazone complexes: solution behavior and antiproliferative activity. Organometallics 2018, 37, 891–899. doi: 10.1021/acs.organomet.7b00875
28. [28]
  Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Cryst. A 2008, 64, 112–122. doi: 10.1107/S0108767307043930
29. [29]
  Vlasenko, V. G.; Burlov, A. S.; Koshchienko, Y. V.; Kolodina, A. A. Zubavichus, Y. V.; Lazarenko, V. A.; Khrustalev, V. N. Synthesis, crystal structure and magnetic properties of copper(II) complexes with 4-methyl-N-[2-[(E)-2-pyridyl[alkyl]iminomethyl] phenyl]benzenesulfamide ligands. J. Mol. Struct. 2020, 1203, 127450–127547. doi: 10.1016/j.molstruc.2019.127450
30. [30]
  (a) Steemers, F. J.; Verboom, W.; Reinhoudt, D. N.; van der Tol, E. B.; Jan, W.; Verhoeven, J. W. New sensitizer-modified calix[4]arenes enabling near-UV excitation of complexed luminescent lanthanide ions. J. Am. Chem. Soc. 1995, 117, 37, 9408–9414. (b) Yang, J.; Tao, G. X.; Xin, G. X.; Meng, T.; Yuan, X. M.; Du, L. T.; Li, X.; Xu, H. J. Syntheses, characterization and crystal Sstructures of metal Coordination Polymers based on L-malic acid. Chin. J. Inorg. Chem. 2018, 34, 1312–1318.
31. [31]
  Shebl, M. Synthesis, spectroscopic characterization and antimicrobial activity of binuclear metal complexes of a new asymmetrical Schiff base ligand: DNA binding affinity of copper(II) complexes. Spectrochim. Acta. A 2014, 117, 127–137. doi: 10.1016/j.saa.2013.07.107
32. [32]
  Adibi, H.; Abdolmaleki, S.; Shahabadi, N.; Golabi, A.; Mandavi, M.; Zendehcheshm, S.; Ghadermazi, M.; Ansari, M.; Rudbari, H. A.; Bruno, G.; Nemati, A. Investigation of crystallographic structure, in vitro cytotoxicity and DNA interaction of two La(III) and Ce(IV) complexes containing dipicolinic acid and 4-dimethylaminopyridine. Polyhedron 2019, 163, 20–32. doi: 10.1016/j.poly.2019.02.009
33. [33]
  Song, X. Q.; Wang, Z. G.; Wang, Y.; Huang, Y. Y.; Sun, Y. X.; Ouyang, Y.; Xie, C. Z.; Xu, J. Y. Syntheses, characterization, DNA/HSA binding ability and antitumor activities of a family of isostructural binuclear lanthanide complexes containing hydrazine Schiff base. J. Biomol. Struct. Dyn. 2019, 38, 733–743.
34. [34]
  Chakraborty, M.; Mondal, S.; Cardin, C.; Rheingold, A. L.; Das Mukhopadhyay, C.; Chattopadhyay, S. K. Yb(III), Sm(III) and La(III) complexes of a tetradentate pyridoxal Schiff base ligand: their DNA-binding activity and bio-imaging applications. Polyhedron 2020, 175, 114167–114178. doi: 10.1016/j.poly.2019.114167
35. [35]
  Haribabu, J.; Sabapathi, G.; Tamizh, M. M.; Balachandran, C.; Bhuvanesh, N. S. P.; Venuvanalingam, P.; Karvembu, R. Water-soluble mono- and binuclear ru(η₆-p-cymene) complexes containing indole thiosemicarbazones: synthesis, DFT modeling, biomolecular interactions, and in vitro anticancer activity through apoptosis. Organometallics 2018, 37, 1242–1257. doi: 10.1021/acs.organomet.8b00004
1. [1]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
2. [2]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
3. [3]
  Lu LIU , Huijie WANG , Haitong WANG , Ying 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
4. [4]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
5. [5]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
6. [6]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
7. [7]
  Yinling HOU , Jia JI , Hong YU , Xiaoyun BIAN , Xiaofen GUAN , Jing QIU , Shuyi REN , Ming FANG . A rhombic Dy₄-based complex showing remarkable single-molecule magnet behavior. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 605-612. doi: 10.11862/CJIC.20240251
8. [8]
  Xiaofen GUAN , Yating LIU , Jia LI , Yiwen HU , Haiyuan DING , Yuanjing SHI , Zhiqiang WANG , Wenmin WANG . Synthesis, crystal structure, and DNA-binding of binuclear lanthanide complexes based on a multidentate Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2486-2496. doi: 10.11862/CJIC.20240122
9. [9]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
10. [10]
  Xiumei LI , Linlin LI , Bo LIU , Yaru PAN . Syntheses, crystal structures, and characterizations of two cadmium(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 613-623. doi: 10.11862/CJIC.20240273
11. [11]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
12. [12]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
13. [13]
  Yan XU , Suzhi LI , Yan LI , Lushun FENG , Wentao SUN , Xinxing LI . Structure variation of cadmium naphthalene-diphosphonates with the changing rigidity of N-donor auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 395-406. doi: 10.11862/CJIC.20240226
14. [14]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
15. [15]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
16. [16]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting 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
17. [17]
  Shuyan ZHAO . Field-induced Co^Ⅱ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
18. [18]
  Zhaodong WANG . In situ synthesis, crystal structure, and magnetic characterization of a trinuclear copper complex based on a multi-substituted imidazo[1,5-a]pyrazine scaffold. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 597-604. doi: 10.11862/CJIC.20240268
19. [19]
  Hai-Ling Wang , Zhong-Hong Zhu , Hua-Hong Zou . Structure and assembly mechanism of high-nuclear lanthanide-oxo clusters. Chinese Journal of Structural Chemistry, 2024, 43(9): 100372-100372. doi: 10.1016/j.cjsc.2024.100372
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(363)
HTML views(5)

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