Citation: Xiao-Shuang ZHU, Xue-Zhi GAO, Rui WANG, Yan-Hong YANG, Jia-Wei LIANG, Bing LI. Bovine serum albumin binding property of Dy(Ⅲ) and Tm(Ⅲ) complexes based on pyridine-2-carboxylic acid[J]. Chinese Journal of Inorganic Chemistry, ;2023, 39(7): 1360-1368. doi: 10.11862/CJIC.2023.111 shu

Bovine serum albumin binding property of Dy(Ⅲ) and Tm(Ⅲ) complexes based on pyridine-2-carboxylic acid

State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering, Department of Chemistry & Chemical Engineering, Ningxia University, Yinchuan 750021, China

Corresponding author: Bing LI, nxdaxue@126.com
Received Date: 28 November 2022
Revised Date: 27 April 2023

Figures(4)

Two isomorphous mononuclear complexes [M(tpc)₃(H₂O)₃]·H₂O, where M=Dy (1), Tm (2), were synthesized through the reaction of 5-(trifluoromethyl) pyridine-2-carboxylic acid (Htpc), DyCl₃·6H₂O, and TmCl₃·3H₂O. The crystallographic details of complexes 1 and 2 reveal a monoclinic crystal system with the P2₁/c space group. Metal ions in the two complexes are eight-coordinated and located in the slightly deformed dodecahedron geometry. The fluorescence data reveal that complexes 1 and 2 could interact with bovine serum albumin (BSA) through the static quenching mechanism with the quenching constant K_sv ranging from 10⁵ to 10⁶ L·mol^-1. Hydrophobic interaction plays an important role in the interaction of complexes and BSA since both ΔH and ΔS values are positive. The binding constant between the two complexes and BSA was about 10⁴ L·mol^-1 at 25 ℃, which indicates the complexes and BSA have moderate interactions.
- lanthanide complexes,
- 5-(trifluoromethyl) pyridine-2-carboxylic acid,
- bovine serum albumin,
- static quenching
1. [1]
  Lacroix A, Edwardson T G, Hancock M A, Dore M D, Sleiman H F. Development of DNA nanostructures for high‑affinity binding to human serum albumin[J]. J. Am. Chem. Soc., 2017,139(21):7355-7362. doi: 10.1021/jacs.7b02917
2. [2]
  Dixon J M, Egusa S. Conformational change-induced fluorescence of bovine serum albumin-gold complexes[J]. J. Am. Chem. Soc., 2018,140(6):2265-2271. doi: 10.1021/jacs.7b11712
3. [3]
  Rogawski R, Sharon M. Characterizing endogenous protein complexes with biological mass spectrometry[J]. Chem. Rev., 2021,122(8):7386-7414.
4. [4]
  Jiang J, Cao B, Chen Y T, Luo H J, Xue J Y, Xiong X L, Zou T T. Alkylgold(Ⅲ) complexes undergo unprecedented photo-induced β-hydride elimination and reduction for targeted cancer therapy[J]. Angew. Chem. Int. Ed., 2022,134(16)e202201103.
5. [5]
  Zhang G, Wang L, Pan J. Probing the binding of the flavonoid diosmetin to human serum albumin by multispectroscopic techniques[J]. J. Agric. Food Chem., 2012,60(10):2721-2729. doi: 10.1021/jf205260g
6. [6]
  Li X F, Ma L G, Yang Y Q, Liu Y J, Meng X R, Yang H X. Synthesis, crystal structure and bovine serum albumin-binding studies of a new Cd(Ⅱ) complex incorporating 2, 2'-(propane-1, 3-diyl) bis(1H-imidazole-4, 5-dicarboxylate)[J]. J. Chem. Res., 2020,44(3/4):198-205.
7. [7]
  Raja D S, Bhuvanesh N S P, Natarajan K. Synthesis, crystal structure and pharmacological evaluation of two new Cu(Ⅱ) complexes of 2-oxo-1, 2-dihydroquinoline-3-carbaldehyde (benzoyl) hydrazone: A comparative investigation[J]. Eur. J. Med. Chem., 2012,47:73-85. doi: 10.1016/j.ejmech.2011.10.024
8. [8]
  Annaraj B, Neelakantan M A. Synthesis, crystal structure, spectral characterization and biological exploration of water soluble Cu(Ⅱ) complexes of vitamin B6 derivative[J]. Eur. J. Med. Chem., 2015,102:1-8. doi: 10.1016/j.ejmech.2015.07.041
9. [9]
  Sahu G, Banerjee A, Samanta R, Mohanty M, Lima S, Tiekink E R, Dinda R. Water-soluble dioxidovanadium? complexes of aroylhydrazones: DNA/BSA interactions, hydrophobicity, and cell-selective anticancer potential[J]. Inorg. Chem., 2021,60(20):15291-15309. doi: 10.1021/acs.inorgchem.1c01899
10. [10]
  Anjomshoa M, Torkzadeh-Mahani M, Sahihi M, Rizzoli C, Ansari M, Janczak J, Esfahani S S, Ataei F, Dehkhodaei M, Amirheidari B. Tris-chelated complexes of nickel(Ⅱ) with bipyridine derivatives: DNA binding and cleavage, BSA binding, molecular docking, and cytotoxicity[J]. J. Biomol. Struct. Dyn., 2019,37:3887-3904. doi: 10.1080/07391102.2018.1534700
11. [11]
  Song H, Wang J K, Chen X Y, Tian X Y, Li Y L, Li B. Synthesis, crystal structure and antifungal activity of a new Zn(Ⅱ) complex based on 4-(5-(pyridin-3-yl)-4H-1, 2, 4-triazol-3-yl) benzoic acid[J]. Chin. J. Struct. Chem., 2021,40(1):103-108.
12. [12]
  Mugnaini C, Kostrzewa M, Bryk M, Mahmoud A M, Brizzi A, Lamponi S, Giorgi G, Ferlenghi F, Vacondio F, Maccioni P, Colombo G, Mor M, Starowicz K, Marzo V D, Ligresti A, Corelli F. Design, synthesis, and physicochemical and pharmacological profiling of 7-hydroxy-5-oxopyrazolo[4, 3-b]pyridine-6-carboxamide derivatives with antiosteoarthritic activity in vivo[J]. J. Med. Chem., 2020,63(13):7369-7391. doi: 10.1021/acs.jmedchem.0c00595
13. [13]
  CHEN L, DENG X, TAN Y X, ZHANG F X, KUANG D Z, JIANG W J. Synthesis, anti-tumor activity, and interaction with DNA of two substituted benzyltin complexes[J]. Chinese J. Inorg. Chem., 2022,38(6):1081-1089.
14. [14]
  Swanson D M. Identification and biological evaluation of 4-(3-trifluoromethylpyridin-2-yl)piperazine-1-carboxylic acid (5-trifluoromethylpyridin-2-yl)amide, a high affinity TRPV1 (VR1) vanilloid receptor antagonist[J]. J. Med. Chem., 2005,48(6):1857-1872. doi: 10.1021/jm0495071
15. [15]
  Asahina Y, Araya I, Iwase K, Iinuma F, Hosaka M, Ishizaki T. Synthesis and antibacterial activity of the 4-quinolone-3-carboxylic acid derivatives having a trifluoromethyl group as a novel N-1 substituent[J]. J. Med. Chem., 2005,48(9):3443-3446. doi: 10.1021/jm040204g
16. [16]
  Akher F B, Farrokhzadeh A, Ravenscroft N, Kuttel M M. Mechanistic study of potent fluorinated EGFR kinase inhibitors with a quinazoline scaffold against L858R/T790M/C797S resistance mutation: Unveiling the fluorine substituent cooperativity effect on the inhibitory activity[J]. J. Phys. Chem. B, 2020,124(28):5813-5824. doi: 10.1021/acs.jpcb.0c03440
17. [17]
  Li B, Wang J K, Song H, Wu H P, Chen X Y, Ma X X. Synthesis, crystal structure, and BSA interaction with a new Co(Ⅱ) complex based on 5-(trifluoromethyl)pyridine-2-carboxylic acid[J]. J. Coord. Chem., 2019,72(15):2562-2573. doi: 10.1080/00958972.2019.1663836
18. [18]
  Vadori M, Pacor S, Vita F, Zorzet S, Cocchietto M, Sava G. Features and full reversibility of the renal toxicity of the ruthenium-based drug NAMI-A in mice[J]. J. Inorg. Biochem., 2013,118:21-27. doi: 10.1016/j.jinorgbio.2012.09.018
19. [19]
  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[J]. Chin. J. Struct. Chem., 2019,8:1349-1355.
20. [20]
  Shang Y P, Feng X, Li J X, Wang Y F, Wang L Y, Li Z J. Two novel hydroxide anions bridged lanthanide coordination polymers based on fluorinated carboxylate ligand: Structures, luminescence and magnetic property[J]. Inorg. Chem. Commun., 2019,105:47-54. doi: 10.1016/j.inoche.2019.04.003
21. [21]
  Asadpour S, Aramesh-Boroujeni Z, Jahani S. In vitro anticancer activity of parent and nano-encapsulated samarium(Ⅲ) complex towards antimicrobial activity studies and FS-DNA/BSA binding affinity[J]. RSC Adv., 2020,10(53):31979-31990. doi: 10.1039/D0RA05280A
22. [22]
  Zhu X P, Li Z P, Ji X X, Chen Q, Wu S Y, Gao E J, Zhu M C. Two new lanthanide complexes with 5-(pyrazol-1-yl)nicotinic acid: Structures and their anti-cancer properties[J]. J. Inorg. Biochem., 2021,222111505. doi: 10.1016/j.jinorgbio.2021.111505
23. [23]
  Aramesh-Boroujeni Z, Jahani S, Khorasani-Motlagh M, Kerman K, Noroozifar M. Evaluation of DNA, BSA binding, DNA cleavage and antimicrobial activity of ytterbium(Ⅲ) complex containing 2, 2'-bipyridine ligand[J]. J. Biomol. Struct. Dyn., 2019,38:1711-1725.
24. [24]
  Singh K, Srivastava P, Patra A K. Binding interactions with biological targets and DNA photocleavage activity of Pr(Ⅲ) and Nd(Ⅲ) complexes of dipyridoquinoxaline[J]. Inorg. Chim. Acta, 2016,451:73-81. doi: 10.1016/j.ica.2016.07.003
25. [25]
  Sheldrick G M. SHELXL-2018. University of Göttingen, Germany, 2018.
26. [26]
  Ren Y W, Hu H N, Zhang J, Zhuang X J, Li D P, Li Y X. Characterization and DNA interaction of lanthanide complexes based on thiourea ligand[J]. Chin. J. Struct. Chem., 2021,40(1):47-54.
27. [27]
  Shan F L, Song H, Gao X Z, Li B, Ma X X. Synthesis, crystal structure and DNA-binding property of a new Cu(Ⅱ) complex based on 4-(trifluoromethyl)nicotinic acid[J]. Chin. J. Struct. Chem., 2022,41(2):57-63.
28. [28]
  Bashir M, Yousuf I, Prasad C P. Mixed Ni(Ⅱ) and Co(Ⅱ) complexes of nalidixic acid drug: Synthesis, characterization, DNA/BSA binding profile and in vitro cytotoxic evaluation against MDA-MB-231 and HepG2 cancer cell lines[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2022,271120910. doi: 10.1016/j.saa.2022.120910
29. [29]
  Anjomshoa M, Fatemi S J, Torkzadeh-Mahani M, Hadadzadeh H. DNA-and BSA-binding studies and anticancer activity against human breast cancer cells (MCF-7) of the zinc(Ⅱ) complex coordinated by 5, 6-diphenyl-3-(2-pyridyl)-1, 2, 4-triazine[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2014,127:511-520. doi: 10.1016/j.saa.2014.02.048
30. [30]
  Pan A, Mitra I, Mukherjee S, Ghosh S, Chatterji U, Moi S C. Development of anticancer activity of the Pt(Ⅱ) complex with N-heterocyclic amine: Its in vitro pharmacokinetics with thiol and thio-ethers, DNA and BSA binding, and cell cycle arrest[J]. ACS Appl. Bio Mater., 2021,4(1):853-868. doi: 10.1021/acsabm.0c01374
31. [31]
  Machicote R G, Pacheco M E, Bruzzone L. Binding of several benzodiazepines to bovine serum albumin: Fluorescence study[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2010,77(2):466-472. doi: 10.1016/j.saa.2010.06.020
32. [32]
  Samari F, Shamsipur M, Hemmateenejad B, Khayamian T, Gharaghani S. Investigation of the interaction between amodiaquine and human serum albumin by fluorescence spectroscopy and molecular modeling[J]. Eur. J. Med. Chem., 2012,54:255-263. doi: 10.1016/j.ejmech.2012.05.007
33. [33]
  Guo J L, Liu G Y, Wang R Y, Sun S X. Synthesis and structure elucidation of two essential metal complexes: In-vitro studies of their BSA/HSA-binding properties, docking simulations, and anticancer activities[J]. Molecules, 2022,27(6)1886. doi: 10.3390/molecules27061886
34. [34]
  Divsalar A, Razmi M, Saboury A A, Mansouri-Torshizi H, Ahmad F. Biological evaluation of a new synthesized Pt(Ⅱ) complex by cytotoxic and spectroscopic studies[J]. Cell Biochem. Biophys., 2015,71(3):1415-1424. doi: 10.1007/s12013-014-0364-z
35. [35]
  Sangeetha S, Murali M. Cytotoxic ruthenium(Ⅱ) complexes containing a dangling pyridine: Selectivity for diseased cells mediated by pH-dependent DNA binding[J]. Inorg. Chem., 2022,61(6):2864-2882. doi: 10.1021/acs.inorgchem.1c03399
36. [36]
  Patel R V, Keum Y S, Park S W. Nitroimidazoles, quinolones and oxazolidinones as fluorine bearing antitubercular clinical candidates[J]. Mini-Rev. Med. Chem., 2015,15(14):1174-1186. doi: 10.2174/1389557515666150709121153
37. [37]
  Ross P D, Subramanian S. Thermodynamics of protein association reactions: Forces contributing to stability[J]. Biochemistry, 1981,20(11):3096-3102. doi: 10.1021/bi00514a017
38. [38]
  Aseman M D, Aryamanesh S, Shojaeifard Z, Hemmateenejad B, Nabavizadeh S M. Cycloplatinated(Ⅱ) derivatives of mercaptopurine capable of binding interactions with HSA/DNA[J]. Inorg. Chem., 2019,58(23):16154-16170. doi: 10.1021/acs.inorgchem.9b02696
1. [1]
  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
2. [2]
  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
3. [3]
  Yuanjiao Liu , Xiaoyang Zhao , Songyao Zhang , Yi Wang , Yutuo Zheng , Xinrui Miao , Wenli Deng . Site-selection and recognition of aromatic carboxylic acid in response to coronene and pyridine derivative. Chinese Chemical Letters, 2024, 35(8): 109404-. doi: 10.1016/j.cclet.2023.109404
4. [4]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
5. [5]
  Shiyu Pan , Bo Cao , Deling Yuan , Tifeng Jiao , Qingrui Zhang , Shoufeng Tang . Complexes of cupric ion and tartaric acid enhanced calcium peroxide Fenton-like reaction for metronidazole degradation. Chinese Chemical Letters, 2024, 35(7): 109185-. doi: 10.1016/j.cclet.2023.109185
6. [6]
  Chaochao Jin , Kai Li , Jiongpei Zhang , Zhihua Wang , Jiajing Tan . N,O-Bidentated difluoroboron complexes based on pyridine-ester enolates: Facile synthesis, post-complexation modification, optical properties, and applications. Chinese Chemical Letters, 2024, 35(9): 109532-. doi: 10.1016/j.cclet.2024.109532
7. [7]
  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
8. [8]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
9. [9]
  Yinglian LI , Chengcheng ZHANG , Xinyu ZHANG , Xinyi WANG . Spin crossover in [Co(pytpy)₂]²⁺ complexes modified by organosulfonate anions. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1162-1172. doi: 10.11862/CJIC.20240087
10. [10]
  Shengwen Guan , Zhaotong Wei , Ningxu Han , Yude Wei , Bin Xu , Ming Wang , Junjuan Shi . Construction of metallo-complexes with 2,2′:6′,2″-terpyridine substituted triphenylamine in different modified positions and their photophysical properties. Chinese Chemical Letters, 2024, 35(7): 109348-. doi: 10.1016/j.cclet.2023.109348
11. [11]
  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
12. [12]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068
13. [13]
  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
14. [14]
  Hao Jiang , Yuan-Yuan He , Hai-Chao Liang , Meng-Jia Shang , Han-Han Lu , Chun-Hua Liu , Yin-Shan Meng , Tao Liu , Yuan-Yuan Zhu . Tuning lanthanide luminescence from bipyridine-bis(oxazoline/thiazoline) tetradentate ligands. Chinese Journal of Structural Chemistry, 2024, 43(9): 100354-100354. doi: 10.1016/j.cjsc.2024.100354
15. [15]
  Tiantian Gong , Yanan Chen , Shuo Wang , Miao Wang , Junwei Zhao . Rigid-flexible-ligand-ornamented lanthanide-incorporated selenotungstates and photoluminescence properties. Chinese Journal of Structural Chemistry, 2024, 43(9): 100370-100370. doi: 10.1016/j.cjsc.2024.100370
16. [16]
  Min Huang , Ru Cheng , Shuai Wen , Liangtong Li , Jie Gao , Xiaohui Zhao , Chunmei Li , Hongyan Zou , Jian Wang . Ultrasensitive detection of microRNA-21 in human serum based on the confinement effect enhanced chemical etching of gold nanorods. Chinese Chemical Letters, 2024, 35(9): 109379-. doi: 10.1016/j.cclet.2023.109379
17. [17]
  Jiaqi Huang , Renjiang Kong , Yanmei Li , Ni Yan , Yeyang Wu , Ziwen Qiu , Zhenming Lu , Xiaona Rao , Shiying Li , Hong Cheng . Feedback enhanced tumor targeting delivery of albumin-based nanomedicine to amplify photodynamic therapy by regulating AMPK signaling and inhibiting GSTs. Chinese Chemical Letters, 2024, 35(8): 109254-. doi: 10.1016/j.cclet.2023.109254
18. [18]
  Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
19. [19]
  Shili Wang , Mamitiana Roger Razanajatovo , Xuedong Du , Shunli Wan , Xin He , Qiuming Peng , Qingrui Zhang . Recent advances on decomplexation mechanisms of heavy metal complexes in persulfate-based advanced oxidation processes. Chinese Chemical Letters, 2024, 35(6): 109140-. doi: 10.1016/j.cclet.2023.109140
20. [20]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(1025)
HTML views(31)

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