Citation: Li ZHANG, Chang JIANG, Lin-Feng GUO, Xiao-Ling ZHANG, Xiong-Qiang LIN, Jie KANG, Wei-Ming SUN. Synthesis, Characterization, Antitumor Activity, and Theoretical Calculations of Co(Ⅱ) Complex Based on Pyridine-2, 6-dicarboxylic Acid[J]. Chinese Journal of Inorganic Chemistry, ;2021, 37(2): 368-374. doi: 10.11862/CJIC.2021.027 shu

Synthesis, Characterization, Antitumor Activity, and Theoretical Calculations of Co(Ⅱ) Complex Based on Pyridine-2, 6-dicarboxylic Acid

Li ZHANG ^{1, #} ,
Chang JIANG ^{2, #} ,
Lin-Feng GUO ¹ ,
Xiao-Ling ZHANG ¹ ,
Xiong-Qiang LIN ¹ ,
Jie KANG ^1,, ,
Wei-Ming SUN ^1,,

1.
School of Pharmacy, Fujian Key Laboratory of Drug Target Discovery and Structural and Functional Research, Fujian Medical University, Fuzhou 350108, China
2.
Fujian Academy of Chinese Medical Sciences, Fuzhou 350003, China

Corresponding author: Jie KANG, davidkj660825@163.com Wei-Ming SUN, sunwm@fjmu.edu.cn

Received Date: 7 July 2020
Revised Date: 28 October 2020

Figures(4)

A new cobalt complex, namely[Co(Hpdc)(bpy)Cl]·C₂H₅OH (bpy=2, 2'-bipyridine), was synthesized by using pyridine-2, 6-dicarboxylic acid (H₂pdc) as ligand under hydrothermal condition, and followed by experimental characterization of infrared spectroscopy and X-ray single-crystal diffraction. To deeply reveal the electronic structure of this complex, density functional theory calculations were employed to investigate its charge distribution, electrostatic potential, frontier molecular orbitals, and relevant electronic properties under aqueous condition. Moreover, the antitumor activity of this complex was evaluated by thiazolyl blue tetrazolium bromide (MTT) assay in chronic myelocytic leukemia (K562) and esophageal carcinoma (OE-19) cancer cell lines, and the resulting IC₅₀ values were estimated to be as low as (0.22±0.05) μg·mL^-1 and (0.82±0.16) μg·mL^-1 (i. e., (0.48±0.11) μmol·L^-1 and (1.77±0.35) μmol·L^-1) for K562 and OE-19, respectively, demonstrating its cytotoxic activity against these two cancer cell lines. CCDC: 1994088.
- cobalt(Ⅱ) complex,
- crystal structure,
- antitumor activity,
- DFT calculation
1. [1]
  Ferlay J, Soerjomataram I, Dikshit R, Eser S, Mathers C, Rebelo M, Parkin D M, Forman D, Bray F. Int. J. Cancer, 2015, 136(5):E359-E386 doi: 10.1002/ijc.29210
2. [2]
  Thun M J, DeLancey J O, Center M M, Jemal A, Ward E M. Carcinogenesis, 2009, 31(1):100-110
3. [3]
  Tomasetti C, Li L, Vogelstein B. Science, 2017, 355(6331):1330-1334 doi: 10.1126/science.aaf9011
4. [4]
  Livingston D M, Silver D P. Nature, 2008, 451(7182):1066-1067 doi: 10.1038/4511066a
5. [5]
  Rosenberg B, Vancamp L, Krigas T. Nature, 1965, 205(4972):698-699 doi: 10.1038/205698a0
6. [6]
  Rosenberg B, Vancamp L, Trosko J E, Mansour V H. Nature, 1969, 222(5191):385-386 doi: 10.1038/222385a0
7. [7]
  Hurley, Laurence H. Nat. Rev. Cancer, 2002, 2(3):188-200 doi: 10.1038/nrc749
8. [8]
  Hartinger C G, Dyson P J. Chem. Soc. Rev., 2009, 38(2):391-401 doi: 10.1039/B707077M
9. [9]
  Thota S, Rodrigues D A, Crans D C, Barreiro E J. J. Med. Chem., 2018, 61(14):5805-5821 doi: 10.1021/acs.jmedchem.7b01689
10. [10]
  Bakalova A, Varbanov H, Buyukliev R, Momekov G, Ferdinandov D, Konstantinov S, Ivanov D. Eur. J. Med. Chem., 2008, 43(5):958-965 doi: 10.1016/j.ejmech.2007.06.025
11. [11]
  Galanski M, Arion V B, Jakupec M A, Keppler B K. Curr. Pharm. Des., 2003, 9(25):2078-2089 doi: 10.2174/1381612033454180
12. [12]
  Tanaka T, Yukawa K, Umesaki N. Oncol. Rep., 2005, 14(5):1365-1369
13. [13]
  Rabik C A, Dolan M E. Cancer Treat. Rev., 2007, 33(1):9-23 doi: 10.1016/j.ctrv.2006.09.006
14. [14]
  Ohmichi M, Hayakawa J, Tasaka K, Kurachi H, Murata Y. Trends Pharmacol. Sci., 2005, 26(3):113-116 doi: 10.1016/j.tips.2005.01.002
15. [15]
  Galanski M. Recent Patents Anti-Canc. Drug Discov., 2006, 1(2):285-295 doi: 10.2174/157489206777442287
16. [16]
  Shaili E. Sci. Prog., 2014, 97(1):20-40 doi: 10.3184/003685014X13904811808460
17. [17]
  CHEN Z F, MA Y D, HUA L G, ZHANG J. Chinese J. Inorg. Chem., 2014, 30(7):1525-1534
18. [18]
  Pires B M, Giacomin L C, Castro F A V, Amanda D S C, Pereira M D, Bortoluzzi A J, Faria R B, Scarpellini M. J. Inorg. Biochem., 2016, 157:104-113 doi: 10.1016/j.jinorgbio.2016.01.024
19. [19]
  XIE Q F, GUO M L, CHEN Y M. Chinese J. Inorg. Chem., 2018, 34(2):309-316
20. [20]
  Li J, Zhang J, Zhang Q, Wang Y, Bai Z, Zhao Q, He D, Wang Z, Zhang J, Chen Y. Bioorg. Med. Chem., 2019, 27(20):115071 doi: 10.1016/j.bmc.2019.115071
21. [21]
  Khan H Y, Ansari M O, Shadab G G H A, Tabassum S, Arjmand F. Bioorg. Chem., 2019, 88(2019):102963
22. [22]
  Chuasaard T, Panyarat K, Rodlamul P, Chainok K, Yimklan S, Rujiwatra A. Cryst. Growth Des., 2017, 17(3):1045-1054 doi: 10.1021/acs.cgd.6b01389
23. [23]
  Xu J, Su W, Hong M. Cryst. Growth Des., 2011, 11(1):337-346 doi: 10.1021/cg101343k
24. [24]
  Ghosh S K, Ribas J, Bharadwaj P K. CrystEngComm, 2004, 6(45):250-256 doi: 10.1039/B407571D
25. [25]
  Bordbar M, Tabatabaee M, Alizadeh-Nouqi M, Mehri-Lighvan Z, Khavasi H R, YeganehFaal A, Fallahian F, Dolati M. J. Iran. Chem. Soc., 2016, 13(6):1125-1132 doi: 10.1007/s13738-016-0826-x
26. [26]
  Ghosh S K, Bharadwaj P K. Inorg. Chem., 2004, 43(7):2293-2298 doi: 10.1021/ic034982v
27. [27]
  Ghosh S K, Bharadwaj P K. Inorg. Chem., 2005, 44(9):3156-3161 doi: 10.1021/ic048159q
28. [28]
  Derikvand Z, Dorosti N, Hassanzadeh F, Shokrollahi A, Mohammadpour Z, Azadbakht A. Polyhedron, 2012, 43(1):140-152 doi: 10.1016/j.poly.2012.06.026
29. [29]
  Deng D, Liu P, Fu W, Li L, Yang F, Ji B. Inorg. Chim. Acta, 2010, 363(5):891-898 doi: 10.1016/j.ica.2009.12.044
30. [30]
  CrystalClear 1.40, Rigaku Americas Corp, The Woodlands, TX, 2008.
31. [31]
  Sheldrick G M. SHELXL-97, Program for the Solution of Crystal Structures, University of Göttingen, Germany, 1997.
32. [32]
  Sheldrick G M. SHELXL-2018/1, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 2018.
33. [33]
  Hutama A S, Huang H, Kurniawan Y S. Spectrochim. Acta. A Mol. Biomol. Spectrosc., 2019, 221:117152
34. [34]
  Parr R G, Donnelly R A, Levy M, Palke W E. J. Chem. Phys., 1978, 68(8):3801-3807 doi: 10.1063/1.436185
35. [35]
  Parr R G, Szentpaly L V, Liu S. J. Am. Chem. Soc., 1999, 121(9):1922-1924
36. [36]
  Cohen A J, Mori-Sánchez P, Yang W. Science, 2008, 321(5890):792-794
37. [37]
  Mori-Sanchez P, Cohen A J, Yang W. J. Chem. Phys., 2006, 125(20):2604-308
38. [38]
  Lu C, Kuang X Y, Lu Z W, Mao A J, Ma Y M. J. Phys. Chem. A, 2011, 115(33):9273-9281
39. [39]
  Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Scalmani G, Barone V, Petersson G A, Nakatsuji H, Li X, Caricato M, Marenich A V, Bloino J, Janesko B G, Gomperts R, Mennucci B, Hratchian H P, Ortiz J V, Izmaylov A F, Sonnenberg J L, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski V G, Rega N, Gao J, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery JrJA, Peralta J E, Ogliaro F, Bearpark M J, Heyd J J, Brothers E N, Kudin K N, Staroverov V N, Keith T A, Kobayashi R, Normand J, Raghavachari K, Rendell A P, Burant J C, Iyengar S S, Tomasi J, Cossi M, Millam J M, Klene M, Adamo C, Cammi R, Ochterski J W, Martin R L, Morokuma K, Farkas O, Foresman J B, Fox D J. Gaussian 16, Revision A.03, Gaussian, Inc., Wallingford, 2016.
40. [40]
  Scalmani G, Frisch M J. J. Chem. Phys., 2010, 132(11):114110
41. [41]
  Dennington R, Keith T, Millam J. GaussView, Ver. 6, KS, USA: Semichem Inc, Shawnee Mission, 2016.
42. [42]
  Lu T, Chen F J. Comput. Chem., 2012, 33(5):580-592
43. [43]
  Humphrey W, Dalke A, Schulten K. J. Mol. Graphics, 1996, 14(1):33-38
44. [44]
  Stamatatos T C, Pringouri K V, Raptopoulou C P, Vicente R, Psycharis V, Escuer A, Perlepes S P. Inorg. Chem. Commun., 2006, 9(12):1178-1182
45. [45]
  Marques L F, Marinho M V, Speziali N L, Visentin L D C, Machado F C. Inorg. Chim. Acta, 2011, 365(1):454-457
46. [46]
  Ghasemi K, Rezvani A R, Shokrollahi A, Moghimi A, Gavahi S, García-Granda S, Mendoza-Meroño R. C. R. Chim., 2014, 17(12):1221-1229
47. [47]
  Gao H. Spectrochim. Acta Part A Mol. Biomol. Spectrosc., 2011, 79(3):687-693
48. [48]
  Štarha P, Marek J, Trávníček Z. Polyhedron, 2012, 33(1):404-409
49. [49]
  Krstic N M, Matic I Z, Juranic Z D, Novakovic I T, Sladic D M. J. Steroid. Biochem. Mol. Biol., 2014, 143:365-375
50. [50]
  Ohe Y, Nakagawa K, Fujiwara Y, Sasaki Y, Minato K, Bungo M. Cancer Res., 1989, 49(15):4098-4102
51. [51]
  Han Q B, Li R T, Zhang J X, Sun H D. Helv. Chim. Acta, 2004, 87(5):1119-1124
52. [52]
  Su W C, Chang S L, Chen T Y, Chen J S, Tsao C J. Jpn. J. Clin. Oncol., 2000, 30(12):562-567
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]
  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
7. [7]
  Dan-Ying Xing , Xiao-Dan Zhao , Chuan-Shu He , Bo Lai . Kinetic study and DFT calculation on the tetracycline abatement by peracetic acid. Chinese Chemical Letters, 2024, 35(9): 109436-. doi: 10.1016/j.cclet.2023.109436
8. [8]
  Haibin Yang , Duowen Ma , Yang Li , Qinghe Zhao , Feng Pan , Shisheng Zheng , Zirui Lou . Mo doped Ru-based cluster to promote alkaline hydrogen evolution with ultra-low Ru loading. Chinese Journal of Structural Chemistry, 2023, 42(11): 100031-100031. doi: 10.1016/j.cjsc.2023.100031
9. [9]
  Jing Wang , Zhongliao Wang , Jinfeng Zhang , Kai Dai . Single-layer crystalline triazine-based organic framework photocatalysts with different linking groups for H2O2 production. Chinese Journal of Structural Chemistry, 2023, 42(12): 100202-100202. doi: 10.1016/j.cjsc.2023.100202
10. [10]
  Ya-Nan Yang , Zi-Sheng Li , Sourav Mondal , Lei Qiao , Cui-Cui Wang , Wen-Juan Tian , Zhong-Ming Sun , John E. McGrady . Metal-metal bonds in Zintl clusters: Synthesis, structure and bonding in [Fe₂Sn₄Bi₈]^3– and [Cr₂Sb₁₂]^3–. Chinese Chemical Letters, 2024, 35(8): 109048-. doi: 10.1016/j.cclet.2023.109048
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  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
16. [16]
  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
17. [17]
  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
18. [18]
  Linshan Peng , Qihang Peng , Tianxiang Jin , Zhirong Liu , Yong Qian . Highly efficient capture of thorium ion by citric acid-modified chitosan gels from aqueous solution. Chinese Chemical Letters, 2024, 35(5): 108891-. doi: 10.1016/j.cclet.2023.108891
19. [19]
  Guangchang Yang , Shenglong Yang , Jinlian Yu , Yishun Xie , Chunlei Tan , Feiyan Lai , Qianqian Jin , Hongqiang Wang , Xiaohui Zhang . Regulating local chemical environment in O3-type layered sodium oxides by dual-site Mg²⁺/B³⁺ substitution achieves durable and high-rate cathode. Chinese Chemical Letters, 2024, 35(9): 109722-. doi: 10.1016/j.cclet.2024.109722
20. [20]
  Lian Sun , Honglei Wang , Ming Ma , Tingting Cao , Leilei Zhang , Xingui Zhou . Shape and composition evolution of Pt and Pt₃M nanocrystals under HCl chemical etching. Chinese Chemical Letters, 2024, 35(9): 109188-. doi: 10.1016/j.cclet.2023.109188

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(780)
HTML views(120)

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