Citation: HASI Qi-Mei-Ge, CHEN Li-Hua, XIAO Chao-Hu. Syntheses, DNA-binding and Antitumor Activities of Water Soluble Copper Porphyrins Complexes[J]. Chinese Journal of Inorganic Chemistry, ;2018, 34(10): 1841-1850. doi: 10.11862/CJIC.2018.239 shu

Syntheses, DNA-binding and Antitumor Activities of Water Soluble Copper Porphyrins Complexes

Experimental Center, Northwest Minzu University, Lanzhou 730070, China

Corresponding author: HASI Qi-Mei-Ge, ha2qimei@163.com
Received Date: 28 May 2018
Revised Date: 23 July 2018

Figures(8)

Three water-soluble copper porphyrin complexes (water-soluble bromine-containing copper porphyrin CuP-1 and its bromine substituted derivatives CuP-2 and CuP-3) have been synthesized and characterized by ¹H NMR, elementary analysis and MS spectra. The interaction of CuP-1, CuP-2 and CuP-3 with CT-DNA have been investigated by UV spectrum, EB-DNA fluorescence quenching, viscosity method and circular dichroism spectrum. Moreover, the antitumor activities of CuP-1~CuP-3 against Hela (cervical cancer) cell lines and MDA (breast carcinoma) cell lines have been studied by MTT assay. L929 (human fibroblast) cell line was used as a normal cell lines. Various spectroscopic approaches indicates that CuP-1 could effectively bind with CT-DNA through intercalation mode, while CuP-2 and CuP-3 may interact with CT-DNA by outside groove binding mode. And the binding affinity of CuP-1 with CT-DNA is better than its derivatives CuP-2 and CuP-3. In vitro antitumor activity experiments showed that CuP-1~CuP-3 can inhibit the growth of Hela and MDA cell lines, and the inhibition shows concentration and time dependent. In addition, antitumor activity in vitro of CuP-1 is much better than CuP-2 and CuP-3.
- water soluble copper porphyrins complexes,
- CT-DNA,
- anticancer activity
1. [1]
  Zhao P, Liu M C, Zheng M, et al. Dyes Pigm., 2016, 128:41-48 doi: 10.1016/j.dyepig.2016.01.009
2. [2]
  Ramakrishnan S, Shakthiptiya D, Suresh E, et al. Inorg. Chem., 2011, 50:6458-6471 doi: 10.1021/ic1024185
3. [3]
  Huang Y M, Zheng S J, Yan J, et al. Luminescence, 2016, 31:1077-1084 doi: 10.1002/bio.v31.5
4. [4]
  Suntharalingam K, White A J P, Vilar R. Inorg. Chem., 2010, 49:8371-8380 doi: 10.1021/ic100884p
5. [5]
  Sendhil K, Vijayan C, Kothiyal M P. Opt. Commun., 2005, 251:292-298 doi: 10.1016/j.optcom.2005.03.014
6. [6]
  Biesaga M, Pyrzyńska K, Trojanowicz M. Talanta, 2000, 51:209-224 doi: 10.1016/S0039-9140(99)00291-X
7. [7]
  Rangasamy S, Ju H, Um S, et al. J. Med. Chem., 2015, 58:6864-6874 doi: 10.1021/acs.jmedchem.5b01095
8. [8]
  Ruan T L, Davis S J, Powell B M, et al. Biochimie, 2017, 132:121-130 doi: 10.1016/j.biochi.2016.11.003
9. [9]
  Huang L J, Zhang L, Yang L, et al. Biosens. Bioelectron., 2018, 104:21-26 doi: 10.1016/j.bios.2017.12.037
10. [10]
  CAO Bo, LIU Tian-Jun, NIU Cong. Chinese Pharmacological Bulletin, 2014, 30(2):170-174 doi: 10.3969/j.issn.1001-1978.2014.02.007
11. [11]
  Yao Y H, Li J, Yuan L F, et al. RSC Adv., 2016, 6(51):45681-45688 doi: 10.1039/C6RA05682B
12. [12]
  Yao Y, Luo Y, Li J, et al. Helv. Chim. Acta, 2016, 99(1):24-29 doi: 10.1002/hlca.v99.1
13. [13]
  Guy M E, Francesca B, Juozas D, et al. Mol. Pharm., 2015, 12:4414-4423 doi: 10.1021/acs.molpharmaceut.5b00606
14. [14]
  Feng X X, Liu J C. J. Inorg. Biochem., 2018, 178:1-8 doi: 10.1016/j.jinorgbio.2017.09.024
15. [15]
  Zhang J X, Zhou J W, Chan C F, et al. Bioconjugate Chem., 2012, 23(18):1623-1638
16. [16]
  Karunakarn S C, Babu P S, Madhuri B, et al. ACS Chem. Biol., 2013, 8(1):127-132 doi: 10.1021/cb3004622
17. [17]
  ZHANG Xian-Xia, CHEN Can-Yu. Acta Chim. Sinica, 2012, 70:2475-2483
18. [18]
  HUANG Jun-Teng, ZHANG Yang, WANG Xiang-Li, et al. Chinese J. Inorg. Chem., 2013, 29(8):1649-1656
19. [19]
  FANG Qi-Chao. Chinese Journal of New Drugs, 2014, 23(13):1540-1545
20. [20]
  Entract G M, Bryden F, Domarkas J, et al. Mol. Pharmaceutics, 2015, 12(12):4414-4423 doi: 10.1021/acs.molpharmaceut.5b00606
21. [21]
  Marmur J. J. Mol. Biol., 1961, 3(2):208-218 doi: 10.1016/S0022-2836(61)80047-8
22. [22]
  Liu J, Shi S, Ji L N, et al. Transition Met. Chem., 2005, 30(6):684-690 doi: 10.1007/s11243-005-5273-y
23. [23]
  Krishna A G, Kumar D V, Khan B M, et al. Biochim. Biophys. Acta, 1998, 1381:104-112 doi: 10.1016/S0304-4165(98)00019-1
24. [24]
  Xu X H, Yang H C, Mallouk T E, et al. J. Am. Chem. Soc., 1994, 116(18):8386-8387 doi: 10.1021/ja00097a064
25. [25]
  Zhao P, Huang J W, Mei W J, et al. Spectrochim. Acta Part A, 2010, 75:1108-1114 doi: 10.1016/j.saa.2009.12.065
26. [26]
  Wei C Y, Jia G Q, Yuan J L, et al. Biochemistry, 2006, 45(21):6681-6691 doi: 10.1021/bi052356z
27. [27]
  LI Wen-Quan, ZHANG Ling, GUO Jiang-Ning, et al. Journal of Guangdong Pharmaceutical University, 2014, 30(3):261-267 doi: 10.3969/j.issn.1006-8783.2014.03.001
28. [28]
  Ghosh K, Kumar P, Tyagi N, et al. Eur. J. Med. Chem., 2010, 45:3770-3779 doi: 10.1016/j.ejmech.2010.05.026
29. [29]
  Perontsis S, Hatzidimitriou A G, Begou O A, et al. J. Inorg. Biochem., 2016, 162:22-30 doi: 10.1016/j.jinorgbio.2016.06.001
30. [30]
  PENG Xiao-Bin, LE Chang-Gao, CAI Jie. Progress in Chemistry, 1999, 11(3):327-332 doi: 10.3321/j.issn:1005-281X.1999.03.011
31. [31]
  Ethirajan M, Chen Y H, Joshi P, et al. Chem. Soc. Rev., 2011, 40:340-362 doi: 10.1039/B915149B
32. [32]
  Feng X X, Zhang J X, Wu Y, et al. Dyes Pigm., 2017, 136:773-778 doi: 10.1016/j.dyepig.2016.09.044
33. [33]
  Kralova J, Koivukorpi J, Kejik Z, et al. Org. Biomol. Chem., 2008, 6:1548-1552 doi: 10.1039/b717528k
1. [1]
  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
2. [2]
  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
3. [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. [4]
  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
5. [5]
  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
6. [6]
  Ji Qi , Jianan Zhu , Yanxu Zhang , Jiahao Yang , Chunting Zhang . Visible Color Change of Copper (II) Complexes in Reversible SCSC Transformation: The Effect of Structure on Color. University Chemistry, 2024, 39(3): 43-57. doi: 10.3866/PKU.DXHX202307050
7. [7]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
8. [8]
  Chang Liu , Tao Wu , Lijiao Deng , Xuzi Li , Xin Fu , Shuzhen Liao , Wenjie Ma , Guoqiang Zou , Hai Yang . Programmed DNA walkers for biosensors. Chinese Chemical Letters, 2024, 35(9): 109307-. doi: 10.1016/j.cclet.2023.109307
9. [9]
  Jia-Li Xie , Tian-Jin Xie , Yu-Jie Luo , Kai Mao , Cheng-Zhi Huang , Yuan-Fang Li , Shu-Jun Zhen . Octopus-like DNA nanostructure coupled with graphene oxide enhanced fluorescence anisotropy for hepatitis B virus DNA detection. Chinese Chemical Letters, 2024, 35(6): 109137-. doi: 10.1016/j.cclet.2023.109137
10. [10]
  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
11. [11]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
12. [12]
  Yang Qin , Jiangtian Li , Xuehao Zhang , Kaixuan Wan , Heao Zhang , Feiyang Huang , Limei Wang , Hongxun Wang , Longjie Li , Xianjin Xiao . Toeless and reversible DNA strand displacement based on Hoogsteen-bond triplex. Chinese Chemical Letters, 2024, 35(5): 108826-. doi: 10.1016/j.cclet.2023.108826
13. [13]
  Xiaohong Wen , Mei Yang , Lie Li , Mingmin Huang , Wei Cui , Suping Li , Haiyan Chen , Chen Li , Qiuping Guo . Enzymatically controlled DNA tetrahedron nanoprobes for specific imaging of ATP in tumor. Chinese Chemical Letters, 2024, 35(8): 109291-. doi: 10.1016/j.cclet.2023.109291
14. [14]
  Jingwen Zhao , Jianpu Tang , Zhen Cui , Limin Liu , Dayong Yang , Chi Yao . A DNA micro-complex containing polyaptamer for exosome separation and wound healing. Chinese Chemical Letters, 2024, 35(9): 109303-. doi: 10.1016/j.cclet.2023.109303
15. [15]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
16. [16]
  Wei Li , Ze Chang , Meihui Yu , Ying Zhang . Curriculum Ideological and Political Design of Piezoelectricity Measurement Experiments of Coordination Compounds. University Chemistry, 2024, 39(2): 77-82. doi: 10.3866/PKU.DXHX202308004
17. [17]
  Cunling Ye , Xitong Zhao , Hongfang Wang , Zhike Wang . A Formula for the Calculation of Complex Concentrations Arising from Side Reactions and Its Applications. University Chemistry, 2024, 39(4): 382-386. doi: 10.3866/PKU.DXHX202310043
18. [18]
  Keweiyang Zhang , Zihan Fan , Liyuan Xiao , Haitao Long , Jing Jing . Unveiling Crystal Field Theory: Preparation, Characterization, and Performance Assessment of Nickel Macrocyclic Complexes. University Chemistry, 2024, 39(5): 163-171. doi: 10.3866/PKU.DXHX202310084
19. [19]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
20. [20]
  Quanliang Chen , Zhaohui Zhou . Research on the Active Site of Nitrogenase over Fifty Years. University Chemistry, 2024, 39(7): 287-293. doi: 10.3866/PKU.DXHX202310133

Get Citation

PDF

XML

Metrics

PDF Downloads(20)
Abstract views(1438)
HTML views(501)

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