Citation: Zhang Li, Yao Yu-Chao, Gao Meng-Ying, Rong Rui-Xue, Wang Ke-Rang, Li Xiao-Liu, Chen Hua. Anticancer activity and DNA binding property of the trimers of triphenylethylene-coumarin hybrids[J]. Chinese Chemical Letters, ;2016, 27(11): 1708-1716. doi: 10.1016/j.cclet.2016.05.027 shu

Anticancer activity and DNA binding property of the trimers of triphenylethylene-coumarin hybrids

Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China

Corresponding author: Li Xiao-Liu, lixl@hbu.cn Chen Hua, hua-todd@163.com
Received Date: 19 April 2016
Revised Date: 17 May 2016
Accepted Date: 24 May 2016
Available Online: 3 November 2016

Figures(6)

Novel trimers of triphenylethylene-coumarin hybrid containing two amino side chains (5a-d and 6a-d) were designed and synthesized by the condensation of 1, 3, 5-benzenetricarboxylic acid with the varied amino monomeric hybrids catalyzed by HATU and DIPEA at room temperature.The extended trimeric compound 6a (R=piperidinyl) exhibited significant anti-proliferative activity against three cancer cells at IC₅₀ of near 10 μmol/L.UV-vis, fluorescence (lifetime) and thermal denaturation exhibited that 6a had significant interaction with Ct-DNA by the intercalative mode of binding.The order of their antiproliferative activities was 6(a, d) > 5(a, d) and (5-6)a > (5-6)d, respectively, in accordance with that of their DNA binding properties, which suggested that the prolonged linker (six carbons) and piperidinyl group on the side chains are beneficial to DNA binding and the anti-tumor activity.
- Coumarin,
- Triphenylethylene,
- Trimer,
- Anti-tumor activity,
- DNA binding property
1. [1]
  Amin K.M., Abdel Gawad N.M., Abdel Rahman D.E., El Ashry M.K.M.. New series of 6-substituted coumarin derivatives as effective factor Xa inhibitors: synthesis, in vivo antithrombotic evaluation and molecular docking[J]. Bioorg. Chem., 2014,52:31-43. doi: 10.1016/j.bioorg.2013.11.002
2. [2]
  Rempel V., Volz N., Gläser F.. Antagonists for the orphan G-protein-coupled receptor GPR55 based on a coumarin scaffold[J]. J. Med. Chem., 2013,56:4798-4810. doi: 10.1021/jm4005175
3. [3]
  Chen Y., Wang S.L., Xu X.Q.. Synthesis and biological investigation of coumarin piperazine (Piperidine) derivatives as potential multireceptor atypical antipsychotics[J]. J. Med. Chem., 2013,56:4671-4690. doi: 10.1021/jm400408r
4. [4]
  Zou Q.L., Fang Y.Y., Zhao Y.X.. Synthesis and in vitro photocytotoxicity of coumarin derivatives for one-and two-photon excited photodynamic therapy[J]. J. Med. Chem., 2013,56:5288-5294. doi: 10.1021/jm400025g
5. [5]
  Keri R.S., Sasidhar B.S., Nagaraja B.M., Santos M.A.. Recent progress in the drug development of coumarin derivatives as potent antituberculosis agents[J]. Eur. J. Med. Chem., 2015,100:257-269. doi: 10.1016/j.ejmech.2015.06.017
6. [6]
  Li B., Pai R., Di M.. Coumarin-based inhibitors of Bacillus anthracis and Staphylococcus aureus replicative DNA helicase: chemical optimization, biological evaluation, and antibacterial activities[J]. J. Med. Chem., 2012,55:10896-10908. doi: 10.1021/jm300922h
7. [7]
  Hamulakova S., Janovec L., Hrabinova M.. Synthesis and biological evaluation of novel tacrine derivatives and tacrine-coumarin hybrids as cholinesterase inhibitors[J]. J. Med. Chem., 2014,57:7073-7084. doi: 10.1021/jm5008648
8. [8]
  Thakur A., Singla R., Jaitak V.. Coumarins as anticancer agents: a review on synthetic strategies, mechanism of action and SAR studies[J]. Eur. J. Med. Chem., 2015,101:476-495. doi: 10.1016/j.ejmech.2015.07.010
9. [9]
  Basanagouda M., Jambagi V.B., Barigidad N.N., Laxmeshwar S.S., Narayanachar V.D.. Synthesis, structure-activity relationship of iodinated-4-aryloxymethylcoumarins as potential anti-cancer and anti-mycobacterial agents[J]. Eur. J. Med. Chem., 2014,74:225-233. doi: 10.1016/j.ejmech.2013.12.061
10. [10]
  Dandriyal J., Singla R., Kumar M., Jaitak V.. Recent developments of C-4 substituted coumarin derivatives as anticancer agents[J]. Eur. J. Med. Chem., 2016,119:141-168. doi: 10.1016/j.ejmech.2016.03.087
11. [11]
  Touisni N., Maresca A., McDonald P.C.. Glycosyl coumarin carbonic anhydrase Ⅸ and Ⅻ inhibitors strongly attenuate the growth of primary breast tumors[J]. J. Med. Chem., 2011,54:8271-8277. doi: 10.1021/jm200983e
12. [12]
  Wang C.J., Hsieh Y.J., Chu C.Y., Lin Y.L., Tseng T.H.. Inhibition of cell cycle progression in human leukemia HL-60 cells by esculetin[J]. Cancer Lett., 2002,183:163-168. doi: 10.1016/S0304-3835(02)00031-9
13. [13]
  Nasr T., Bondock S., Youns M.. Anticancer activity of new coumarin substituted hydrazide-hydrazone derivatives[J]. Eur. J. Med. Chem., 2014,76:539-548. doi: 10.1016/j.ejmech.2014.02.026
14. [14]
  Avin B.R.V., Thirusangu P., Ranganatha V.L.. Synthesis and tumor inhibitory activity of novel coumarin analogs targeting angiogenesis and apoptosis[J]. Eur. J. Med. Chem., 2014,75:211-221. doi: 10.1016/j.ejmech.2014.01.050
15. [15]
  Chu C.Y., Tsai Y.Y., Wang C.J., Lin W.L., Tseng T.H.. Induction of apoptosis by esculetin in human leukemia cells[J]. Eur. J. Pharmacol., 2001,416:25-32. doi: 10.1016/S0014-2999(01)00859-7
16. [16]
  McKie J.A., Bhagwat S.S., Brady H.. Lead identification of a potent benzopyranone selective estrogen receptor modulator[J]. Bioorg. Med. Chem. Lett., 2004,14:3407-3410. doi: 10.1016/j.bmcl.2004.04.081
17. [17]
  Bailly C.. Contemporary challenges in the design of topoisomerase Ⅱ inhibitors for cancer chemotherapy[J]. Chem. Rev., 2012,112:3611-3640. doi: 10.1021/cr200325f
18. [18]
  Facompré M., Tardy C., Bal-Mahieu C.. Lamellarin D: a novel potent inhibitor of topoisomerase I[J]. Cancer Res., 2003,63:7392-7399.
19. [19]
  Emami S., Dadashpour S.. Current developments of coumarin-based anti-cancer agents in medicinal chemistry[J]. Eur. J. Med. Chem., 2015,102:611-630. doi: 10.1016/j.ejmech.2015.08.033
20. [20]
  Liu M.M., Chen X.Y., Huang Y.Q.. Hybrids of phenylsulfonylfuroxan and coumarin as potent antitumor agents[J]. J. Med. Chem., 2014,57:9343-9356. doi: 10.1021/jm500613m
21. [21]
  Zhang W.J., Li Z., Zhou M.. Synthesis and biological evaluation of 4-(1, 2, 3-triazol-1-yl)coumarin derivatives as potential antitumor agents[J]. Bioorg. Med. Chem. Lett., 2014,24:799-807. doi: 10.1016/j.bmcl.2013.12.095
22. [22]
  Pé rez-Cruz F., Vazquez-Rodriguez S., João Matos M.. Synthesis and electrochemical and biological studies of novel coumarin-chalcone hybrid compounds[J]. J. Med. Chem., 2013,56:6136-6145. doi: 10.1021/jm400546y
23. [23]
  Gupta A., Mandal S.K., Leblanc V.. Synthesis and cytotoxic activity of benzopyran-based platinum(Ⅱ) complexes[J]. Bioorg. Med. Chem. Lett., 2008,18:3982-3987. doi: 10.1016/j.bmcl.2008.06.013
24. [24]
  Sashidhara K.V., Kumar A., Kumar M., Sarkar J., Sinha S.. Synthesis and in vitro evaluation of novel coumarin-chalcone hybrids as potential anticancer agents[J]. Bioorg. Med. Chem. Lett., 2010,20:7205-7211. doi: 10.1016/j.bmcl.2010.10.116
25. [25]
  Liu X.H., Liu H.F., Chen J.. Synthesis and molecular docking study of novel coumarin derivatives containing 4, 5-dihydropyrazole moiety as potential antitumor agents[J]. Bioorg. Med. Chem. Lett., 2010,20:5705-5708. doi: 10.1016/j.bmcl.2010.08.017
26. [26]
  Belluti F., Fontana G., Dal Bo L.. Design, synthesis and anticancer activities of stilbene-coumarin hybrid compounds: identification of novel proapoptotic agents[J]. Bioorg. Med. Chem. Lett., 2010,18:3543-3550. doi: 10.1016/j.bmc.2010.03.069
27. [27]
  Zhao H.P., Donnelly A.C., Kusuma B.R.. Engineering an antibiotic to fight cancer: optimization of the novobiocin scaffold to produce anti-proliferative agents[J]. J. Med. Chem., 2011,54:3839-3853. doi: 10.1021/jm200148p
28. [28]
  Siddiqui Z.N., Mohammed Musthafa T.N., Ahmad A., Khan A.U.. Synthesis of 4-hydroxycoumarin heteroarylhybrids as potential antimicrobial agents[J]. Arch. Pharm. Chem. Life Sci., 2011,344:394-401. doi: 10.1002/ardp.201000218
29. [29]
  Kusuma B.R., Peterson L.B., Zhao H.P.. Targeting the heat shock protein 90 dimer with dimeric inhibitors[J]. J. Med. Chem., 2011,54:6234-6253. doi: 10.1021/jm200553w
30. [30]
  Burlison J.A., Blagg B.S.J.. Synthesis and evaluation of coumermycin A1 analogues that inhibit the Hsp90 protein folding machinery[J]. Org. Lett., 2006,8:4855-4858. doi: 10.1021/ol061918j
31. [31]
  Tan G.H., Yao Y.C., Gu Y.J.. Cytotoxicity and DNA binding property of the dimers of triphenylethylene-coumarin hybrid with one amino side chain[J]. Bioorg. Med. Chem. Lett., 2014,24:2825-2830. doi: 10.1016/j.bmcl.2014.04.106
32. [32]
  Zhu M., Zhou L.K., Yao Y.C.. Anticancer activity and DNA binding property of the dimers of triphenylethylene-coumarin hybrid with two amino side chains[J]. Med. Chem. Res., 2015,24:2314-2324. doi: 10.1007/s00044-014-1296-2
33. [33]
  Zhao L., Yao Y.C., Li S.. Cytotoxicity and DNA binding property of triphenylethylene-coumarin hybrids with two amino side chains[J]. Bioorg. Med. Chem. Lett., 2014,24:900-904. doi: 10.1016/j.bmcl.2013.12.084
34. [34]
  Chen H., Li S., Yao Y.C.. Design, synthesis, and anti-tumor activities of novel triphenylethylene-coumarin hybrids, and their interactions with Ct-DNA[J]. Bioorg. Med. Chem. Lett., 2013,23:4785-4789. doi: 10.1016/j.bmcl.2013.07.009
35. [35]
  Mosmann T.J.. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays[J]. J. Immunol. Methods, 1983,65:55-63. doi: 10.1016/0022-1759(83)90303-4
36. [36]
  Sahoo D., Bhattacharya P., Chakravorti S.. Reverse micelle induced flipping of binding site and efficiency of albumin protein with an ionic styryl dye[J]. J. Phys. Chem. B, 2010,114:10442-10450. doi: 10.1021/jp102937y
37. [37]
  Breslow R., Overman I.E.. "Artificial enzyme" combining a metal catalytic group and a hydrophobic binding cavity[J]. J. Am. Chem. Soc., 1970,92:1075-1077. doi: 10.1021/ja00707a062
38. [38]
  Pasternack R.F., Gibbs E.J., Villatrnaca J.J.. Interactions of porphyrins with nucleic acids[J]. Biochemistry, 1983,22:2406-2414. doi: 10.1021/bi00279a016
39. [39]
  Purcell M., Neault J.F., Tajmir-Riahi H.A.. Interaction of taxol with human serum albumin[J]. Biochim. Biophys. Acta, 2000,1478:61-68. doi: 10.1016/S0167-4838(99)00251-4
40. [40]
  Faulhaber K., Granzhan A., Ihmels H.. Studies of the fluorescence light-up effect of amino-substituted benzo[J]. Photochem. Photobiol. Sci., 2011,10:1535-1545. doi: 10.1039/c1pp05106g
41. [41]
  Ramadass R., Bereiter-Hahn J.. Photophysical properties of DASPMI as revealed by spectrally resolved fluorescence decays[J]. J. Phys. Chem. B, 2007,111:7681-7690. doi: 10.1021/jp070378k
42. [42]
  Pandey S., Baker G.A., Kane M.A., Bonzagni N.J., Bright F.V.. O₂ Quenching of ruthenium(Ⅱ) tris(2, 2'-bypyridyl)²⁺ within the water pool of perfluoropolyetherbased reverse micelles formed in supercritical carbon dioxide[J]. Langmuir, 2000,16:5593-5599. doi: 10.1021/la991719r
43. [43]
  Wang J., Wang D.L., Miller E.K.. Photoluminescence of water-soluble conjugated polymers: origin of enhanced quenching by charge transfer[J]. Macromolecules, 2000,33:5153-5158. doi: 10.1021/ma000081j
44. [44]
  Chaveerach U., Meenongwa A., Trongpanich Y., Soikum C., Chaveerach P.. DNA binding and cleavage behaviors of copper(Ⅱ) complexes with amidino-O-methylurea and N-methylphenyl-amidino-O-methylurea, and their antibacterial activities[J]. Polyhedron, 2010,29:731-738. doi: 10.1016/j.poly.2009.10.031
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]
  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
3. [3]
  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
4. [4]
  Jiangshan Xu , Weifei Zhang , Zhengwen Cai , Yong Li , Long Bai , Shaojingya Gao , Qiang Sun , Yunfeng Lin . Tetrahedron DNA nanostructure/iron-based nanomaterials for combined tumor therapy. Chinese Chemical Letters, 2024, 35(11): 109620-. doi: 10.1016/j.cclet.2024.109620
5. [5]
  Xiaoyao Ma , Jinling Zhang , Ge Fang , He Gao , Jie Gao , Li Fu , Yuanyuan Hou , Gang Bai . Förster resonance energy transfer reveals phillygenin and swertiamarin concurrently target AKT on different binding domains to increase the anti-inflammatory effect. Chinese Chemical Letters, 2024, 35(5): 108823-. doi: 10.1016/j.cclet.2023.108823
6. [6]
  Yanfei Liu , Yaqin Hu , Yifu Tan , Qiwen Chen , Zhenbao Liu . Tumor acidic microenvironment activatable DNA nanostructure for precise cancer cell targeting and inhibition. Chinese Chemical Letters, 2025, 36(1): 110289-. doi: 10.1016/j.cclet.2024.110289
7. [7]
  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
8. [8]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Qiang Sun , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Li Wang . Recent progress on surface chemistry Ⅱ: Property and characterization. Chinese Chemical Letters, 2025, 36(1): 110100-. doi: 10.1016/j.cclet.2024.110100
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]
  Wu-Jian Long , Yang Yu , Chuang He . A novel and promising engineering application of carbon dots: Enhancing the chloride binding performance of cement. Chinese Chemical Letters, 2024, 35(6): 108943-. doi: 10.1016/j.cclet.2023.108943
11. [11]
  Yulin Mao , Jingyu Ma , Jiecheng Ji , Yuliang Wang , Wanhua Wu , Cheng Yang . Crown aldoxime ethers: Their synthesis, structure, acid-catalyzed/photo-induced isomerization and adjustable guest binding. Chinese Chemical Letters, 2024, 35(11): 109927-. doi: 10.1016/j.cclet.2024.109927
12. [12]
  Lihua Gao , Yinglei Han , Chensheng Lin , Huikang Jiang , Guang Peng , Guangsai Yang , Jindong Chen , Ning Ye . Halogen-assisted octet binding electrons construction of pnictogens towards wide-bandgap nonlinear optical pnictides. Chinese Chemical Letters, 2024, 35(12): 109529-. doi: 10.1016/j.cclet.2024.109529
13. [13]
  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
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]
  Zhongyu Wang , Lijun Wang , Huaixin Zhao . DNA-based nanosystems to generate reactive oxygen species for nanomedicine. Chinese Chemical Letters, 2024, 35(11): 109637-. doi: 10.1016/j.cclet.2024.109637
16. [16]
  Zhijia Zhang , Shihao Sun , Yuefang Chen , Yanhao Wei , Mengmeng Zhang , Chunsheng Li , Yan Sun , Shaofei Zhang , Yong Jiang . Epitaxial growth of Cu_2-xSe on Cu (220) crystal plane as high property anode for sodium storage. Chinese Chemical Letters, 2024, 35(7): 108922-. doi: 10.1016/j.cclet.2023.108922
17. [17]
  Hao Cai , Xiaoyan Wu , Lei Jiang , Feng Yu , Yuxiang Yang , Yan Li , Xian Zhang , Jian Liu , Zijian Li , Hong Bi . Lysosome-targeted carbon dots with a light-controlled nitric oxide releasing property for enhanced photodynamic therapy. Chinese Chemical Letters, 2024, 35(4): 108946-. doi: 10.1016/j.cclet.2023.108946
18. [18]
  Ziyi Liu , Xunying Liu , Lubing Qin , Haozheng Chen , Ruikai Li , Zhenghua Tang . Alkynyl ligand for preparing atomically precise metal nanoclusters: Structure enrichment, property regulation, and functionality enhancement. Chinese Journal of Structural Chemistry, 2024, 43(11): 100405-100405. doi: 10.1016/j.cjsc.2024.100405
19. [19]
  Peipei CUI , Xin LI , Yilin CHEN , Zhilin CHENG , Feiyan GAO , Xu GUO , Wenning YAN , Yuchen DENG . Transition metal coordination polymers with flexible dicarboxylate ligand: Synthesis, characterization, and photoluminescence property. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2221-2231. doi: 10.11862/CJIC.20240234
20. [20]
  Tian TIAN , Meng ZHOU , Jiale WEI , Yize LIU , Yifan MO , Yuhan YE , Wenzhi JIA , Bin HE . Ru-doped Co₃O₄/reduced graphene oxide: Preparation and electrocatalytic oxygen evolution property. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 385-394. doi: 10.11862/CJIC.20240298

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(603)
HTML views(2)

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