Citation: REN Li-Lei, PENG Xiao-Xia, WANG Shu-Jun, XIAO Li-Wei, LI Ze-Qiang. Syntheses, Spectral and Electrochemical Properties, Antitumor Activities of Manganese/Zinc Complexes with Porphyrin Modified by 5-Fluorouracil[J]. Chinese Journal of Inorganic Chemistry, ;2019, 35(6): 965-970. doi: 10.11862/CJIC.2019.106 shu

Syntheses, Spectral and Electrochemical Properties, Antitumor Activities of Manganese/Zinc Complexes with Porphyrin Modified by 5-Fluorouracil

Faculty of Chemistry and Material Science, Langfang Teachers University, Langfang, Hebei 065000, China

Corresponding author: REN Li-Lei, renll1409@163.com WANG Shu-Jun, d022036@mail.nankai.edu.cn
Received Date: 25 October 2018
Revised Date: 13 March 2019

Figures(3)

One novel free porphyrin modified with 5-fluorouracil (5-(2-(5-fluorouracil-3-yl)-ethoxyphenyl)-10, 15, 20-triphenyl porphyrin, L) and its manganese complex (MnL), zinc complex (ZnL) were synthesized. They were characterized by UV-Vis, IR, ¹H NMR and MS. Their fluorescence properties and electrochemical properties were examined. The antitumor activities of them were evaluated by SRB assay in vitro against three human cancer cell lines. The results indicate that metal ions have a significant influence on the fluorescence intensity of complexes under the same experimental conditions:the fluorescence quenching was exhibited for zinc complex, but fluorescence signal had not been detected for manganese complex. The cyclic voltammetry of manganese complex was different from those of free porphyrin and zinc complex, which showed not only the redox of porphyrin ring but also the redox of Mn²⁺ ion. The biological tests revealed that manganese complex has a higher inhibitory rate than L and ZnL, but is less active than 5-fluorouracil.
- metalloporphyrin,
- 5-fluorouracil,
- fluorescence,
- electrochemical property,
- antitumor activity
1. [1]
  Yang Y W, Lee J S, Kim I, et al. Eur. J. Pharm. Biopharm., 2007, 66:260-267 doi: 10.1016/j.ejpb.2006.11.002
2. [2]
  Toden S, Okugawa Y, Jascur T, et al. Carcinogenesis, 2015, 36(3):355-367 doi: 10.1093/carcin/bgv006
3. [3]
  Vincent J, Mignot G, Chalmin F, et al. Cancer Res., 2010, 70(8):3052-3061 doi: 10.1158/0008-5472.CAN-09-3690
4. [4]
  Anitha A, Maya S, Krishna P C, et al. Eur. J. Pharm. Biopharm., 2014, 8(1):238-251 doi: 10.1016/j.ejpb.2014.04.017
5. [5]
  Moylan C, Sweed A M K, Shaker Y M, et al. Tetrahedron, 2015, 71(24):4145-4153 doi: 10.1016/j.tet.2015.04.097
6. [6]
  Zhang L, Lei J P, Ma F J, et al. Chem. Commun., 2015, 51:10831-10834 doi: 10.1039/C5CC03028E
7. [7]
  Maytin E V, Anand S, Riha M, et al. Clin. Cancer Res., 2018, 3:1-30 doi: 10.1158/1078-0432.CCR-17-2020
8. [8]
  Ol'shevskaya V A, Zaitsev A V, Kalinin V N, et al. Russ. Chem. Bull., 2014, 63(10):2383-2387 doi: 10.1007/s11172-014-0751-z
9. [9]
  Prakash K, Sankar M. Sens. Actuators B, 2017, 240:709-717 doi: 10.1016/j.snb.2016.09.016
10. [10]
  Naik A, Rubbiani R, Gasser G. Angew. Chem., 2014, 126:7058-7061 doi: 10.1002/ange.201400533
11. [11]
  Arba M, Ihsan S, Ramadhan L O A N, et al. Comput. Biol. Chem., 2017, 67:9-14 doi: 10.1016/j.compbiolchem.2016.12.005
12. [12]
  WANG Shu-Jun, PENG Yu-Ling, ZHOU Xue-Wen. Chinese J. Inorg. Chem., 2010, 26(5):793-800
13. [13]
  Gouterman M. J. Chem. Phys., 1959, 30:1139-1161 doi: 10.1063/1.1730148
14. [14]
  Thomas D W, Martell A E. J. Am. Chem. Soc., 1956, 78(7):1335-1338 doi: 10.1021/ja01588a020
15. [15]
  Pierini G D, Pinto V H A, Maia C G C, et al. Luminescence, 2017, 32:1-6 doi: 10.1002/bio.v32.1
16. [16]
  REN Li-Lei, PENG Xiao-Xia, ZHAO Xiu-Li, et al. Chinese Journal of Applied Chemistry, 2016, 33(12):1415-1419 doi: 10.11944/j.issn.1000-0518.2016.12.160054
17. [17]
  PENG Yu-Ling, WANG Shu-Jun, GUO Yu-Ming. Chinese J. Inorg. Chem., 2012, 28(7):1315-1323
18. [18]
  SHA Qiu-Yue, YUAN Xue-Mei, WANG Xiao-Yu, et al. Chinese J. Inorg. Chem., 2016, 32(7):1293-1302
19. [19]
  Kadish K M, WANG Er-Kang. Chinese Journal of Applied Chemistry, 1986, 3(3):1-7
20. [20]
  Zemer M, Gouterman M. Theor. Chim. Acta, 1966, 4:44-63 doi: 10.1007/BF00526010
21. [21]
  Ke X Y, Kumar R, Sankar M, et al. Inorg. Chem., 2018, 57:1490-1503 doi: 10.1021/acs.inorgchem.7b02856
22. [22]
  Norel L, Tourbillon C, Warnan J, et al. Dalton Trans., 2018, 47:8364-8374 doi: 10.1039/C8DT01493K
23. [23]
  LI Ya, WANG Xiao-Mei, HAN Shi-Tian, et al. Chinese Journal of Applied Chemistry, 2009, 26(3):316-320 doi: 10.3969/j.issn.1000-0518.2009.03.015
1. [1]
  Qin Li , Kexin Yang , Qinglin Yang , Xiangjin Zhu , Xiaole Han , Tao Huang . Illuminating Chlorophyll: Innovative Chemistry Popularization Experiment. University Chemistry, 2024, 39(9): 359-368. doi: 10.3866/PKU.DXHX202309059
2. [2]
  YanYuan Jia , Rong Rong , Jie Liu , Jing Guo , GuoYu Jiang , Shuo Guo . Unity is Strength, and Independence Shines: A Science Popularization Experiment on AIE and ACQ Effects. University Chemistry, 2024, 39(9): 349-358. doi: 10.12461/PKU.DXHX202402035
3. [3]
  Kun Xu , Xinxin Song , Zhilei Yin , Jian Yang , Qisheng Song . Comprehensive Experimental Design of Preferential Orientation of Zinc Metal by Heat Treatment for Enhanced Electrochemical Performance. University Chemistry, 2024, 39(4): 192-197. doi: 10.3866/PKU.DXHX202309050
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]
  Shuwen SUN , Gaofeng WANG . Two cadmium coordination polymers constructed by varying Ⅴ-shaped co-ligands: Syntheses, structures, and fluorescence properties. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 613-620. doi: 10.11862/CJIC.20230368
6. [6]
  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
7. [7]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
8. [8]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
9. [9]
  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
10. [10]
  Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431
11. [11]
  Jing SU , Bingrong LI , Yiyan BAI , Wenjuan JI , Haiying YANG , Zhefeng Fan . Highly sensitive electrochemical dopamine sensor based on a highly stable In-based metal-organic framework with amino-enriched pores. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1337-1346. doi: 10.11862/CJIC.20230414
12. [12]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
13. [13]
  Jiahong ZHENG , Jiajun SHEN , Xin BAI . Preparation and electrochemical properties of nickel foam loaded NiMoO₄/NiMoS₄ composites. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 581-590. doi: 10.11862/CJIC.20230253
14. [14]
  Zhihuan XU , Qing KANG , Yuzhen LONG , Qian YUAN , Cidong LIU , Xin LI , Genghuai TANG , Yuqing LIAO . Effect of graphene oxide concentration on the electrochemical properties of reduced graphene oxide/ZnS. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1329-1336. doi: 10.11862/CJIC.20230447
15. [15]
  Qin ZHU , Jiao MA , Zhihui QIAN , Yuxu LUO , Yujiao GUO , Mingwu XIANG , Xiaofang LIU , Ping NING , Junming GUO . Morphological evolution and electrochemical properties of cathode material LiAl_0.08Mn_1.92O₄ single crystal particles. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1549-1562. doi: 10.11862/CJIC.20240022
16. [16]
  Qingtang ZHANG , Xiaoyu WU , Zheng WANG , Xiaomei WANG . Performance of nano Li₂FeSiO₄/C cathode material co-doped by potassium and chlorine ions. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1689-1696. doi: 10.11862/CJIC.20240115
17. [17]
  Xinyi Hong , Tailing Xue , Zhou Xu , Enrong Xie , Mingkai Wu , Qingqing Wang , Lina Wu . Non-Site-Specific Fluorescent Labeling of Proteins as a Chemical Biology Experiment. University Chemistry, 2024, 39(4): 351-360. doi: 10.3866/PKU.DXHX202310010
18. [18]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
19. [19]
  Shengbiao Zheng , Liang Li , Nini Zhang , Ruimin Bao , Ruizhang Hu , Jing Tang . Metal-Organic Framework-Derived Materials Modified Electrode for Electrochemical Sensing of Tert-Butylhydroquinone: A Recommended Comprehensive Chemistry Experiment for Translating Research Results. University Chemistry, 2024, 39(7): 345-353. doi: 10.3866/PKU.DXHX202310096
20. [20]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(1227)
HTML views(128)

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