Synthesis and Antitumor Activity of Porphyrin Modified with 5-Fluorouracil

doi:10.11944/j.issn.1000-0518.2016.12.160054

Chinese Journal of Applied Chemistry ›› 2016, Vol. 33 ›› Issue (12): 1415-1419.DOI: 10.11944/j.issn.1000-0518.2016.12.160054

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Synthesis and Antitumor Activity of Porphyrin Modified with 5-Fluorouracil

REN Lilei(),PENG Xiaoxia,ZHAO Xiuli,ZHU Hongmei

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

Received:2016-02-01 Accepted:2016-05-11 Published:2016-12-05 Online:2016-12-05
Contact: REN Lilei
Supported by:
Supported by the Youth Foundation of Hebei Province Education Department(No.QN2014117), the Youth Foundation of Langfang Teachers University(No.LSZQ201204)

Abstract

Abstract:

The porphyrin modified with 5-fluorouracil(5-[2-(5-fluorouracil-3-yl)-ethoxyphenyl]-10,15,20-tri(4-methoxyphenyl) porphyrin) and its two metal porphyrin complexes: 5-[2-(5-fluorouracil-3-yl)-ethoxyphenyl]-10,15,20-tri(4-methoxyphenyl) Mn porphyrin and 5-[2-(5-fluorouracil-3-yl)-ethoxyphenyl]-10,15,20-tri(4-methoxyphenyl) Zn porphyrin were synthesized. The structures of the three compounds were characterized by ultraviolet visible spectroscopy(UV-Vis), infred spectroscopy(IR) and proton nuclear magnetic resonance spectroscopy(¹H NMR). The antitumor activities of these compounds to A549, Bel7402, HCT-8 were tested using the methyl thiazolyl tetrazolium(MTT) method. The results show that the IC₅₀ value of Mn porphyrin to HCT-8 is 17.8 mg/L.

Key words: porphyrin, fluorouracil, antitumor activity

REN Lilei, PENG Xiaoxia, ZHAO Xiuli, ZHU Hongmei. Synthesis and Antitumor Activity of Porphyrin Modified with 5-Fluorouracil[J]. Chinese Journal of Applied Chemistry, 2016, 33(12): 1415-1419.

References

[1]	Li M,Zhang J,Feng L,et al. The In Vitro Anti-tumor Efficacy and the Pharmacokinetics of N3-o-toluylfluorouracil Loaded Nanosuspension(TFu-LNS)[J]. J Biomed Nanotechnol,2013,9(5):801-810.
[2]	Sun W T,Zhang N,Li X. Release Mechanism Studies on TFu Nanoparticles-in-microparticles System[J]. Colloids Surf B,2012,95(6):115-120.
[3]	TONG Chunyi,TANG Fengxia,LIU Bin,et al. Preparation of Micro-spheres Co-carried Anti-tumor Drug and Sensitizer(5-Fu-COS/SeNP) and Their Inhibiting Tumorous Cellular Growths Activity[J]. Chem J Chinese Univ,2014,35(7):1603-1607(in Chinese). 童春义,唐凤霞,刘斌,等. 氟尿嘧啶-壳寡糖/硒纳米微球的制备及抑制肿瘤细胞生长活性[J]. 高等学校化学学报,2014,35(7):1603-1607.
[4]	LIU Yanqin,ZHANG Huijuan,HAN Shitian. Synthesis and Antitumor Activity of 5-Fluorouracil-porphyrin Compounds[J]. Chinese J Org Chem,2002,22(4):279-282(in Chinese). 刘彦钦,张慧娟,韩士田. 5-氟尿嘧啶-卟啉化合物的合成及抗癌活性[J]. 有机化学,2002,22(4):279-282.
[5]	HAN Junxing,LIU Yanqin,HAN Shitian. Synthesis of m-Chlorophenyl Mn-porphyrin-5-Fluorouracil Complexes and Their Inhibition Activity to Cancer Cells[J]. Chinese J Appl Chem,2012,29(6):718-720(in Chinese). 韩军兴,刘彦钦,韩士田. 间氯苯基锰卟啉-5-氟尿嘧啶配合物的合成及其对癌细胞的抑制活性[J]. 应用化学,2012,29(6):718-720.
[6]	PENG Yuling,WANG Shujun,FU Li,et al. Synthesis of Tailed Porphyrin Modified with Nicotinic Acid and Interactions with Human Serum Albumin[J]. Acta Phys-Chim Sin,2012,28(5):1054-1062(in Chinese). 彭玉苓,王树军,傅丽,等. 烟酸修饰尾式卟啉的合成及其与人血清白蛋白的相互作用[J]. 物理化学学报,2012,28(5):1054-1062.
[7]	Gouterman M. Spectra of Porphyrins[J]. J Mol Spectrosc,1961,6:138-163.
[8]	SUN Erjun,WANG Dong,CHENG Xiuli,et al. Preparation and Properties of 5,10,15,20-Tetra(4-myristylimidophenyl) Porphyrin and Its Zn and Mn Complexes[J]. Chem J Chinese Univ,2007,28(7):1208-1213(in Chinese). 孙二军,王栋,程秀利,等. 5,10,15,20-四(对-十四酰亚胺基苯基)卟啉及其锰、锌配合物的合成及性质[J]. 高等学校化学学报,2007,28(7):1208-1213.
[9]	ZHAO Shengfang,CHEN Nianyou,XIA Jingping,et al. Microwave Synthesis and Spectroscopic Property of Tetra(2-hydroxphenyl) Porphyrin and Its Matal Complexes[J]. J Wuhan Univ Technol,2013,35(11):43-46(in Chinese). 赵胜芳,陈年友,夏静平,等. 四(2-羟基苯基)卟啉及系列金属配合物的微波合成和光谱性质[J]. 武汉理工大学学报,2013,35(11):43-46.
[10]	YANG Qiuqing,HAN Shitian,ZHANG Huijuan. Spectral and Antitumor Activity Studies of Tail-porphyin-5-Fluorouracil and Their Metallic Manganese Complexes[J]. Chinese J Anal Chem,2001,29(12):1379-1383(in Chinese). 杨秋青,韩士田,张慧娟. 尾式卟啉-5-氟尿嘧啶及其金属络合物的光谱分析[J]. 分析化学,2001,29(12):1379-1383.
[11]	LI Meirong,CAI Xiaoqing,ZHU Yifeng,et al. Synthesis and Biological Evaluation of Novel Coupling Derivatives of Photosensitizer and 5-Fluorouracil as Antineoplastic Agents[J]. Acta Chim Sin,2011,69(4):425-430(in Chinese). 李美容,蔡晓庆,朱易峰,等. 5-氟尿嘧啶光敏性偶联衍生物的合成、表征及抗癌活性研究[J]. 化学学报,2011,69(4):425-430.

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Synthesis and Antitumor Activity of Porphyrin Modified with 5-Fluorouracil

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