Microwave-assisted synthesis of cupric(Ⅱ) complex with porphyrin and its interaction with c-myc G4 DNA

doi:10.3969/j.issn.0438-1157.2014.z1.065

Abstract

Abstract: 5,10,15,20-tetra(4-merhoxyphenyl)porphyrin (TMOPP) was synthesized from pyrrole and p-methoxybenzaldehyde in propanoic acid solution at 130℃. Then, TMOPP and 1,4-dibromobutane were mixed in DMF solution at 100℃ to prepare target complex(CuTMOPP) under microwave-assisted with the yield of 64.7% in 20 min. The target compound was characterized by using ESI-MS, UV and IR spectra. Further, the binding behaviour of CuTMOPP with c-myc G4 DNA was investigated via FRET melting point methods, as well as spectroscopy methods. The results indicated that the target compound CuTMOPP may bind c-myc G4 DNA by electrostatic binding mode, as a result, the replication of c-myc G4 DNA was blocked, and an evaluation of biological activity is now in progress.

Key words: microwave-assisted, synthesis, porphyrin copper, complex, c-myc G4 DNA

摘要： 以吡咯、p-甲氧基苯甲醛为原料，丙酸为溶剂，130℃ 条件下制得四（p-甲氧苯基）卟啉（TMOPP）；然后在100℃ 微波辐射条件下，以TMOPP和乙酸铜为原料，DMF为溶剂，制得目标化合物四（p-甲氧苯基）卟啉铜（Ⅱ）配合物（CuTMOPP）。采用电喷雾质谱、紫外光谱和红外光谱等分析方法对所合成的目标化合物进行了表征，目标化合物的理论值和实验值基本一致。进一步采用紫外光谱、CD光谱、FRET熔点实验、PCR-Stop实验考察了目标化合物与c-myc G4 DNA的相互作用，结果表明目标化合物可能与c-myc G4 DNA以静电方式结合，从而抑制其复制，进一步对其生物功能的影响还在研究中。

关键词: 微波辅助, 合成, 卟啉铜, 配合物, c-myc G4 DNA

CLC Number:

O622.6

SUN Fuqiang, MEI Wenjie, WU Weili, WU Jian, ZHANG Zhao, ZHANG Ziyi, CUI Yingde. Microwave-assisted synthesis of cupric(Ⅱ) complex with porphyrin and its interaction with c-myc G4 DNA[J]. CIESC Journal, 2014, 65(S1): 403-408.

孙福强, 梅文杰, 吴韦黎, 吴剑, 张召, 张紫伊, 崔英德. 微波辅助四（p-甲氧苯基）卟啉铜（Ⅱ）的合成及其与c-myc G4 DNA的相互作用[J]. 化工学报, 2014, 65(S1): 403-408.

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