Synthesis of porphyrin-formononetin derivatives and their anti-tumor activity studies.

IF 3.8 2区化学 Q2 CHEMISTRY, APPLIED Molecular Diversity Pub Date : 2025-04-09 DOI:10.1007/s11030-025-11183-w

Lingyan Yang, Shan He, Chen Tang, Lei Shi, Zhenhua Liu, Zejie Tian, Hui Li, Xufeng He, Jiding Liao, Yunmei Liu

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Abstract

Photodynamic therapy (PDT) has received much attention in cancer treatment because of its low toxicity and side effects. In this study, we successfully synthesized 14 novel porphyrin-formononetin derivatives. In reactive oxygen species detection experiments, the target compounds 4a-6d caused a significant decrease in the fluorescence intensity of DPBF compared with the porphyrin parent and formononetin feedstock after illumination, and it was found that the target compound had a higher ROS quantum yield, among which the quantum yield of compound 6c was higher. In the in vitro anti-tumor activity assay, the target compounds 4a-6d exhibited a certain degree of growth inhibition against six cancer cells (A549, MDA-MB-231, HCT-116, HGC-27, DU145, and TCCSUP) under light conditions, whereas the cytotoxicity of the target compounds against the normal cells H9c2 was less. The results of the scratch assay showed that 6c could inhibit the growth of tumor cells by inhibiting the migration of DU145 cells. The experimental results indicate that the target compounds achieve the synergistic effect of PDT and chemotherapy.

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卟啉-刺芒柄花素衍生物的合成及其抗肿瘤活性研究。

光动力疗法（PDT）因其毒副作用小而在癌症治疗中受到广泛关注。在本研究中，我们成功合成了14个新的卟啉-刺芒柄花素衍生物。在活性氧检测实验中，与卟啉亲本和刺芒花素原料相比，靶化合物4a-6d在光照后使DPBF的荧光强度显著降低，并且发现靶化合物具有更高的ROS量子产率，其中化合物6c的量子产率更高。体外抗肿瘤活性实验发现，靶化合物4a-6d在光照条件下对6种肿瘤细胞（A549、MDA-MB-231、HCT-116、HGC-27、DU145、TCCSUP）均有一定的生长抑制作用，而对正常细胞H9c2的细胞毒性较弱。划痕实验结果表明，6c通过抑制DU145细胞的迁移来抑制肿瘤细胞的生长。实验结果表明，目标化合物实现了PDT和化疗的协同作用。

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来源期刊

Molecular Diversity 化学-化学综合

CiteScore

7.30

自引率

7.90%

发文量

219

审稿时长

2.7 months

期刊介绍： Molecular Diversity is a new publication forum for the rapid publication of refereed papers dedicated to describing the development, application and theory of molecular diversity and combinatorial chemistry in basic and applied research and drug discovery. The journal publishes both short and full papers, perspectives, news and reviews dealing with all aspects of the generation of molecular diversity, application of diversity for screening against alternative targets of all types (biological, biophysical, technological), analysis of results obtained and their application in various scientific disciplines/approaches including: combinatorial chemistry and parallel synthesis; small molecule libraries; microwave synthesis; flow synthesis; fluorous synthesis; diversity oriented synthesis (DOS); nanoreactors; click chemistry; multiplex technologies; fragment- and ligand-based design; structure/function/SAR; computational chemistry and molecular design; chemoinformatics; screening techniques and screening interfaces; analytical and purification methods; robotics, automation and miniaturization; targeted libraries; display libraries; peptides and peptoids; proteins; oligonucleotides; carbohydrates; natural diversity; new methods of library formulation and deconvolution; directed evolution, origin of life and recombination; search techniques, landscapes, random chemistry and more;