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Synthesis, characterization, and biological evaluations of substituted phenethylamine-based urea as anticancer and antioxidant agents
Monatshefte für Chemie - Chemical Monthly ( IF 1.7 ) Pub Date : 2021-08-25 , DOI: 10.1007/s00706-021-02830-7
Fatma Betül Özgeriş 1 , Bünyamin Özgeriş 2
Affiliation  

Cancer is one of the most important diseases. It is the second leading cause of death worldwide following cardiovascular disease. There is a need to develop new chemotherapeutic agents for the treatment of cancer and it is still a significant task for medicinal chemists. Symmetrical and unsymmetrical urea derivatives have been reported to play a significant role in biological systems. Phenethylamine is a precursor of dopamine and related compounds. In this study, we disclose the first examples of phenethylamine-based urea derivatives bearing fluoro, methoxy, and methyl groups. We also report cytotoxicity and toxicity profiles of novel urea derivatives on HeLa (human cervical cancer), A549 (non-small cell lung carcinoma), and HDF (human dermal fibroblast) cell lines. Moreover, we demonstrate antioxidant properties of synthesized compounds by DPPH, ABTS, and CUPRAC method. The results revealed that 1,3-bis(4-methylphenethyl)urea was up to eightfold more potent than cisplatin against HeLa cell line and also displayed very low toxic effect on HDF cell line compared to cisplatin. On the other hand, the anticancer activity of 1-(3,4-dimethoxyphenethyl)-3-(4-fluorophenethyl)urea and 1-(3,4-dimethoxyphenethyl)-3-(4-methylphenethyl)urea were close to that of cisplatin on A549 cell line, although 1-(3,4-dimethoxyphenethyl)-3-(4-fluorophenethyl)urea was more toxic than compound 1-(3,4-dimethoxyphenethyl)-3-(4-methylphenethyl)urea on HDF cell line. All tested compounds displayed remarkable activity compared to the standard antioxidants. Considering these properties, they may be a lead compounds for the treatment of human cervical and non-small cell lung cancer. These findings may be helpful for the discovery of more biologically active phenethylamine-based urea for clinical studies.

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中文翻译:

取代苯乙胺基尿素作为抗癌剂和抗氧化剂的合成、表征和生物学评价

癌症是最重要的疾病之一。它是仅次于心血管疾病的全球第二大死亡原因。需要开发新的化学治疗剂来治疗癌症,这仍然是药物化学家的一项重要任务。据报道,对称和不对称尿素衍生物在生物系统中发挥着重要作用。苯乙胺是多巴胺和相关化合物的前体。在这项研究中,我们公开了带有氟、甲氧基和甲基的苯乙胺基尿素衍生物的第一个例子。我们还报告了新型尿素衍生物对 HeLa(人宫颈癌)、A549(非小细胞肺癌)和 HDF(人真皮成纤维细胞)细胞系的细胞毒性和毒性特征。此外,我们通过 DPPH 证明了合成化合物的抗氧化特性,ABTS 和 CUPRAC 方法。结果表明,与顺铂相比,1,3-双(4-甲基苯乙基)脲对 HeLa 细胞系的效力是顺铂的八倍,并且对 HDF 细胞系的毒性作用非常低。另一方面,1-(3,4-二甲氧基苯乙基)-3-(4-氟苯乙基)脲和1-(3,4-二甲氧基苯乙基)-3-(4-甲基苯乙基)脲的抗癌活性接近顺铂对 A549 细胞系的影响,尽管 1-(3,4-二甲氧基苯乙基)-3-(4-氟苯乙基)脲比化合物 1-(3,4-二甲氧基苯乙基)-3-(4-甲基苯乙基)脲在HDF 细胞系。与标准抗氧化剂相比,所有测试的化合物都显示出显着的活性。考虑到这些特性,它们可能是治疗人类宫颈癌和非小细胞肺癌的先导化合物。

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更新日期:2021-08-26
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