Das Vishal, Kaishap Partha Pratim, Duarah Gauri, Chikkaputtaiah Channakeshavaiah, Deka Boruah Hari Prasanna, Pal Mintu
Biotechnology Group, Biological Sciences and Technology Division, CSIR-North East Institute of Science & Technology, Jorhat, Assam, 785006, India.
Academy of Scientific and Innovative Research, Headquarters, CSIR-HRDC Campus , Sector 19, Kamla Nehru Nagar ,Ghaziabaad-201002, India.
Naunyn Schmiedebergs Arch Pharmacol. 2021 Jul;394(7):1437-1449. doi: 10.1007/s00210-021-02063-9. Epub 2021 Mar 2.
Isocoumarin is a lactone, a type of natural organic compound that is used as synthetic intermediates of several natural products and pharmaceutical compounds explored for their potential therapeutic applications like antifungal, antimicrobial, anti-inflammatory, and anticancer activities. In our previous work, we were the first group to report the use of amide C-N bond of isatins as the oxidizing directing group for the synthesis of 8-amido isocoumarin derivatives. Whereas in our present work, we have screened the cytotoxic effects of novel 8-amido isocoumarin derivatives (S1-S10) in human breast cancer MCF-7 and MDA-MB-231 cells. Our novel results revealed that N-(3-(4-methoxyphenyl)-1-oxo-4-(4-propylphenyl)-1H-isochromen-8yl)acetamide (S1) and N-(4-(3,5-difluorophenyl)-1-oxo-3-(p-tolyl)-1H-isochromen-8-yl) acetamide (S2) are the two potent compounds among the rest synthesized isocoumarin derivatives that are cytotoxic against MCF-7 and MDA-MB-231 cells, whereas less toxic to the non-tumorigenic IOSE-364 cells. Flow cytometry studies have confirmed the induction of apoptotic effects of compounds by Annexin V/PI double staining. We also observed the cytotoxic effects of S1 and S2, as evaluated by DAPI-PI immunostaining and H&E staining. The morphological alterations consistent with apoptotic blebs were observed in both cancer cells treated with compounds assessed by scanning electron microscopy. Overall, this present study strongly demonstrates that 8-amido isocoumarin derivatives have potent cytotoxic and apoptotic effects in breast cancer cells.
异香豆素是一种内酯,属于天然有机化合物,用作几种天然产物和药物化合物的合成中间体,这些化合物因其潜在的治疗应用而被研究,如抗真菌、抗菌、抗炎和抗癌活性。在我们之前的工作中,我们是第一个报道使用异吲哚酮的酰胺C-N键作为氧化导向基团合成8-酰胺基异香豆素衍生物的团队。而在我们目前的工作中,我们筛选了新型8-酰胺基异香豆素衍生物(S1-S10)对人乳腺癌MCF-7和MDA-MB-231细胞的细胞毒性作用。我们的新结果表明,N-(3-(4-甲氧基苯基)-1-氧代-4-(4-丙基苯基)-1H-异色烯-8-基)乙酰胺(S1)和N-(4-(3,5-二氟苯基)-1-氧代-3-(对甲苯基)-1H-异色烯-8-基)乙酰胺(S2)是其余合成的异香豆素衍生物中对MCF-7和MDA-MB-231细胞具有细胞毒性的两种有效化合物,而对非致瘤性IOSE-364细胞毒性较小。流式细胞术研究通过Annexin V/PI双重染色证实了化合物诱导的凋亡作用。我们还通过DAPI-PI免疫染色和苏木精-伊红染色评估了S1和S2的细胞毒性作用。通过扫描电子显微镜评估,在用化合物处理的两种癌细胞中均观察到与凋亡小泡一致的形态学改变。总体而言,本研究有力地证明了8-酰胺基异香豆素衍生物在乳腺癌细胞中具有强大的细胞毒性和凋亡作用。