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4-硝基苯甲醛衍生新型席夫碱的制备、表征及其细胞毒性活性

Preparation and Characterization of Novel Schiff Base Derived From 4-Nitro Benzaldehyde and Its Cytotoxic Activities.

作者信息

Abdul Majeed Rana Hassan, Hussein Hanaa Ali, Abdullah Mohd Azmuddin

机构信息

College of Dentistry, University of Basrah, Basrah, Iraq.

SIBCo Medical and Pharmaceuticals Sdn. Bhd., No. 2, Level 5, Jalan Tengku Ampuan Zabedah, D9/D, Seksyen 9, 40000 Shah Alam, Selangor, Malaysia.

出版信息

Int J Mol Cell Med. 2022;11(4):285-296. doi: 10.22088/IJMCM.BUMS.11.4.285.

Abstract

Normal drugs exhibit activities against both normal and cancer cells. Furthermore, cancer cells may develop resistance to these drugs that alternative treatment must be explored. The main objective of this study was to examine the anticancer activity of Schiff base against Tongue Squamous Cell Carcinoma Fibroblasts (TSCCF) and normal human gingival fibroblasts (NHGF) and to propose its mechanism. A Novel Schiff base ligand was synthesized from the reaction of 5-C-2-4-NABA (5-chloro-2-((4-nitrobenzylidene) amino) benzoic acid). These Schiff bases possessed azomethine group (-HC=N-) and aromatic group (CH) as analyzed by Fourier transforms infrared (FTIR) spectroscopy and UV-Vis spectra. The cytotoxicity screening assay suggested promising activity against TSCCF with IC of 446.68 µg/mL, but insignificant activity against NHGF cells (IC of 977.24 µg/mL) after 72 h. The evidence of apoptotic induction was supported by DAPI staining of apoptotic nuclei with reduced cell numbers, suggesting that Schiff base could induce apoptotic bodies in cancer cells being observed. Based on the Schiff base structure, the anti-cancer mechanism may be attributed to the -HC=N- azomethine group. For the first time, our findings highlighted the anticancer activities of the new Schiff base against oral cancer cell lines.

摘要

常规药物对正常细胞和癌细胞均有活性。此外,癌细胞可能会对这些药物产生耐药性,因此必须探索替代治疗方法。本研究的主要目的是检测席夫碱对舌鳞状细胞癌成纤维细胞(TSCCF)和正常人牙龈成纤维细胞(NHGF)的抗癌活性,并提出其作用机制。一种新型席夫碱配体由5-C-2-4-NABA(5-氯-2-((4-硝基亚苄基)氨基)苯甲酸)反应合成。通过傅里叶变换红外(FTIR)光谱和紫外可见光谱分析,这些席夫碱含有偶氮甲碱基团(-HC=N-)和芳香基团(CH)。细胞毒性筛选试验表明,该席夫碱对TSCCF具有良好的活性,72小时后的IC50为446.68 µg/mL,但对NHGF细胞的活性不显著(IC50为977.24 µg/mL)。凋亡诱导的证据得到了凋亡细胞核的DAPI染色支持,细胞数量减少,表明观察到席夫碱可在癌细胞中诱导凋亡小体。基于席夫碱结构,抗癌机制可能归因于-HC=N-偶氮甲碱基团。我们的研究结果首次突出了新型席夫碱对口腔癌细胞系的抗癌活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0036/10506673/7a653ec8d8a1/ijmcm-11-285-g001.jpg

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