Synthesis and Anticancer Potential of New Benzimidazole Theranostic.

IF 2.5 4区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

ChemistryOpen Pub Date : 2025-07-15 DOI:10.1002/open.202500263

Sahani Sandalima Uthumange, Muhammad Azri Faiz Bin Abdul Zaki, Keng Yoon Yeong

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Abstract

A series of novel benzimidazole analogs is designed, synthesized, and screened against a panel of selected cancer cell lines, including H103 (oral squamous cell carcinoma, OSCC), H314 (OSCC), and HCT116 (colorectal carcinoma). Structural characterization of the compounds is successfully confirmed using nuclear magnetic resonance spectroscopy (¹H and ¹³C) and liquid chromatography-mass spectrometry. Within the series, compound V7 emerged as a promising anticancer candidate, displaying broad-spectrum activity with high selectivity toward the tested cancer cell lines (half-maximal inhibitory concentration, IC₅₀: H103 = 11.64 μM, H314 = 16.68 μM, HCT11 = 13.30 μM). Furthermore, the observed sirtuin 2 (SIRT2) inhibitory activity of V7 suggests a potential link to its anticancer effects. Molecular docking analysis reveals the importance of a hydroxyl group at the ortho position of the 2-phenyl ring in rendering SIRT2 inhibitory activity. Notably, the high autofluorescent properties of V7 (molar absorptivity ε = 34,477 M^-1 cm^-1, quantum yield Φ = 26%, and Stokes shift Δλ = 166 nm) indicate potential for further development as a theranostic agent for cancer.

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新型苯并咪唑治疗剂的合成及其抗癌潜力。

设计、合成了一系列新型苯并咪唑类似物，并对一系列选定的癌细胞系进行了筛选，包括H103（口腔鳞状细胞癌，OSCC）、H314 （OSCC）和HCT116（结直肠癌）。用核磁共振波谱（1H和13C）和液相色谱-质谱成功地证实了化合物的结构表征。其中，化合物V7对肿瘤细胞具有广谱活性和高选择性，IC50分别为：H103 = 11.64 μM, H314 = 16.68 μM, HCT11 = 13.30 μM。此外，观察到的V7的sirtuin 2 （SIRT2）抑制活性提示其抗癌作用的潜在联系。分子对接分析揭示了2-苯基环邻位羟基对SIRT2抑制活性的重要性。值得注意的是，V7的高自荧光特性（摩尔吸收率ε = 34,477 M-1 cm-1，量子产率Φ = 26%， Stokes位移Δλ = 166 nm）表明其作为癌症治疗药物的进一步发展潜力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

ChemistryOpen CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

4.80

自引率

4.30%

发文量

143

审稿时长

1 months

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