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目的 首次合成一种具有靶向线粒体抗肿瘤活性的半花菁衍生物。方法 以半花菁结构中的吲哚阳离子和4-(双(4-(吡啶-4-基)苯基)氨基)苯甲醛为底物，设计并合成了PNIN((E)-2-(4-(双(4-(吡啶-4-基)苯基)氨基)苯乙烯基)-1-乙基-3,3-二甲基-3H-吲哚-1-碘化物)。通过核磁和高分辨质谱对化合物的结构进行表征，荧光光谱法和紫外-可见光吸收光谱法研究该化合物的光物理化学性质。通过理论计算得到ESP、HOMO、LUMO的化学结构以及能隙值。MTT实验以及细胞活/死双染实验研究化合物的细胞毒性；激光共聚焦显微镜对线粒体荧光共定位成像进行拍照。结果 所合成的半花菁衍生物具有抗癌毒性，以及红光成像能力，并且具有优异的线粒体靶向效果。结论 PNIN具有靶向线粒体红光成像能力以及细胞毒性，可作为潜在的靶向线粒体抗肿瘤药物。
Abstract：Objective To first synthesize a mitochondria-targeting hemicyanine derivative with antitumor activity.Methods The compound PNIN((E)-2-(4-(bis(4-(pyridin-4-yl)phenyl)amino)styryl)-1-ethyl-3,3-dimethyl-3H-indole-1-iodide) was designed and synthesized by using the indole cation in the hemicarbocyanine structure and 4-(bis(4-(pyridin-4-yl)phenyl)amino)benzaldehyde as substrate.The structural characterization of the compound was identified through nuclear magnetic resonance(NMR) and high-resolution mass spectrometry, while the photophysical and chemical properties were investigated by means of fluorescence and UV-visible absorption spectroscopy.The electronic structure parameters, including the electron spin-up(ESP),the electron hole(HOMO),the electron spin-down(LUMO),and the energy gap(Eg),were derived through theoretical calculations.The toxicity of the compound was detected by using MTT assay and live/dead double staining of cells.Mitochondrial fluorescence co-localization imaging was photographed by laser confocal microscopy.Results The synthesized hemicyanine derivatives exhibited anticancer toxicity, red-light imaging ability, and excellent mitochondrial targeting.Conclusion PNIN has the capacity to mitochondrial-target red-light imaging and exhibits cytotoxicity, makeing it a potential mitochondria-targeting antitumor drug.
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基本信息:
DOI：10.16751/j.cnki.2095-4646.2025052905
中图分类号:R914.5
引用信息:
[1]晏可,闵爽,王都喜,等.基于半花菁结构的线粒体靶向抗肿瘤药物的合成及性能研究[J].湖北科技学院学报(医学版),2026,40(01):1-5+101.DOI:10.16751/j.cnki.2095-4646.2025052905.
2026-01-20
2026-01-20