探索蒽衍生物作为生物医学应用荧光发射体的潜力,Journal of Materials Chemistry B

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探索蒽衍生物作为生物医学应用荧光发射体的潜力
Journal of Materials Chemistry B ( IF 6.1 ) Pub Date : 2023-04-17 , DOI: 10.1039/d3tb00449j
Murat Aydemir ₁ , Gulcin Haykir ₂ , Harun Selvitopi ₃ , Ozge Caglar Yildirim ₄ , Mehmet Enes Arslan ₄ , Bahattin Abay ₅ , Figen Turksoy ₂

Affiliation

合成了两种新型蒽衍生物，并使用各种光谱技术进行了详细的光物理和生物学研究。发现氰基 (-CN) 取代的效果可有效改变电荷数和前沿轨道能级密度泛函理论 (DFT) 计算。特别是，引入与蒽核相连的苯乙烯基和三苯胺基团有助于增加相对于蒽部分的共轭。结果表明，这些分子具有分子内电荷转移 (ICT) 特性，发生在溶液中从给电子三苯胺到接受电子蒽部分。此外，光物理性质强烈依赖于氰基，其中氰基取代的 ( E / Z )-(2-anthracen-9-yl)-3-(4'-(diphenylamino)biphenyl-4yl)acrylonitrile 分子与 ( E )-4'-(2-(anthracen-9-yl)vinyl)- N相比，由于增强的内部空间位阻，显示出更强的电子亲和力，N-二苯基联苯-4-胺分子，导致较低的光致发光量子产率 (PLQY) 值和较短的分子寿命。此外，分子对接方法用于研究可能的细胞染色靶标，以确认化合物的细胞成像潜力。^{此外，细胞活力分析表明，合成的分子在 125 μg mL −1}以下不会表现出显着的细胞毒性对人真皮成纤维细胞系 (HDFa) 的浓度。此外，这两种化合物在 HDFa 细胞的细胞成像方面都显示出巨大的潜力。与用于核染色的常用荧光染料 Hoechst 33258 相比，这些化合物通过染色整个细胞室显示出更高的细胞结构成像能力放大倍数。另一方面，细菌染色表明溴化乙锭在监测金黄色葡萄球菌( S. aureus ) 细胞培养方面具有更高的分辨率。

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Exploring the potential of anthracene derivatives as fluorescence emitters for biomedical applications

Two novel anthracene derivatives were synthesized, and detailed photo-physical and biological investigations were carried out using a variety of spectroscopy techniques. The effect of cyano (–CN) substitution was found to be effective to alter the charge population and frontier orbital energy levels via Density Functional Theory (DFT) calculations. Particularly, the introduction of styryl and triphenylamine groups attached to the anthracene core helped to increase the conjugation relative to the anthracene moiety. The results revealed that the molecules have intramolecular charge transfer (ICT) properties, occurring from the electron donating triphenylamine to the electron accepting anthracene moiety in solutions. In addition, the photo-physical properties are strongly cyano-dependent, where the cyano-substituted (E/Z)-(2-anthracen-9-yl)-3-(4′-(diphenylamino)biphenyl-4yl)acrylonitrile molecule showed stronger electron affinity due to the enhanced internal steric hindrance compared to the (E)-4′-(2-(anthracen-9-yl)vinyl)-N,N-diphenylbiphenyl-4-amine molecule, which resulted in a lower photoluminescence quantum yield (PLQY) value and a shorter lifetime in the molecule. Besides, the Molecular Docking approach was used to investigate possible cellular staining targets to confirm cellular imaging potential of the compounds. Moreover, cell viability analyses put forth that synthesized molecules do not exhibit significant cytotoxicity under 125 μg mL⁻¹ concentration on the human dermal fibroblast cell line (HDFa). Moreover, both of the compounds showed great potential in cellular imaging of HDFa cells. Compared to Hoechst 33258, a common fluorescent dye used for nuclear staining, the compounds showed higher magnification of cellular structure imaging capacity by staining the whole cellular compartment. On the other hand, bacterial staining showed that ethidium bromide has higher resolution in monitoring Staphylococcus aureus (S. aureus) cell culture.

更新日期：2023-04-17

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