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1,8‐Naphthalimide‐Substituted BODIPY Dyads: Synthesis, Structure, Properties, and Live‐Cell Imaging
Chemistry - An Asian Journal ( IF 4.1 ) Pub Date : 2018-09-04 , DOI: 10.1002/asia.201800816
Madhurima Poddar 1 , Vinay Sharma 2 , Shaikh M. Mobin 1, 2 , Rajneesh Misra 1
Affiliation  

A set of 1,8‐naphthalimide (NPI)‐substituted 4,4‐difluoroboradiaza‐s‐indacene (BODIPY) dyads 1 a1 c were designed and synthesized by the Pd‐catalyzed Sonogashira cross‐coupling reaction of ethynyl substituted NPI 1 with the meso‐, β‐, and α‐halogenated BODIPYs a, b, and c, respectively. The BODIPY 1 c exhibits redshifted absorption, which suggests better electronic communication with substitution at the α‐position of BODIPY compared with at the meso and β positions, which was further supported by time‐dependent DFT calculations. The optical band gap follows the order 1 a>1 b>1 c. The single‐crystal X‐ray structures of dyads 1 a1 c are reported, which reflect planar orientations of the BODIPY units with respect to the NPIs. The DFT‐optimized structures show good correlation with the experimental data obtained from the single‐crystal X‐ray structures. The packing diagram of 1 a shows a sheet‐like arrangement, 1 b forms a ladder‐like structural motif, and 1 c forms a complex 3D structural arrangement. The dyads 1 a1 c show low cytotoxicity (IC50>100 μm). The confocal microscopy studies with HeLa and A375 cells (when treated with dyads 1 a1 c) show that all the dyads easily enter the cell membrane and show significant multicolor intracellular fluorescence covering the entire visible range with clear emissions in blue, green, and red channels.

中文翻译:

1,8-萘二甲酰亚胺取代的BODIPY染料:合成,结构,性质和活细胞成像

一组1,8-萘二甲酰亚胺的(NPI) -取代的4,4- difluoroboradiaza-小号-indacene(BODIPY)二价基1 - 1c中设计并合成由乙炔基的取代的NPI的Pd-催化的Sonogashira交叉偶联反应1内消旋- ,β-,和α-卤代BODIPYs一个b,和ç分别。BODIPY 1 c表现出红移吸收,这表明与中和β位置相比,BODIPY的α位置的取代具有更好的电子通信,这进一步得到了时变DFT计算的支持。光学带隙遵循顺序1 a > 1 b > 1 c。据报道,二元组1a - 1c的单晶X射线结构反映了BODIPY单元相对于NPI的平面取向。DFT优化的结构与从单晶X射线结构获得的实验数据显示出良好的相关性。1a的包装图显示了片状布置,1b形成了梯子状的结构图案,1c形成了复杂的3D结构。所述成对层1 -图1c示出低细胞毒性(IC 50 > 100μ)。用HeLa和A375细胞进行共聚焦显微镜研究(用1a1c染料进行处理)显示,所有染料均容易进入细胞膜,并显示出明显的多色细胞内荧光,覆盖了整个可见范围,并发出清晰的蓝色,绿色和绿色荧光。红色通道。
更新日期:2018-09-04
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