Journal of Photochemistry and Photobiology A: Chemistry ( IF 4.1 ) Pub Date : 2019-06-18 , DOI: 10.1016/j.jphotochem.2019.111944 Majka Duda , Maria Rąpała-Kozik , Katarzyna M. Stadnicka , Bogdan Musielak , Piotr Goszczycki , Łukasz J. Witek , Marcin Zawrotniak , Miriam González-González , Katarzyna Ostrowska
In the present study, a new 'turn on' fluorescent sensor, (E/Z)-enaminone containing a pyrrolo[2,3-b]quinoxaline group as the fluorophore and a N,N-bis(pyridin-2-ylmethyl)ethylenediamine group as a specific chelator capable of selective detection of Zn2+ is reported. The structure of the ligand was determined by IR, MS, and 1D and 2D NMR, including 1H-15N HMBC correlations. X-ray analysis for (E/Z)-2 confirmed the presence of 90.3% E-diastereoisomer and 9.7% Z-one in the structure of the crystals obtained from acetonitrile. The mechanism of zinc ion recognition is related to the restriction of E/Z-isomerisation of enaminone occurring upon Zn2+ binding that alters the electronic structure of the ligand. Sensing of Zn2+ was confirmed in detail using UV–vis, fluorescent, and 1H NMR titrations, which allowed us to propose the binding mode for complexes formed in the solution during the zinc ion recognition. The ligand functions under physiological conditions and retains its activity in buffer solutions over a wide pH range 2.4–10.6. The developed sensor allowed for intracellular sensing of Zn2+ in human (fibroblast) and fungal (Candida albicans) cells through fluorescence imaging studies.
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
N,N-双(吡啶-2-基甲基)乙二胺链的吡咯并[2,3- b ]喹喔啉在白色念珠菌和成纤维细胞中Zn(II)检测中的应用
在本研究中,一种新的“开启”荧光传感器,(E / Z)-烯胺酮,含有吡咯并[2,3- b ]喹喔啉基团作为荧光团和N,N-双(吡啶-2-基甲基)报道了乙二胺基团作为能够选择性检测Zn 2+的特定螯合剂。配体的结构通过IR,MS,1D和2D NMR确定,包括1 H- 15 N HMBC相关性。X射线分析(E / Z)-2证实存在90.3%的E-非对映异构体和9.7%的Z-从乙腈获得的晶体的结构中的一个。锌离子识别的机制与在改变配体的电子结构的Zn 2+结合时发生的烯胺酮的E / Z-异构化的限制有关。使用UV-vis,荧光和1 H NMR滴定法已详细证实了Zn 2+的传感,这使我们能够提出识别锌离子过程中溶液中形成的络合物的结合模式。配体在生理条件下起作用,并在2.4-10.6的宽pH范围内在缓冲溶液中保留其活性。允许的Zn的胞内传感发达传感器2+人类(成纤维细胞)和真菌(白色念珠菌)细胞通过荧光成像研究。