Dumat Blaise, Faurel-Paul Elodie, Fornarelli Pauline, Saettel Nicolas, Metgé Germain, Fiorini-Debuisschert Céline, Charra Fabrice, Mahuteau-Betzer Florence, Teulade-Fichou Marie-Paule
Institut Curie, PSL Research University, CNRS, INSERM, UMR9187/U1196, F-91405, Orsay, France.
Org Biomol Chem. 2016 Jan 7;14(1):358-70. doi: 10.1039/c5ob02225h. Epub 2015 Nov 24.
On the basis of our previous work on DNA fluorophores derived from vinylpyridinium-triphenylamine, we explored the structure space around the electron-rich triphenylamine (TP) core by changing the vinyl bond to an oxazole ring. As 2,5-diaryloxazoles are known to be highly fluorescent and efficient two photon absorbers, we synthesized analogues with two different connections of the oxazole to the triphenylamine core: TP-Ox2Py and TP-Ox5Py sets. Since the benzimidazolium group was proven to be more effective in the TP series than the pyridinium, we also synthesized a TP-Ox5Bzim set. The TP-Ox5Py series retains the TP-Py properties: on/off behavior on DNA, good two-photon cross-section and bright staining of nuclear DNA by microscopy under both one or two-photon excitation. On the other hand, the TP-Ox2Py series does not display fluorescence upon binding to DNA. The TP-Ox5Bzim set is fluorescent even in the absence of DNA and displays lower affinity than the corresponding TP-Ox5Py. CD experiments and docking were performed to understand these different behaviors.
基于我们之前在由乙烯基吡啶鎓 - 三苯胺衍生的DNA荧光团方面的工作，我们通过将乙烯基键变为恶唑环来探索富电子三苯胺（TP）核心周围的结构空间。由于已知2,5 - 二芳基恶唑具有高荧光性且是高效的双光子吸收剂，我们合成了恶唑与三苯胺核心具有两种不同连接方式的类似物：TP - Ox2Py和TP - Ox5Py系列。由于已证明苯并咪唑鎓基团在TP系列中比吡啶鎓更有效，我们还合成了TP - Ox5Bzim系列。TP - Ox5Py系列保留了TP - Py的性质：对DNA有开/关行为、良好的双光子截面以及在单光子或双光子激发下通过显微镜对核DNA进行明亮染色。另一方面，TP - Ox2Py系列在与DNA结合时不显示荧光。TP - Ox5Bzim系列即使在没有DNA的情况下也有荧光，并且显示出比相应的TP - Ox5Py更低的亲和力。进行了圆二色性（CD）实验和对接以了解这些不同的行为。
