New 1,3-Disubstituted Benzo[h]Isoquinoline Cyclen-Based Ligand Platform: Synthesis, Eu3+ Multiphoton Sensitization and Imaging Applications

Molecules

Valeria Di Bussolo¹  Dalila Iacopini¹  Sebastiano Di Pietro²  Mauro Pineschi²  Riccardo Nifosì³  Giovanni Signore³  Barbara Storti³  Aldo Moscardini³  Ranieri Bizzarri³ 

[1] Chemistry and Industrial Chemistry Department, University of Pisa, Via G. Moruzzi 3, 56126 Pisa, Italy;Department of Pharmacy, University of Pisa, Via Bonanno Pisano 6, 56126 Pisa, Italy;NEST, Scuola Normale Superiore and Istituto Nanoscienze-CNR, Piazza San Silvestro 12, 56127 Pisa, Italy;

关键词: europium complex;    benzoisoquinoline;    cyclen;    bioprobe;    structured illumination microscopy;   

DOI  :  10.3390/molecules26010058

来源: DOAJ

【 摘 要 】

The development of lanthanide-based luminescent probes with a long emission lifetime has the potential to revolutionize imaging-based diagnostic techniques. By a rational design strategy taking advantage of computational predictions, a novel, water-soluble Eu3+ complex from a cyclen-based ligand bearing 1,3-disubstituted benzo[h]isoquinoline arms was realized. The ligand has been obtained overcoming the lack of reactivity of position 3 of the isoquinoline moiety. Notably, steric hindrance of the heteroaromatic chromophore allowed selective and stoichiometry-controlled insertion of two or three antennas on the cyclen platform without any protection strategy. The complex bears a fourth heptanoic arm for easy conjugation to biomolecules. This new chromophore allowed the sensitization of the metal center either with one or two photons excitation. The suitability as a luminescent bioprobe was validated by imaging BMI1 oncomarker in lung carcinoma cells following an established immunofluorescence approach. The use of a conventional epifluorescence microscope equipped with a linear structured illumination module disclosed a simple and inexpensive way to image confocally Ln-bioprobes by single photon excitation in the 350–400 nm window, where ordinary confocal systems have no excitation sources.

【 授权许可】

Unknown