Combinatorial discovery of full-color-tunable emissive fluorescent probes using a single core skeleton, 1,2-dihydropyrrolo[3,4-beta]indolizin-3-one.
We developed a novel fluorescent core skeleton, 1,2-dihydropyrrolo[3,4-beta]indolizin-3-one, by complexity-generating one-pot reactions through 1,3-dipolar cyclization followed by oxidative aromatization. This fluorescent core skeleton can accommodate various wavelengths of emission maxima by changing the electronic properties of substituents, which was postulated by computational studies. The full-color-tunable emission maxima were achieved with a single core skeleton by changing the substituents using the combinatorial approach. These novel fluorophores have excellent photophysical and photochemical properties: moderate to excellent quantum yields, resistance to the photobleaching, pH-independent fluorescence, large Stokes shifts, druglike lipophilicity for membrane permeability, etc. Further, we successfully demonstrated the bioapplication of fluorophores B1 and B5 in the immunofluorescence for visualizing cellular compartments of HeLa cells.
Kim
Eunha
E
Department of Chemistry, Seoul National University, Seoul 151-747, Korea.
Koh
Minseob
M
Ryu
Jihoon
J
Park
Seung Bum
SB
D020650:Combinatorial Chemistry Techniques / Q000379:methods; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D007150:Immunohistochemistry; D007212:Indolizines / Q000138:chemical synthesis / Q000737:chemistry*; D010777:Photochemistry; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
D005456:Fluorescent Dyes; D007212:Indolizines; D011758:Pyrroles