Design of dual-emission chemosensors for ratiometric detection of ATP derivatives.
Nucleoside pyrophosphate (nucleoside PP) derivatives are widespread in living cells and play pivotal roles in various biological events. We report novel fluorescence chemosensors for nucleoside PPs that make use of coordination chemistry. The chemosensors, which contain two Zn(II)-dipicolylamine units, bind strongly to nucleoside PPs (K(app)>10(6) M(-1)) in aqueous solution and sense them by a dual-emission change. Detailed fluorescence and UV/Vis spectral studies revealed that the emission changes of the chemosensors upon binding to nucleoside PPs can be ascribed to the loss of coordination between Zn(II) and the acridine fluorophore. This is a unique sensing system based on the anion-induced rearrangement of the coordination. Furthermore, we demonstrated the utility of these chemosensors in real-time monitoring of two important biological processes involving nucleoside PP conversion: the apyrase-catalyzed hydrolysis of nucleoside PPs and the glycosyl transfer catalyzed by beta-1,4-galactosyltransferase.
Ojida
Akio
A
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Nishikyo-ku, Kyoto, 615-8510, Japan.
Miyahara
Yoshifumi
Y
Wongkongkatep
Jirarut
J
Tamaru
Shun-ichi
S
Sada
Kazuki
K
Hamachi
Itaru
I
D000255:Adenosine Triphosphate / Q000737:chemistry*; D000838:Anions; D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D011756:Diphosphates / Q000737:chemistry; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D008956:Models, Chemical; D008968:Molecular Conformation; D009705:Nucleosides / Q000737:chemistry; D013050:Spectrometry, Fluorescence / Q000295:instrumentation* / Q000379:methods
D000838:Anions; D011756:Diphosphates; D005456:Fluorescent Dyes; D009705:Nucleosides; D000255:Adenosine Triphosphate