Unique sandwich stacking of pyrene-adenine-pyrene for selective and ratiometric fluorescent sensing of ATP at physiological pH.
A pincer-like benzene-bridged sensor 1 with a pyrene excimer as a signal source and imidazolium as a phosphate anion receptor was synthesized and investigated for ATP sensing. A unique switch of excimer vs monomer pyrene fluorescence of 1 is observed in the presence of ATP due to the charcteristic sandwich pi-pi stacking of pyrene-adenine-pyrene. On the other hand, four other bases of nucleoside triphosphates such as GTP, CTP, UTP, and TTP can interact only from the outside with the already stabilized stacked pyrene-pyrene dimer of 1, resulting in excimer fluorescence quenching. The fluorescent intensity ratio of monomer-to-excimer for 1 upon binding with ATP (I(375)/I(487)) is much larger than that upon binding with ADP and AMP. This difference is large enough to discriminate ATP from ADP and AMP. As one of the biological applications, sensor 1 is successfully applied to the ATP staining experiments. Sensor 1 is also applied to monitor the hydrolysis of ATP and ADP by apyrase. The results indicate that 1 is a useful fluorescent sensor for investigations of ATP-relevant biological processes.
Xu
Zhaochao
Z
Department of Chemistry and Nano Science and Department of Bioinspired Science, Ewha Womans University, Seoul, 120-750, Korea.
Singh
N Jiten
NJ
Lim
Jeesun
J
Pan
Jie
J
Kim
Ha Na
HN
Park
Sungsu
S
Kim
Kwang S
KS
Yoon
Juyoung
J
D000225:Adenine / Q000737:chemistry*; D000255:Adenosine Triphosphate / Q000032:analysis*; D005456:Fluorescent Dyes / Q000032:analysis* / Q000737:chemistry; D006367:HeLa Cells; D006801:Humans; D006863:Hydrogen-Ion Concentration; D008958:Models, Molecular; D015394:Molecular Structure; D011721:Pyrenes / Q000737:chemistry*
D005456:Fluorescent Dyes; D011721:Pyrenes; D000255:Adenosine Triphosphate; C030984:pyrene; D000225:Adenine