Detection of metal cations by self-assembled fluorescent probes based on Pyrenyl-labeled-8-phenyl-2'-dG analogs

CHED 374

Andrés M. González, a_gonzalez02b@hotmail.com, Department of Chemistry, University of Puerto Rico, Rio Piedras Campus, PO Box 23346, San Juan, PR 00931, Vladimir Gubala, gubala@adam.uprr.pr, Department of Chemistry, University of Puerto Rico at Rio Piedras, Río Piedras, PR 00931, and José M. Rivera, jrivera@cnnet.upr.edu, Department of Chemistry, University of Puerto Rico at Río Piedras, PO Box 23346, San Juan, PR 00931-3346.
Self-assembly is an attractive synthetic strategy for the construction of sensitive, reliable and cheap fluorescent probes for metal cations. Guanosine and related compounds have a propensity to form planar tetramers (tetrads), which are held together by H-bonds and cation complexation; further stacking of such tetrads leads to G-quadruplex formation. We will present the synthesis of 3'- and 5'-(pyrenyl-labeled)-8-phenyl-2'-deoxyguanosine analogues as well as studies of their photophysical properties before and after their self-assembly templated by a variety of metal cations (See figure below). The fluorescence properties of these probes are modulated by the supramolecular structure as supported by fluorescence and NMR spectroscopies. These results bode well for development of sensors for metal cations for biomedical and environmental applications.