Synthesis and self-assembly of 8-Aryl-2'-deoxyguanosine derivatives in aqueous media

ORGN 705

Marilyn García-Arriaga, mgayjnr@yahoo.com, Department of Chemistry, University of Puerto Rico, Río Piedras Campus, San Juan, PR 00931-3346 and José M. Rivera, Department of Chemistry, University of Puerto Rico at Rio Piedras, P.O.Box 23346, San Juan, Puerto Rico 00931-3346, San Juan, PR 00931.
Guanosine forms supramolecular structures known as G-quadruplexes in which four gua-nine bases form a tetrad and two or more of such tetrads stack using a metal cation like potassium as a template. Recently, we showed that lipophilic 8-aryl-2'-deoxyguanosine derivatives (8ArGs) can also form quadruplexes in organic media and that the 8-aryl group could be used to modulate the supramolecular properties of the resulting assembly. On the other hand, little is known of the self-assembly of hydrophilic 8ArGs in aqueous environments. We will discuss a general method for the synthesis of such 8ArGs as well as their characterization of the supramolecular properties in aqueous media by spectro-scopic methods (NMR, UV and CD).