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Selectivity in the interactions between positively charged small molecules and negatively charged biopolymers
Abstract
There are multiple negative charged biopolymers that exist within the context of the cell including cell surface proteoglycans, the cell membrane, RNA and DNA. Guanidinoglycosides, a family of small, positively charged molecules bind with surprising selectivity to cell surface heparan sulfate proteoglycans. This binding event allows these compounds to internalize into the cell via receptor mediated endocytosis, and be released into the cytoplasm. Guanidinoglycosides also have a high affinity for RNA and show selectivity for the RRE over other RNA and DNA. Guanidinoglycosides have significant potential as both cellular delivery agents and as scaffolds for the design of anti-HIV therapeutics. Through conjugation to therapeutic agents, guanidinoglycosides can increase the efficacy of these compounds by allowing them to cross cellular membranes and localize within the cytoplasm, and through modifications which increase their selectivity for specific RNA targets guanidinoglycosides can achieve more potent anti-viral activity
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