Abstract
Pyridinium chlorides with long alkyl substituents were prepared, sometimes in quantitative yields, using a macroporous, strongly basic, anion exchange resin of the styrene-divinylbenzene type. This procedure opens the way to convert readily available and highly pure pyrylium salts with tailored amphiphilicity inducing substituents, into pyridinium perchlorates, and then by this optimized anion exchange procedure into the corresponding chlorides. Previous transfection studies using long chain pyridinium perchlorates have proven acute cell toxicity whereas the corresponding chlorides were benign and had good to high transfection efficiencies, superior to commercial nonviral vectors. All new compounds were fully characterized and can now be made available in large quantities.
Highlights
Recent in depth studies of cationic amphiphiles have demonstrated practical utility for the latter for delivery of DNA and RNA into cells
The groups of Jan Engberts and Dick Hoekestra describe the synthesis of pyridinium chlorides as amphiphiles by the quaternization of 4methylpyridine, in order to identify lead structures and to optimize the efficiency of these quaternary salts in transfection experiments
Synthesis of pyridinium chlorides from pyrylium perchlorates followed by anion exchange
Summary
Recent in depth studies of cationic amphiphiles have demonstrated practical utility for the latter for delivery of DNA and RNA into cells. Synthesis of pyridinium chlorides from pyrylium perchlorates followed by anion exchange.
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