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Chemical synthesis and biological activities of 3-alkyl pyridinium polymeric analogues of marine toxins

Houssen, W.E. and Luo, Z. and Edrada-Ebel, R.A. and Chatzi, C. and Tucker, S.J. and Sepcic, K. and Turk, T. and Zovko, A. (2010) Chemical synthesis and biological activities of 3-alkyl pyridinium polymeric analogues of marine toxins. Journal of Chemical Biology, 3 (3). pp. 113-125. ISSN 1864-6158

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Two new large poly-1,3-dodecylpyridinium salts, APS12 and APS12-2 of 12.5- and 14.7-kDa size, respectively, were synthesised and tested for their pore-forming and transfection capabilities in HEK 293 and undifferentiated mouse ES cells using patch-clamp recording, Ca2+ imaging and flow cytometry. Polymerisation reactions were enhanced by microwaves, and the product sizes were controlled by altering the irradiation time. This method can also be applied to obtain polymers with variable linking chains as shown by the preparation of poly-(1,3-octylpyridinium) salt of 11.9-kDa size. Molecular weights of the final products were determined using ESIMS analysis, which also indicated the products to be amongst the largest macro-cycles ever recorded, up to a 900-membered ring. Anti-bacterial, haemolytic and anti-acetylcholinesterase activities were also reported for the two dodecyl pyridinium polymers. These biological activities are characteristic to the structurally related marine toxin, poly-APS.