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

Journal of Chemical Biology

Ines Mancini³  Christina Chatzi⁶  Marcel Jaspars²  Ana Zovko¹  Kristina Sepčić¹  Zhibao Lu²  Sanbing Shen⁵  Tom Turk¹  RuAngelie Edrada-Ebel⁴  Roderick H. Scott⁵  Steven J. Tucker⁵  Wael E. Houssen² 

[1] Department of Biology, Biotechnical Faculty, University of Ljubljana, Večna pot 111, 1111 Ljubljana, Slovenia;Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Aberdeen, AB24 3UE Scotland, UK;Laboratorio di Chimica Bioorganica, Università di Trento, via Sommarive 14, 38100 Trent, Italy;Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, John Arbuthnott Building, 27 Taylor Street, Glasgow, G4 0NR UK;Institute of Medical Sciences, University of Aberdeen, Aberdeen, AB25 2ZD Scotland, UK;Burnham Institute for Medical Research, Development and Ageing, 10901, North Torrey Pines Rd, La Jolla, CA 92037 USA

关键词: Marine toxins;    Transfection;    Poly-APS;    Pore formers;    Microwave-assisted polymerisation;   

DOI  :  10.1007/s12154-010-0036-4

学科分类：分子生物学，细胞生物学和基因

来源: Springer

【 摘 要 】

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.

【 授权许可】

Unknown