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

Wael E Houssen , Zhibao Lu, RuAngelie Edrada-Ebel, Christina Chatzi, Steven J. Tucker, Kristina Sepcic, Tom Turk, Ana Zovko, Sanbing Shen, Ines Mancini, Roderick H. Scott, Marcel Jaspars

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)113-125
Number of pages13
JournalJournal of Chemical Biology
Volume3
Issue number3
Early online date17 Feb 2010
DOIs
Publication statusPublished - Aug 2010

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Marine Toxins
Bioactivity
Polymers
Salts
Flow cytometry
Clamping devices
Acetylcholinesterase
Microwaves
Polymerization
Transfection
Macros
Flow Cytometry
Molecular Weight
Molecular weight
Irradiation
Imaging techniques

Keywords

  • marine toxins
  • transfection
  • Poly-APS
  • pore formers
  • microwave-assisted polymerisation

Cite this

Chemical synthesis and biological activities of 3-alkyl pyridinium polymeric analogues of marine toxins. / Houssen , Wael E; Lu, Zhibao; Edrada-Ebel, RuAngelie; Chatzi, Christina; Tucker, Steven J.; Sepcic, Kristina; Turk, Tom; Zovko, Ana; Shen, Sanbing; Mancini, Ines; Scott, Roderick H.; Jaspars, Marcel.

In: Journal of Chemical Biology, Vol. 3, No. 3, 08.2010, p. 113-125.

Research output: Contribution to journalArticle

Houssen , WE, Lu, Z, Edrada-Ebel, R, Chatzi, C, Tucker, SJ, Sepcic, K, Turk, T, Zovko, A, Shen, S, Mancini, I, Scott, RH & Jaspars, M 2010, 'Chemical synthesis and biological activities of 3-alkyl pyridinium polymeric analogues of marine toxins' Journal of Chemical Biology, vol. 3, no. 3, pp. 113-125. https://doi.org/10.1007/s12154-010-0036-4
Houssen , Wael E ; Lu, Zhibao ; Edrada-Ebel, RuAngelie ; Chatzi, Christina ; Tucker, Steven J. ; Sepcic, Kristina ; Turk, Tom ; Zovko, Ana ; Shen, Sanbing ; Mancini, Ines ; Scott, Roderick H. ; Jaspars, Marcel. / Chemical synthesis and biological activities of 3-alkyl pyridinium polymeric analogues of marine toxins. In: Journal of Chemical Biology. 2010 ; Vol. 3, No. 3. pp. 113-125.
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