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Synthesis, Surface‐Active Properties, and Anthelmintic Activities of New Cationic Gemini Surfactants Against the Gastrointestinal Nematode, Heligmosomoides polygyrus bakeri , In Vitro
Author(s) -
Sánchez Victoria G.,
Giudici Claudio J.,
Bassi Amilcar R.,
Murguía Marcelo C.
Publication year - 2012
Publication title -
journal of surfactants and detergents
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.349
H-Index - 48
eISSN - 1558-9293
pISSN - 1097-3958
DOI - 10.1007/s11743-012-1337-0
Subject(s) - chemistry , anthelmintic , cationic polymerization , heligmosomoides polygyrus , micelle , chromatography , critical micelle concentration , organic chemistry , aqueous solution , helminths , ecology , biology , zoology
A novel series of cationic dimeric surfactants was prepared involving the ketalization reaction, Williamson etherification, and regioselective oxirane ring opening with tertiary alkyl amines. The synthesized compounds were obtained in high purity by a simple purification procedure using column chromatography. The critical micelle concentration (CMC), effectiveness of surface tension reduction (γ CMC ), surface excess concentration (Γ), and area per molecule at the interface ( A ) were determined and values indicate that the cationic series is characterized by good surface‐active and self‐aggregation properties. For the first time, we reported the anthelmintic activities against the rodent gastrointestinal nematode Heligmosomoides polygyrus bakeri , in vitro for cationic gemini compounds. In the series of five tested cationic compounds ( 4a – e ), three of them ( 4a , 4b and 4d ) were shown to have an excellent anthelmintic activity in vitro at different concentrations. The anthelmintic activity was found to be dependent on the type of cationic compound, concentration and incubation time. The cationic di‐C 12 ( 4a ) derivate of the series was the best anthelmintic agent, its use was optimal at a minimum concentration of 50 ppm and with 60 min of incubation.