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Inhibition of Clostridium botulinum by aliphatic amines and long chain aliphatic aminodiamides
Author(s) -
Huhtanen C. N.,
Micich T. J.
Publication year - 1978
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02671405
Subject(s) - clostridium botulinum , moiety , chemistry , amine gas treating , stereochemistry , minimum inhibitory concentration , inhibitory postsynaptic potential , medicinal chemistry , organic chemistry , biochemistry , in vitro , toxin , biology , neuroscience
N‐substituted aminodiamides of the general structure, RNHCO (CH 2 ) x ‐CONH(CH 2 ) y N(CH 3 ) 2 , and the corresponding N‐sulfopropyl derivatives were studied for their inhibiting effect on growth of Clostridium botulinum in culture media. With R = C 16 H 33 , more activity was observed with x = 2, 3, or 4 and y = 2, 3, or 4 than with R = C 12 H 25 or C 10 H 21 . There was little or no correlation of activity with the length of the x or y chains, but the addition of the sulfopropyl group resulted in decreased inhibitory activity. The C 3 to C 18 saturated aliphatic amines used for synthesizing the aminodiamides were effective inhibitors of C. botulinum ; tetradecyl‐, pentadecyl‐, and hexadecylamines were the most active with minimum inhibitory concentrations (MIC) of 0.8 μ/ml‐The ratio of molecular weights of the diamides to the corresponding aliphatic amines indicated that most if not all of the inhibitory activity of the aminodiamides could be attributed to the amine moiety.