Culler M D, Bitman J, Thompson M J, Robbins W E, Dutky S R
J Dairy Sci. 1979 Apr;62(4):584-95. doi: 10.3168/jds.S0022-0302(79)83294-4.
The activities of branched and straight chain amines (10 to 18 carbons chain length) were compared in inhibiting the growth of five microorganisms that cause about 95% of bovine mastitis. Three gram-positive (Streptococcus agalactiae, Streptococcus uberis, Staphylococcus aureus) and two gram-negative (Escherichia coli, Klebsiella pneumoniae) bacteria were used in a trypticase soy broth tube culture growth assay. Sixty-two compounds were screened at concentrations of 200, 100, 50, 25, 10, 5, and 1 ppm in broth culture to determine the effective minimum inhibitory concentration. Alkyl secondary N-substituted monoethyl [CH3(CH2)nNHCH2CH3] and tertiary N,N-substituted dimethyl [CH3(CH2) nN(CH3)2] amines with chain lengths of 11 to 14 carbon atoms were active against both gram-positive and gram-negative organisms. Antimicrobial activity against gram-positive organisms increased with increasing chain length and carbon-14 to 18 amines were active at 1 to 5 ppm. The carbon-11 to 13 alkyl amines were most active against gram-positive organisms; longer chain amines (more than 14 carbons) were inactive. Branching of the alkyl chain caused a loss of activity against gram-negative but not against gram-positive bacteria. Antimicrobial testing of monoamines, polyamines, and the influence of order substituents were investigated to correlate structure-acitivity relationships.
比较了支链和直链胺(碳链长度为10至18个碳原子)对五种导致约95%牛乳腺炎的微生物生长的抑制活性。在胰蛋白酶大豆肉汤试管培养生长试验中使用了三种革兰氏阳性菌(无乳链球菌、乳房链球菌、金黄色葡萄球菌)和两种革兰氏阴性菌(大肠杆菌、肺炎克雷伯菌)。在肉汤培养中以200、100、50、25、10、5和1 ppm的浓度筛选了62种化合物,以确定有效最低抑菌浓度。碳链长度为11至14个碳原子的烷基仲N-取代单乙胺[CH3(CH2)nNHCH2CH3]和叔N,N-取代二甲胺[CH3(CH2)nN(CH3)2]对革兰氏阳性菌和革兰氏阴性菌均有活性。对革兰氏阳性菌的抗菌活性随碳链长度增加而增强,碳-14至18胺在1至5 ppm时具有活性。碳-11至13烷基胺对革兰氏阳性菌最具活性;碳链更长的胺(超过14个碳原子)无活性。烷基链的分支导致对革兰氏阴性菌的活性丧失,但对革兰氏阳性菌没有影响。研究了单胺、多胺的抗菌测试以及有序取代基的影响,以关联结构-活性关系。