Structure -: Activity relationships of oligoguanidines-influence of counterion, diamine, and average molecular weight on blocidal activities
Structure -: Activity relationships of oligoguanidines-influence of counterion, diamine, and average molecular weight on blocidal activities
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DOI：
10.1021/bm0342180
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发表时间：
2003-11-01
影响因子：
6.2
通讯作者：
Hönig, H
中科院分区：
文献类型：
--
作者：
Albert, M;Feiertag, P;Hönig, H
通过胍盐和四种不同的二胺在不同条件下的缩聚反应，制备了一系列不同的寡聚胍。对两种至四种微生物进行了抗菌活性评价。使用MALDI-TOF-MS分析不同的低聚物。结果发现，在每种情况下，三种主要产品类型系列占据主导地位。这些系列是线性的，分别用一个胍和一个氨基（A型）、两个氨基（B型）或两个胍基（C型）封端。通过使用1，2-双（2-氨基乙氧基）乙烷作为氨基组分，检测到相当数量的由环状结构组成的两个另外的产物系列（类型D和E）。结果表明，约800 Da的平均分子量对于有效的抗微生物活性是必需的。较低的M-w导致活性迅速降低。以碳酸胍为起始原料，得到的低聚物具有较低的生物杀灭活性，这是由于在缩聚过程中引入了脲基团所致。二胺决定两个胍基之间的距离。结果表明，1，2-二（2-氨基乙氧基）乙烷和六亚甲基二胺均能生成具有高杀菌活性的低聚物。通过增加二胺的链长，杀菌活性再次下降。
A series of different oligomeric guanidines was prepared by polycondensation of guanidinium salts and four different diamines under varying conditions. The antimicrobial activities were evaluated against two to four microorganisms. MALDI-TOF-MS was used to analyze the different oligomers. It was found that in each case three major product type series are dominating. These series are linear and terminated with one guanidine and one amino group (type A), two amino groups (type B), or two guanidine groups (type C), respectively. By using 1,2-bis(2-aminoethoxy)ethane as the amino component, a considerable amount of two additional product series, consisting of cyclic structures, was detected (type D and E). It turned out that an average molecular mass of about 800 Da is necessary for an efficient antimicrobial activity. Lower M-w's result in a rapid decrease of activity. By using guanidinium carbonate as the starting material, oligomers with low biocidal activity were obtained, which was caused by incorporation of urea groups during the polycondensation. The diamine determines the distance between two guanidinium groups. It was shown that both 1,2-bis(2-aminoethoxy)ethane and hexamethylenediamine give oligomers with high biocidal activity. By increasing the chain length of the diamine, the biocidal activity drops again.