用实验和理论方法研究磺胺类药物与β-环糊精的络合作用。
Complexation of sulfonamides with beta-cyclodextrin studied by experimental and theoretical methods.
机构信息
Departamento de Farmacia, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Córdoba, Ciudad Universitaria, 5000 Córdoba, Argentina.
出版信息
J Pharm Sci. 2010 Jul;99(7):3166-76. doi: 10.1002/jps.22062.
The complex formation between three structurally related sulfonamides (sulfadiazine (SDZ), sulfamerazine (SMR), and sulfamethazine (SMT)) and beta-cyclodextrin (beta-CD) was studied, by exploring its structure affinity relationship. In all the cases, 1:1 stoichiometries were determined with different relative affinities found by phase solubility (SDZ:beta-CD > SMR:beta-CD > SMT:beta-CD) and nuclear magnetic resonance (NMR) (SMT:beta-CD > SMR:beta-CD > SDZ:beta-CD) studies. The spatial configurations determined by NMR were in agreement with those obtained by molecular modeling, showing that SDZ included its aniline ring into beta-CD, while SMR and SMT included the substituted pyrimidine ring. Energetic analyses demonstrated that hydrophobicity is the main driving force to complex formation.
研究了三种结构相关的磺胺类药物（磺胺嘧啶（SDZ）、磺胺甲噁唑（SMR）和磺胺间甲氧嘧啶（SMT））与β-环糊精（β-CD）之间的配合物形成，以探讨其结构亲和力关系。在所有情况下，均确定了 1:1 的化学计量比，通过相溶解度（SDZ：β-CD＞SMR：β-CD＞SMT：β-CD）和核磁共振（NMR）（SMT：β-CD＞SMR：β-CD＞SDZ：β-CD）研究发现了不同的相对亲和力。NMR 确定的空间构型与分子建模得到的构型一致，表明 SDZ 将其苯胺环纳入β-CD 中，而 SMR 和 SMT 将取代的嘧啶环纳入其中。能量分析表明，疏水性是形成配合物的主要驱动力。
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