Dubes Alix, Degobert Ghania, Fessi Hatem, Parrot-Lopez Hélène
Laboratoire de Méthodologies de Synthèse et Molécules Bioactives, F-69622 Villeurbanne, France.
Carbohydr Res. 2003 Oct 10;338(21):2185-93. doi: 10.1016/s0008-6215(03)00356-2.
The synthesis of sulfated amphiphilic alpha-, beta- and gamma-cyclodextrins was achieved according to the standard protection-deprotection procedure. The formation of inclusion complexes between the amphiphilic alpha-, beta- and gamma-cyclodextrins and an antiviral molecule, acyclovir (ACV) was investigated by UV-visible spectroscopy (UV-Vis) and electrospray ionisation mass spectrometry (ESIMS). UV-Vis spectroscopy allowed determination of the stoichiometry and stability constants of complexes, whereas ESIMS, a soft ionisation technique, allowed the detection of the inclusion complexes. The results showed that the non-sulfated amphiphilic cyclodextrins exhibit a 1:2 stoichiometry with acyclovir, while sulfated amphiphilic cyclodextrins, except gamma-cyclodextrin, exhibit a 1:1 stoichiometry indicating the loss of one interaction site. Non-covalent interactions between acyclovir and non-sulfated amphiphilic cyclodextrins appear to take place both in the cavity of the cyclodextrin and inside the hydrophobic zone generated by alkanoyl chains. In contrast, in the case of sulfated amphiphilic cyclodextrins, the interactions appear to involve only the hydrophobic region of the alkanoyl chains.
根据标准的保护-脱保护程序实现了硫酸化两亲性α-、β-和γ-环糊精的合成。通过紫外可见光谱（UV-Vis）和电喷雾电离质谱（ESIMS）研究了两亲性α-、β-和γ-环糊精与抗病毒分子阿昔洛韦（ACV）之间包合物的形成。紫外可见光谱可用于确定配合物的化学计量比和稳定常数，而ESIMS作为一种软电离技术，可用于检测包合物。结果表明，非硫酸化两亲性环糊精与阿昔洛韦的化学计量比为1:2，而除γ-环糊精外的硫酸化两亲性环糊精的化学计量比为1:1，这表明失去了一个相互作用位点。阿昔洛韦与非硫酸化两亲性环糊精之间的非共价相互作用似乎发生在环糊精的腔内以及由烷酰基链产生的疏水区域内。相比之下，在硫酸化两亲性环糊精的情况下，相互作用似乎仅涉及烷酰基链的疏水区域。
