Veignie Etienne, Rafin Catherine, Landy David, Fourmentin Sophie, Surpateanu Gheorghe
Laboratoire de Synthèse Organique et Environnement (EA2599), Université du Littoral Côte d'Opale, 59140 Dunkerque, France.
J Hazard Mater. 2009 Sep 15;168(2-3):1296-301. doi: 10.1016/j.jhazmat.2009.03.012. Epub 2009 Mar 14.
This paper investigates the effect of native beta-cyclodextrin (beta-CD) and its CD derivatives, such as hydroxypropyl-beta-cyclodextrin (HPBCD) and randomly methylated-beta-cyclodextrin (RAMEB), on the solubilization of a high molecular weight polycyclic aromatic hydrocarbon benzo[a]pyrene (BaP) and on its degradation by Fenton's reaction. The results show that BaP apparent solubility was significantly increased in the presence of cyclodextrin (CD) in the following order: beta-CD<RAMEB<HPCD. BaP Fenton degradation was strongly dependent on the capacity of cyclodextrin to solubilize BaP. In the presence of a radical scavenger (mannitol), BaP Fenton degradation was inhibited with RAMEB but not in the presence of HPCD. Molecular modelisation was used to visualize the steric complementarity of these host-guest systems. No significant difference of encapsulation between the two modified CDs was observed. Nevertheless, the results suggest a probable existence of a ternary complex HPCD-BaP-iron permitting the generation of hydroxyl radicals in close proximity to BaP. On the basis of these results, it appears that HPCD may be useful for developing targeted BaP degradation system.
本文研究了天然β-环糊精（β-CD）及其环糊精衍生物，如羟丙基-β-环糊精（HPBCD）和随机甲基化-β-环糊精（RAMEB），对高分子量多环芳烃苯并[a]芘（BaP）的增溶作用及其在芬顿反应中的降解情况。结果表明，在环糊精（CD）存在下，BaP的表观溶解度显著增加，顺序如下：β-CD < RAMEB < HPBCD。BaP的芬顿降解强烈依赖于环糊精增溶BaP的能力。在存在自由基清除剂（甘露醇）的情况下，RAMEB会抑制BaP的芬顿降解，但HPBCD存在时则不会。分子建模用于可视化这些主客体系统的空间互补性。未观察到两种改性环糊精之间的包封有显著差异。然而，结果表明可能存在三元复合物HPBCD-BaP-铁，从而允许在靠近BaP的位置产生羟基自由基。基于这些结果，看来HPBCD可能有助于开发靶向BaP降解系统。
