Orientational effect of surface-confined cyclodextrin on the inclusion of bisphenols.
Orientational effect of surface-confined cyclodextrin on the inclusion of bisphenols.
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DOI：
10.1021/la048595p
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发表时间：
2005-01
期刊：
影响因子：
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通讯作者：
H. Endo;T. Nakaji-Hirabayashi;Shinta Morokoshi;Makoto Gemmei-Ide;H. Kitano
中科院分区：
文献类型：
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作者：
H. Endo;T. Nakaji-Hirabayashi;Shinta Morokoshi;Makoto Gemmei-Ide;H. Kitano
采用循环伏安法（CV）研究了巯基化β -环糊精（CD）自组装单层（SAM）在金电极上对多种双酚（bp）和双酚a-聚合物共轭物（BPA-polymer）的分子识别。基于bp对作为探针的对苯二酚（HQ）被表面约束的CD包合的抑制作用，估计了bp与固定化β -CD的结合常数K（assoc）。bp与3-二硫比（十一烷酰胺）-3-脱氧- β -环糊精（dtua - β - cd） SAM的K（assoc）值小于之前报道的游离β - cd体系。用6-（脂酰基酰胺）-6-脱氧- β -环糊精（lp - β - cd）代替dtua - β - cd时，也有类似的趋势。除双酚B外，lp - β - cd中除双酚B外的所有bp的K（assoc）值均大于dtua - β - cd的SAM，这是由于SAM中β - cd部分的取向不同所致。此外，利用局部表面等离子体共振光谱研究了双酚a-聚合物从表面受限的β - cd上的吸附和解吸过程。
The molecular recognition of various kinds of bisphenols (BPs) and a bisphenol A-polymer conjugate (BPA-polymer) by a self-assembled monolayer (SAM) of thiolated beta-cyclodextrin (CD) on a gold electrode was examined using cyclic voltammetry (CV). Based on the inhibitory effect of BPs on the inclusion of hydroquinone (HQ) as a probe by the surface-confined CD, the association constants (K(assoc)) of BPs with the immobilized beta-CD were estimated. The K(assoc) values for BPs with the SAM of 3-dithiobis(undecanoylamido)-3-deoxy-beta-cyclodextrin (DTUA-beta-CD) were smaller than those in the free beta-CD system reported previously. A similar tendency was obtained when 6-(lipoylamido)-6-deoxy-beta-cyclodextrin (LP-beta-CD) was used in place of DTUA-beta-CD. The K(assoc) values for all the BPs except for bisphenol B with the SAM of LP-beta-CD were always larger than those with the SAM of DTUA-beta-CD, due to a difference in the orientation of the beta-CD moiety in the SAMs. Furthermore, adsorption and desorption processes of the BPA-polymer from the surface-confined beta-CD was followed using local surface plasmon resonance spectroscopy.