Encapsulation of serotonin in β-cyclodextrin nano-cavities: Fluorescence spectroscopic and molecular modeling studies
Encapsulation of serotonin in β-cyclodextrin nano-cavities: Fluorescence spectroscopic and molecular modeling studies
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DOI：
10.1016/j.molstruc.2010.04.014
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发表时间：
2010-06-30
影响因子：
3.8
通讯作者：
Sengupta, Pradeep K.
中科院分区：
文献类型：
--
作者：
Chaudhuri, Sudip;Chakraborty, Sandipan;Sengupta, Pradeep K.
5-羟色胺是一种生理上重要的生物胺，缺乏5-羟色胺会导致精神障碍，如阿尔茨海默病、精神分裂症、幼儿自闭症和抑郁症。β-环糊精（β-CD）及其化学取代的合成品种（通常具有增强的水溶性和改善的药物络合能力）作为药物递送载体正在得到广泛的应用。在这里，我们已经研究了包封的5-羟色胺在β-CD和琥珀酰-2-羟丙基β-环糊精（SHP-β-CD），利用内在的5-羟色胺荧光。在环糊精的存在下观察到增强的荧光发射强度（其在β-CD和SHP β-CD中分别增加约18%和34%）和各向异性（r）（在β-CD和SHP β-CD中分别r = 0.075和0.1）。从荧光数据可以看出，主体-客体以1：1的化学计量相互作用是明显的，β-CD和SHP β-CD的缔合常数（K）分别为126.06 M-1和461.62 M-1。此外，分子对接和半经验的计算已经进行了提供，第一次，详细的见解有关的封装过程。特别是，很明显吲哚环插入β-CD空腔内，脂肪胺侧链向β-CD空腔的主要边缘突出。对接计算表明，氢键相互作用参与了包合物的形成。半经验计算表明，1：1包合物的形成是积极有利的，这是与荧光数据一致。(C)2010爱思唯尔有限公司版权所有。
Serotonin is a physiologically important biogenic amine, deficiency of which leads to mental disorders such as Alzheimer's disease, schizophrenia, infantile autism, and depression. Both beta-cyclodextrin (beta-CD) and its chemically substituted synthetic varieties (often possessing enhanced aqueous solubility and improved drug complexing abilities) are finding wide applications as drug delivery vehicles. Here we have studied the encapsulation of serotonin in beta-CD and succinyl-2-hydroxypropyl p-cyclodextrin (SHP-beta-CD) by exploiting the intrinsic serotonin fluorescence. Enhanced fluorescence emission intensity (which increases by similar to 18% and 34% in beta-CD and SHP beta-CD respectively) and anisotropy (r) (r = 0.075 and 0.1 in beta-CD and SHP beta-CD respectively) are observed in presence of the cyclodextrins. From the fluorescence data host-guest interaction with 1:1 stoichiometry is evident, the association constants (K) being 126.06 M-1 and 461.62 M-1 for beta-CD and SHP beta-CD respectively. Additionally, molecular docking and semiempirical calculations have been carried out which provide, for the first time, detailed insights regarding the encapsulation process. In particular, it is evident that the indole ring is inserted within the beta-CD cavity with the aliphatic amine side chain protruding towards the primary rim of the beta-CD cavity. Docking calculations reveal that hydrogen bonding interactions are involved in the formation of the inclusion complex. Semiempirical calculations indicate that formation of the 1:1 inclusion complex is energetically favorable which is consistent with the fluorescence data. (C) 2010 Elsevier B.V. All rights reserved.