Kinetics and thermodynamics of β-cyclodextrin-NH2/β-carotene complexation: how much energy is required to include a hydrophobic group in the macrocycle cavity?

IF 2.3 4区 化学 Q2 Agricultural and Biological Sciences Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2024-05-03 DOI:10.1007/s10847-024-01240-6
Yara Luiza Coelho, Hauster Maximiler Campos de Paula, Lívia Neves Santa Rosa, Isabela Araujo Marques, Nícolas Glanzmann, Camilla Fonseca Silva, Adilson David da Silva, Clebio Soares Nascimento Jr., Ana Clarissa dos Santos Pires, Luis Henrique Mendes da Silva
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Abstract

To improve the efficiency of cyclodextrins as carotenoid carriers, the kinetics and thermodynamics of the inclusion complex formation between modified β-cyclodextrin (βCD-NH2) and β-carotene (βCT) were studied using surface plasmon resonance (SPR) at pH 7.4 and theoretical calculations. The observed dissociation rate of the [βCD-NH2/βCT]° inclusion complex is small \((2.59\times 1{0}^{-1} {\text{s}}^{-1}\)), indicating that βCD-NH2 only interacted with the βCT ionone group to form inclusion complex. The βCD-NH2/βCT binding constant is \(2.80\times 1{0}^{4} \text{L} {\text{m}\text{o}\text{l}}^{-1}\) (at 298.15 K), and its temperature dependence indicates that the [βCD-NH2/βCT]° formation is driven by hydrophobic interactions (\({\Delta }H^\circ = 28.83 \text{k}\text{J} \text{m}\text{o}{\text{l}}^{-1}\) and \(T{\Delta }S^\circ = 54.21 \text{k}\text{J} \text{m}\text{o}{\text{l}}^{-1}\)) caused mainly by the βCT end group desolvation. In contrast, the formation of the [βCD-NH2/βCT] activated complex via association between free molecules and dissociation of [βCD-NH2/βCT]° occurred with the overcoming of an energy barrier (\(E_{a}^{\ddag } = 40.77~{\text{kJ mol}}^{{ - 1}} ~\) and \({E}_{d}^{\ddag}=11.94 \text{k}\text{J} \text{m}\text{o}{\text{l}}^{-1}\)) and decrease in entropy (\(T{\varDelta S}_{a}^{\ddag}=-11.70 \text{k}\text{J} \text{m}\text{o}{\text{l}}^{-1}\) and \(T{\varDelta S}_{d}^{\ddag}=- 65.92 \text{k}\text{J} \text{m}\text{o}{\text{l}}^{-1}\)).

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β-环糊精-NH2/β-胡萝卜素复合物的动力学和热力学:在大环空腔中加入疏水基团需要多少能量?
为了提高环糊精作为类胡萝卜素载体的效率,我们利用表面等离子体共振(SPR)技术和理论计算研究了改性β-环糊精(βCD-NH2)和β-胡萝卜素(βCT)在 pH 值为 7.4 时形成包合物的动力学和热力学。观察到[βCD-NH2/βCT]°包合复合物的解离率很小((2.59/times 1{0}^{-1} {\text{s}}^{-1} )),表明βCD-NH2只与βCT的离子基相互作用形成包合复合物。βCD-NH2/βCT的结合常数为\(2.80\times 1{0}^{4} \text{L} {text{m}\text{o}\text{l}}^{-1}\) (298.15 K时),其温度依赖性表明[βCD-NH2/βCT]°的形成是由疏水相互作用驱动的(\({\Delta }H^\circ = 28.83 \text{k}\text{J} \text{m}\text{o}\{text{l}}^{-1}\) 和 (T{\Delta }S^\circ = 54.21 \text{k}\text{J} \text{m}\text{o}{text{l}}^{-1}\)) 主要由 βCT 端基脱溶引起。相反,[βCD-NH2/βCT]‡活化复合物的形成是通过自由分子之间的结合和[βCD-NH2/βCT]°的解离而发生的,并克服了能障(E_{a}^{\dag } = 40.77~{text{kJ mol}}^{ - 1}} ~\) and\({E}_{d}^{\ddag}=11.94 \text{k}\text{J} \text{m}\text{o}{\text{l}}^{-1}}\)) and decrease in entropy (\(T{varDelta S}_{a}^{\ddag}=-11.70 \text{k}\text{J})\和 ( T{varDelta S}_{d}^{ddag}=- 65.92 \text{k}\text{J}\text{m}\text{o}{\text{l}}^{-1}\)).
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来源期刊
CiteScore
3.30
自引率
8.70%
发文量
0
审稿时长
3-8 weeks
期刊介绍: The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites. The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.
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