Journal of Chemical Sciences ( IF 1.7 ) Pub Date : 2022-02-05 , DOI: 10.1007/s12039-021-02014-0 Abhinanda Chowdhury 1 , Prashant Chandra Singh 1
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Abstract
The conformational state and noncovalent interaction of protonated dopamine (p-dopamine) play an important role in its key and lock binding with its receptors. Hence, understanding of the role of weak noncovalent interactions in the stability of the higher order structures of the p-dopamine is desired. In this study, we have combined the spectroscopic and quantum chemical calculation studies to understand the role of noncovalent interactions in the stability of the dimers and trimers of p-dopamine in the aqueous medium. The intensity of the UV–Visible spectra of p-dopamine increases and shows a red shift with increasing concentrations suggesting the presence of the higher order structures of p-dopamine in the aqueous medium. The quantum chemical calculations and AIM studies of the different structures of its dimer and trimers suggest the presence of N–H3+…π, C–H…π, π…π weak interactions along with conventional N–H…O hydrogen bond. The calculated peak positions of the UV–Visible spectra of different clusters show that the higher order of clusters show red shifted peak position compared to the monomer and the red shifted peak is more evident in the clusters having noncovalent interactions.
Graphical abstract
Weak noncovalent interactions stabilise higher order clusters of protonated dopamine leading to red shift in the UV-visible spectra as shown by quantum chemical calculations.
中文翻译：
弱非共价相互作用在水溶液中聚集的质子化多巴胺稳定性中的作用：光谱和量子化学计算研究
摘要
质子化多巴胺（p-多巴胺）的构象状态和非共价相互作用在其与其受体的键和锁结合中起重要作用。因此，需要了解弱非共价相互作用在对多巴胺的高阶结构稳定性中的作用。在这项研究中，我们结合了光谱和量子化学计算研究，以了解非共价相互作用在水介质中对多巴胺二聚体和三聚体稳定性中的作用。对多巴胺的紫外-可见光谱的强度随着浓度的增加而增加并显示出红移，表明在水性介质中存在对多巴胺的高级结构。3 + … π, C–H … π, π … π 弱相互作用以及传统的 N–H … O 氢键。计算的不同簇的紫外-可见光谱的峰位置表明，与单体相比，较高阶的簇显示出红移峰位置，并且在具有非共价相互作用的簇中红移峰更明显。
图形概要
如量子化学计算所示，弱的非共价相互作用稳定了质子化多巴胺的高阶簇，导致紫外-可见光谱中的红移。
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