A combined physicochemical and computational investigation of the inclusion behaviour of 3-(1-Naphthyl)-D-alanine Hydrochloride insights into β-Cyclodextrin

• Published in: Journal of molecular liquids 2023-05, Vol.378, p.121583, Article 121583
• Main Authors: Mondal, Modhusudan, Basak, Shatarupa, Ghosh, Biswajit, Ali, Salim, Saha, Baishali, Mallick, Kangkan, Roy, Kanak, Nath Roy, Mahendra
• Format: Article
• Language: English
• Subjects: 3-(1-Naphthyl)-D-alanine Hydrochloride; DNA Binding; Inclusion Complex; Photostability; β-Cyclodextrin
• ISSN: 0167-7322
• DOI: 10.1016/j.molliq.2023.121583

[Display omitted] •The photo stabilised D-1NA@CD IC was exposed to have a 1:1 stoichiometry.•The complex characterised by NMR and FTIR spectroscopy.•The insertion behaviour of D-1NA into BCD is explored by Physicochemical and Docking studies.•The effect of BCD on D-1NA to DNA binding was explored.•The inclusion phenomena found to be thermodynamically favourable. In numerous biological activities, 3-(1-Naphthyl)-D-alanine Hydrochloride (D-1NA) serves as an essential metabolic precursor and amino acid receptor. Therefore, a sufficient supply of D-1NA is very much important. Here, we look into how D-1NA interacts with the hydrophobic cavity of β-cyclodextrin (BCD) to form the host–guest assembly. Analysis of experimental and theoretical findings demonstrates the creation of a stable IC, which is suggestive of the usefulness of BCD as a delivery method for D-1NA. The binding behaviour of this newly created 1:1 inclusion system of D-1NA with BCD has been examined by UV–visible spectroscopy and discovered that BCD showed a considerable affinity for D-1NA and the binding process was thermodynamically possible. Molecular docking analysis demonstrated the most reliable D-1NA binding orientation inside the BCD, as shown by Fourier transforms infrared and 1H-Nuclear magnetic resonance spectroscopic analyses. Studies using PXRD and SEM images also showed that inclusion complexes had formed. After complexing with BCD, D-1NA's photostability is increased. Additionally, it was described how the produced IC is bound to the Deoxyribonucleic acid (DNA) of the calf thymus (CT).