Please use this identifier to cite or link to this item: https://ir.swu.ac.th/jspui/handle/123456789/29568
Title: Stability improvement of UV-filter between methoxy cinnamic acid derivatives and cyclodextrins inclusion complexes based on DFT and TD-DFT investigations
Authors: Promkatkaew M.
Boonsri P.
Suramitr S.
Karpkird T.
Wolschann P.
Hannongbua S.
Keywords: Cyclodextrin
Density functional theory (DFT)
Methoxy cinnamic acid
Sunscreen
Time-dependent DFT (TD-DFT)
UV-filters
Issue Date: 2023
Publisher: Elsevier Inc.
Abstract: Structures and UV–vis absorption spectra of the host-guest interaction of the methoxy cinnamic acid (MCA) derivatives and cyclodextrins (CDs) were performed by using the density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations. All geometries of MCA derivatives (4-MCA, 245-MCA, 246-MCA), three types of CD (αCD, βCD, γCD), and five host-guest inclusion complexes between MCA and CD consisting of 4-MCA/αCD (1), 4-MCA/βCD (2), 245-MCA/βCD (3), 246-MCA/βCD (4), and 246-MCA/γCD (5) were fully optimized by using the M06-2X/6-31G (d,p) levels of theory. Two orientations (A and B) of the MCA guest molecule were considered. Upon examining the optimized geometry, five complexes of the methoxy cinnamic acid molecules are located inside the cavity of CD. Orientation B was more stable than orientation A because of the stronger intermolecular hydrogen bonds between the hydroxyl group of CD and the carboxylic group of MCA. The results indicated that the intermolecular hydrogen bond is mainly the driving force of formation between methoxy cinnamic acid and cyclodextrins. To reveal the host-guest interaction that is relevant to UV-filter compounds, the UV–vis absorption spectra were performed using TD-DFT calculations. The obtained results confirmed that orientation B is the most stable orientation and can absorb in both UVB and UVA regions which is similar to the parent MCA. Therefore, this knowledge will bring to understand the host-guest interaction between methoxy cinnamic acid and cyclodextrin complexes. The theoretical results are expected to provide valuable information for improving the stability of further UV-filter compounds. © 2023 Elsevier Inc.
URI: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85169584019&doi=10.1016%2fj.jmgm.2023.108619&partnerID=40&md5=d19f1669dcd60cf1f040c7aaa673ba08
https://ir.swu.ac.th/jspui/handle/123456789/29568
Appears in Collections:Scopus 2023

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