{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T19:50:53Z","timestamp":1792698653017,"version":"4.5.0"},"reference-count":43,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2023,1,12]],"date-time":"2023-01-12T00:00:00Z","timestamp":1673481600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Thammasat University Research Fund","award":["TUFT 42\/2565"],"award-info":[{"award-number":["TUFT 42\/2565"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>The complexation of \u03b2-cyclodextrin (\u03b2-CD) with cannabidiol (CBD) and \u03949-tetrahydrocannabinol (THC) was investigated using molecular docking and M062X\/6-31G(d,p) calculations. The calculations suggested two possible complex formations of 1:1 and 2:1 host-guest molecular ratio of \u03b2-CD with CBD and THC. The preferred orientation of all complexes in this study exhibited the hydrogen bonding between hydroxy-substituted benzene ring of CBD and THC with the \u03b2-CD\u2019s secondary hydroxy groups at the wide rim. The calculated complexation energies indicate that formation of the 2:1 complexes (\u221283.53 to \u2212135.36 kcal\/mol) was more energetically favorable and chemically stable than the 1:1 complexes (\u221230.00 to \u221234.92 kcal\/mol). However, the deformation energies of the host and the guest components in the 2:1 complexes (37.47\u201396.91 kcal\/mol) are much higher than those in the 1:1 complexes (3.49\u20138.69 kcal\/mol), which means the formation processes of the 2:1 complexes are more difficult due to the rigidity of the dimeric \u03b2-CDs. Therefore, the inclusion complexes of \u03b2-CD with CBD and THC are more likely to be in 1:1 host-guest ratio than in 2:1 molecular ratio. The results of this study supported the experimental results that the complexation constant of 1:1 \u03b2-CD\/CBD (Ks = 300 M\u22121) is greater than that of 2:1 \u03b2-CDs\/CBD (Kss = 0.833 M\u22121). Altogether, this study introduced the fitting parameters that could indicate the stability of the molecular fits in complex formation of each stoichiometry host-guest ratio, which are important for the assessment of the inclusion mechanisms as well as the relationships of reactants and products in chemical reactions.<\/jats:p>","DOI":"10.3390\/ijms24021525","type":"journal-article","created":{"date-parts":[[2023,1,13]],"date-time":"2023-01-13T01:30:26Z","timestamp":1673573426000},"page":"1525","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["Structural Investigation of Beta-Cyclodextrin Complexes with Cannabidiol and Delta-9-Tetrahydrocannabinol in 1:1 and 2:1 Host-Guest Stoichiometry: Molecular Docking and Density Functional Calculations"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3229-4456","authenticated-orcid":false,"given":"Nat","family":"Triamchaisri","sequence":"first","affiliation":[{"name":"School of Bio-Chemical Engineering and Technology, Sirindhorn International Institute of Technology, Thammasat University, Pathum Thani 12120, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pisanu","family":"Toochinda","sequence":"additional","affiliation":[{"name":"School of Bio-Chemical Engineering and Technology, Sirindhorn International Institute of Technology, Thammasat University, Pathum Thani 12120, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1104-2700","authenticated-orcid":false,"given":"Luckhana","family":"Lawtrakul","sequence":"additional","affiliation":[{"name":"School of Bio-Chemical Engineering and Technology, Sirindhorn International Institute of Technology, Thammasat University, Pathum Thani 12120, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,1,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Mlost, J., Bryk, M., and Starowicz, K. 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