Design and theoretical calculation of chitosan derivatives: Amphiphilic chitosan micelles loaded with Chinese fir essential oil

Ying Lu; Xiangzhou Li; Jun Zhou; Peng Zhou; Jiajia Lai; Yanhong Yang; Liqun Shen

doi:10.1016/j.ijbiomac.2025.139833

Design and theoretical calculation of chitosan derivatives: Amphiphilic chitosan micelles loaded with Chinese fir essential oil

Int J Biol Macromol. 2025 Jan 13:297:139833. doi: 10.1016/j.ijbiomac.2025.139833. Online ahead of print.

Authors

Ying Lu¹, Xiangzhou Li², Jun Zhou¹, Peng Zhou¹, Jiajia Lai¹, Yanhong Yang¹, Liqun Shen³

Affiliations

¹ College of Chemistry and Chemical Engineering, Central South University of Forestry and Technology, Hunan Province Key Laboratory of Materials Surface/Interface Science and Technology, Changsha 410004, Hunan, China.
² College of Chemistry and Chemical Engineering, Central South University of Forestry and Technology, Hunan Province Key Laboratory of Materials Surface/Interface Science and Technology, Changsha 410004, Hunan, China; Institute of Natural Products Research and Development, Central South University of Forestry and Technology, Changsha 410004, Hunan, China. Electronic address: RLXZ@163.com.
³ Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products, Guangxi Minzu University, Nanning 530006, Guangxi, China.

PMID: 39814307
DOI: 10.1016/j.ijbiomac.2025.139833

Abstract

The unique structure of chitosan-based micelles can be loaded with essential oil, so it is significant to study the modification of chitosan and the interactions between chitosan and essential oil, while molecular dynamics (MD) simulation and density functional theory (DFT) provide a solution. In this study, three kinds of amphiphilic chitosan derivatives (CSDs) were constructed by grafting of different hydrophilic and hydrophobic groups. Amphiphilic chitosan micelles loaded with Chinese fir essential oil (CFEO) were prepared by self-assembly. The aggregation behavior of CFEO component (cedrol and α-cedrene) in the solutions of chitosan and three CSDs were simulated using MD, and the mean square displacement was calculated. DFT analyzed the mechanism for regulating the molecular properties of CSDs by different modification methods, and explored the intensity and type of interaction force between cedrol/α-cedrene and three CSDs. The results show that cedrol and α-cedrene were more easily aggregated near the modified CSDs, with CS-g-PLA showing the strongest trapping ability. The grafting of polylactic acid on chitosan resulted in a significant decrease in HOMO-LUMO energy gap and an increase in reactivity activity. Widely distributed hydrogen bonding and van der Waals forces were confirmed to be the key to enhanced loading capacity.

Keywords: Density functional theory; Load mechanism; Modification; Molecular dynamics.