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Coumarin/β-Cyclodextrin Inclusion Complexes Promote Acceleration and Improvement of Wound Healing

2024; American Chemical Society; Volume: 16; Issue: 24 Linguagem: Inglês

10.1021/acsami.4c05069

1944-8252

Flávia Viana Avelar Dutra, Carla Santana Francisco, Bruna Carneiro Pires, Marcella Matos Cordeiro Borges, A. Torres, Vivian Alexandra Resende, Marcella Fernandes Mano Mateus, Daniel F. Cipriano, Flávio B. Miguez, Jair C. C. Freitas, Jéssika Poliana Teixeira, Warley de Souza Borges, Luciana Guimarães, Elaine F. F. da Cunha, Teodorico C. Ramalho, Clébio S. Nascimento, Frederico B. De Sousa, Raquel Alves Costa, Valdemar Lacerda, Keyller Bastos Borges,

Hydrogels: synthesis, properties, applications

Coumarins have great pharmacotherapeutic potential, presenting several biological and pharmaceutical applications, like antibiotic, fungicidal, anti-inflammatory, anticancer, anti-HIV, and healing activities, among others. These molecules are practically insoluble in water, and for biological applications, it became necessary to complex them with cyclodextrins (CDs), which influence their bioavailability in the target organism. In this work, we studied two coumarins, and it was possible to conclude that there were structural differences between 4,7-dimethyl-2H-chromen-2-one (DMC) and 7-methoxy-4-methyl-2H-chromen-2-one (MMC)/β-CD that were solubilized in ethanol, frozen, and lyophilized (FL) and the mechanical mixtures (MM). In addition, the inclusion complex formation improved the solubility of DMC and MMC in an aqueous medium. According to the data, the inclusion complexes were formed and are more stable at a molar ratio of 2:1 coumarin/β-CD, and hydrogen bonds along with π–π stacking interactions are responsible for the better stability, especially for (MMC)2@β-CD. In vivo wound healing studies in mice showed faster re-epithelialization and the best deposition of collagen with the (DMC)2@β-CD (FL) and (MMC)2@β-CD (FL) inclusion complexes, demonstrating clearly that they have potential in wound repair. Therefore, (DMC)2@β-CD (FL) deserves great attention because it presented excellent results, reducing the granulation tissue and mast cell density and improving collagen remodeling. Finally, the protein binding studies suggested that the anti-inflammatory activities might exert their biological function through the inhibition of MEK, providing the possibility of development of new MEK inhibitors.