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Comparative study of monoterpenes complexation in cyclodextrins: preparation, physicochemical characterization, technological development and biological evaluation

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Author(s):
Gabriel Primini Feltran
Total Authors: 1
Document type: Master's Dissertation
Press: Campinas, SP.
Institution: Universidade Estadual de Campinas (UNICAMP). Instituto de Biologia
Defense date:
Examining board members:
Marcos José Salvador; Cristiane Yumi Koga Ito; Paulo César Pires Rosa
Advisor: Marcos José Salvador
Abstract

Monoterpenes are an important class of natural products with intense flavor and odor and can exhibit biological activity including antimicrobial activity, and applications in the pharmaceutical, cosmetic and food industry. However, monoterpenes are lipophilic and volatile substances which demonstrate some chemical instability. Cyclodextrins (CDs) are macrocyclic carriers capable of complexing a wide range of substances and increase their water solubility currently been the subject of research and development of new products for the pharmaceutical industry. In this project a comparative study was carried complexing four monoterpenes (citral, ?-myrcene, limonene and 1,8-cineole) in ?-cyclodextrin and hydroxypropyl-?-cyclodextrin, and biological evaluation of such monoterpenes, complexed or not. After these assessments was performed to develop a mouthwash containing the most promising monoterpene to combat dental biofilm. For physico-chemical characterization of the inclusion complex monoterpene-CD spectroscopic (UV-Vis), chromatographic (GC-MS) and calorimetric (DSC) were used to evaluate the solubility of the complex in water and percentage of inclusion of these monoterpenes in cyclodextrin. Antimicrobial activity screening for the monoterpenes was conducted across four strains of bacteria (Staphylococcus aureus ATCC 6538, Pseudomonas aeruginosa ATCC 27853, Escherichia coli ATCC 10538 and Streptococcus mutans ATCC 25175) and four strains of fungi (Candida albicans ATCC 10231, Candida dubliniensis ATCC 22019, Candida tropicalis ATCC 157 and Candida parapsilosis ATCC 22019). This evaluation was performed by determining the minimum inhibitory concentration (concentration that inhibited 50% of microbial growth, MIC) and Minimum Biocide Concentration (concentration that inhibited 100% microbial development, MBC). The monoterpene citral was more effective (MBC citral = 2.5?L/mL) against the strain of S. mutans (ATCC 25175). From these results the monoterpene citral was chosen to continue the studies in the proposed project. Were evaluated the effect of citral alone, complexed and incorporated into mouthwash formulations, to the growth and adherence of S. mutans (ATCC25175) on a solid surface. It was also assessed the cytotoxicity of citral and some mouthwash formulations afford low cytotoxicity against human keratinocytes (HaCat) cell culture. Both citral and citral complexed with CDs presented activity against the indicator strain of S. mutans (ATCC25175), preventing the formation of biofilms in vitro in the sub-inhibitory concentration (MBC/2 = 1.25?L/mL). When evaluating citral and their inclusion complexes embedded in mouthwash formulations, the in vitro antibacterial effect against S. mutans (ATCC 25175) was maintained and an increased solubility of the inclusion complex citral-HP?CD compared to monoterpene uncomplexed with CD (AU)

FAPESP's process: 13/08696-4 - Comparative study of monoterpenes complexation with cyclodextrins: preparation, chemical characterization, technological development and biological activity
Grantee:Gabriel Primini Feltran
Support Opportunities: Scholarships in Brazil - Master