Project summary

The controlled release of bioactive compounds is a widely studied topic. Cyclodextrin derivatives capable of solubilizing in water lipophilic drugs by inclusion complexation1,2 are now produced in ton quantities. Nevertheless, the combination of inclusion complexation and covalent binding of bioactive compounds by a labile bond to cyclodextrin3 is a relatively new area of research. Such a combination brings advantages from both areas – it protects the active compound, increases its solubility by the inclusion complexation, and allows to control the speed of its release by choice of the covalent linker.

The Ph.D. project extends our recently published work on the controlled release of fragrant aldehydes bound by imine bonds to cyclodextrin4. In cooperation with prof. Fourmentin (Dunkerque, France), we plan to study further combinations of types of labile bonds (e.g., acyl hydrazone linkers) and single isomer cyclodextrin derivatives. The aim is to find the optimal combination of well-complexing and unequivocally defined CD units and the active compound's release speed.

A Ph.D. applicant is expected to be a skillful and independent synthetic chemist capable of performing syntheses of organic compounds under an inert atmosphere, separating the products using chromatography and other separation techniques, and characterizing the prepared compounds by NMR, MS, IR, and UV. Moreover, the ability to perform analytical kinetic measurements is welcome.

References

(1) Crini, G.; Fourmentin, S.; Fenyvesi, É.; Torri, G.; Fourmentin, M.; Morin-Crini, N. Cyclodextrins, from Molecules to Applications. Environmental Chemistry Letters 2018, 16 (4), 1361–1375. https://doi.org/10.1007/s10311-018-0763-2.

(2) Szejtli, J. Introduction and General Overview of Cyclodextrin Chemistry. Chemical Reviews 1998, 98 (5), 1743–1754. https://doi.org/10.1021/cr970022c.

(3) Chu, H. M.; Zhang, R. X.; Huang, Q.; Bai, C. C.; Wang, Z. Z. Chemical Conjugation with Cyclodextrins as a Versatile Tool for Drug Delivery. J Incl Phenom Macrocycl Chem 2017, 89 (1), 29–38. https://doi.org/10.1007/s10847-017-0743-3.

(4) Palágyi, A.; Jindřich, J.; Dian, J.; Fourmentin, S. Cyclodextrin-Based Schiff Base pro-Fragrances: Synthesis and Release Studies. Beilstein J. Org. Chem. 2022, 18 (1), 1346–1354. https://doi.org/10.3762/bjoc.18.140.


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