PhD Scientific Days 2025
Budapest, 7-9 July 2025
Poster Session II. - G: Pharmaceutical Sciences and Health Technologies
Efficient Synthesis of a Folic Acid-Modified Sulfobutylether-β-Cyclodextrin Derivative via Click Chemistry
Előadó neve
Herr Dominika Mária
Neptun code
XSW9RR
Előadó munkahelye
Semmelweis University Department of Pharmaceutical Chemistry and CycloLab Ltd
Előadó telefonszáma
+36306557707
Előadó e-mail címe
herr.dominika@phd.semmelweis.hu
Az előadás címe
Efficient Synthesis of a Folic Acid-Modified Sulfobutylether-β-Cyclodextrin Derivative via Click Chemistry
Szerző(k) neve és munkahelye
Dominika Mária Herr1, Róbert Iványi2, Erzsébet Varga2, György Tibor Balogh3
1: Semmelweis University Department of Pharmaceutical Chemistry and CycloLab Ltd
2: CycloLab Ltd.
3: Semmelweis University Department of Pharmaceutical Chemistry
Bemutatás módja
Poszter
Szekció
Poster Session II. - G: Pharmaceutical Sciences and Health Technologies
Language of the presentation
English
Preferred session
Pharmaceutical Sciences and Health Technologies
Összefoglaló szövege
Introduction:
Cyclodextrins (CDs) are widely used as drug delivery vehicles due to their biocompatibility and ability to form inclusion complexes. Sulfobutylether-β-cyclodextrin (SBECD) is a particularly promising derivative with improved aqueous solubility and safety profile. Targeting ligands, such as folic acid (FA), can be introduced to enhance cellular uptake in folate receptor-overexpressing tumors. However, the conjugation of FA onto CDs often requires multi-step procedures with limited yields or harsh reaction conditions.
Aims:
The aim of this study was to develop a straightforward and efficient method for the synthesis of a folic acid-modified SBECD derivative using copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC, “click” reaction), employing mono-azido-SBECD and a folic acid–propargylamine conjugate as starting materials.
Methods:
Mono-azido-SBECD was prepared using mono-tosyl-β-cyclodextrin and subsequent nucleophilic substitution with sodium azide. The alkyne-modified folic acid derivative was synthesized by coupling propargylamine (PA) to folic acid using DCC and basis in anhydrous reaction. After the isolation of the desired PA-FA isomer click reaction between the two components was carried out under mild, aqueous-compatible conditions using a copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) approach. The resulting conjugate was purified and structural characterization was performed by NMR spectroscopy and purity determination by HPLC.
Results:
The CuAAC reaction yielded the folic acid-functionalized SBECD derivative in good yield under mild conditions. NMR analysis confirmed the successful attachment of the folate moiety through the triazole linker. The product exhibited structural integrity, suggesting potential for further biological evaluation as a targeted drug delivery system.
Conclusion:
A novel folic acid–SBECD conjugate was successfully synthesized using a modular and efficient click chemistry approach. The method offers a reproducible and scalable route to targeted cyclodextrin-based carriers with potential application in tumor-selective drug delivery.
Funding:
Project no. 2023-2.1.2-KDP-2023-00016 has been implemented with the support provided by the Ministry of Culture and Innovation of Hungary from the National Research, Development and Innovation Fund, financed under the KDP-2023 funding scheme.
University
Semmelweis University
Supervisor
György Tibor Balogh
Publication of my abstract
I do not give consent to the publication of my abstract on the website of the congress.
phd.section.field
in doctoral studies before complex exam (PhD)
Kind
Szabad
Status
elfogadva
Accepted presentation method
poszter
Előadás fájl jóváhagyás
nem rendelkezett róla
Előadó
9129
Start
18:36
End
18:42