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Effect of chemical structure on complexation efficiency of aromatic drugs with cyclodextrins: The example of dibenzazepine derivatives.
Hemine, Koleta; Skwierawska, Anna; Kleist, Cyprian; Olewniczak, Michal; Szwarc-Karabyka, Katarzyna; Wyrzykowski, Dariusz; Mieszkowska, Anna; Chojnacki, Jaroslaw; Czub, Jacek; Nierzwicki, Lukasz.
Afiliación
  • Hemine K; Department of Chemistry and Technology of Functional Materials, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland.
  • Skwierawska A; Department of Chemistry and Technology of Functional Materials, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland. Electronic address: anna.skwierawska@pg.edu.pl.
  • Kleist C; Department of Physical Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland.
  • Olewniczak M; Department of Physical Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland.
  • Szwarc-Karabyka K; Nuclear Magnetic Resonance Laboratory, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland.
  • Wyrzykowski D; Department of General and Inorganic Chemistry, University of Gdansk, Wita Stwosza 63, 80-308 Gdansk, Poland.
  • Mieszkowska A; Department of Pharmaceutical Technology and Biochemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland.
  • Chojnacki J; Department of Inorganic Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland.
  • Czub J; Department of Physical Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland.
  • Nierzwicki L; Department of Physical Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland.
Carbohydr Polym ; 250: 116957, 2020 Dec 15.
Article en En | MEDLINE | ID: mdl-33049861
It is widely believed that the hydrophobic effect governs the binding of guest molecules to cyclodextrins (CDs). However, it is also known that high hydrophobicity of guest molecules does not always translate to the formation of stable inclusion complexes with CDs. Indeed, a plethora of other factors can play a role in the efficiency of guest-CD interactions, rendering structure-based prediction of the complexation efficiency with CDs a non trivial task. In this combined experimental and computational study, we examine the major structural factors governing complexation efficiency of polycyclic aromatic drug-like compounds with natural CDs, using as an example iminostilbene and its N-substituted derivatives. We find that purely hydrophobic IS derivatives show negligible complexation efficiency with CDs and only IS with hydrophilic substituents form stable inclusion complexes in water. We show that the balance between the guest solubility and its affinity to CDs is critical for the effective formation of inclusion complexes. Finally, our results demonstrate that guest-host hydrogen bonds facilitate the formation of crystalline inclusion complexes with CDs.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Hidrocarburos Policíclicos Aromáticos / Preparaciones Farmacéuticas / Ciclodextrinas / Dibenzazepinas Tipo de estudio: Prognostic_studies Idioma: En Revista: Carbohydr Polym Año: 2020 Tipo del documento: Article País de afiliación: Polonia Pais de publicación: Reino Unido
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Hidrocarburos Policíclicos Aromáticos / Preparaciones Farmacéuticas / Ciclodextrinas / Dibenzazepinas Tipo de estudio: Prognostic_studies Idioma: En Revista: Carbohydr Polym Año: 2020 Tipo del documento: Article País de afiliación: Polonia Pais de publicación: Reino Unido