Structural diversity in the host–guest complexes of the antifolate pemetrexed with native cyclodextrins: gas phase, solution and solid state studies
| Autor: | Aneta Aniela Kowalska, Magdalena Ceborska, Barbara Repeć, Magdalena Zimnicka, Kajetan Dąbrowa |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
Stereochemistry
Supramolecular chemistry 02 engineering and technology 010402 general chemistry 01 natural sciences Full Research Paper supramolecular chemistry lcsh:QD241-441 Hydrophobic effect antifolate chemistry.chemical_compound symbols.namesake lcsh:Organic chemistry Molecule lcsh:Science inclusion complexes pemetrexed chemistry.chemical_classification Cyclodextrin Organic Chemistry hydrophobic interactions 021001 nanoscience & nanotechnology 0104 chemical sciences Crystallography Chemistry Monomer chemistry cyclodextrin symbols lcsh:Q Titration 0210 nano-technology Raman spectroscopy Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry, Vol 13, Iss 1, Pp 2252-2263 (2017) |
| ISSN: | 1860-5397 |
| Popis: | The complexation of the antifolate pemetrexed (PTX) with native cyclodextrins was studied. This process, along with the findings gathered for the structurally related folic acid was treated as a model for exploiting host–guest interactions of this class of guest molecules in the gas phase, in solution and in the solid state. Mass spectrometry was employed for the investigation of the architecture and relative gas-phase stabilities of these supramolecular complexes. The mode of complexation was further tracked by 1D and 2D NMR proving the formation of the exclusion-type complex with α-CD and pseudorotaxane inclusion-type complexes with β-, and γ-CDs. UV–vis titrations at pH 7.4 gave association constants for the obtained complexes. The stability of the complexes increases in the series: α-CD/PTX < γ-CD/PTX << β-CD/PTX. The association of PTX with a monomer cyclodextrin equivalent – methyl α-D-glucopyranoside – was investigated for a deeper understanding of the type of host–guest interactions. Solid state studies of PTX/CDs were performed using FTIR–ATR and Raman spectroscopy techniques. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|