Comprehensive Characterisation of the Ketoprofen-β-Cyclodextrin Inclusion Complex Using X-ray Techniques and NMR Spectroscopy
Racemic ketoprofen (KP) and β-cyclodextrin (β-CD) powder samples from co-precipitation (<b>1</b>), evaporation (<b>2</b>), and heating-under-reflux (<b>3</b>) were analysed using X-ray techniques and nuclear magnetic resonance (NMR) spectroscopy. On the basis of N...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-07-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/26/13/4089 |
| _version_ | 1797527960368971776 |
|---|---|
| author | Katarzyna Betlejewska-Kielak Elżbieta Bednarek Armand Budzianowski Katarzyna Michalska Jan K. Maurin |
| author_facet | Katarzyna Betlejewska-Kielak Elżbieta Bednarek Armand Budzianowski Katarzyna Michalska Jan K. Maurin |
| author_sort | Katarzyna Betlejewska-Kielak |
| collection | DOAJ |
| description | Racemic ketoprofen (KP) and β-cyclodextrin (β-CD) powder samples from co-precipitation (<b>1</b>), evaporation (<b>2</b>), and heating-under-reflux (<b>3</b>) were analysed using X-ray techniques and nuclear magnetic resonance (NMR) spectroscopy. On the basis of NMR studies carried out in an aqueous solution, it was found that in the samples obtained by methods <b>1</b> and <b>2,</b> there were large excesses of β-CD in relation to KP, 10 and 75 times, respectively, while the sample obtained by method <b>3</b> contained equimolar amounts of β-CD and KP. NMR results indicated that KP/β-CD inclusion complexes were formed and the estimated binding constants were approximately 2400 M<sup>−1</sup>, showing that KP is quite strongly associated with β-CD. On the other hand, the X-ray single-crystal technique in the solid state revealed that the (<i>S</i>)-KP/β-CD inclusion complex with a stoichiometry of 2:2 was obtained as a result of heating-under-reflux, for which the crystal and molecular structure were examined. Among the methods used for the preparation of the KP/β-CD complex, only method <b>3</b> is suitable. |
| first_indexed | 2024-03-10T09:51:17Z |
| format | Article |
| id | doaj.art-e16da15e50374e17b32ce2ae9f330748 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T09:51:17Z |
| publishDate | 2021-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e16da15e50374e17b32ce2ae9f3307482023-11-22T02:47:58ZengMDPI AGMolecules1420-30492021-07-012613408910.3390/molecules26134089Comprehensive Characterisation of the Ketoprofen-β-Cyclodextrin Inclusion Complex Using X-ray Techniques and NMR SpectroscopyKatarzyna Betlejewska-Kielak0Elżbieta Bednarek1Armand Budzianowski2Katarzyna Michalska3Jan K. Maurin4Department of Synthetic Drugs, National Medicines Institute, Chełmska 30/34, 00-725 Warsaw, PolandFalsified Medicines and Medical Devices Department, National Medicines Institute, Chełmska 30/34, 00-725 Warsaw, PolandNational Centre for Nuclear Research, A. Sołtana 7, 05-400 Otwock, PolandDepartment of Synthetic Drugs, National Medicines Institute, Chełmska 30/34, 00-725 Warsaw, PolandFalsified Medicines and Medical Devices Department, National Medicines Institute, Chełmska 30/34, 00-725 Warsaw, PolandRacemic ketoprofen (KP) and β-cyclodextrin (β-CD) powder samples from co-precipitation (<b>1</b>), evaporation (<b>2</b>), and heating-under-reflux (<b>3</b>) were analysed using X-ray techniques and nuclear magnetic resonance (NMR) spectroscopy. On the basis of NMR studies carried out in an aqueous solution, it was found that in the samples obtained by methods <b>1</b> and <b>2,</b> there were large excesses of β-CD in relation to KP, 10 and 75 times, respectively, while the sample obtained by method <b>3</b> contained equimolar amounts of β-CD and KP. NMR results indicated that KP/β-CD inclusion complexes were formed and the estimated binding constants were approximately 2400 M<sup>−1</sup>, showing that KP is quite strongly associated with β-CD. On the other hand, the X-ray single-crystal technique in the solid state revealed that the (<i>S</i>)-KP/β-CD inclusion complex with a stoichiometry of 2:2 was obtained as a result of heating-under-reflux, for which the crystal and molecular structure were examined. Among the methods used for the preparation of the KP/β-CD complex, only method <b>3</b> is suitable.https://www.mdpi.com/1420-3049/26/13/4089KP/β-CD inclusion complexNMRXRPDcrystal and molecular structure |
| spellingShingle | Katarzyna Betlejewska-Kielak Elżbieta Bednarek Armand Budzianowski Katarzyna Michalska Jan K. Maurin Comprehensive Characterisation of the Ketoprofen-β-Cyclodextrin Inclusion Complex Using X-ray Techniques and NMR Spectroscopy Molecules KP/β-CD inclusion complex NMR XRPD crystal and molecular structure |
| title | Comprehensive Characterisation of the Ketoprofen-β-Cyclodextrin Inclusion Complex Using X-ray Techniques and NMR Spectroscopy |
| title_full | Comprehensive Characterisation of the Ketoprofen-β-Cyclodextrin Inclusion Complex Using X-ray Techniques and NMR Spectroscopy |
| title_fullStr | Comprehensive Characterisation of the Ketoprofen-β-Cyclodextrin Inclusion Complex Using X-ray Techniques and NMR Spectroscopy |
| title_full_unstemmed | Comprehensive Characterisation of the Ketoprofen-β-Cyclodextrin Inclusion Complex Using X-ray Techniques and NMR Spectroscopy |
| title_short | Comprehensive Characterisation of the Ketoprofen-β-Cyclodextrin Inclusion Complex Using X-ray Techniques and NMR Spectroscopy |
| title_sort | comprehensive characterisation of the ketoprofen β cyclodextrin inclusion complex using x ray techniques and nmr spectroscopy |
| topic | KP/β-CD inclusion complex NMR XRPD crystal and molecular structure |
| url | https://www.mdpi.com/1420-3049/26/13/4089 |
| work_keys_str_mv | AT katarzynabetlejewskakielak comprehensivecharacterisationoftheketoprofenbcyclodextrininclusioncomplexusingxraytechniquesandnmrspectroscopy AT elzbietabednarek comprehensivecharacterisationoftheketoprofenbcyclodextrininclusioncomplexusingxraytechniquesandnmrspectroscopy AT armandbudzianowski comprehensivecharacterisationoftheketoprofenbcyclodextrininclusioncomplexusingxraytechniquesandnmrspectroscopy AT katarzynamichalska comprehensivecharacterisationoftheketoprofenbcyclodextrininclusioncomplexusingxraytechniquesandnmrspectroscopy AT jankmaurin comprehensivecharacterisationoftheketoprofenbcyclodextrininclusioncomplexusingxraytechniquesandnmrspectroscopy |