Two Crystal Forms of a Hydrated 2:1 β-Cyclodextrin Fluconazole Complex: Single Crystal X-ray Structures, Dehydration Profiles, and Conditions for Their Individual Isolation
| dc.contributor.author | Sala, Andrea | |
| dc.contributor.author | Hoossen, Zakiena | |
| dc.contributor.author | Bacchi, Alessia | |
| dc.contributor.author | Caira, Mino R | |
| dc.date.accessioned | 2021-10-08T08:53:03Z | |
| dc.date.available | 2021-10-08T08:53:03Z | |
| dc.date.issued | 2021-07-22 | |
| dc.date.updated | 2021-08-06T15:19:24Z | |
| dc.description.abstract | Inclusion complexes between cyclodextrins (CDs) and active pharmaceutical ingredients (APIs) have potential for pharmaceutical formulation. Since crystallization of a given complex may result in the isolation of multiple crystal forms, it is essential to characterize these forms with respect to their structures and physicochemical properties to optimize pharmaceutical candidate selection. Here, we report the preparation and characterization of two crystallographically distinct hydrated forms of an inclusion complex between β-cyclodextrin (β-CD) and the antifungal API fluconazole (FLU) as well as temperature–concentration conditions required for their individual isolation. Determination of crystal water contents was achieved using thermoanalytical methods. X-ray analyses revealed distinct structural differences between the triclinic (TBCDFLU, space group P1) and monoclinic (MBCDFLU, space group C2) crystal forms. Removal of the crystals from their mother liquors led to rapid dehydration of the MBCDFLU crystal, while the TBCDFLU crystal was stable, a result that could be reconciled with the distinct packing arrangements in the respective crystals. This study highlights (a) the importance of identifying possible multiple forms of a cyclodextrin API complex and controlling the crystallization conditions, and (b) the need to characterize such crystal forms to determine the extent to which their physicochemical properties may differ. | en_US |
| dc.identifier | 10.3390/molecules26154427 | |
| dc.identifier.apacitation | Sala, A., Hoossen, Z., Bacchi, A., & Caira, M. R. (2021). Two Crystal Forms of a Hydrated 2:1 β-Cyclodextrin Fluconazole Complex: Single Crystal X-ray Structures, Dehydration Profiles, and Conditions for Their Individual Isolation. <i>Molecules</i>, 26(15), 4427. http://hdl.handle.net/11427/35039 | en_ZA |
| dc.identifier.chicagocitation | Sala, Andrea, Zakiena Hoossen, Alessia Bacchi, and Mino R Caira "Two Crystal Forms of a Hydrated 2:1 β-Cyclodextrin Fluconazole Complex: Single Crystal X-ray Structures, Dehydration Profiles, and Conditions for Their Individual Isolation." <i>Molecules</i> 26, 15. (2021): 4427. http://hdl.handle.net/11427/35039 | en_ZA |
| dc.identifier.citation | Sala, A., Hoossen, Z., Bacchi, A. & Caira, M.R. 2021. Two Crystal Forms of a Hydrated 2:1 β-Cyclodextrin Fluconazole Complex: Single Crystal X-ray Structures, Dehydration Profiles, and Conditions for Their Individual Isolation. <i>Molecules.</i> 26(15):4427. http://hdl.handle.net/11427/35039 | en_ZA |
| dc.identifier.ris | TY - Journal Article AU - Sala, Andrea AU - Hoossen, Zakiena AU - Bacchi, Alessia AU - Caira, Mino R AB - Inclusion complexes between cyclodextrins (CDs) and active pharmaceutical ingredients (APIs) have potential for pharmaceutical formulation. Since crystallization of a given complex may result in the isolation of multiple crystal forms, it is essential to characterize these forms with respect to their structures and physicochemical properties to optimize pharmaceutical candidate selection. Here, we report the preparation and characterization of two crystallographically distinct hydrated forms of an inclusion complex between β-cyclodextrin (β-CD) and the antifungal API fluconazole (FLU) as well as temperature–concentration conditions required for their individual isolation. Determination of crystal water contents was achieved using thermoanalytical methods. X-ray analyses revealed distinct structural differences between the triclinic (TBCDFLU, space group P1) and monoclinic (MBCDFLU, space group C2) crystal forms. Removal of the crystals from their mother liquors led to rapid dehydration of the MBCDFLU crystal, while the TBCDFLU crystal was stable, a result that could be reconciled with the distinct packing arrangements in the respective crystals. This study highlights (a) the importance of identifying possible multiple forms of a cyclodextrin API complex and controlling the crystallization conditions, and (b) the need to characterize such crystal forms to determine the extent to which their physicochemical properties may differ. DA - 2021-07-22 DB - OpenUCT DP - University of Cape Town IS - 15 J1 - Molecules LK - https://open.uct.ac.za PY - 2021 T1 - Two Crystal Forms of a Hydrated 2:1 β-Cyclodextrin Fluconazole Complex: Single Crystal X-ray Structures, Dehydration Profiles, and Conditions for Their Individual Isolation TI - Two Crystal Forms of a Hydrated 2:1 β-Cyclodextrin Fluconazole Complex: Single Crystal X-ray Structures, Dehydration Profiles, and Conditions for Their Individual Isolation UR - http://hdl.handle.net/11427/35039 ER - | en_ZA |
| dc.identifier.uri | http://hdl.handle.net/11427/35039 | |
| dc.identifier.vancouvercitation | Sala A, Hoossen Z, Bacchi A, Caira MR. Two Crystal Forms of a Hydrated 2:1 β-Cyclodextrin Fluconazole Complex: Single Crystal X-ray Structures, Dehydration Profiles, and Conditions for Their Individual Isolation. Molecules. 2021;26(15):4427. http://hdl.handle.net/11427/35039. | en_ZA |
| dc.language.iso | en | en_US |
| dc.publisher.department | Department of Chemistry | en_US |
| dc.publisher.faculty | Faculty of Science | en_US |
| dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | en_US |
| dc.source | Molecules | en_US |
| dc.source.journalissue | 15 | en_US |
| dc.source.journalvolume | 26 | en_US |
| dc.source.pagination | 4427 | en_US |
| dc.source.uri | https://www.mdpi.com/journal/molecules | |
| dc.title | Two Crystal Forms of a Hydrated 2:1 β-Cyclodextrin Fluconazole Complex: Single Crystal X-ray Structures, Dehydration Profiles, and Conditions for Their Individual Isolation | en_US |
| dc.type | Journal Article | en_US |