Formation of ibrutinib solvates: so similar, yet so different
The transformation processes of non-solvated ibrutinib into a series of halogenated benzene solvates are explored in detail here. The transformation was studied in real time by X-ray powder diffraction in a glass capillary. Crystal structures of chlorobenzene, bromobenzene and iodobenzene solvates a...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2023-03-01
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| Series: | IUCrJ |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2052252523001197 |
| _version_ | 1811161181757374464 |
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| author | Jan Jirát Jan Rohlíček Jakub Kaminský Tomáš Jirkal Luděk Ridvan Eliška Skořepová Vít Zvoníček Michal Dušek Miroslav Šoóš |
| author_facet | Jan Jirát Jan Rohlíček Jakub Kaminský Tomáš Jirkal Luděk Ridvan Eliška Skořepová Vít Zvoníček Michal Dušek Miroslav Šoóš |
| author_sort | Jan Jirát |
| collection | DOAJ |
| description | The transformation processes of non-solvated ibrutinib into a series of halogenated benzene solvates are explored in detail here. The transformation was studied in real time by X-ray powder diffraction in a glass capillary. Crystal structures of chlorobenzene, bromobenzene and iodobenzene solvates are isostructural, whereas the structure of fluorobenzene solvate is different. Four different mechanisms for transformation were discovered despite the similarity in the chemical nature of the solvents and crystal structures of the solvates formed. These mechanisms include direct transformations and transformations with either a crystalline or an amorphous intermediate phase. The binding preference of each solvate in the crystal structure of the solvates was examined in competitive slurry experiments and further confirmed by interaction strength calculations. Overall, the presented system and online X-ray powder diffraction measurement provide unique insights into the formation of solvates. |
| first_indexed | 2024-04-10T06:10:15Z |
| format | Article |
| id | doaj.art-043c446e1ced43629bfa9c1f839c4b63 |
| institution | Directory Open Access Journal |
| issn | 2052-2525 |
| language | English |
| last_indexed | 2024-04-10T06:10:15Z |
| publishDate | 2023-03-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | IUCrJ |
| spelling | doaj.art-043c446e1ced43629bfa9c1f839c4b632023-03-02T16:45:21ZengInternational Union of CrystallographyIUCrJ2052-25252023-03-0110221021910.1107/S2052252523001197lq5049Formation of ibrutinib solvates: so similar, yet so differentJan Jirát0Jan Rohlíček1Jakub Kaminský2Tomáš Jirkal3Luděk Ridvan4Eliška Skořepová5Vít Zvoníček6Michal Dušek7Miroslav Šoóš8Chemical Engineering, University of Chemistry and Technology in Prague, Technická 3, Praha, Czech RepublicInstitute of Physics of the Czech Academy of Sciences, Na Slovance 2, Prague 8 182 00, Czech RepublicInstitute of Organic Chemistry and Biochemistry of the CAS, Flemingovo náměstí 542/2, Prague 6, Czech RepublicChemical Engineering, University of Chemistry and Technology in Prague, Technická 3, Praha, Czech RepublicZentiva, k.s., U kabelovny 130, Prague 10 10237, Czech RepublicChemical Engineering, University of Chemistry and Technology in Prague, Technická 3, Praha, Czech RepublicZentiva, k.s., U kabelovny 130, Prague 10 10237, Czech RepublicInstitute of Physics of the Czech Academy of Sciences, Na Slovance 2, Prague 8 182 00, Czech RepublicChemical Engineering, University of Chemistry and Technology in Prague, Technická 3, Praha, Czech RepublicThe transformation processes of non-solvated ibrutinib into a series of halogenated benzene solvates are explored in detail here. The transformation was studied in real time by X-ray powder diffraction in a glass capillary. Crystal structures of chlorobenzene, bromobenzene and iodobenzene solvates are isostructural, whereas the structure of fluorobenzene solvate is different. Four different mechanisms for transformation were discovered despite the similarity in the chemical nature of the solvents and crystal structures of the solvates formed. These mechanisms include direct transformations and transformations with either a crystalline or an amorphous intermediate phase. The binding preference of each solvate in the crystal structure of the solvates was examined in competitive slurry experiments and further confirmed by interaction strength calculations. Overall, the presented system and online X-ray powder diffraction measurement provide unique insights into the formation of solvates.http://scripts.iucr.org/cgi-bin/paper?S2052252523001197ibrutinibmulticomponent crystal solvatestransformation mechanisms |
| spellingShingle | Jan Jirát Jan Rohlíček Jakub Kaminský Tomáš Jirkal Luděk Ridvan Eliška Skořepová Vít Zvoníček Michal Dušek Miroslav Šoóš Formation of ibrutinib solvates: so similar, yet so different IUCrJ ibrutinib multicomponent crystal solvates transformation mechanisms |
| title | Formation of ibrutinib solvates: so similar, yet so different |
| title_full | Formation of ibrutinib solvates: so similar, yet so different |
| title_fullStr | Formation of ibrutinib solvates: so similar, yet so different |
| title_full_unstemmed | Formation of ibrutinib solvates: so similar, yet so different |
| title_short | Formation of ibrutinib solvates: so similar, yet so different |
| title_sort | formation of ibrutinib solvates so similar yet so different |
| topic | ibrutinib multicomponent crystal solvates transformation mechanisms |
| url | http://scripts.iucr.org/cgi-bin/paper?S2052252523001197 |
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