Crystal Structures of New Ivermectin Pseudopolymorphs
New pseudopolymorphs of ivermectin (IVM), a potential anti-COVID-19 drug, were prepared. The crystal structure for three pseudopolymorphic crystalline forms of IVM has been determined using single-crystal X-ray crystallographic analysis. The molecular conformation of IVM in crystals has been compare...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-02-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/11/2/172 |
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| author | Kirill Shubin Agris Bērziņš Sergey Belyakov |
| author_facet | Kirill Shubin Agris Bērziņš Sergey Belyakov |
| author_sort | Kirill Shubin |
| collection | DOAJ |
| description | New pseudopolymorphs of ivermectin (IVM), a potential anti-COVID-19 drug, were prepared. The crystal structure for three pseudopolymorphic crystalline forms of IVM has been determined using single-crystal X-ray crystallographic analysis. The molecular conformation of IVM in crystals has been compared with the conformation of isolated molecules modeled by DFT calculations. In a solvent with relatively small molecules (ethanol), IVM forms monoclinic crystal structure (space group <i>I</i>2), which contains two types of voids. When crystallized from solvents with larger molecules, like γ-valerolactone (GVL) and methyl <i>tert-</i>butyl ether (MTBE), IVM forms orthorhombic crystal structure (space group <i>P</i>2<sub>1</sub>2<sub>1</sub>2<sub>1</sub>). Calculations of the lattice energy indicate that interactions between IVM and solvents play a minor role; the main contribution to energy is made by the interactions between the molecules of IVM itself, which form a framework in the crystal structure. Interactions between IVM and molecules of solvents were evaluated using Hirshfeld surface analysis. Thermal analysis of the new pseudopolymorphs of IVM was performed by differential scanning calorimetry and thermogravimetric analysis. |
| first_indexed | 2024-03-09T05:00:15Z |
| format | Article |
| id | doaj.art-928e63e528114324928c78a64d88efd4 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-09T05:00:15Z |
| publishDate | 2021-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-928e63e528114324928c78a64d88efd42023-12-03T13:01:14ZengMDPI AGCrystals2073-43522021-02-0111217210.3390/cryst11020172Crystal Structures of New Ivermectin PseudopolymorphsKirill Shubin0Agris Bērziņš1Sergey Belyakov2Latvian Institute of Organic Synthesis, 21 Aizkraukles St., LV-1006 Riga, LatviaFaculty of Chemistry, University of Latvia, 1 Jelgavas St., LV-1004 Riga, LatviaLatvian Institute of Organic Synthesis, 21 Aizkraukles St., LV-1006 Riga, LatviaNew pseudopolymorphs of ivermectin (IVM), a potential anti-COVID-19 drug, were prepared. The crystal structure for three pseudopolymorphic crystalline forms of IVM has been determined using single-crystal X-ray crystallographic analysis. The molecular conformation of IVM in crystals has been compared with the conformation of isolated molecules modeled by DFT calculations. In a solvent with relatively small molecules (ethanol), IVM forms monoclinic crystal structure (space group <i>I</i>2), which contains two types of voids. When crystallized from solvents with larger molecules, like γ-valerolactone (GVL) and methyl <i>tert-</i>butyl ether (MTBE), IVM forms orthorhombic crystal structure (space group <i>P</i>2<sub>1</sub>2<sub>1</sub>2<sub>1</sub>). Calculations of the lattice energy indicate that interactions between IVM and solvents play a minor role; the main contribution to energy is made by the interactions between the molecules of IVM itself, which form a framework in the crystal structure. Interactions between IVM and molecules of solvents were evaluated using Hirshfeld surface analysis. Thermal analysis of the new pseudopolymorphs of IVM was performed by differential scanning calorimetry and thermogravimetric analysis.https://www.mdpi.com/2073-4352/11/2/172ivermectinpseudopolymorphcrystal structure analysisHirshfeld surface analysis |
| spellingShingle | Kirill Shubin Agris Bērziņš Sergey Belyakov Crystal Structures of New Ivermectin Pseudopolymorphs Crystals ivermectin pseudopolymorph crystal structure analysis Hirshfeld surface analysis |
| title | Crystal Structures of New Ivermectin Pseudopolymorphs |
| title_full | Crystal Structures of New Ivermectin Pseudopolymorphs |
| title_fullStr | Crystal Structures of New Ivermectin Pseudopolymorphs |
| title_full_unstemmed | Crystal Structures of New Ivermectin Pseudopolymorphs |
| title_short | Crystal Structures of New Ivermectin Pseudopolymorphs |
| title_sort | crystal structures of new ivermectin pseudopolymorphs |
| topic | ivermectin pseudopolymorph crystal structure analysis Hirshfeld surface analysis |
| url | https://www.mdpi.com/2073-4352/11/2/172 |
| work_keys_str_mv | AT kirillshubin crystalstructuresofnewivermectinpseudopolymorphs AT agrisberzins crystalstructuresofnewivermectinpseudopolymorphs AT sergeybelyakov crystalstructuresofnewivermectinpseudopolymorphs |