X-ray crystal structure of cytotoxic oxidized cholesterols: 7-ketocholesterol and 25-hydroxycholesterol
The cytotoxic cholesterol derivative, 7-ketocholesterol, crystallizes in a monoclinic unit cell, space group P2(1) with a = 11.405 A, b = 6.288 A, c = 35.393 A and beta = 92.75 degrees (Z = 4). Its room temperature crystal structure was solved by direct methods, i.e., the minimal principle via the S...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
1997-05-01
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| Series: | Journal of Lipid Research |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S0022227520372254 |
| _version_ | 1818676245599092736 |
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| author | M P McCourt K Ashraf R Miller C M Weeks N Li W Pangborn D L Dorset |
| author_facet | M P McCourt K Ashraf R Miller C M Weeks N Li W Pangborn D L Dorset |
| author_sort | M P McCourt |
| collection | DOAJ |
| description | The cytotoxic cholesterol derivative, 7-ketocholesterol, crystallizes in a monoclinic unit cell, space group P2(1) with a = 11.405 A, b = 6.288 A, c = 35.393 A and beta = 92.75 degrees (Z = 4). Its room temperature crystal structure was solved by direct methods, i.e., the minimal principle via the Shake-and-Bake (SnB) algorithm. In contrast to the continuous chain pattern found for the cholesterol monohydrate structure, hydrogen bonding in the 7-ketocholesterol structure is localized to specific sites via one water molecule that forms linkages between two O3 hydroxyl groups and one keto oxygen. The final weighted R factor for 4562 reflections was 0.144. The 25-hydroxycholesterol also crystallizes in a monoclinic unit cell (P2(1)), with a = 10.840 A, b = 14.533 A, c = 16.093 A and beta = 95.91 degrees (Z = 4). The low temperature structure was solved by DIRDIF. In this instance, molecular packing is anti-parallel in layers stabilized by hydrogen bonding networks via both hydroxyl functions, differing both from cholesterol monohydrate and the 7-ketocholesterol. The final weighted R-factor for 6566 reflections was 0.034. Functional differences of the oxysterols therefore, may be expressed by observed variations in the molecular packing and geometry. |
| first_indexed | 2024-12-17T08:40:25Z |
| format | Article |
| id | doaj.art-da0816729b714252947ac1b3760a5531 |
| institution | Directory Open Access Journal |
| issn | 0022-2275 |
| language | English |
| last_indexed | 2024-12-17T08:40:25Z |
| publishDate | 1997-05-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Lipid Research |
| spelling | doaj.art-da0816729b714252947ac1b3760a55312022-12-21T21:56:21ZengElsevierJournal of Lipid Research0022-22751997-05-0138510141021X-ray crystal structure of cytotoxic oxidized cholesterols: 7-ketocholesterol and 25-hydroxycholesterolM P McCourt0K Ashraf1R Miller2C M Weeks3N Li4W Pangborn5D L Dorset6Electron Diffraction Department, Hauptman Woodward Medical Research Institute, USA.Electron Diffraction Department, Hauptman Woodward Medical Research Institute, USA.Electron Diffraction Department, Hauptman Woodward Medical Research Institute, USA.Electron Diffraction Department, Hauptman Woodward Medical Research Institute, USA.Electron Diffraction Department, Hauptman Woodward Medical Research Institute, USA.Electron Diffraction Department, Hauptman Woodward Medical Research Institute, USA.Electron Diffraction Department, Hauptman Woodward Medical Research Institute, USA.The cytotoxic cholesterol derivative, 7-ketocholesterol, crystallizes in a monoclinic unit cell, space group P2(1) with a = 11.405 A, b = 6.288 A, c = 35.393 A and beta = 92.75 degrees (Z = 4). Its room temperature crystal structure was solved by direct methods, i.e., the minimal principle via the Shake-and-Bake (SnB) algorithm. In contrast to the continuous chain pattern found for the cholesterol monohydrate structure, hydrogen bonding in the 7-ketocholesterol structure is localized to specific sites via one water molecule that forms linkages between two O3 hydroxyl groups and one keto oxygen. The final weighted R factor for 4562 reflections was 0.144. The 25-hydroxycholesterol also crystallizes in a monoclinic unit cell (P2(1)), with a = 10.840 A, b = 14.533 A, c = 16.093 A and beta = 95.91 degrees (Z = 4). The low temperature structure was solved by DIRDIF. In this instance, molecular packing is anti-parallel in layers stabilized by hydrogen bonding networks via both hydroxyl functions, differing both from cholesterol monohydrate and the 7-ketocholesterol. The final weighted R-factor for 6566 reflections was 0.034. Functional differences of the oxysterols therefore, may be expressed by observed variations in the molecular packing and geometry.http://www.sciencedirect.com/science/article/pii/S0022227520372254 |
| spellingShingle | M P McCourt K Ashraf R Miller C M Weeks N Li W Pangborn D L Dorset X-ray crystal structure of cytotoxic oxidized cholesterols: 7-ketocholesterol and 25-hydroxycholesterol Journal of Lipid Research |
| title | X-ray crystal structure of cytotoxic oxidized cholesterols: 7-ketocholesterol and 25-hydroxycholesterol |
| title_full | X-ray crystal structure of cytotoxic oxidized cholesterols: 7-ketocholesterol and 25-hydroxycholesterol |
| title_fullStr | X-ray crystal structure of cytotoxic oxidized cholesterols: 7-ketocholesterol and 25-hydroxycholesterol |
| title_full_unstemmed | X-ray crystal structure of cytotoxic oxidized cholesterols: 7-ketocholesterol and 25-hydroxycholesterol |
| title_short | X-ray crystal structure of cytotoxic oxidized cholesterols: 7-ketocholesterol and 25-hydroxycholesterol |
| title_sort | x ray crystal structure of cytotoxic oxidized cholesterols 7 ketocholesterol and 25 hydroxycholesterol |
| url | http://www.sciencedirect.com/science/article/pii/S0022227520372254 |
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