Revisiting capsaicin and nonivamide: Their analogs exert strong inhibitory activity against cholinesterases
The scientific community has long been interested in capsaicin, and the extensive hunt for AChE and BChE enzyme inhibitors is still ongoing. In this investigation analogs of capsaicin, such as the pharmaceutical nonivamide, which is preferred in clinical settings for the topical treatment of pain, w...
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Elsevier
2024-12-01
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| Series: | European Journal of Medicinal Chemistry Reports |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2772417424000724 |
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| author | Niels V. Heise Jeremy Quast René Csuk |
| author_facet | Niels V. Heise Jeremy Quast René Csuk |
| author_sort | Niels V. Heise |
| collection | DOAJ |
| description | The scientific community has long been interested in capsaicin, and the extensive hunt for AChE and BChE enzyme inhibitors is still ongoing. In this investigation analogs of capsaicin, such as the pharmaceutical nonivamide, which is preferred in clinical settings for the topical treatment of pain, were explored in the search for appropriate inhibitors. Thus, to test their inhibitory effect on AChE and BChE, we synthesized a short series of derivatives derived from vanillylamide. Consequently, it was discovered that compounds 12, 34, and 35, which have Ki values in the sub-micromolar concentration range, are especially effective inhibitors. Compound 12 demonstrated dual mixed-type (competitive/uncompetitive) inhibitory activity for both enzymes; compound 34 showed selective mixed-type inhibitory activity for AChE, and compound 35 was found to have selective uncompetitive activity for AChE. |
| format | Article |
| id | doaj-art-4bf4932214da4f569189226fe2ecbab2 |
| institution | OA Journals |
| issn | 2772-4174 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | European Journal of Medicinal Chemistry Reports |
| spelling | doaj-art-4bf4932214da4f569189226fe2ecbab22025-08-20T02:30:42ZengElsevierEuropean Journal of Medicinal Chemistry Reports2772-41742024-12-011210020010.1016/j.ejmcr.2024.100200Revisiting capsaicin and nonivamide: Their analogs exert strong inhibitory activity against cholinesterasesNiels V. Heise0Jeremy Quast1René Csuk2Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120, Halle (Saale), GermanyMartin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120, Halle (Saale), GermanyCorresponding author.; Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120, Halle (Saale), GermanyThe scientific community has long been interested in capsaicin, and the extensive hunt for AChE and BChE enzyme inhibitors is still ongoing. In this investigation analogs of capsaicin, such as the pharmaceutical nonivamide, which is preferred in clinical settings for the topical treatment of pain, were explored in the search for appropriate inhibitors. Thus, to test their inhibitory effect on AChE and BChE, we synthesized a short series of derivatives derived from vanillylamide. Consequently, it was discovered that compounds 12, 34, and 35, which have Ki values in the sub-micromolar concentration range, are especially effective inhibitors. Compound 12 demonstrated dual mixed-type (competitive/uncompetitive) inhibitory activity for both enzymes; compound 34 showed selective mixed-type inhibitory activity for AChE, and compound 35 was found to have selective uncompetitive activity for AChE.http://www.sciencedirect.com/science/article/pii/S2772417424000724CapsaicinNonivamideCholinesteraseInhibitor |
| spellingShingle | Niels V. Heise Jeremy Quast René Csuk Revisiting capsaicin and nonivamide: Their analogs exert strong inhibitory activity against cholinesterases European Journal of Medicinal Chemistry Reports Capsaicin Nonivamide Cholinesterase Inhibitor |
| title | Revisiting capsaicin and nonivamide: Their analogs exert strong inhibitory activity against cholinesterases |
| title_full | Revisiting capsaicin and nonivamide: Their analogs exert strong inhibitory activity against cholinesterases |
| title_fullStr | Revisiting capsaicin and nonivamide: Their analogs exert strong inhibitory activity against cholinesterases |
| title_full_unstemmed | Revisiting capsaicin and nonivamide: Their analogs exert strong inhibitory activity against cholinesterases |
| title_short | Revisiting capsaicin and nonivamide: Their analogs exert strong inhibitory activity against cholinesterases |
| title_sort | revisiting capsaicin and nonivamide their analogs exert strong inhibitory activity against cholinesterases |
| topic | Capsaicin Nonivamide Cholinesterase Inhibitor |
| url | http://www.sciencedirect.com/science/article/pii/S2772417424000724 |
| work_keys_str_mv | AT nielsvheise revisitingcapsaicinandnonivamidetheiranalogsexertstronginhibitoryactivityagainstcholinesterases AT jeremyquast revisitingcapsaicinandnonivamidetheiranalogsexertstronginhibitoryactivityagainstcholinesterases AT renecsuk revisitingcapsaicinandnonivamidetheiranalogsexertstronginhibitoryactivityagainstcholinesterases |