An improved partial synthesis of corosolic acid and its conversion to highly cytotoxic mitocans
Ursolic acid was used as a convenient starting material for a three-step partial synthesis of corosolic acid. Corosolic acid was acetylated, and an amide linker was attached followed by a rhodamine B unit at the distal end of the linker. Especially compounds holding a piperazinyl or homopiperazinyl...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2022-12-01
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| Series: | European Journal of Medicinal Chemistry Reports |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2772417422000450 |
| _version_ | 1811178181301895168 |
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| author | Niels V. Heise Sophie Hoenke Immo Serbian René Csuk |
| author_facet | Niels V. Heise Sophie Hoenke Immo Serbian René Csuk |
| author_sort | Niels V. Heise |
| collection | DOAJ |
| description | Ursolic acid was used as a convenient starting material for a three-step partial synthesis of corosolic acid. Corosolic acid was acetylated, and an amide linker was attached followed by a rhodamine B unit at the distal end of the linker. Especially compounds holding a piperazinyl or homopiperazinyl linker held exceptional cytotoxicity for several human tumor cell lines. For example, homopiperazinyl spacered 11 showed EC50 = 2 nM for A2780 cells combined with high tumor cell/non-tumor cell selectivity (compound 11: EC50 = 0.122 μM for non-malignant NIH 3T3). Thus, compound 11 currently represents one of the most cytotoxic triterpene derivatives holding both superior cytotoxicity combined with high selectivity (SI A2780 vs NIH 3T3 > 60). Staining experiments showed this compound to act as a mitocan. This makes 11 an interesting compound for further studies or as a lead substance. |
| first_indexed | 2024-04-11T06:14:07Z |
| format | Article |
| id | doaj.art-6d96264c0c43454d8fd484652daf758a |
| institution | Directory Open Access Journal |
| issn | 2772-4174 |
| language | English |
| last_indexed | 2024-04-11T06:14:07Z |
| publishDate | 2022-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | European Journal of Medicinal Chemistry Reports |
| spelling | doaj.art-6d96264c0c43454d8fd484652daf758a2022-12-22T04:41:06ZengElsevierEuropean Journal of Medicinal Chemistry Reports2772-41742022-12-016100073An improved partial synthesis of corosolic acid and its conversion to highly cytotoxic mitocansNiels V. Heise0Sophie Hoenke1Immo Serbian2René Csuk3Martin–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), 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), GermanyUrsolic acid was used as a convenient starting material for a three-step partial synthesis of corosolic acid. Corosolic acid was acetylated, and an amide linker was attached followed by a rhodamine B unit at the distal end of the linker. Especially compounds holding a piperazinyl or homopiperazinyl linker held exceptional cytotoxicity for several human tumor cell lines. For example, homopiperazinyl spacered 11 showed EC50 = 2 nM for A2780 cells combined with high tumor cell/non-tumor cell selectivity (compound 11: EC50 = 0.122 μM for non-malignant NIH 3T3). Thus, compound 11 currently represents one of the most cytotoxic triterpene derivatives holding both superior cytotoxicity combined with high selectivity (SI A2780 vs NIH 3T3 > 60). Staining experiments showed this compound to act as a mitocan. This makes 11 an interesting compound for further studies or as a lead substance.http://www.sciencedirect.com/science/article/pii/S2772417422000450TriterpenesCorosolic acidCytotoxicityMitocans |
| spellingShingle | Niels V. Heise Sophie Hoenke Immo Serbian René Csuk An improved partial synthesis of corosolic acid and its conversion to highly cytotoxic mitocans European Journal of Medicinal Chemistry Reports Triterpenes Corosolic acid Cytotoxicity Mitocans |
| title | An improved partial synthesis of corosolic acid and its conversion to highly cytotoxic mitocans |
| title_full | An improved partial synthesis of corosolic acid and its conversion to highly cytotoxic mitocans |
| title_fullStr | An improved partial synthesis of corosolic acid and its conversion to highly cytotoxic mitocans |
| title_full_unstemmed | An improved partial synthesis of corosolic acid and its conversion to highly cytotoxic mitocans |
| title_short | An improved partial synthesis of corosolic acid and its conversion to highly cytotoxic mitocans |
| title_sort | improved partial synthesis of corosolic acid and its conversion to highly cytotoxic mitocans |
| topic | Triterpenes Corosolic acid Cytotoxicity Mitocans |
| url | http://www.sciencedirect.com/science/article/pii/S2772417422000450 |
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