Synthesis and cytotoxicity of apoptosis-inducing N-heterocyclic triterpene amides
The modification of lipophilic triterpenes to enhance their cytotoxicity, is a viable strategy for finding new anti-cancer agents. Herein we report the synthesis, analysis of 18 pentacyclic triterpenoic acid N-heterocyclic amides and their cytotoxicity, tumor cell/non-tumor cell selectivity, as well...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2022-12-01
|
| Series: | European Journal of Medicinal Chemistry Reports |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2772417422000577 |
| _version_ | 1811294629223464960 |
|---|---|
| author | Benjamin Brandes Sophie Hoenke Niclas Starke Immo Serbian Hans-Peter Deigner Ahmed Al-Harrasi René Csuk |
| author_facet | Benjamin Brandes Sophie Hoenke Niclas Starke Immo Serbian Hans-Peter Deigner Ahmed Al-Harrasi René Csuk |
| author_sort | Benjamin Brandes |
| collection | DOAJ |
| description | The modification of lipophilic triterpenes to enhance their cytotoxicity, is a viable strategy for finding new anti-cancer agents. Herein we report the synthesis, analysis of 18 pentacyclic triterpenoic acid N-heterocyclic amides and their cytotoxicity, tumor cell/non-tumor cell selectivity, as well as their putative mode of action. EC50 values were measured by SRB-assays, and found to be as low as 3.13 μM, with a selectivity as high as S = 5.05. Moreover, supportive assays were performed to further analyze their cytotoxicity; these experiments showed the compounds to act mainly by apoptosis. |
| first_indexed | 2024-04-13T05:20:17Z |
| format | Article |
| id | doaj.art-77a74539bd80436a8d1435c42ada84b6 |
| institution | Directory Open Access Journal |
| issn | 2772-4174 |
| language | English |
| last_indexed | 2024-04-13T05:20:17Z |
| publishDate | 2022-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | European Journal of Medicinal Chemistry Reports |
| spelling | doaj.art-77a74539bd80436a8d1435c42ada84b62022-12-22T03:00:46ZengElsevierEuropean Journal of Medicinal Chemistry Reports2772-41742022-12-016100085Synthesis and cytotoxicity of apoptosis-inducing N-heterocyclic triterpene amidesBenjamin Brandes0Sophie Hoenke1Niclas Starke2Immo Serbian3Hans-Peter Deigner4Ahmed Al-Harrasi5René Csuk6Martin-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), GermanyMartin-Luther University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120, Halle (Saale), GermanyFurtwangen University, Institute of Precision Medicine, Medical and Life Science Faculty, Jakob–Kienzle–Str. 17, D-78054, Villingen–Schwenningen, GermanyUniversity of Nizwa, Chair of Oman's Medicinal Plants and Marine Natural Products, P.O. Box 33, PC 616, Birkat Al-Mauz, Nizwa, Sultanate of OmanMartin-Luther University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120, Halle (Saale), Germany; Corresponding author.The modification of lipophilic triterpenes to enhance their cytotoxicity, is a viable strategy for finding new anti-cancer agents. Herein we report the synthesis, analysis of 18 pentacyclic triterpenoic acid N-heterocyclic amides and their cytotoxicity, tumor cell/non-tumor cell selectivity, as well as their putative mode of action. EC50 values were measured by SRB-assays, and found to be as low as 3.13 μM, with a selectivity as high as S = 5.05. Moreover, supportive assays were performed to further analyze their cytotoxicity; these experiments showed the compounds to act mainly by apoptosis.http://www.sciencedirect.com/science/article/pii/S2772417422000577Triterpenoic acidsCytotoxicityAmides |
| spellingShingle | Benjamin Brandes Sophie Hoenke Niclas Starke Immo Serbian Hans-Peter Deigner Ahmed Al-Harrasi René Csuk Synthesis and cytotoxicity of apoptosis-inducing N-heterocyclic triterpene amides European Journal of Medicinal Chemistry Reports Triterpenoic acids Cytotoxicity Amides |
| title | Synthesis and cytotoxicity of apoptosis-inducing N-heterocyclic triterpene amides |
| title_full | Synthesis and cytotoxicity of apoptosis-inducing N-heterocyclic triterpene amides |
| title_fullStr | Synthesis and cytotoxicity of apoptosis-inducing N-heterocyclic triterpene amides |
| title_full_unstemmed | Synthesis and cytotoxicity of apoptosis-inducing N-heterocyclic triterpene amides |
| title_short | Synthesis and cytotoxicity of apoptosis-inducing N-heterocyclic triterpene amides |
| title_sort | synthesis and cytotoxicity of apoptosis inducing n heterocyclic triterpene amides |
| topic | Triterpenoic acids Cytotoxicity Amides |
| url | http://www.sciencedirect.com/science/article/pii/S2772417422000577 |
| work_keys_str_mv | AT benjaminbrandes synthesisandcytotoxicityofapoptosisinducingnheterocyclictriterpeneamides AT sophiehoenke synthesisandcytotoxicityofapoptosisinducingnheterocyclictriterpeneamides AT niclasstarke synthesisandcytotoxicityofapoptosisinducingnheterocyclictriterpeneamides AT immoserbian synthesisandcytotoxicityofapoptosisinducingnheterocyclictriterpeneamides AT hanspeterdeigner synthesisandcytotoxicityofapoptosisinducingnheterocyclictriterpeneamides AT ahmedalharrasi synthesisandcytotoxicityofapoptosisinducingnheterocyclictriterpeneamides AT renecsuk synthesisandcytotoxicityofapoptosisinducingnheterocyclictriterpeneamides |