Design, Synthesis and Biological Evaluation of Jahanyne Analogs as Cell Cycle Arrest Inducers
Jahanyne, a lipopeptide with a unique terminal alkynyl and OEP (2-(1-oxo-ethyl)-pyrrolidine) moiety, exhibits anticancer activity. We synthesized jahanyne and analogs modified at the OEP moiety, employing an α-fluoromethyl ketone (FMK) strategy. Preliminary bioassays indicated that compound...
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| Format: | Article |
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MDPI AG
2020-03-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/18/3/176 |
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| author | Baijun Ye Jianmiao Gong Qiuying Li Shiqi Bao Xuemei Zhang Jing Chen Qing Meng Bolin Chen Peng Jiang Liang Wang Yue Chen |
| author_facet | Baijun Ye Jianmiao Gong Qiuying Li Shiqi Bao Xuemei Zhang Jing Chen Qing Meng Bolin Chen Peng Jiang Liang Wang Yue Chen |
| author_sort | Baijun Ye |
| collection | DOAJ |
| description | Jahanyne, a lipopeptide with a unique terminal alkynyl and OEP (2-(1-oxo-ethyl)-pyrrolidine) moiety, exhibits anticancer activity. We synthesized jahanyne and analogs modified at the OEP moiety, employing an α-fluoromethyl ketone (FMK) strategy. Preliminary bioassays indicated that compound <b>1b</b> (FMK−jahanyne) exhibited decreased activities to varying degrees against most of the cancer cells tested, whereas the introduction of a fluorine atom to the α-position of a hydroxyl group (<b>2b</b>) enhanced activities against all lung cancer cells. Moreover, jahanyne and <b>2b</b> could induce G0/G1 cell cycle arrest in a concentration-dependent manner. |
| first_indexed | 2024-04-11T18:43:17Z |
| format | Article |
| id | doaj.art-b8653d6b56404efeabfb8c48b69cec25 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T18:43:17Z |
| publishDate | 2020-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-b8653d6b56404efeabfb8c48b69cec252022-12-22T04:08:54ZengMDPI AGMarine Drugs1660-33972020-03-0118317610.3390/md18030176md18030176Design, Synthesis and Biological Evaluation of Jahanyne Analogs as Cell Cycle Arrest InducersBaijun Ye0Jianmiao Gong1Qiuying Li2Shiqi Bao3Xuemei Zhang4Jing Chen5Qing Meng6Bolin Chen7Peng Jiang8Liang Wang9Yue Chen10The State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300350, ChinaAccendatech Co., Ltd., Tianjin 300384, ChinaAccendatech Co., Ltd., Tianjin 300384, ChinaAccendatech Co., Ltd., Tianjin 300384, ChinaAccendatech Co., Ltd., Tianjin 300384, ChinaAccendatech Co., Ltd., Tianjin 300384, ChinaThe State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300350, ChinaThe State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300350, ChinaThe State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300350, ChinaThe State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300350, ChinaThe State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300350, ChinaJahanyne, a lipopeptide with a unique terminal alkynyl and OEP (2-(1-oxo-ethyl)-pyrrolidine) moiety, exhibits anticancer activity. We synthesized jahanyne and analogs modified at the OEP moiety, employing an α-fluoromethyl ketone (FMK) strategy. Preliminary bioassays indicated that compound <b>1b</b> (FMK−jahanyne) exhibited decreased activities to varying degrees against most of the cancer cells tested, whereas the introduction of a fluorine atom to the α-position of a hydroxyl group (<b>2b</b>) enhanced activities against all lung cancer cells. Moreover, jahanyne and <b>2b</b> could induce G0/G1 cell cycle arrest in a concentration-dependent manner.https://www.mdpi.com/1660-3397/18/3/176jahanyneα-fluoromethyl ketonelipopeptideg0/g1 phase arrest |
| spellingShingle | Baijun Ye Jianmiao Gong Qiuying Li Shiqi Bao Xuemei Zhang Jing Chen Qing Meng Bolin Chen Peng Jiang Liang Wang Yue Chen Design, Synthesis and Biological Evaluation of Jahanyne Analogs as Cell Cycle Arrest Inducers Marine Drugs jahanyne α-fluoromethyl ketone lipopeptide g0/g1 phase arrest |
| title | Design, Synthesis and Biological Evaluation of Jahanyne Analogs as Cell Cycle Arrest Inducers |
| title_full | Design, Synthesis and Biological Evaluation of Jahanyne Analogs as Cell Cycle Arrest Inducers |
| title_fullStr | Design, Synthesis and Biological Evaluation of Jahanyne Analogs as Cell Cycle Arrest Inducers |
| title_full_unstemmed | Design, Synthesis and Biological Evaluation of Jahanyne Analogs as Cell Cycle Arrest Inducers |
| title_short | Design, Synthesis and Biological Evaluation of Jahanyne Analogs as Cell Cycle Arrest Inducers |
| title_sort | design synthesis and biological evaluation of jahanyne analogs as cell cycle arrest inducers |
| topic | jahanyne α-fluoromethyl ketone lipopeptide g0/g1 phase arrest |
| url | https://www.mdpi.com/1660-3397/18/3/176 |
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