Design, synthesis, and biological evaluation of thiomatrine derivatives as potential anticancer agents
Abstract A series of new thiomatrine derivatives was designed and synthesized for their potential application as anticancer agents. The structure of these compounds was characterized by 1H-NMR, 13C-NMR, and ESI-MS spectral analyses. Single crystals of compound 3k were obtained by recrystallization a...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Li, Zheng [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2018 |
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| Schlagwörter: |
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| Anmerkung: |
© Springer Science+Business Media, LLC, part of Springer Nature 2018 |
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| Übergeordnetes Werk: |
Enthalten in: Medicinal chemistry research - Cambridge, Mass. [u.a.] : Birkhäuser Boston, 1991, 27(2018), 8 vom: 23. Juni, Seite 1941-1955 |
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| Übergeordnetes Werk: |
volume:27 ; year:2018 ; number:8 ; day:23 ; month:06 ; pages:1941-1955 |
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| DOI / URN: |
10.1007/s00044-018-2205-x |
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| Katalog-ID: |
SPR000417106 |
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| 520 | |a Abstract A series of new thiomatrine derivatives was designed and synthesized for their potential application as anticancer agents. The structure of these compounds was characterized by 1H-NMR, 13C-NMR, and ESI-MS spectral analyses. Single crystals of compound 3k were obtained by recrystallization and the structure was further confirmed by X-ray diffraction determination. All the target compounds were evaluated for their in vitro cytotoxicity against human cancer cell lines A549 and HepG2. Among these compounds, the derivative 3aa displayed the most significant anticancer activity against four cancer cell lines with $ IC_{50} $ values in range of 7.8–11.4 μM, indicating much better activity than the parent compound (matrine). The cell cycle analysis revealed that compound 3aa could cause cell cycle arrest of SMMC-7721 and CNE2 cells at G2/M phase. Furthermore, the Annexin V-FITC/PI dual staining assay revealed that compound 3aa could significantly induce the apoptosis of SMMC-7721 and CNE2 cells in a dose-dependent manner. Western blot analysis revealed that compound 3aa could induce apoptosis by activating caspase-3, increasing expression of cleaved caspase-3 and reducing the ratio of Bcl-2/Bax. | ||
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| 650 | 4 | |a Anticancer |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Cell cycle |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Apoptosis |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Crystal structure |7 (dpeaa)DE-He213 | |
| 700 | 1 | |a Wu, Lichuan |4 aut | |
| 700 | 1 | |a Cai, Bin |4 aut | |
| 700 | 1 | |a Luo, Mengyang |4 aut | |
| 700 | 1 | |a Huang, Mengtian |4 aut | |
| 700 | 1 | |a Ur Rashid, Haroon |4 aut | |
| 700 | 1 | |a Yang, Yuwen |4 aut | |
| 700 | 1 | |a Jiang, Jun |4 aut | |
| 700 | 1 | |a Wang, Lisheng |4 aut | |
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10.1007/s00044-018-2205-x doi (DE-627)SPR000417106 (SPR)s00044-018-2205-x-e DE-627 ger DE-627 rakwb eng Li, Zheng verfasserin aut Design, synthesis, and biological evaluation of thiomatrine derivatives as potential anticancer agents 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Springer Science+Business Media, LLC, part of Springer Nature 2018 Abstract A series of new thiomatrine derivatives was designed and synthesized for their potential application as anticancer agents. The structure of these compounds was characterized by 1H-NMR, 13C-NMR, and ESI-MS spectral analyses. Single crystals of compound 3k were obtained by recrystallization and the structure was further confirmed by X-ray diffraction determination. All the target compounds were evaluated for their in vitro cytotoxicity against human cancer cell lines A549 and HepG2. Among these compounds, the derivative 3aa displayed the most significant anticancer activity against four cancer cell lines with $ IC_{50} $ values in range of 7.8–11.4 μM, indicating much better activity than the parent compound (matrine). The cell cycle analysis revealed that compound 3aa could cause cell cycle arrest of SMMC-7721 and CNE2 cells at G2/M phase. Furthermore, the Annexin V-FITC/PI dual staining assay revealed that compound 3aa could significantly induce the apoptosis of SMMC-7721 and CNE2 cells in a dose-dependent manner. Western blot analysis revealed that compound 3aa could induce apoptosis by activating caspase-3, increasing expression of cleaved caspase-3 and reducing the ratio of Bcl-2/Bax. Thiomatrine derivatives (dpeaa)DE-He213 Anticancer (dpeaa)DE-He213 Cell cycle (dpeaa)DE-He213 Apoptosis (dpeaa)DE-He213 Crystal structure (dpeaa)DE-He213 Wu, Lichuan aut Cai, Bin aut Luo, Mengyang aut Huang, Mengtian aut Ur Rashid, Haroon aut Yang, Yuwen aut Jiang, Jun aut Wang, Lisheng aut Enthalten in Medicinal chemistry research Cambridge, Mass. [u.a.] : Birkhäuser Boston, 1991 27(2018), 8 vom: 23. Juni, Seite 1941-1955 (DE-627)490223427 (DE-600)2191978-1 1554-8120 nnns volume:27 year:2018 number:8 day:23 month:06 pages:1941-1955 https://dx.doi.org/10.1007/s00044-018-2205-x lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 27 2018 8 23 06 1941-1955 |
| spelling |
10.1007/s00044-018-2205-x doi (DE-627)SPR000417106 (SPR)s00044-018-2205-x-e DE-627 ger DE-627 rakwb eng Li, Zheng verfasserin aut Design, synthesis, and biological evaluation of thiomatrine derivatives as potential anticancer agents 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Springer Science+Business Media, LLC, part of Springer Nature 2018 Abstract A series of new thiomatrine derivatives was designed and synthesized for their potential application as anticancer agents. The structure of these compounds was characterized by 1H-NMR, 13C-NMR, and ESI-MS spectral analyses. Single crystals of compound 3k were obtained by recrystallization and the structure was further confirmed by X-ray diffraction determination. All the target compounds were evaluated for their in vitro cytotoxicity against human cancer cell lines A549 and HepG2. Among these compounds, the derivative 3aa displayed the most significant anticancer activity against four cancer cell lines with $ IC_{50} $ values in range of 7.8–11.4 μM, indicating much better activity than the parent compound (matrine). The cell cycle analysis revealed that compound 3aa could cause cell cycle arrest of SMMC-7721 and CNE2 cells at G2/M phase. Furthermore, the Annexin V-FITC/PI dual staining assay revealed that compound 3aa could significantly induce the apoptosis of SMMC-7721 and CNE2 cells in a dose-dependent manner. Western blot analysis revealed that compound 3aa could induce apoptosis by activating caspase-3, increasing expression of cleaved caspase-3 and reducing the ratio of Bcl-2/Bax. Thiomatrine derivatives (dpeaa)DE-He213 Anticancer (dpeaa)DE-He213 Cell cycle (dpeaa)DE-He213 Apoptosis (dpeaa)DE-He213 Crystal structure (dpeaa)DE-He213 Wu, Lichuan aut Cai, Bin aut Luo, Mengyang aut Huang, Mengtian aut Ur Rashid, Haroon aut Yang, Yuwen aut Jiang, Jun aut Wang, Lisheng aut Enthalten in Medicinal chemistry research Cambridge, Mass. [u.a.] : Birkhäuser Boston, 1991 27(2018), 8 vom: 23. Juni, Seite 1941-1955 (DE-627)490223427 (DE-600)2191978-1 1554-8120 nnns volume:27 year:2018 number:8 day:23 month:06 pages:1941-1955 https://dx.doi.org/10.1007/s00044-018-2205-x lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 27 2018 8 23 06 1941-1955 |
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10.1007/s00044-018-2205-x doi (DE-627)SPR000417106 (SPR)s00044-018-2205-x-e DE-627 ger DE-627 rakwb eng Li, Zheng verfasserin aut Design, synthesis, and biological evaluation of thiomatrine derivatives as potential anticancer agents 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Springer Science+Business Media, LLC, part of Springer Nature 2018 Abstract A series of new thiomatrine derivatives was designed and synthesized for their potential application as anticancer agents. The structure of these compounds was characterized by 1H-NMR, 13C-NMR, and ESI-MS spectral analyses. Single crystals of compound 3k were obtained by recrystallization and the structure was further confirmed by X-ray diffraction determination. All the target compounds were evaluated for their in vitro cytotoxicity against human cancer cell lines A549 and HepG2. Among these compounds, the derivative 3aa displayed the most significant anticancer activity against four cancer cell lines with $ IC_{50} $ values in range of 7.8–11.4 μM, indicating much better activity than the parent compound (matrine). The cell cycle analysis revealed that compound 3aa could cause cell cycle arrest of SMMC-7721 and CNE2 cells at G2/M phase. Furthermore, the Annexin V-FITC/PI dual staining assay revealed that compound 3aa could significantly induce the apoptosis of SMMC-7721 and CNE2 cells in a dose-dependent manner. Western blot analysis revealed that compound 3aa could induce apoptosis by activating caspase-3, increasing expression of cleaved caspase-3 and reducing the ratio of Bcl-2/Bax. Thiomatrine derivatives (dpeaa)DE-He213 Anticancer (dpeaa)DE-He213 Cell cycle (dpeaa)DE-He213 Apoptosis (dpeaa)DE-He213 Crystal structure (dpeaa)DE-He213 Wu, Lichuan aut Cai, Bin aut Luo, Mengyang aut Huang, Mengtian aut Ur Rashid, Haroon aut Yang, Yuwen aut Jiang, Jun aut Wang, Lisheng aut Enthalten in Medicinal chemistry research Cambridge, Mass. [u.a.] : Birkhäuser Boston, 1991 27(2018), 8 vom: 23. Juni, Seite 1941-1955 (DE-627)490223427 (DE-600)2191978-1 1554-8120 nnns volume:27 year:2018 number:8 day:23 month:06 pages:1941-1955 https://dx.doi.org/10.1007/s00044-018-2205-x lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 27 2018 8 23 06 1941-1955 |
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10.1007/s00044-018-2205-x doi (DE-627)SPR000417106 (SPR)s00044-018-2205-x-e DE-627 ger DE-627 rakwb eng Li, Zheng verfasserin aut Design, synthesis, and biological evaluation of thiomatrine derivatives as potential anticancer agents 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Springer Science+Business Media, LLC, part of Springer Nature 2018 Abstract A series of new thiomatrine derivatives was designed and synthesized for their potential application as anticancer agents. The structure of these compounds was characterized by 1H-NMR, 13C-NMR, and ESI-MS spectral analyses. Single crystals of compound 3k were obtained by recrystallization and the structure was further confirmed by X-ray diffraction determination. All the target compounds were evaluated for their in vitro cytotoxicity against human cancer cell lines A549 and HepG2. Among these compounds, the derivative 3aa displayed the most significant anticancer activity against four cancer cell lines with $ IC_{50} $ values in range of 7.8–11.4 μM, indicating much better activity than the parent compound (matrine). The cell cycle analysis revealed that compound 3aa could cause cell cycle arrest of SMMC-7721 and CNE2 cells at G2/M phase. Furthermore, the Annexin V-FITC/PI dual staining assay revealed that compound 3aa could significantly induce the apoptosis of SMMC-7721 and CNE2 cells in a dose-dependent manner. Western blot analysis revealed that compound 3aa could induce apoptosis by activating caspase-3, increasing expression of cleaved caspase-3 and reducing the ratio of Bcl-2/Bax. Thiomatrine derivatives (dpeaa)DE-He213 Anticancer (dpeaa)DE-He213 Cell cycle (dpeaa)DE-He213 Apoptosis (dpeaa)DE-He213 Crystal structure (dpeaa)DE-He213 Wu, Lichuan aut Cai, Bin aut Luo, Mengyang aut Huang, Mengtian aut Ur Rashid, Haroon aut Yang, Yuwen aut Jiang, Jun aut Wang, Lisheng aut Enthalten in Medicinal chemistry research Cambridge, Mass. [u.a.] : Birkhäuser Boston, 1991 27(2018), 8 vom: 23. Juni, Seite 1941-1955 (DE-627)490223427 (DE-600)2191978-1 1554-8120 nnns volume:27 year:2018 number:8 day:23 month:06 pages:1941-1955 https://dx.doi.org/10.1007/s00044-018-2205-x lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 27 2018 8 23 06 1941-1955 |
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10.1007/s00044-018-2205-x doi (DE-627)SPR000417106 (SPR)s00044-018-2205-x-e DE-627 ger DE-627 rakwb eng Li, Zheng verfasserin aut Design, synthesis, and biological evaluation of thiomatrine derivatives as potential anticancer agents 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Springer Science+Business Media, LLC, part of Springer Nature 2018 Abstract A series of new thiomatrine derivatives was designed and synthesized for their potential application as anticancer agents. The structure of these compounds was characterized by 1H-NMR, 13C-NMR, and ESI-MS spectral analyses. Single crystals of compound 3k were obtained by recrystallization and the structure was further confirmed by X-ray diffraction determination. All the target compounds were evaluated for their in vitro cytotoxicity against human cancer cell lines A549 and HepG2. Among these compounds, the derivative 3aa displayed the most significant anticancer activity against four cancer cell lines with $ IC_{50} $ values in range of 7.8–11.4 μM, indicating much better activity than the parent compound (matrine). The cell cycle analysis revealed that compound 3aa could cause cell cycle arrest of SMMC-7721 and CNE2 cells at G2/M phase. Furthermore, the Annexin V-FITC/PI dual staining assay revealed that compound 3aa could significantly induce the apoptosis of SMMC-7721 and CNE2 cells in a dose-dependent manner. Western blot analysis revealed that compound 3aa could induce apoptosis by activating caspase-3, increasing expression of cleaved caspase-3 and reducing the ratio of Bcl-2/Bax. Thiomatrine derivatives (dpeaa)DE-He213 Anticancer (dpeaa)DE-He213 Cell cycle (dpeaa)DE-He213 Apoptosis (dpeaa)DE-He213 Crystal structure (dpeaa)DE-He213 Wu, Lichuan aut Cai, Bin aut Luo, Mengyang aut Huang, Mengtian aut Ur Rashid, Haroon aut Yang, Yuwen aut Jiang, Jun aut Wang, Lisheng aut Enthalten in Medicinal chemistry research Cambridge, Mass. [u.a.] : Birkhäuser Boston, 1991 27(2018), 8 vom: 23. Juni, Seite 1941-1955 (DE-627)490223427 (DE-600)2191978-1 1554-8120 nnns volume:27 year:2018 number:8 day:23 month:06 pages:1941-1955 https://dx.doi.org/10.1007/s00044-018-2205-x lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 27 2018 8 23 06 1941-1955 |
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Enthalten in Medicinal chemistry research 27(2018), 8 vom: 23. Juni, Seite 1941-1955 volume:27 year:2018 number:8 day:23 month:06 pages:1941-1955 |
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Li, Zheng @@aut@@ Wu, Lichuan @@aut@@ Cai, Bin @@aut@@ Luo, Mengyang @@aut@@ Huang, Mengtian @@aut@@ Ur Rashid, Haroon @@aut@@ Yang, Yuwen @@aut@@ Jiang, Jun @@aut@@ Wang, Lisheng @@aut@@ |
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The structure of these compounds was characterized by 1H-NMR, 13C-NMR, and ESI-MS spectral analyses. Single crystals of compound 3k were obtained by recrystallization and the structure was further confirmed by X-ray diffraction determination. All the target compounds were evaluated for their in vitro cytotoxicity against human cancer cell lines A549 and HepG2. Among these compounds, the derivative 3aa displayed the most significant anticancer activity against four cancer cell lines with $ IC_{50} $ values in range of 7.8–11.4 μM, indicating much better activity than the parent compound (matrine). The cell cycle analysis revealed that compound 3aa could cause cell cycle arrest of SMMC-7721 and CNE2 cells at G2/M phase. Furthermore, the Annexin V-FITC/PI dual staining assay revealed that compound 3aa could significantly induce the apoptosis of SMMC-7721 and CNE2 cells in a dose-dependent manner. 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design, synthesis, and biological evaluation of thiomatrine derivatives as potential anticancer agents |
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Design, synthesis, and biological evaluation of thiomatrine derivatives as potential anticancer agents |
| abstract |
Abstract A series of new thiomatrine derivatives was designed and synthesized for their potential application as anticancer agents. The structure of these compounds was characterized by 1H-NMR, 13C-NMR, and ESI-MS spectral analyses. Single crystals of compound 3k were obtained by recrystallization and the structure was further confirmed by X-ray diffraction determination. All the target compounds were evaluated for their in vitro cytotoxicity against human cancer cell lines A549 and HepG2. Among these compounds, the derivative 3aa displayed the most significant anticancer activity against four cancer cell lines with $ IC_{50} $ values in range of 7.8–11.4 μM, indicating much better activity than the parent compound (matrine). The cell cycle analysis revealed that compound 3aa could cause cell cycle arrest of SMMC-7721 and CNE2 cells at G2/M phase. Furthermore, the Annexin V-FITC/PI dual staining assay revealed that compound 3aa could significantly induce the apoptosis of SMMC-7721 and CNE2 cells in a dose-dependent manner. Western blot analysis revealed that compound 3aa could induce apoptosis by activating caspase-3, increasing expression of cleaved caspase-3 and reducing the ratio of Bcl-2/Bax. © Springer Science+Business Media, LLC, part of Springer Nature 2018 |
| abstractGer |
Abstract A series of new thiomatrine derivatives was designed and synthesized for their potential application as anticancer agents. The structure of these compounds was characterized by 1H-NMR, 13C-NMR, and ESI-MS spectral analyses. Single crystals of compound 3k were obtained by recrystallization and the structure was further confirmed by X-ray diffraction determination. All the target compounds were evaluated for their in vitro cytotoxicity against human cancer cell lines A549 and HepG2. Among these compounds, the derivative 3aa displayed the most significant anticancer activity against four cancer cell lines with $ IC_{50} $ values in range of 7.8–11.4 μM, indicating much better activity than the parent compound (matrine). The cell cycle analysis revealed that compound 3aa could cause cell cycle arrest of SMMC-7721 and CNE2 cells at G2/M phase. Furthermore, the Annexin V-FITC/PI dual staining assay revealed that compound 3aa could significantly induce the apoptosis of SMMC-7721 and CNE2 cells in a dose-dependent manner. Western blot analysis revealed that compound 3aa could induce apoptosis by activating caspase-3, increasing expression of cleaved caspase-3 and reducing the ratio of Bcl-2/Bax. © Springer Science+Business Media, LLC, part of Springer Nature 2018 |
| abstract_unstemmed |
Abstract A series of new thiomatrine derivatives was designed and synthesized for their potential application as anticancer agents. The structure of these compounds was characterized by 1H-NMR, 13C-NMR, and ESI-MS spectral analyses. Single crystals of compound 3k were obtained by recrystallization and the structure was further confirmed by X-ray diffraction determination. All the target compounds were evaluated for their in vitro cytotoxicity against human cancer cell lines A549 and HepG2. Among these compounds, the derivative 3aa displayed the most significant anticancer activity against four cancer cell lines with $ IC_{50} $ values in range of 7.8–11.4 μM, indicating much better activity than the parent compound (matrine). The cell cycle analysis revealed that compound 3aa could cause cell cycle arrest of SMMC-7721 and CNE2 cells at G2/M phase. Furthermore, the Annexin V-FITC/PI dual staining assay revealed that compound 3aa could significantly induce the apoptosis of SMMC-7721 and CNE2 cells in a dose-dependent manner. Western blot analysis revealed that compound 3aa could induce apoptosis by activating caspase-3, increasing expression of cleaved caspase-3 and reducing the ratio of Bcl-2/Bax. © Springer Science+Business Media, LLC, part of Springer Nature 2018 |
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| title_short |
Design, synthesis, and biological evaluation of thiomatrine derivatives as potential anticancer agents |
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https://dx.doi.org/10.1007/s00044-018-2205-x |
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Wu, Lichuan Cai, Bin Luo, Mengyang Huang, Mengtian Ur Rashid, Haroon Yang, Yuwen Jiang, Jun Wang, Lisheng |
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Wu, Lichuan Cai, Bin Luo, Mengyang Huang, Mengtian Ur Rashid, Haroon Yang, Yuwen Jiang, Jun Wang, Lisheng |
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10.1007/s00044-018-2205-x |
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|
| score |
7.39935 |