Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues
Naturally occurring anthraquinones, damnacanthal (1) and nordamnacanthal (2) were synthesized with modified reaction steps and investigated for their cytotoxicity against the MCF-7 and K-562 cancer cell lines, respectively. Intermediate analogues 2-bromomethyl-1,3-dimethoxyanthraquinone (5, IC50 = 5...
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| Format: | Article |
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MDPI AG
2013-08-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/18/8/10042 |
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| author | Kong Mun Lo Aurangzeb Hasan Seema Zareen Wan Yong Ho Swee Keong Yeap Muhammad Nadeem Akhtar Noorjahan Banu Alitheen |
| author_facet | Kong Mun Lo Aurangzeb Hasan Seema Zareen Wan Yong Ho Swee Keong Yeap Muhammad Nadeem Akhtar Noorjahan Banu Alitheen |
| author_sort | Kong Mun Lo |
| collection | DOAJ |
| description | Naturally occurring anthraquinones, damnacanthal (1) and nordamnacanthal (2) were synthesized with modified reaction steps and investigated for their cytotoxicity against the MCF-7 and K-562 cancer cell lines, respectively. Intermediate analogues 2-bromomethyl-1,3-dimethoxyanthraquinone (5, IC50 = 5.70 ± 0.21 and 8.50 ± 1.18 mg/mL), 2-hydroxymethyl-1,3-dimethoxyanthraquinone (6, IC50 = 12.10 ± 0.14 and 14.00 ± 2.13), 2-formyl-1,3-dimethoxyantharquinone (7, IC50 = 13.10 ± 1.02 and 14.80 ± 0.74), 1,3-dimethoxy-2-methylanthraquinone (4, IC50 = 9.40 ± 3.51 and 28.40 ± 2.33), and 1,3-dihydroxy-2-methylanthraquinone (3, IC50 = 25.60 ± 0.42 and 28.40 ± 0.79) also exhibited moderate cytotoxicity against MCF-7 and K-562 cancer cell lines, respectively. Other structurally related compounds like 1,3-dihydroxyanthraquinone (13a, IC50 = 19.70 ± 0.35 and 14.50 ± 1.28), 1,3-dimethoxyanthraquinone (13b, IC50 = 6.50 ± 0.66 and 5.90 ± 0.95) were also showed good cytotoxicity. The target compound damnacanthal (1) was found to be the most cytotoxic against the MCF-7 and K-562 cancer cell lines, with IC50 values of 3.80 ± 0.57 and 5.50 ± 1.26, respectively. The structures of all compounds were elucidated with the help of detailed spectroscopic techniques. |
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| language | English |
| last_indexed | 2024-12-17T01:12:21Z |
| publishDate | 2013-08-01 |
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| series | Molecules |
| spelling | doaj.art-e3e1a4403c684d48a462094a4cc2611c2022-12-21T22:09:07ZengMDPI AGMolecules1420-30492013-08-01188100421005510.3390/molecules180810042Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone AnaloguesKong Mun LoAurangzeb HasanSeema ZareenWan Yong HoSwee Keong YeapMuhammad Nadeem AkhtarNoorjahan Banu AlitheenNaturally occurring anthraquinones, damnacanthal (1) and nordamnacanthal (2) were synthesized with modified reaction steps and investigated for their cytotoxicity against the MCF-7 and K-562 cancer cell lines, respectively. Intermediate analogues 2-bromomethyl-1,3-dimethoxyanthraquinone (5, IC50 = 5.70 ± 0.21 and 8.50 ± 1.18 mg/mL), 2-hydroxymethyl-1,3-dimethoxyanthraquinone (6, IC50 = 12.10 ± 0.14 and 14.00 ± 2.13), 2-formyl-1,3-dimethoxyantharquinone (7, IC50 = 13.10 ± 1.02 and 14.80 ± 0.74), 1,3-dimethoxy-2-methylanthraquinone (4, IC50 = 9.40 ± 3.51 and 28.40 ± 2.33), and 1,3-dihydroxy-2-methylanthraquinone (3, IC50 = 25.60 ± 0.42 and 28.40 ± 0.79) also exhibited moderate cytotoxicity against MCF-7 and K-562 cancer cell lines, respectively. Other structurally related compounds like 1,3-dihydroxyanthraquinone (13a, IC50 = 19.70 ± 0.35 and 14.50 ± 1.28), 1,3-dimethoxyanthraquinone (13b, IC50 = 6.50 ± 0.66 and 5.90 ± 0.95) were also showed good cytotoxicity. The target compound damnacanthal (1) was found to be the most cytotoxic against the MCF-7 and K-562 cancer cell lines, with IC50 values of 3.80 ± 0.57 and 5.50 ± 1.26, respectively. The structures of all compounds were elucidated with the help of detailed spectroscopic techniques.http://www.mdpi.com/1420-3049/18/8/10042AnthraquinonedamnacanthalnordamnacanthalMCF-7K-562cytotoxic effects |
| spellingShingle | Kong Mun Lo Aurangzeb Hasan Seema Zareen Wan Yong Ho Swee Keong Yeap Muhammad Nadeem Akhtar Noorjahan Banu Alitheen Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues Molecules Anthraquinone damnacanthal nordamnacanthal MCF-7 K-562 cytotoxic effects |
| title | Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues |
| title_full | Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues |
| title_fullStr | Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues |
| title_full_unstemmed | Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues |
| title_short | Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues |
| title_sort | total synthesis cytotoxic effects of damnacanthal nordamnacanthal and related anthraquinone analogues |
| topic | Anthraquinone damnacanthal nordamnacanthal MCF-7 K-562 cytotoxic effects |
| url | http://www.mdpi.com/1420-3049/18/8/10042 |
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