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...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI - Open Access Publishing
2013
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| Subjects: | |
| Online Access: | http://umpir.ump.edu.my/id/eprint/5262/1/FIST%2C_2013._Nadeem.pdf |
| _version_ | 1796989939329531904 |
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| author | Akhtar, Muhammad Nadeem Seema, Zareen Swee, Keong Yeap Wan, Yong Ho Kong, Mun Lo Hasan, Aurangzeb Noorjahan Banu, Alitheen |
| author_facet | Akhtar, Muhammad Nadeem Seema, Zareen Swee, Keong Yeap Wan, Yong Ho Kong, Mun Lo Hasan, Aurangzeb Noorjahan Banu, Alitheen |
| author_sort | Akhtar, Muhammad Nadeem |
| collection | UMP |
| 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 µg/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. |
| first_indexed | 2024-03-06T11:44:26Z |
| format | Article |
| id | UMPir5262 |
| institution | Universiti Malaysia Pahang |
| language | English |
| last_indexed | 2024-03-06T11:44:26Z |
| publishDate | 2013 |
| publisher | MDPI - Open Access Publishing |
| record_format | dspace |
| spelling | UMPir52622018-04-18T04:14:08Z http://umpir.ump.edu.my/id/eprint/5262/ Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues Akhtar, Muhammad Nadeem Seema, Zareen Swee, Keong Yeap Wan, Yong Ho Kong, Mun Lo Hasan, Aurangzeb Noorjahan Banu, Alitheen QD Chemistry 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 µg/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. MDPI - Open Access Publishing 2013-08-20 Article PeerReviewed application/pdf en http://umpir.ump.edu.my/id/eprint/5262/1/FIST%2C_2013._Nadeem.pdf Akhtar, Muhammad Nadeem and Seema, Zareen and Swee, Keong Yeap and Wan, Yong Ho and Kong, Mun Lo and Hasan, Aurangzeb and Noorjahan Banu, Alitheen (2013) Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues. Molecules, 18 (8). pp. 10042-10055. ISSN 1420-3049 (print); 1420-3049 (online). (Published) http://dx.doi.org/10.3390/molecules180810042 DOI: 10.3390/molecules180810042 |
| spellingShingle | QD Chemistry Akhtar, Muhammad Nadeem Seema, Zareen Swee, Keong Yeap Wan, Yong Ho Kong, Mun Lo Hasan, Aurangzeb Noorjahan Banu, Alitheen Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues |
| title | Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues
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| title_full | Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues
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| title_fullStr | Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues
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| title_full_unstemmed | Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues
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| title_short | Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues
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| title_sort | total synthesis cytotoxic effects of damnacanthal nordamnacanthal and related anthraquinone analogues |
| topic | QD Chemistry |
| url | http://umpir.ump.edu.my/id/eprint/5262/1/FIST%2C_2013._Nadeem.pdf |
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