Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues

Molecules

Muhammad Nadeem Akhtar¹  Seema Zareen¹  Swee Keong Yeap²  Wan Yong Ho³  Kong Mun Lo⁴  Aurangzeb Hasan⁴ 

[1] Faculty of Industrial Sciences & Technology, Universiti Malaysia Pahang, Lebuhraya Tun Razak 26300, Kuantan Pahang, Malaysia; E-Mail:;Institute of Bioscience, Universiti Putra Malaysia, UPM Serdang 43400, Selangor Darul Ehsan, Malaysia; E-Mail:;School of Biomedical Sciences, The University of Nottingham Malaysia Campus, Jalan Broga, Semenyih 43500, Selangor, Malaysia; E-Mail:;Department of Chemistry, University of Malaya, Kuala Lumpur 50603, Malaysia; E-Mails:

关键词: Anthraquinone;    damnacanthal;    nordamnacanthal;    MCF-7;    K-562;    cytotoxic effects;   

DOI  :  10.3390/molecules180810042

来源: mdpi

【 摘 要 】

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.

【 授权许可】

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