Next Article in Journal
Modeling the Interaction of Dodecylphosphocholine Micelles with the Anticoccidial Peptide PW2 Guided by NMR Data
Previous Article in Journal
Volatile Aroma Compounds in Various Brewed Green Teas
Molecules 2013, 18(8), 10042-10055; doi:10.3390/molecules180810042
Communication

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

1,2,* , 1
, 2
, 3
, 4
, 4
 and 5
1 Faculty of Industrial Sciences & Technology, Universiti Malaysia Pahang, Lebuhraya Tun Razak 26300, Kuantan Pahang, Malaysia 2 Institute of Bioscience, Universiti Putra Malaysia, UPM Serdang 43400, Selangor Darul Ehsan, Malaysia 3 School of Biomedical Sciences, The University of Nottingham Malaysia Campus, Jalan Broga, Semenyih 43500, Selangor, Malaysia 4 Department of Chemistry, University of Malaya, Kuala Lumpur 50603, Malaysia 5 Faculty of Biotechnology and Bimolecular Sciences, Universiti Putra Malaysia, UPM Serdang 43400, Selangor Darul Ehsan, Malaysia
* Author to whom correspondence should be addressed.
Received: 22 May 2013 / Revised: 29 June 2013 / Accepted: 16 July 2013 / Published: 20 August 2013
(This article belongs to the Section Organic Synthesis)
Download PDF [317 KB, uploaded 18 June 2014]

Abstract

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.
Keywords: Anthraquinone; damnacanthal; nordamnacanthal; MCF-7; K-562; cytotoxic effects Anthraquinone; damnacanthal; nordamnacanthal; MCF-7; K-562; cytotoxic effects
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Export to BibTeX |
EndNote


MDPI and ACS Style

Akhtar, M.N.; Zareen, S.; Yeap, S.K.; Ho, W.Y.; Lo, K.M.; Hasan, A.; Alitheen, N.B. Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues. Molecules 2013, 18, 10042-10055.

View more citation formats

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert