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...

Full description

Bibliographic Details
Main Authors:	Akhtar, Muhammad Nadeem, Seema, Zareen, Swee, Keong Yeap, Wan, Yong Ho, Kong, Mun Lo, Hasan, Aurangzeb, Noorjahan Banu, Alitheen
Format:	Article
Language:	English
Published:	MDPI - Open Access Publishing 2013
Subjects:	QD Chemistry
Online Access:	http://umpir.ump.edu.my/id/eprint/5262/ http://umpir.ump.edu.my/id/eprint/5262/ http://umpir.ump.edu.my/id/eprint/5262/ http://umpir.ump.edu.my/id/eprint/5262/1/FIST%2C_2013._Nadeem.pdf

id	ump-5262
recordtype	eprints
spelling	ump-52622018-04-18T04:14:08Z 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) http://dx.doi.org/10.3390/molecules180810042 DOI: 10.3390/molecules180810042
repository_type	Digital Repository
institution_category	Local University
institution	Universiti Malaysia Pahang
building	UMP Institutional Repository
collection	Online Access
language	English
topic	QD Chemistry
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
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.
format	Article
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
title	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_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_sort	total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues
publisher	MDPI - Open Access Publishing
publishDate	2013
url	http://umpir.ump.edu.my/id/eprint/5262/ http://umpir.ump.edu.my/id/eprint/5262/ http://umpir.ump.edu.my/id/eprint/5262/ http://umpir.ump.edu.my/id/eprint/5262/1/FIST%2C_2013._Nadeem.pdf
first_indexed	2023-09-18T22:00:30Z
last_indexed	2023-09-18T22:00:30Z
_version_	1777414366248828928

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

Similar Items