Open Access

Structure-activity relationship study of novel anticancer aspirin-based compounds

  • Authors: Stancy Joseph, Ting Nie, Liqun Huang, Hui Zhou, Krishnaiah Atmakur, Ramesh C. Gupta, Francis Johnson, Basil Rigas
  • View Affiliations

  • Published online on: Wednesday, July 6, 2011
  • Pages: 891-899
  • DOI: 10.3892/mmr.2011.534

Abstract

We performed a structure-activity relationship (SAR) study of a novel aspirin (ASA) derivative, which shows strong anticancer activity in vitro and in vivo. A series of ASA-based benzyl esters (ABEs) were synthesized and their inhibitory activity against human colon (HT-29 and SW480) and pancreatic (BxPC-3 and MIA PaCa-2) cancer cell lines was evaluated. The ABEs that we studied largely comprise organic benzyl esters bearing an ASA or acyloxy group (X) at the meta or para position of the benzyl ring and one of four different leaving groups. The nature of the salicyloyl/acyloxy function, the leaving group, and the additional substituents affecting the electron density of the benzyl ring, all were influential determinants of the inhibitory activity on cancer cell growth for each ABE. Positional isomerism also played a significant role in this effect. The mechanism of action of these compounds appears consistent with the notion that they generate either a quinone methide or an m-oxybenzyl zwitterion (or an m-hydroxybenzyl cation), which then reacts with a nucleophile, mediating their biological effect. Our SAR study provides an insight into the biological properties of this novel class of compounds and underscores their potential as anticancer agents.
Journal Cover

September 2011
Volume 4 Issue 5

Print ISSN: 1791-2997
Online ISSN:1791-3004

2012 Impact Factor: 1.17
Ranked #78/121 Medicine Research and Experimental
(total number of cites)

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APA
Joseph, S., Nie, T., Huang, L., Zhou, H., Atmakur, K., Gupta, R., Johnson, F., & Rigas, B. (2011). Structure-activity relationship study of novel anticancer aspirin-based compounds. Molecular Medicine Reports, 4(5), 891-899.
MLA
Joseph, Nie, Huang, Zhou, Atmakur, Gupta, Johnson, and Basil Rigas. "Structure-activity relationship study of novel anticancer aspirin-based compounds." Molecular Medicine Reports Molecular Medicine Reports 4.5 (2011): 891-899.
Chicago
Joseph, Nie, Huang, Zhou, Atmakur, Gupta, Johnson, and Basil Rigas. "Structure-activity relationship study of novel anticancer aspirin-based compounds." Molecular Medicine Reports Molecular Medicine Reports 4 no. 5 (2011): 891-899.