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Molecular Medicine Reports
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Print ISSN: 1791-2997 Online ISSN: 1791-3004
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September-October 2011 Volume 4 Issue 5

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International Journal of Molecular Medicine

International Journal of Molecular Medicine

International Journal of Molecular Medicine is an international journal devoted to molecular mechanisms of human disease.

International Journal of Oncology

International Journal of Oncology

International Journal of Oncology is an international journal devoted to oncology research and cancer treatment.

Molecular Medicine Reports

Molecular Medicine Reports

Covers molecular medicine topics such as pharmacology, pathology, genetics, neuroscience, infectious diseases, molecular cardiology, and molecular surgery.

Oncology Reports

Oncology Reports

Oncology Reports is an international journal devoted to fundamental and applied research in Oncology.

Experimental and Therapeutic Medicine

Experimental and Therapeutic Medicine

Experimental and Therapeutic Medicine is an international journal devoted to laboratory and clinical medicine.

Oncology Letters

Oncology Letters

Oncology Letters is an international journal devoted to Experimental and Clinical Oncology.

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Explores a wide range of biological and medical fields, including pharmacology, genetics, microbiology, neuroscience, and molecular cardiology.

Molecular and Clinical Oncology

Molecular and Clinical Oncology

International journal addressing all aspects of oncology research, from tumorigenesis and oncogenes to chemotherapy and metastasis.

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Multidisciplinary open-access journal spanning biochemistry, genetics, neuroscience, environmental health, and synthetic biology.

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International Journal of Functional Nutrition

Open-access journal combining biochemistry, pharmacology, immunology, and genetics to advance health through functional nutrition.

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International Journal of Epigenetics

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Article 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 / Copyright

    Affiliations: Division of Cancer Prevention, Department of Medicine, Stony Brook University, Health Sciences Center T17-080, Stony Brook, NY 11794-8173, USA, Chem-Master International, Inc., Graduate Chemistry Building, Stony Brook University, Stony Brook, NY 11794-3400, USA, Department of Chemistry, Stony Brook University, Stony Brook, NY 11794-3400, USA
  • Pages: 891-899
    |
    Published online on: July 6, 2011
       https://doi.org/10.3892/mmr.2011.534
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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.

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Copy and paste a formatted citation
Spandidos Publications style
Joseph S, Nie T, Huang L, Zhou H, Atmakur K, Gupta RC, Johnson F and Rigas B: Structure-activity relationship study of novel anticancer aspirin-based compounds. Mol Med Rep 4: 891-899, 2011.
APA
Joseph, S., Nie, T., Huang, L., Zhou, H., Atmakur, K., Gupta, R.C. ... Rigas, B. (2011). Structure-activity relationship study of novel anticancer aspirin-based compounds. Molecular Medicine Reports, 4, 891-899. https://doi.org/10.3892/mmr.2011.534
MLA
Joseph, S., Nie, T., Huang, L., Zhou, H., Atmakur, K., Gupta, R. C., Johnson, F., Rigas, B."Structure-activity relationship study of novel anticancer aspirin-based compounds". Molecular Medicine Reports 4.5 (2011): 891-899.
Chicago
Joseph, S., Nie, T., Huang, L., Zhou, H., Atmakur, K., Gupta, R. C., Johnson, F., Rigas, B."Structure-activity relationship study of novel anticancer aspirin-based compounds". Molecular Medicine Reports 4, no. 5 (2011): 891-899. https://doi.org/10.3892/mmr.2011.534
Copy and paste a formatted citation
x
Spandidos Publications style
Joseph S, Nie T, Huang L, Zhou H, Atmakur K, Gupta RC, Johnson F and Rigas B: Structure-activity relationship study of novel anticancer aspirin-based compounds. Mol Med Rep 4: 891-899, 2011.
APA
Joseph, S., Nie, T., Huang, L., Zhou, H., Atmakur, K., Gupta, R.C. ... Rigas, B. (2011). Structure-activity relationship study of novel anticancer aspirin-based compounds. Molecular Medicine Reports, 4, 891-899. https://doi.org/10.3892/mmr.2011.534
MLA
Joseph, S., Nie, T., Huang, L., Zhou, H., Atmakur, K., Gupta, R. C., Johnson, F., Rigas, B."Structure-activity relationship study of novel anticancer aspirin-based compounds". Molecular Medicine Reports 4.5 (2011): 891-899.
Chicago
Joseph, S., Nie, T., Huang, L., Zhou, H., Atmakur, K., Gupta, R. C., Johnson, F., Rigas, B."Structure-activity relationship study of novel anticancer aspirin-based compounds". Molecular Medicine Reports 4, no. 5 (2011): 891-899. https://doi.org/10.3892/mmr.2011.534
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