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Synthesis, bioactivity evaluation, and docking study of 5-aminosalicylic acid’s fatty acid derivatives

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Abstract

Some new oleic acid, linoleic acid, lauric acid derivatives of 5-aminosalicylic acid were produced in order to enhance bioactivity properties of 5-aminosalicylic acid. All new compounds’ structures were confirmed by spectroscopic methods. Moreover, in vitro antibacterial, anticancer, and anti-inflammatory activities of new synthesized compounds were investigated. Antibacterial activity was studied against pathogenic Gram-negative bacteria, Escherichia coli and Gram-positive bacteria, Staphylococcus aureus via disc diffusion method. Additionally, all derivatives’ anti-inflammatory activity were evaluated through NO suppression assay using interferon gamma (IFN-γ)/lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Furthermore, in vitro cytotoxicity assay was probed using MTT test against 3T3 and HT-29 cell lines. In another effort, docking studies were performed to predict the possible interactions and binding energy of new compounds against cyclooxygenase (COX-1/COX-2) and lipoxygenase (5-LOX) proteins. In conclusion, all new compounds exhibited moderate to better bioactivity improvements in comparison with parent drug. Also study of interactions between the new derivatives with active sites of proteins presented greater binding affinities than 5-aminosalicylic acid.

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Acknowledgments

We are grateful for financial support of this work by ERGS (KPM) with Grant No. 5527054 and University of Putra Malaysia (UPM).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Universiti Putra Malaysia (UPM), 43400, Serdang, Selangor, Malaysia

    Samira Yousefi, Saadi Bayat, Mohd Basyaruddin Abdul Rahman, Intan Safinar Ismail & Emilia Abdulmalek

  2. Structural and Synthetic Biology Research Centre, Malaysia Genome Institute, 43600, Bangi, Selangor, Malaysia

    Mohd Basyaruddin Abdul Rahman

  3. Laboratory of Natural Products, Institute of Bioscience, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia

    Intan Safinar Ismail & Sze Wei Leong

  4. Department of Cell and Molecular Biology, Faculty of Biotechnology and Biomolecular Sciences, Serdang, Malaysia

    Elnaz Saki

Authors
  1. Samira Yousefi
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  2. Saadi Bayat
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  3. Mohd Basyaruddin Abdul Rahman
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  4. Intan Safinar Ismail
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  5. Elnaz Saki
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  7. Emilia Abdulmalek
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Correspondence to Samira Yousefi or Emilia Abdulmalek.

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Yousefi, S., Bayat, S., Rahman, M.B.A. et al. Synthesis, bioactivity evaluation, and docking study of 5-aminosalicylic acid’s fatty acid derivatives. Monatsh Chem 146, 2139–2149 (2015). https://doi.org/10.1007/s00706-015-1538-0

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  • DOI: https://doi.org/10.1007/s00706-015-1538-0

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