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Antibacterial, Antioxidant and Raw 264.7 Cell Line Proliferative Effect of 5-[(4-Nitro-Benzylidene)-Amino]-2H-Pyrazol-3-ol

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Chemistry for a Clean and Healthy Planet (ICPAC 2018)

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Abstract

Pyrazole derivatives are considered important scaffold that possesses cocktails of pharmacological activities. However, no study has assessed their effects on the proliferation of macrophages. In this study, 4-nitrophenyl derivative containing the 1H-pyrazol-3-ol moiety HL1 was synthesised, characterised and assessed for antibacterial as well as cell proliferative effects. HL1 was characterised using an elemental analyser, TGA, XRD, and various spectrophotometric methods. The antibacterial effect of HL1 on three Gram-positive bacterial strains: Enterococcus faecalis, Staphylococcus aureus and Staphylococcus epidermidis and three Gram-negative bacterial strains: Klebsiella pneumoniae, Escherichia coli, and Pseudomonas aeruginosa were determined using the minimal inhibition assays. The RAW 264.7 macrophage cell line was used to assess the effect of HL1 on mitochondrial activity using the CellTiter® Blue Cell Viability Assay. The thermogram and diffractogram plots registered thermal stability slightly above the melting point of HL1 and a crystal size of 13.01 nm, respectively. The characterisation studies indicated the presence of azomethine moiety at 1701.65 cm−1, \(\delta_{H}\) 9.13 and \(\delta_{C}\) 156.85 ppm in the FT-IR, 1H, and 13C NMR spectra, respectively. The synthesised pyrazole moiety exhibited significant antioxidant activity (IC50 ≤ 0.41 ± 0.02 µM) compared to gallic and ascorbic acid (IC50 ≤ 0.58 ± 0.01 µM) and preserved pharmacological integrity at high temperature but was found not to have any antibacterial effects. The effect of HL1 on the Raw 264.7 cell line intimated a significant increase in the mitochondrial function of the macrophage cells (12.5 μg/ml [127 ± 3%; P < 0.0007] vs. control) indicating an increase in cell proliferation.

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Acknowledgements

Our appreciation goes to the Institute of Chemical and Biotechnology, Vaal University of Technology, South Africa, for supporting the research.

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Authors and Affiliations

  1. Institute of Chemical and Biotechnology, Vaal University of Technology, Science Park, Private Bag X021, Vanderbijlpark, South Africa

    Bamidele J. Okoli, Cornelius Cano Ssemakalu & Johannes Sekomeng Modise

  2. Department of Biotechnology, Vaal University of Technology, Science Park, Private Bag X021, Vanderbijlpark, South Africa

    Unisa Terblanche & Michael Pillay

  3. Department of Chemistry, Faculty of Applied and Computer Sciences, Vaal University of Technology, Science Park, Private Bag X021, Vanderbijlpark, South Africa

    Fanyana M. Mtunzi

Authors
  1. Bamidele J. Okoli
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  2. Unisa Terblanche
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  4. Fanyana M. Mtunzi
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  5. Michael Pillay
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  6. Johannes Sekomeng Modise
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Corresponding author

Correspondence to Bamidele J. Okoli .

Editor information

Editors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Mauritius, Reduit, Mauritius

    Ponnadurai Ramasami

  2. Dept of Chemistry, Faculty of Scien, University of Mauritius, Reduit, Mauritius

    Minu Gupta Bhowon

  3. Dept. of Chemistry, Faculty of Scie, University of Mauritius, Reduit, Mauritius

    Sabina Jhaumeer Laulloo

  4. Dept. of Chem., Fac. of Science, University of Mauritius, Reduit, Mauritius

    Henri Li Kam Wah

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Okoli, B.J., Terblanche, U., Ssemakalu, C.C., Mtunzi, F.M., Pillay, M., Modise, J.S. (2019). Antibacterial, Antioxidant and Raw 264.7 Cell Line Proliferative Effect of 5-[(4-Nitro-Benzylidene)-Amino]-2H-Pyrazol-3-ol. In: Ramasami, P., Gupta Bhowon, M., Jhaumeer Laulloo, S., Li Kam Wah, H. (eds) Chemistry for a Clean and Healthy Planet. ICPAC 2018. Springer, Cham. https://doi.org/10.1007/978-3-030-20283-5_21

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