Simultaneous measurement of hydrogen carbonate and acetate anions using biologically active receptor based on azo derivatives of naphthalene

Spectrochim Acta A Mol Biomol Spectrosc. 2020 Mar 15:229:117925. doi: 10.1016/j.saa.2019.117925. Epub 2019 Dec 9.

Abstract

A novel receptor based on azo-derivatives of 1-naphthylamine (2-((E)-((4-chloro-3-(trifluoromethyl)phenyl)imino)methyl)-4-((E)-naphthalene-1-yldiazenyl)phenol(2) abbreviated CTNP was successfully designed and synthesized. Its sensing properties were studied deeply. Systematic studies of CTNP with HCO3- and AcO- anions in DMSO disclosed that there is hydrogen-bonding between CTNP and incoming anions. Significant changes in the visible region of the spectrum, as well as a drastic color change of CTNP from pale yellow to red, observed due to interaction as mentioned earlier. The stoichiometry of [CTNP: HCO3- or AcO-] complexes and association constants determined through Job's method and Benesi-Hildebrand (B-H) plot, respectively. Taking into account the analysis results, CTNP performs the selective recognition of sub-millimolar concentrations of HCO3- and AcO- efficiently. The antifungal activity of the receptor was tested against Aspergillus brasiliensis and Aspergillus niger. CTNP exhibited excellent antifungal activity against both strains. CTNP also represented antibacterial activity against Gram-positive bacteria: Staphylococcus epidermidis. It was cleared that designed receptor can be applied under physiological conditions for a long duration.

Keywords: Acetate anion; Biological activity; Chemosensor; Hydrogen carbonate anion.

MeSH terms

  • Acetates / analysis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Aspergillus / drug effects
  • Aspergillus / metabolism
  • Azo Compounds / chemistry*
  • Bicarbonates / analysis*
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Staphylococcus epidermidis / drug effects
  • Staphylococcus epidermidis / metabolism

Substances

  • Acetates
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Azo Compounds
  • Bicarbonates
  • Naphthalenes