Modification of agarose: 6-Aminoagarose mediated syntheses of fluorogenic pyridine carboxylic acid amides

  • Kondaveeti S
  • Mehta G
  • Siddhanta A
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Abstract

A facile 6-aminoagarose (AA) mediated synthesis of new fluorogenic amides of agarose with nicotinic (AA-NA) and picolinic acids (AA-PA) employing carbodiimide chemistry have been described. 6-Amino agarose (AA) was synthesized in a facile Mitsunobu-inspired microwave mediated method involving the reaction of agarose with phthalimide in presence of diisopropyl azodicarboxylate and triphenylphosphene (DIAD/TPP) followed by hydrazinolysis. All compounds were characterized by GPC, UV spectrophotometry, fluorescence spectroscopy, FT-IR,1H and13C NMR spectra. The fluorescence emissions (λmax430 and 412 nm) of 1 × 10-3M solutions of AA-NA and AA-PA in water were significantly higher (ca. 82% and ca. 90%) than those of the molar equivalents (0.2 mg) of NA and PA present in the 1 × 10-3M solutions of the amides, respectively. These fluorogenic pyridine carboxylic acid amides of agarose may find applications as sensors in biomedical and pharmaceutical industries. © 2014 Elsevier Ltd.

Author-supplied keywords

  • Amide
  • Aminoagarose
  • Fluorescence
  • Hydrogel
  • Nicotinic acid
  • Picolinic acid

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Authors

  • Stalin Kondaveeti

  • Gaurav K. Mehta

  • A. K. Siddhanta

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