A facile one-pot synthesis of a fluorescent agarose-O-naphthylacetyl adduct with slow release properties

Carbohydr Polym. 2013 Oct 15;98(1):589-95. doi: 10.1016/j.carbpol.2013.06.046. Epub 2013 Jun 29.

Abstract

A microwave assisted facile synthesis of a fluorescent 6-O-naphthylacetyl agarose (NA-agarose) employing carbodiimide chemistry (dicyclohexylcarbodiimide/4-dimethylaminopyridine) has been described. NA-agarose was characterized by TGA, GPC, UV spectrophotometry, fluorescence spectroscopy, FT-IR, (1)H and (13)C NMR spectra, exhibiting that in NA-agarose the naphthylacetyl group was attached to the backbone of the agarose polymer. The hydrolysis of NA-agarose in heterogeneous aqueous phase showed that the 1-naphthyl acetic acid (NAA), a plant growth regulator, got released in a controlled manner, the release rate being dependent on the hydrophilicity of the polymer adduct as well as on pH and temperature. The fluorescence emission (λmax 332 nm) of NA-agarose (1×10(-3) M) in ethylene glycol was significantly higher (ca. 82%) than that of the molar equivalent of NAA content in the product i.e. 0.08 mg in 1×10(-3) M solution. The resulting polymer would be of potential utility as a sustained release plant growth regulator and sensory applications.

Keywords: 1-Naphthylacetic acid; Agarose; Fluorescence; Sustained release property.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Aminopyridine / analogs & derivatives
  • 4-Aminopyridine / chemistry
  • Chemical Phenomena
  • Chemistry Techniques, Synthetic
  • Delayed-Action Preparations
  • Dicyclohexylcarbodiimide / chemistry
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry*
  • Hydrolysis
  • Naphthaleneacetic Acids / chemistry*
  • Sepharose / chemistry*
  • Temperature

Substances

  • Delayed-Action Preparations
  • Fluorescent Dyes
  • Naphthaleneacetic Acids
  • 1-naphthaleneacetic acid
  • Dicyclohexylcarbodiimide
  • Sepharose
  • 4-Aminopyridine
  • 4-dimethylaminopyridine