Modification of agarose: 6-aminoagarose mediated syntheses of fluorogenic pyridine carboxylic acid amides.
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, (1)H and (13)C NMR spectra. The fluorescence emissions (λmax 430 and 412 nm) of 1 × 10(-3)M solutions of AA-NA and AA-PA in water were significantly higher (ca. 82% and ca. 90%) than those of the molar equivalents (0.2mg) of NA and PA present in the 1 × 10(-3)M solutions of the amides, respectively. These fluorogenic pyridine carboxylic acid amides of agarose may find applications as sensors in biomedical and pharmaceutical industries.
Marine Biotechnology and Ecology Discipline, CSIR-Central Salt & Marine Chemicals Research Institute, G. B. Marg, Bhavnagar 364002, Gujarat, India.
Stalin
S
Kondaveeti
Marine Biotechnology and Ecology Discipline, CSIR-Central Salt & Marine Chemicals Research Institute, G. B. Marg, Bhavnagar 364002, Gujarat, India.
Gaurav K
GK
Mehta
Marine Biotechnology and Ecology Discipline, CSIR-Central Salt & Marine Chemicals Research Institute, G. B. Marg, Bhavnagar 364002, Gujarat, India; Academy of Scientific & Innovative Research, Anusandhan Bhavan, 2 Rafi Marg, New Delhi 110001, India. Electronic address: aks@csmcri.org.
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AK
Siddhanta
D000577:Amides / Q000138:chemical synthesis*; D000606:Amino Sugars / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry; D002236:Carbohydrate Conformation; D002264:Carboxylic Acids / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D020100:Hydrogels; D039823:Iridoids / Q000737:chemistry; D008872:Microwaves; D009525:Niacin / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D009943:Organophosphorus Compounds; D010797:Phthalimides / Q000737:chemistry; D010848:Picolinic Acids / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis*; D012685:Sepharose / Q000031:analogs & derivatives / Q000737:chemistry*; D012996:Solutions; D013053:Spectrophotometry; D017550:Spectroscopy, Fourier Transform Infrared
D000577:Amides; D000606:Amino Sugars; D001391:Azo Compounds; D002264:Carboxylic Acids; D003432:Cross-Linking Reagents; D005456:Fluorescent Dyes; D020100:Hydrogels; D039823:Iridoids; D009943:Organophosphorus Compounds; D010797:Phthalimides; D010848:Picolinic Acids; D011725:Pyridines; D012996:Solutions; C037431:phthalimide; D009525:Niacin; C061896:triphenylphosphine; D012685:Sepharose; C007834:genipin; C030614:picolinic acid
Amide; Aminoagarose; Fluorescence; Hydrogel; Nicotinic acid; Picolinic acid