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An method for highly efficient chemiluminescence of imidazopyrazinone in water Katsunori Teranishi* Kamihama 1515, Tsu, Mie 514-8507, Japan      *(teranisi@bio.mie-u.ac.jp) In order to provide chemiluminescent substrates that have high light-emitting efficiency in aqueous medium, the structural design on the substrates was studied in the covalent attachment of a light-producing chromophore, imidazo[1,2-a]pyrazin-3(7H)-one, to a cyclodextrin (CD) molecule. The synthesis of mono-CD-bound 6-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one was achieved by the formation of amido bond between imidazo[1,2-a]pyrazin-3(7H)-one carboxylic acid derivative and mono-amino CD. Light-emitting efficiency of the oxygen-induced chemiluminescence in phosphate buffer (pH 8.0) was remarkably dependent on the kind of bound CD, the binding site of chromophore to CD, and the length of spacer between the chromophore and CD. When C3-carbon of g-CD was covalently attached to 2-position of imidazo[1,2-a]pyrazin- 3(7H)-one ring system by a short spacer, the light-emitting efficiency showed an up to 44-fold enhancement than that of 2-methyl-6-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one (MCLA). Moreover, decrease of the dihedral angle between phenyl group and pyrazine in 6-(4-methoxyphenyl) imidazo[1,2-a]pyrazin-3(7H)-one of the g-CD-bound compound gave an up to 170-fold enhancement as against MCLA. [Poster: teranish.katsun.11532]

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