Cypridina luciferin analogue

Nakano, M., Sugioka, K., Ushijima, Y., and Goto, T. (1986). Chemiluminescence probe with Cypridina luciferin analogue, 2-methyl-6-phenyl-3,7-dihydroimidazo[l,2-a]pyrazine-3-one, for estimating the ability of human granulocytes to generate superoxide anion. Anal. Biochem. 159 363-369. 

SUPEROXIDE OR SINGLET OXYGEN THE CHEMILUMINESCENCE OF CYPRIDINA LUCIFERIN ANALOGUES IN PHOTODYNAMIC SOLUTIONS... 

Various chemiluminescent compounds (e.g. luminol) have been studied in order to find suitable and specific probes for detection of ROS. Recently Cypridina luciferin analogues CLA and MCLA are thought to emit light only when reacting with superoxide anion and singlet oxygen. ... 

Scheme 1. Postulated chemiluminescence mechanism for Cypridina luciferin analogue (CLA) and its derivatives. The parentheses donate possible protonations.

Fujimori BC, Nakajima H, Akutsu K, Mitani M. Chemiluminescence of Cypridina luciferin analogues part 1. Effect of pH on rates of spontaneous autoxidation of CLA in aqueous buffer solutions. J Chem Soc PCTkin Trans 2 1993 2405-9. 

T. Reaction rates for the chemiluminescence of Cypridina luciferin analogues with superoxide A quenching experiment with superoxide dismutase. Agric Biol Chem 1991 55 157-60. 

Hirano T, Takahashi Y, Kondo H, Maki S, Kojima S, Ikeda H, Niwa H. The reaction mechanism for the high quantum yield of the Cypridina (Vargula) bioluminescence supported by chemiluminescence of 6-aryl-2-methylimidazo-[l,2-a]pyrazin-3(7H)-ones (Cypridina luciferin analogues). Photochem Photobiol Sci 2008 7 197-207. 

In this study, we report the effect of sugars (fructose, glucose, sucrose and trehalose) on Al3+-induced cell death and 02 generation in tomato cell suspension culture using cell death detection dye, Evans blue and 02o -specific chemiluminescent probe, Cypridina luciferin analogue.. Then, the possible roles for trehalose in reduction of Al3+ toxic effects in plants are discussed. 

Nakamura, H., et al. (2000). Convergent and short-step synthesis of dl-Cypridina luciferin and its analogues based on Pd-mediated cross coupling. Tetrahedron Lett. 41 2185-2188. 

Several papers were concerned with the synthesis of and mechanism of luminescence of Cypridina luciferin and its analogues <06T6272 06TL753 06TL6057>. 

Cypridina luciferin, in the presence of oxygen and the enzyme Cypridina luciferase, is oxidized with emission of light to give products called oxyluciferin and etioluciferin. On the basis of PMR and mass spectra the structure 21 was assigned to oxyluciferin. This is now known to be incorrect. Work on simple analogues of luciferin in aprotic solvents showed that oxidation of compounds such as 22 and 11 was accompanied... 

The initial syntheses of Cypridina luciferin and its analogues were performed in low yields by reaction of appropriate 2-aminopyrazines with a-keto acids, followed by reduction with aluminum amalgam or catalytic hydrogenation, and treatment of the product with dicyclohexyl-carbodiimide. For example, 2-amino-5-phenylpyrazine (36) on reaction with pyruvic acid gave the product 37, which was reduced to give an intermediate formulated as 38, which was then cyclized to give the 0x0 compound 39 in 7% yield. It was later discovered that these products could be obtained in high yield in one step by reaction of aminopyrazines such as 36 with a-keto aldehydes such as pyruvaldehyde (MeCOCHO). Condensation of the appropriate aminopyrazine with... 

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