Coelenterazine analogs as chemiluminescent probe for superoxide anion

Analytical Biochemistry
K Teranishi, O Shimomura

Abstract

Eleven new coelenterazine analogs containing the 3,7-dihydroimidazo[1,2-alpha]pyrazin-3-one structure were synthesized. The superoxide-triggered chemiluminescence of these compounds was investigated using the hypoxanthine-xanthine oxidase system in comparison with four known compounds. The results showed that an alkyl substitution at the position 5 of the imidazopyrazinone ring causes a drastic decrease in the superoxide-dependent chemiluminescence intensity, whereas a dimethylene bridge added between the position 5 and the phenyl group bound to the position 6 dramatically increases the luminescence intensity, indicating the potential usefulness of this type of compound as a probe for superoxide anion. The luminescence intensity of the bridged analog was 33 times greater than that of MCLA [2-methyl-6-(4-methoxyphenyl)-3, 7-dihydroimidazo[1,2-alpha]pyrazin-3-one], the most sensitive superoxide probe of Cypridina luciferin-type. Two of the analogs synthesized, each with a covalently bound cyclodextrin, had a good solubility in water, an advantage in actual use. Moreover, one of them having a beta-cyclodextrin group showed a unique property; its luminescence was little affected by various substances in the environment.

References

Jun 1, 1978·Proceedings of the National Academy of Sciences of the United States of America·O Shimomura, F H Johnson
Feb 15, 1989·Clinica Chimica Acta; International Journal of Clinical Chemistry·A NishidaT Goto
Aug 1, 1989·The Biochemical Journal·O ShimomuraY Kishi
Jun 30, 1988·Biochemical and Biophysical Research Communications·H MinakamiA Sotomatsu
Jul 30, 1974·Biochemistry·O ShimomuraH Morise
Apr 25, 1972·Biochemistry·O Shimomura, F H Johnson
Oct 1, 1970·Photochemistry and Photobiology·O Shimomura, F H Johnson
Jun 1, 1962·Journal of Cellular and Comparative Physiology·O SHIMOMURAY SAIGA
Jan 1, 1973·Proceedings of the National Academy of Sciences of the United States of America·K Hori, M J Cormier

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Citations

Jan 28, 2009·Plant Methods·Livia Saleh, Christoph Plieth
Mar 24, 2004·Free Radical Biology & Medicine·Bertrand de WergifosseJean-François Rees
Jun 23, 2009·Free Radical Biology & Medicine·Helen I Osipova-GoldbergJosef M Pfeilschifter
Mar 1, 2012·Luminescence : the Journal of Biological and Chemical Luminescence·N VasselA K Campbell
Dec 5, 2003·Analytical Biochemistry·Marko KervinenIlmo E Hassinen
Oct 1, 2015·Molecular Imaging and Biology : MIB : the Official Publication of the Academy of Molecular Imaging·Laura L BronsartChristopher H Contag
Jul 22, 2015·Organic Letters·Takamitsu HosoyaSatoshi Inouye
Jan 12, 2016·PloS One·Laura L BronsartChristopher H Contag
Feb 6, 2004·American Journal of Physiology. Regulatory, Integrative and Comparative Physiology·Margaret M TarpeyMatthew B Grisham
Mar 25, 2016·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Tianyu JiangMinyong Li
Nov 20, 2014·Chemical Communications : Chem Comm·Ryo NishiharaKoji Suzuki
Nov 8, 2006·Luminescence : the Journal of Biological and Chemical Luminescence·Katsunori Teranishi
Aug 30, 2008·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Vasilisa V BorisovaEugene S Vysotski
Aug 20, 2004·The Journal of Biological Chemistry·Florian L MullerHolly Van Remmen
Feb 14, 2016·Molecular Imaging and Biology : MIB : the Official Publication of the Academy of Molecular Imaging·Laura BronsartChristopher Contag
Nov 3, 2020·Chemistry : a European Journal·Glwadys GagnotYves L Janin
Aug 31, 2001·Bioorganic & Medicinal Chemistry Letters·I DevillersJ Marchand-Brynaert
Sep 11, 2019·Analytical Chemistry·Hossein RahmaniReza H Sajedi
Nov 5, 2021·Journal of Oleo Science·Manabu NakazonoKenji Hamase

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