40040-81-1Relevant articles and documents
ATP-INDEPENDENT BIOLUMINESCENT REPORTER VARIANTS TO IMPROVE IN VIVO IMAGING
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Page/Page column 55-56, (2020/09/12)
Provided herein are chemically modified luciferase substrates for spectrally shifted emission and enhanced water solubility. Provided herein are engineered luciferases. Moreover, provided herein are new ATP-independent bioluminescent reporters which have improved biochemical and photophysical properties and are expected to have broad applications. Finally, provided herein are spectral-resolved triple-color bioluminescent systems, suitable for flexible and convenient approaches to monitor multiple biological events in either qualitative or quantitative manners.
New bioluminescent coelenterazine derivatives with various C-6 substitutions
Jiang, Tianyu,Yang, Xingye,Zhou, Yubin,Yampolsky, Ilia,Du, Lupei,Li, Minyong
, p. 7008 - 7018 (2017/09/01)
A series of new coelenterazine analogs with varying substituents at the C-6 position of the imidazopyrazinone core have been designed and synthesized for the extension of bioluminescence substrates. Some of them display excellent bioluminescence properties compared to DeepBlueC or native coelenterazine with both in vitro and in vivo biological evaluations, thus placing these derivatives among the most ideal substrates for Renilla bioluminescence applications.
Coelenterazine analog and preparing method and application thereof
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Paragraph 0144; 0145; 0195-0197, (2018/02/04)
The invention discloses a coelenterazine analog and a preparing method and application thereof. The coelenterazine analog has the general structure formula (I) shown in the description, wherein R1, R2 and R3 in the formula are different substituents. According to application of the compound as a bioluminescence substrate, the existence and quantity (including the enzyme level, the cell level and the animal level) of coelenterazine luciferase can be detected with bioluminescence, and the in vitro, cell and in vivo distribution imaging of luciferase can be detected; the compound can serve as a report signal to detect the pharmacologic action and the toxic effect of medicine on the enzyme level, the cell level and the animal level under the existence of luciferase.
IMIDAZO[1,2-α]PYRAZIN-3(7H)-ONE DERIVATIVES BEARING A NEW ELECTRON-RICH STRUCTURE
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Page/Page column 27-28, (2011/02/24)
The present invention relates to compound of formula I : and their use as chemiluminescent and/or bioluminescent reagents.
Novel synthetic route of aryl-aminopyrazine
Kuse, Masaki,Kondo, Nobuhiro,Ohyabu, Yuki,Isobe, Minoru
, p. 835 - 840 (2007/10/03)
We report a novel synthetic route of aryl-aminopyrazine through a new cyclization reaction by using a hydroxylamine. Starting from Boc-glycine and aminonitrile, the aminopyrazine ring was prepared in several steps. After trifluoromethane sulfonylation of the aminopyrazinone, the resultant triflate was subjected to Suzuki-Miyaura coupling reaction with aryl boronic acid to afford coelenteramine.
Highly efficient and flexible total synthesis of coelenterazine
Keenan, Martine,Jones, Keith,Hibbert, Frank
, p. 323 - 324 (2007/10/03)
A new total synthesis of the bioluminescent chromophore coelenterazine 1 is described.
Low-temperature photooxygenation of coelenterate luciferin analog synthesis and proof of 1,2-dioxetanone as luminescence intermediate
Usami, Ken,Isobe, Minoru
, p. 12061 - 12090 (2007/10/03)
Coelenterate luciferin analog having bulky tert-butyl group at the 2-position was suitable for studies on chemiluminescence under various conditions. Photooxygenation of the analog(s) at low temperature (-78°C) afforded luminous intermediates which were proved as peroxides by reduction with PPh3 with resultant loss of luminescence ability. In order to clarify these structures of accumulated luminous intermediates by means of 13C NMR, three 13C enriched analogs were synthesized at the 2, 3 and 5 positions of 3,7-dihydroimidazo[1,2-a]pyrazin-3-one skeleton in 99% enrichment with site-specificity. These 13C-enriched coelenterate luciferin analogs were photooxygenated at -78°C to form two peroxidic products as luminescent intermediates. Structures of these unstable intermediates were deduced by means of 13C NMR spectra at low temperature using substrates enriched at three sites by 13C. Photooxygenation in a mixture of CF3CD2OD and CD3OD as highly protic solvents afforded the dioxetanone and 2-hydroperoxide. These two peroxides emitted light independently at different temperatures either at 400 nm (neutral species) and/or 475 nm (anionic species) after diluting to 10-5 M in diglyme (DGM) containing acid or base.
Chemi- and Bio-luminescence of Coelenterazine Analogues with Phenyl Homologues at the C-2 Position
Qi, Chen Feng,Gomi, Yasushiro,Hirano, Takashi,Ohashi, Mamoru,Ohmiya, Yoshihiro,Tsuji, Frederick I.
, p. 1607 - 1612 (2007/10/02)
A series of phenyl homologues of coelenterazine substituted at the C-2 position were synthesized and their bio- and chemi-luminescence properties were investigated including the measurement of chemiluminescence spectra in various media.The light emitting species of each analogue was found to be a neutral form of a coelenteramide derivative in diethylene glycol dimethyl ether (DGM) containing a trace amount of acetate buffer (pH 5.60), while a monoanion was found only in dimethyl sulfoxide (DMSO) and a dianion was observed in DMSO containing a trace amount of aqueous sodium hydroxide.Based on pseudo first-order reaction kinetics, chemiluminescence rate constants were obtained in DGM containing a trace amount of acetate buffer.Each of the synthetic coelenterazine analogues was incorporated into recombinant apoaequorin to obtain a series of semisynthetic aequorins.Measurements of bioluminescence activities of the aequorins revealed that a benzyl group in the C-2 position was essential for efficient luminescence activity.A two-step incubation procedure was used to determine why some analogues gave less luminescence activity than the benzyl analogue and natural coelenterazine.
