Category: Pyrazines

O′Sullivan, Justin J.; Medici, Valentina; Heffern, Marie C. published an article in 2022, the title of the article was A caged imidazopyrazinone for selective bioluminescence detection of labile extracellular copper(II).Category: pyrazines And the article contains the following content:

Copper is an essential redox-active metal that plays integral roles in biol. ranging from enzymic catalysis to mitochondrial respiration. However, if not adequately regulated, this redox activity has the potential to cause oxidative stress through the production of reactive oxygen species. Indeed, the dysregulation of copper has been associated with a variety of disease states including diabetes, neurodegenerative disorders, and multiple cancers. While increasing tools are being developed for illuminating labile intracellular copper pools and the trafficking pathways in which they are involved, significantly less attention has been given to the analogus extracellular labile pool. To address this gap, we have developed a bioluminescence-based imaging probe, picolinic ester caged-diphenylterazine (pic-DTZ) for monitoring labile, extracellular copper using a coelenterazine-like imidazopyrazinone and the genetically-engineered, marine-based luciferase, nanoluciferase. Unlike the more commonly-used firefly luciferase, nanoluciferase does not require ATP, allowing its application to the extracellular milieu. pic-DTZ demonstrates high metal and oxidation state selectivity for Cu(II) in aqueous buffer as well as selectivity for labile pools over coordinatively inaccessible protein-bound Cu(II). We demonstrate the potential of pic-DTZ as a diagnostic tool in human serum and plasma for copper-associated diseases. Addnl., we apply pic-DTZ to lend insight into the extracellular copper dynamic in anticancer treatments. The experimental process involved the reaction of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one(cas: 55779-48-1).Category: pyrazines

The Article related to extracellular copper imidazopyrazinone selective bioluminescence detection, Placeholder for records without volume info and other aspects.Category: pyrazines

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Mizui, Yuki; Eguchi, Masatoshi; Tanaka, Masanobu; Ikeda, Yuma; Yoshimura, Hideaki; Ozawa, Takeaki; Citterio, Daniel; Hiruta, Yuki published an article in 2021, the title of the article was Long-term single cell bioluminescence imaging with C-3 position protected coelenterazine analogues.Quality Control of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one And the article contains the following content:

Bioluminescence is a powerful imaging modality for monitoring biol. phenomena both in vitro and in vivo. Bioluminescence imagin (BLI) is becoming a seamless imaging technol. covering the range from cells to organs of small animals. Long-term imaging at the single cell level would lead to a true understanding of the dynamics of life phenomena. This work presents a long-term single cell bioluminescence imaging technol. accomplished with C-3 position protected furimazines (FMZs), a CTZ analogs, which generate intense blue emission when paired with a highly stable engineered luciferase, Nanoluc. Four types of FMZs protected at the C-3 position have been synthesized. The type and steric bulkiness of the protection group strongly contributed to storage stability and the kinetics of the bioluminescence reactions of the analogs in human living cells. In particular, two developed FMZ analogs resulted in significantly longer bioluminescence emission with higher S/N ratio than FMZ at single cell level. Long-term bioluminescence single cell imaging technol. with the developed FMZ analogs will lead to seamless imaging in the range from cells to organs of small animals. The experimental process involved the reaction of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one(cas: 55779-48-1).Quality Control of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one

The Article related to bioluminescence imaging coelenterazine storage stability reaction kinetics, Placeholder for records without volume info and other aspects.Quality Control of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Aulestia, Francisco J.; Webb, Sarah E.; Chan, Ching Man; Tse, Man Kit; Neant, Isabelle; Moreau, Marc; Miller, Andrew L.; Leclerc, Catherine published an article in 2021, the title of the article was A simple bioluminescence-based method for recording Ca2+ signaling in the cytosol or mitochondria of neural progenitor cells from the adult zebrafish brain.Synthetic Route of 55779-48-1 And the article contains the following content:

Neurospheres derived from the adult zebrafish brain are a convenient model for investigating the initial stages of neurogenesis. Neurospheres are composed of stem cells, which have the ability to either self-renew or differentiate into specialized cells (i.e., neurons and glial cells) if cultured in an appropriate medium. It has previously been suggested that Ca2+ signaling in the cytosol and mitochondria might play some role in neurogenesis. Ca2+ signals can be recorded using the non-toxic bioluminescent Ca2+ reporter complex, holoaequorin. We have developed a novel electroporation protocol to load neurospheres with cDNA encoding either mitochondrial-targeted EGFP-apoaequorin (MitGA) or the cytosolic-targeted EGFP-apoaequorin (CytGA). We show that within ∼24 h after electroporation, each of these apoaequorin proteins were expressed in ∼20% of the neurosphere cells. In addition, after reconstitution of holoaequorin by incubation of the cells with its luminophore, coelenterazine, dynamic changes in [Ca2+] in the cytosol and mitochondria were imaged using a custom-built electron multiplying charge coupled device (EMCCD)-based photon imaging microscope (PIM) system or measured using a photomultiplier tube (PMT)-based luminescence detection system, after activation of store-operated Ca2+ entry (SOCE). The experimental process involved the reaction of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one(cas: 55779-48-1).Synthetic Route of 55779-48-1

The Article related to calcium adult zebrafish brain cytosol mitochondria neural progenitor cell, Placeholder for records without volume info and other aspects.Synthetic Route of 55779-48-1

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On August 16, 2022, Cumberbatch, Derrick; Mori, Tetsuya; Yang, Jie; Mi, Dehui; Vinson, Paige; Weaver, C. David; Johnson, Carl Hirschie published an article.Computed Properties of 55779-48-1 The title of the article was A BRET Ca2+ sensor enables high-throughput screening in the presence of background fluorescence. And the article contained the following:

The intrinsic fluorescence of samples confounds the use of fluorescence-based sensors. This is of particular concern in high-throughput screening (HTS) applications using large chem. libraries containing intrinsically fluorescent compounds To overcome this problem, we developed a bioluminescence resonance energy transfer (BRET) Ca2+ sensor, CalfluxCTN. We demonstrated that it reliably reported changes in intracellular Ca2+ concentrations evoked by an agonist and an antagonist of the human muscarinic acetylcholine receptor M1 (hM1R) even in the presence of the fluorescent compound fluorescein, which interfered with a standard fluorescent HTS sensor (Fluo-8). In an HTS using a chem. library containing fluorescent compounds, CalfluxCTN accurately identified agonists and antagonists that were missed or miscategorized using Fluo-8. Moreover, we showed that a luciferase substrate that becomes activated only when inside cells generated long-lasting BRET signals in HTS, enabling results to be reliably compared among replicate samples for hours. Thus, the use of a self-luminescent sensor instead of a fluorescent sensor could facilitate the complete screening of chem. libraries in a high-throughput context and enable anal. of autofluorescent samples in many different applications. The experimental process involved the reaction of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one(cas: 55779-48-1).Computed Properties of 55779-48-1

The Article related to bioluminescence resonance energy transfer sensor fluorescence screening, Placeholder for records without volume info and other aspects.Computed Properties of 55779-48-1

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On September 3, 2021, Burakova, Ludmila P.; Lyakhovich, Maria S.; Mineev, Konstantin S.; Petushkov, Valentin N.; Zagitova, Renata I.; Tsarkova, Aleksandra S.; Kovalchuk, Sergey I.; Yampolsky, Ilia V.; Vysotski, Eugene S.; Kaskova, Zinaida M. published an article.Computed Properties of 55779-48-1 The title of the article was Unexpected Coelenterazine Degradation Products of Beroe abyssicola Photoprotein Photoinactivation. And the article contained the following:

Ca2+-regulated photoproteins of ctenophores lose bioluminescence activity when exposed to visible light. Little is known about the chem. nature of chromophore photoinactivation. Using a total synthesis strategy, we have established the structures of 2 unusual coelenterazine products, isolated from recombinant berovin of the ctenophore Beroe abyssicola, which are Z/E isomers. We propose that during light irradiation, these derivatives are formed from 2-hydroperoxycoelenterazine via the intermediate 8a-peroxide by a mechanism reminiscent of that previously described for the auto-oxidation of green-fluorescent-protein-like chromophores. The experimental process involved the reaction of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one(cas: 55779-48-1).Computed Properties of 55779-48-1

The Article related to ctenophore photoprotein inactivation light coelenterazine degradation, Placeholder for records without volume info and other aspects.Computed Properties of 55779-48-1

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On April 30, 2021, Giuliani, Germano; Merolla, Assunta; Paolino, Marco; Reale, Annalisa; Saletti, Mario; Blancafort, Lluis; Cappelli, Andrea; Benfenati, Fabio; Cesca, Fabrizia published an article.Reference of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one The title of the article was Stability Studies of New Caged bis-deoxy-coelenterazine Derivatives and Their Potential Use as Cellular pH Probes. And the article contained the following:

The synthesis of new bis-deoxy-coelenterazine (1) derivatives bearing ester protective groups (acetate, propionate and butyrate esters) was accomplished. Moreover, their hydrolytic stability at room temperature was evaluated in dimethylsulfoxide (DMSO) as solvent, using the NMR (NMR) spectra of the key products at different time intervals. The results showed an increasing hydrolysis rate according to longest aliphatic chain, with a half-life of 24 days of the more stable acetate derivative (4a). Furthermore, the anal. of the exptl. data revealed the greater stability of the enol tautomer in this aprotic polar solvent. This result was confirmed by theor. calculations using the d. functional theory (DFT) approach, which gave us the opportunity to propose a detailed decomposition mechanism. Addnl., the derivatives obtained were tested by bioluminescence luciferase assays to evaluate their potential use as extracellular pH-sensitive reporter substrates of luciferase. The biol. data support the idea that further structural modifications of these mols. may open promising perspectives in this field of research. The experimental process involved the reaction of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one(cas: 55779-48-1).Reference of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one

The Article related to bis deoxy coelenterazine derivative ph probe stability, Placeholder for records without volume info and other aspects.Reference of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Gao, Meng; Liu, Ya-Jun published an article in 2019, the title of the article was Photoluminescence Rainbow from Coelenteramide-A Theoretical Study.Application of 55779-48-1 And the article contains the following content:

A wide variety of marine bioluminescent organisms emit light via the excited-state coelenteramide, which is produced from the coelenterazine oxidation via a series of complicated chem. reactions in protein. Photoluminescence of coelenteramide is a simple way to produce light without experiencing the intricate reactions starting from coelenterazine. To extend the color range of light emission, many coelenterazine analogs were synthesized, but mostly only produce blue and cyan fluorescence. Based on the 42 synthesized coelenterazine analogs, we theor. studied the absorption and fluorescence properties of the corresponding coelenteramide analogs. The electronic effect, steric effect, conjugated effect and solvated effect were considered. The results indicated that conjugated effect has great influence on the strength and wavelength of fluorescence and large electron transfer is beneficial to red shift. Based on the regularities, we theor. designed six coelenteramide analogs, and together with the original coelenteramide, the seven-ones emit the seven colors of rainbow via their photoluminescences. This study expands the coelenteramide fluorescence to the whole visible light region and could inspire new application. The experimental process involved the reaction of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one(cas: 55779-48-1).Application of 55779-48-1

The Article related to photoluminescence rainbow coelenteramide theor study, Placeholder for records without volume info and other aspects.Application of 55779-48-1

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On October 31, 2020, Ding, Bo-Wen; Eremeeva, Elena V.; Vysotski, Eugene S.; Liu, Ya-Jun published an article.SDS of cas: 55779-48-1 The title of the article was Luminescence Activity Decreases When v-coelenterazine Replaces Coelenterazine in Calcium-Regulated Photoprotein-A Theoretical and Experimental Study. And the article contained the following:

Calcium-regulated photoproteins are found in at least five phyla of organisms. The light emitted by those photoproteins can be tuned by mutating the photoprotein and/or by modifying the substrate coelenterazine (CTZ). Thirty years ago, Shimomura observed that the luminescence activity of aequorin was dramatically reduced when the substrate CTZ was replaced by its analog v-CTZ. The latter is formed by adding a Ph ring to the π-conjugated moiety of CTZ. The decrease in luminescence activity has not been understood until now. In this paper, through combined quantum mechanics and mol. mechanics calculations as well as mol. dynamics simulations, we discovered the reason for this observation. Modification of the substrate changes the conformation of nearby aromatic residues and enhances the π-π stacking interactions between the conjugated moiety of v-CTZ and the residues, which weakens the charge transfer to form light emitter and leads to a lower luminescence activity. The microenvironments of CTZ in obelin and in aequorin are very similar, so we predicted that the luminescence activity of obelin will also dramatically decrease when CTZ is replaced by v-CTZ. This prediction has received strong evidence from currently theor. calculations and has been verified by experiments The experimental process involved the reaction of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one(cas: 55779-48-1).SDS of cas: 55779-48-1

The Article related to coelenterazine calcium photoprotein a luminescence, General Biochemistry: Subcellular Processes and other aspects.SDS of cas: 55779-48-1

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On September 30, 2022, Inouye, Satoshi; Nakamura, Mitsuhiro; Hosoya, Takamitsu published an article.Product Details of 55779-48-1 The title of the article was Formation of Coelenteramine from 2-Peroxycoelenterazine in the Ca2+-Binding Photoprotein Aequorin. And the article contained the following:

Aequorin consists of apoprotein (apoAequorin) and (S)-2-peroxycoelenterazine (CTZ-OOH) and is considered to be a transient-state complex of an enzyme (apoAequorin) and a substrate (coelenterazine and mol. oxygen) in the enzymic reaction. The degradation process of CTZ-OOH in aequorin was characterized under various conditions of protein denaturation. By acid treatment, the major product from CTZ-OOH was coelenteramine (CTM), but not coelenteramide (CTMD), and no significant luminescence was observed The counterparts of CTM from CTZ-OOH were identified as 4-hydroxyphenylpyruvic acid (4HPPA) and 4-hydroxyphenylacetic acid (4HPAA) by liquid chromatog./electrospray ionization-time-of-flight mass spectrometry (LC/ESI-TOF-MS). In the luminescence reaction of aequorin with Ca2+, similar amounts of 4HPPA and 4HPAA were detected, indicating that CTM is formed by two pathways from CTZ-OOH through dioxetanone anion and not by hydrolysis from CTMD. The experimental process involved the reaction of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one(cas: 55779-48-1).Product Details of 55779-48-1

The Article related to aequorin coelenteramine peroxycoelenterazine calcium, Biochemical Methods: Chromatographic and other aspects.Product Details of 55779-48-1

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Abe, Masahiro; Nishihara, Ryo; Ikeda, Yuma; Nakajima, Takahiro; Sato, Moritoshi; Iwasawa, Naoko; Nishiyama, Shigeru; Paulmurugan, Ramasamy; Citterio, Daniel; Kim, Sung Bae; Suzuki, Koji published an article in 2019, the title of the article was Near-Infrared Bioluminescence Imaging with a through-Bond Energy Transfer Cassette.Electric Literature of 55779-48-1 And the article contains the following content:

A coelenterazine (CTZ) analog emitting near-IR (NIR) bioluminescence was synthesized for through-bond energy transfer (TBET)-based imaging modalities. The analog, named Cy5-CTZ, was prepared by conjugating cyanine-5 (Cy5) dye to CTZ through an acetylene linker. This novel derivative is intrinsically fluorescent and emits NIR-shifted luminescence upon reacting with an appropriate luciferase, the Renilla luciferase. This Cy5-CTZ substrate is optically stable in physiol. samples and rapidly permeabilize through the plasma membrane into the cytosolic compartment of live cells. The experimental process involved the reaction of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one(cas: 55779-48-1).Electric Literature of 55779-48-1

The Article related to breast cancer fibroblast like cell nir bioluminescence imaging, bioluminescence, dyes/pigments, energy transfer, fluorescence, imaging agents, Biochemical Methods: Spectral and Related Methods and other aspects.Electric Literature of 55779-48-1

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem