Month: October 2022

On March 24, 2005, Heeres, Jan; de Jonge, Marc R.; Koymans, Lucien M. H.; Daeyaert, Frits F. D.; Vinkers, Maarten; Van Aken, Koen J. A.; Arnold, Edward; Das, Kalyan; Kilonda, Amuri; Hoornaert, Georges J.; Compernolle, Frans; Cegla, Marek; Azzam, Rasha A.; Andries, Koen; de Bethune, Marie-Pierre; Azijn, Hilde; Pauwels, Rudi; Lewi, Paul J.; Janssen, Paul A. J. published an article.Reference of 3,5-Dibromo-1-methylpyrazin-2(1H)-one The title of the article was Design, Synthesis, and SAR of a Novel Pyrazinone Series with Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitory Activity. And the article contained the following:

A series of novel pyrazinones designed as non-nucleoside reverse transcriptase inhibitors (NNRTIs) was synthesized and their anti-HIV structure-activity relationship (SAR) was studied. Optimization of activity was guided by mol. modeling, which in turn was based on x-ray structures of HIV-1 reverse transcriptase-bound 4-[[4-[(2,4,6-trimethylphenyl)amino]-2-pyrimidinyl]amino]benzonitrile (dapivirine). An example compound thus prepared and studied was 3-[(4-chlorophenyl)amino]-5-(2,4-dimethylphenoxy)-1-methyl-2(1H)-pyrazinone (I). The experimental process involved the reaction of 3,5-Dibromo-1-methylpyrazin-2(1H)-one(cas: 87486-34-8).Reference of 3,5-Dibromo-1-methylpyrazin-2(1H)-one

The Article related to design synthesis structure activity pyrazinone nonnucleoside hiv reverse transcriptase, mol modeling phenylamino phenoxy pyrazinone hiv reverse transcriptase dapivirine, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Reference of 3,5-Dibromo-1-methylpyrazin-2(1H)-one

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On April 9, 2015, Chen, Yi published a patent.Formula: C5H4Br2N2O The title of the patent was Preparation of substituted [(6-phenyl-4-methyl-3-oxo-3,4-dihydropyrazin-2-yl)amino]benzene derivatives as inhibitors of bruton’s tyrosine kinase. And the patent contained the following:

The present invention provides compounds I [R0 and R1 = independently H, alkyl, alkenyl, alkynyl, cycloalkyl, etc.; L = N(Rd)(CH2)m; Rd = H, alkyl, alkenyl, alkynyl, cycloalkyl or heterocycloalkyl; m = 0-4; R2 = H or alkyl; R3 = H, halo, alkyl, or hydroxyalkyl; R4 = W, X, Y or Z; R5, R6, R7, R8, R9, R10, R11 and R12 = independently H, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, halo, or alkoxy], or their N-oxides, pharmaceutically acceptable salts, solvates, polymorphs or tautomers. For example, compound II was prepared by coupling of compound III (preparation given) with compound IV (preparation given) followed by hydrolysis. The Kd value of compound II for bruton’s tyrosine kinase (BTK) was 0.86 nM, which clearly shows that compound II is a highly potent BTK inhibitor. The invention compounds are useful as inhibitors of bruton’s tyrosine kinase for the treatment of neoplastic disease, autoimmune disease and inflammatory disorder. The experimental process involved the reaction of 3,5-Dibromo-1-methylpyrazin-2(1H)-one(cas: 87486-34-8).Formula: C5H4Br2N2O

The Article related to phenylmethyloxodihydropyrazinylaminobenzene compound preparation bruton tyrosine kinase inhibitor, neoplastic disease autoimmune disease inflammatory disorder treatment, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Formula: C5H4Br2N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On July 28, 2016, Chen, Yi published a patent.Product Details of 87486-34-8 The title of the patent was Preparation of substituted [(6-phenyl-4-methyl-3-oxo-3,4-dihydropyrazin-2-yl)amino]benzene derivatives as selective Bruton’s tyrosine kinase inhibitors. And the patent contained the following:

The invention provides compounds I [R0 and R1 = independently H, alkyl, alkenyl, alkynyl, cycloalkyl, etc.; L = N(Rd)(CH2)m; Rd = H, alkyl, alkenyl, alkynyl, cycloalkyl or heterocycloalkyl; m = 0-4; R2 = H or alkyl; R3 = H, halo, alkyl, or hydroxyalkyl; R4 = W, X, Y or Z; R5, R6, R7, R8, R9, R10, R11 and R12 = independently H, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, halo, or alkoxy], or their N-oxides, pharmaceutically acceptable salts, solvates, polymorphs or tautomers. For example, compound II was prepared by coupling of compound III (preparation given) with compound IV (preparation given) followed by hydrolysis. The Kd value of compound II for Bruton’s tyrosine kinase (BTK) was 0.86 nM, which clearly shows that compound II is a highly potent BTK inhibitor. The invention compounds are useful as inhibitors of Bruton’s tyrosine kinase for the treatment of neoplastic disease, autoimmune disease and inflammatory disorder. The experimental process involved the reaction of 3,5-Dibromo-1-methylpyrazin-2(1H)-one(cas: 87486-34-8).Product Details of 87486-34-8

The Article related to phenylmethyloxodihydropyrazinylaminobenzene compound preparation bruton tyrosine kinase inhibitor, neoplastic disease autoimmune disease inflammatory disorder treatment, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Product Details of 87486-34-8

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Coutant, Eloi P.; Goyard, Sophie; Hervin, Vincent; Gagnot, Glwadys; Baatallah, Racha; Jacob, Yves; Rose, Thierry; Janin, Yves L. published an article in 2019, the title of the article was Gram-scale synthesis of luciferins derived from coelenterazine and original insights into their bioluminescence properties.Formula: C26H21N3O3 And the article contains the following content:

An original gram-scale synthesis of O-acetylated forms of coelenterazine, furimazine or hydroxy-bearing analogs of luciferins is described. The comparison over two hours of their bioluminescence, using the nanoKAZ/NanoLuc luciferase, provides remarkable insights useful for the selection of a substrate adapted for a given 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).Formula: C26H21N3O3

The Article related to luciferin coelenterazine preparation bioluminescence kinetics light absorption, luciferase inhibition kinetics luciferin, Biomolecules and Their Synthetic Analogs: Others, Including Purines, Pyrimidine Nucleic Acid Bases, Flavins, Lignans and other aspects.Formula: C26H21N3O3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On June 9, 2022, Magalhaes, Carla M.; Esteves da Silva, Joaquim C. G.; Pinto da Silva, Luis published an article.Name: 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one The title of the article was Theoretical Study of the Thermolysis Reaction and Chemiexcitation of Coelenterazine Dioxetanes. And the article contained the following:

Coelenterazine and other imidazopyrazinones are important bioluminescent substrates widespread in marine species and can be found in eight phyla of luminescent organisms. Light emission from these systems is caused by the formation and subsequent thermolysis of a dioxetanone intermediate, whose decomposition allows for efficient chemiexcitation to singlet excited states. Interestingly, some studies have also reported the involvement of unexpected dioxetane intermediates in the chemi- and bioluminescent reactions of Coelenterazine, albeit with little information on the underlying mechanisms of these new species. Herein, we have employed a theor. approach based on d. functional theory to study for the first time the thermolysis reaction and chemiexcitation profile of two Coelenterazine dioxetanes. We have found that the thermolysis reactions of these species are feasible but with relevant energetic differences. More importantly, we found that the singlet chemiexcitation profiles of these dioxetanes are significantly less efficient than the corresponding dioxetanones. Furthermore, we identified triplet chemiexcitation pathways for the Coelenterazine dioxetanes. Given this, the chemiexcitation of these dioxetanes should lead only to minimal luminescence. Thus, our theor. investigation of these systems indicates that the thermolysis of these dioxetanes should only provide “dark” pathways for the formation of nonluminescent degradation products of the chemi- and bioluminescent reactions of Coelenterazine and other imidazopyrazinones. 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).Name: 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one

The Article related to dft thermolysis reaction chemiexcitation coelenterazine dioxetanes, Physical Organic Chemistry: Theoretical Organic Chemical Concepts, Including Quantum and Molecular Mechanical Studies and other aspects.Name: 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On July 31, 2020, Inouye, Satoshi; Sahara-Miura, Yuiko; Nakamura, Mitsuhiro; Hosoya, Takamitsu published an article.Category: pyrazines The title of the article was Expression, purification, and characterization of recombinant apoPholasin. And the article contained the following:

Pholasin is a reactive oxygen-sensitive photoprotein that consists of an apoprotein (apoPholasin) and an unknown chromophore. The preferred human codon-optimized apoPholasin gene was transiently expressed in mammalian cells and apoPholasin was detected using an anti-recombinant apoPholasin antibody. For the first time, we found that apoPholasin secreted into the culture medium could catalyze the oxidation of coelenterazine (CTZ, a luciferin) to produce continuous luminescence. The fusion protein of apoPholasin and glutathione S-transferase (GST-apoPholasin) was successfully expressed as a soluble form in bacterial cells using the cold induction system. The purified GST-apoPholasin also had luminescence activity with CTZ, showing the bioluminescence emission peak at 461 nm, and the resultant product showed purple blue fluorescence under 365 nm light. Unexpectedly, the main oxidation product of CTZ was identified as coelenteramine (CTM), not coelenteramide (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).Category: pyrazines

The Article related to apopholasin glutathione transferase coelenterazine reactive oxygen species oxidation, coelenteramide, coelenteramine, dehydrocoelenterazine, photoproteins, reactive oxygen and other aspects.Category: pyrazines

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On October 31, 2020, Peltomaa, Riikka; Fikacek, Sabrina; Benito-Pena, Elena; Barderas, Rodrigo; Head, Trajen; Deo, Sapna; Daunert, Sylvia; Moreno-Bondi, Maria C. published an article.Category: pyrazines The title of the article was Bioluminescent detection of zearalenone using recombinant peptidomimetic Gaussia luciferase fusion protein. And the article contained the following:

The development of a bioluminescent immunosensor is reported for the determination of zearalenone (ZEA) based on a peptide mimetic identified by phage display. The peptide mimetic GW, with a peptide sequence GWWGPYGEIELL, was used to create recombinant fusion proteins with the bioluminescent Gaussia luciferase (GLuc) that were directly used as tracers for toxin detection in a competitive immunoassay without the need for secondary antibodies or further labeling. The bioluminescent sensor, based on protein G-coupled magnetic beads for antibody immobilization, enabled determination of ZEA with a detection limit of 4.2 ng mL-1 (corresponding to 420μg kg-1 in food samples) and an IC50 value of 11.0 ng mL-1. The sensor performance was evaluated in spiked maize and wheat samples, with recoveries ranging from 87 to 106% (RSD < 20%, n = 3). Finally, the developed method was applied to the anal. of a naturally contaminated reference matrix material and good agreement with the reported concentrations was obtained. 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 zearalenone recombinant peptidomimetic gaussia luciferase fusion protein bioluminescent detection, bioluminescence, food safety, gaussia luciferase, mycotoxin, zearalenone and other aspects.Category: pyrazines

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Coutant, Eloi P.; Gagnot, Glwadys; Hervin, Vincent; Baatallah, Racha; Goyard, Sophie; Jacob, Yves; Rose, Thierry; Janin, Yves L. published an article in 2020, the title of the article was Bioluminescence profiling of NanoKAZ/NanoLuc luciferase using a chemical library of coelenterazine analogues.Safety of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one And the article contains the following content:

We describe here an extensive structure-bioluminescence relationship study of a chem. library of analogs of coelenterazine, using nanoKAZ/NanoLuc, a mutated luciferase originated from the catalytic subunit of the deep-sea shrimp Oplophorus gracilirostris. Out of the 135 O-acetylated precursors that were prepared by using our recently reported synthesis and following their hydrolysis to give solutions of the corresponding luciferins, notable bioluminescence improvements were achieved in comparison with furimazine, which is currently amongst the best substrates of nanoKAZ/NanoLuc. For instance, the rather more lipophilic analog 8-(2,3-difluorobenzyl)-2-((5-methylfuran-2-yl)methyl)-6-phenylimidazo[1,2-a]pyrazin-3(7H)-one provided a 1.5-fold improvement of the total light output over a 2 h period, a close to threefold increase of the initial signal intensity and a signal-to-background ratio five times greater than furimazine. The kinetic parameters for the enzymic reaction were obtained for a selection of luciferin analogs and provided unexpected insights into the luciferase activity. Most prominently, along with a general substrate-dependent and irreversible inactivation of this enzyme, in the case of the optimized luciferin mentioned above, the consumption of 2664 mols. was found to be required for the detection of a single Relative Light Unit (RLU; a luminometer-dependent fraction of a photon). 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).Safety of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one

The Article related to luciferase nanokaz nanoluc bioluminescence coelenterazine analog library proluciferin hikarazine, enzyme catalysis, heterocycles, luciferins, luminescence, natural products and other aspects.Safety of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Abe, Masahiro; Nishihara, Ryo; Kim, Sung-Bae; Suzuki, Koji published an article in 2021, the title of the article was Near-infrared bioluminescence imaging of animal cells with through-bond energy transfer cassette.HPLC of Formula: 55779-48-1 And the article contains the following content:

A review. Coelenterazine (CTZ) is the most general substrate for marine luciferases. The present protocol introduces a near-IR (NIR) bioluminescence (BL) imaging of mammalian cells with a cyanine-5 (Cy5) dye-conjugated CTZ. This unique Cy5-conjugated CTZ, named Cy5-CTZ, can act as a dual optical readout emitting both fluorescence (FL) and BL. The Cy5-CTZ exerts through-bond energy transfer (TBET)-based imaging modalities for mammalian cells. This novel derivative, Cy5-CTZ, is intrinsically fluorescent and emits NIR-shifted BL when reacting with an appropriate luciferase, such as Renilla luciferase (RLuc). The protocol exemplifies a unique live-cell imaging with Cy5-CTZ that is optically stable in physiol. samples and rapidly permeabilize through plasma membrane and emit NIR-BL in live mammalian 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).HPLC of Formula: 55779-48-1

The Article related to review energy transfer cassette bioluminescence imaging, bioluminescence (bl), coelenterazine (ctz), cyanine-5 (cy5), near infrared (nir), through-bond energy transfer (tbet) and other aspects.HPLC of Formula: 55779-48-1

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Zenchak, Jessica R.; Palmateer, Brandon; Dorka, Nicolai; Brown, Tariq M.; Wagner, Lina-Marie; Medendorp, William E.; Petersen, Eric D.; Prakash, Mansi; Hochgeschwender, Ute published an article in 2020, the title of the article was Bioluminescence-driven optogenetic activation of transplanted neural precursor cells improves motor deficits in a Parkinson′s disease mouse model.SDS of cas: 55779-48-1 And the article contains the following content:

The need to develop efficient therapies for neurodegenerative diseases is urgent, especially given the increasing percentages of the population living longer, with increasing chances of being afflicted with conditions like Parkinson′s disease (PD). A promising curative approach toward PD and other neurodegenerative diseases is the transplantation of stem cells to halt and potentially reverse neuronal degeneration. However, stem cell therapy does not consistently lead to improvement for patients. Using remote stimulation to optogenetically activate transplanted cells, we attempted to improve behavioral outcomes of stem cell transplantation. We generated a neuronal precursor cell line expressing luminopsin 3 (LMO3), a luciferase-channelrhodopsin fusion protein, which responds to the luciferase substrate coelenterazine (CTZ) with emission of blue light that in turn activates the opsin. Neuronal precursor cells were injected bilaterally into the striatum of homozygous aphakia mice, which carry a spontaneous mutation leading to lack of dopaminergic neurons and symptoms of PD. Following transplantation, the cells were stimulated over a period of 10 days by intraventricular injections of CTZ. Mice receiving CTZ demonstrated significantly improved motor skills in a rotarod test compared to mice receiving vehicle. Thus, bioluminescent optogenetic stimulation of transplanted neuronal precursor cells shows promising effects in improving locomotor behavior in the aphakia PD mouse model and encourages further studies to elucidate the mechanisms and long-term outcomes of these beneficial effects. 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 bioluminescence optogenetic neural precursor cell parkinson disease mouse, pitx3, chemogenetic, embryonic stem cells, luminopsin, multielectrode array, neural differentiation and other aspects.SDS of cas: 55779-48-1

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem