Category: 55779-48-1

Kanie, Shusei; Komatsu, Mami; Mitani, Yasuo published an article in 2020, the title of the article was Luminescence of Cypridina luciferin in the presence of human plasma alpha 1-acid glycoprotein.Computed Properties of 55779-48-1 And the article contains the following content:

The enzyme Cypridina luciferase (CLase) enables Cypridina luciferin to emit light efficiently through an oxidation reaction. The catalytic mechanism on the substrate of CLase has been studied, but the details remain to be clarified. Here, we examined the luminescence of Cypridina luciferin in the presence of several proteins with drug-binding ability. Luminescence measurements showed that the mixture of human plasma alpha 1-acid glycoprotein (hAGP) and Cypridina luciferin produced light. The total value of the luminescence intensity over 60 s was over 12.6-fold higher than those in the presence of ovalbumin, human serum albumin, or bovine serum albumin. In the presence of heat-treated hAGP, the luminescence intensity of Cypridina luciferin was lower than in the presence of intact hAGP. Chlorpromazine, which binds to hAGP, showed an inhibitory effect on the luminescence of Cypridina luciferin, both in the presence of hAGP and a recombinant CLase. Furthermore, BlastP anal. showed that hAGP had partial amino acid sequence similarity to known CLases in the region including amino acid residues involved in the drug-binding ability of hAGP. These findings indicate enzymol. similarity between hAGP and CLase and provide insights into both the enzymol. understanding of CLase and development of a luminescence detection method for hAGP. 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 cypridina luciferin plasma alpha 1 acid glycoprotein luminescence, cypridina luciferase, cypridina luciferin, bioluminescence, cypridinid luciferase, cypridinid luciferin, human plasma alpha 1-aicd glycoprotein and other aspects.Computed Properties of 55779-48-1

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Sousa, Joao; Magalhaes, Carla M.; Gonzalez-Berdullas, Patricia; Esteves da Silva, Joaquim C. G.; Pinto da Silva, Luis published an article in 2022, the title of the article was Comparative Investigation of the Chemiluminescent Properties of a Dibrominated Coelenterazine Analog.Recommanded Product: 55779-48-1 And the article contains the following content:

Chemi- and bioluminescence are remarkable light-emitting phenomena, in which thermal energy is converted into excitation energy due to a (bio)chem. reaction. Among a wide variety of chemi-/bioluminescent systems, one of the most well-known and studied systems is that of marine imidazopyrazinones, such as Coelenterazine and Cypridina luciferin. Due to the increasing usefulness of their chemi-/bioluminescent reactions in terms of imaging and sensing applications, among others, significant effort has been made over the years by researchers to develop new derivatives with enhanced properties. Herein, we report the synthesis and chemiluminescent characterization of a novel dibrominated Coelenterazine analog. This novel compound consistently showed superior luminescence, in terms of total light output and emission lifetime, to natural imidazopyrazinones and com. available analogs in aprotic media, while being capable of yellow light emission. Finally, this new compound showed enhanced chemiluminescence in an aqueous solution when triggered by superoxide anion, showing potential to be used as a basis for optimized probes for reactive oxygen species. In conclusion, bromination of the imidazopyrazinone scaffold appears to be a suitable strategy for obtaining Coelenterazines with enhanced properties. 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).Recommanded Product: 55779-48-1

The Article related to dibrominated coelenterazine comparative investigation chemiluminescent property, cypridina luciferin, bioluminescence, chemiluminescence, coelenterazine, coelenterazine analogues, luminescence, superoxide anion and other aspects.Recommanded Product: 55779-48-1

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Pinto da Silva, Luis; Magalhaes, Carla M.; Nunez-Montenegro, Ara; Ferreira, Paulo J. O.; Duarte, Diana; Rodriguez-Borges, Jose E.; Vale, Nuno; Esteves da Silva, Joaquim C. G. published an article in 2019, the title of the article was Study of the combination of self-activating photodynamic therapy and chemotherapy for cancer treatment.Category: pyrazines And the article contains the following content:

Cancer is a very challenging disease to treat, both in terms of treatment efficiency and side-effects. To overcome these problems, there have been extensive studies regarding the possibility of improving treatment by employing combination therapy, and by exploring therapeutic modalities with reduced side-effects (such as photodynamic therapy (PDT)). Herein, this work has two aims: (i) to develop self-activating photosensitizers for use in light-free photodynamic therapy, which would eliminate light-related restrictions that this therapy currently possesses; (ii) to assess their co-treatment potential when combined with reference chemotherapeutic agents (Tamoxifen and Metformin). We synthesized three new photosensitizers capable of self-activation and singlet oxygen production via a chemiluminescent reaction involving only a cancer marker and without requiring a light source. Cytotoxicity assays demonstrated the cytotoxic activity of all photosensitizers for prostate and breast tumor cell lines. Anal. of co-treatment effects revealed significant improvements for breast cancer, producing better results for all combinations than just for the individual photosensitizers and even Tamoxifen. By its turn, co-treatment for prostate cancer only presented better results for one combination than for just the isolated photosensitizers and Metformin. Nevertheless, it should be noted that the cytotoxicity of the isolated photosensitizers in prostate tumor cells was already very appreciable. 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 breast neoplasm cell tamoxifen photodynamic therapy chemotherapy, anticancer drug, breast cancer, chemiluminescence, chemotherapy, multidrug combinations, photodynamic therapy, photosensitizer, prostate cancer and other aspects.Category: pyrazines

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Nishihara, Ryo; Paulmurugan, Ramasamy; Nakajima, Takahiro; Yamamoto, Eiji; Natarajan, Arutselvan; Afjei, Rayhaneh; Hiruta, Yuki; Iwasawa, Naoko; Nishiyama, Shigeru; Citterio, Daniel; Sato, Moritoshi; Kim, Sung Bae; Suzuki, Koji published an article in 2019, the title of the article was Highly bright and stable NIR-BRET with blue-shifted coelenterazine derivatives for deep-tissue imaging of molecular events in vivo.Category: pyrazines And the article contains the following content:

Bioluminescence imaging (BLI) is one of the most widely used optical platforms in mol. imaging, but it suffers from severe tissue attenuation and autoluminescence in vivo. Here, we developed a novel BLI platform on the basis of bioluminescence resonance energy transfer (BRET) for achieving a ∼300 nm blue-to-near IR shift of the emission (NIR-BRET) by synthesizing an array of 18 novel coelenterazine (CTZ) derivatives, named “Bottle Blue (BBlue)” and a unique iRFP-linked RLuc8.6-535SG fusion protein as a probe. The best NIR-BRET was achieved by tuning the emission peaks of the CTZ derivatives to a Soret band of the iRFP. In mammalian cells, BBlue2.3, one of the CTZ derivatives, emits light that is ∼50-fold brighter than DBlueC when combined with RLuc8.6-535SG, which shows stable BL kinetics. When we used a caged version of BBLue2.3, it showed a BL half decay time of over 60 min while maintaining the higher signal sensitivity. This NIR BL is sufficiently brighter to be used for imaging live mammalian cells at single cell level, and also for imaging metastases in deep tissues in live mice without generating considerable autoluminescence. A single-chain probe developed based on this BLI platform allowed us to sensitively image ligand antagonist-specific activation of estrogen receptor in the NIR region. This unique optical platform provides the brightest NIR BLI template that can be used for imaging a diverse group of cellular events in living subjects including protein-protein interactions and cancer metastasis. 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 nir bioluminescence resonance energy transfer coelenterazine, bioluminescence imaging, bioluminescence resonance energy transfer (bret), blue-to-near infrared shift, coelenterazine derivatives, metastasis and other aspects.Category: pyrazines

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Griffiths, Thomas M.; Oakley, Aaron J.; Yu, Haibo published an article in 2020, the title of the article was Atomistic insights into photoprotein formation: Computational prediction of the properties of coelenterazine and oxygen binding in obelin.COA of Formula: C26H21N3O3 And the article contains the following content:

Bioluminescence in marine systems is dominated by the use of coelenterazine for light production The bioluminescent reaction of coelenterazine is an enzyme catalyzed oxidative decarboxylation: coelenterazine reacts with mol. oxygen to form carbon dioxide, coelenteramide, and light. One such class is the Ca2+-regulated photoproteins. These proteins bind coelenterazine and oxygen, and trap 2-hydroperoxycoelenterazine, an intermediate along the reaction pathway. The reaction is halted until Ca2+ binding triggers the completion of the reaction. There are currently no reported exptl., atomistic descriptions of this ternary Michaelis complex. This study utilized computational techniques to develop an atomistic model of the Michaelis complex. Extensive mol. dynamics simulations were carried out to study the interactions between four tautomeric/protonation states of coelenterazine and wide-type and mutant obelin. Only minor differences in binding modes were observed across all systems. Interestingly, no basic residues were identified in the vicinity of the N7-nitrogen of coelenterazine. This observation was surprising considering that deprotonation at this position is a key mechanistic step in the proposed bioluminescent reaction. This work suggests that coelenterazine binds either as the O10H tautomer, or in the deprotonated form. Implicit ligand sampling simulations were used to identify potential O2 binding and migration pathways within obelin. A key oxygen binding site was identified close to the coelenterazine imidazopyrazinone core. The O2 binding free energy was observed to be dependent on the protonation state of coelenterazine. Taken together, the description of the obelin-coelenterazine-O2 complexes established in this study provides the basis for future computational studies of the bioluminescent mechanism. © 2019 Wiley Periodicals, Inc. 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).COA of Formula: C26H21N3O3

The Article related to bioluminescence obelin obelia mechanism mol dynamics simulation coelenterazine oxygen, bioluminescence, implicit ligand sampling, molecular dynamics simulations, oxygen binding, photoprotein formation and other aspects.COA of Formula: C26H21N3O3

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Nishihara, Ryo; Hoshino, Emi; Kakudate, Yoshiki; Suzuki, Koji; Kim, Sung-Bae published an article in 2021, the title of the article was Azide- and Dye-Conjugated Coelenterazine Analogues for Imaging Mammalian Cells.Recommanded Product: 55779-48-1 And the article contains the following content:

Coelenterazine (CTZ) is a common substrate to most marine luciferases and photoproteins. The present protocol introduces mammalian cell imaging with nine novel dye- and azide-conjugated CTZ analogs, which were synthesized by conjugating a series of fluorescent dyes or an azide group to the C-2 or C-6 position of CTZ backbone. The investigation on the optical properties revealed that azide-conjugated CTZs emit greatly selective bioluminescence (BL) to artificial luciferases (ALucs) and ca. 130 nm blue-shifted BL with Renilla luciferase variant 8.6 (RLuc8.6) in mammalian cells. The corresponding kinetic study explains that azide-conjugated CTZ exerts higher catalytic efficiency than CTZ. Nile red-conjugated CTZ completely showed red-shifted CRET spectra and characteristic BRET spectra with artificial luciferase 16 (ALuc16). The present protocol shows that the minimal spectral overlap occurs among the pairs of [Furimazine/NanoLuc], [6-N3-CTZ/ALuc26], [6-pi-OH-CTZ/RLuc8.6], and [6-N3-CTZ/RLuc8.6] because of the substrate-driven luciferase specificity or color shifts, convincing a cross talk-free multiplex bioassay platform. The present protocol introduces a new toolbox to bioassays and multiplex mol. imaging platforms for 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).Recommanded Product: 55779-48-1

The Article related to artificial luciferase (aluc®), bioluminescence, bioluminescence resonance energy transfer (bret), chemiluminescence resonance energy transfer (cret), coelenterazine (ctz), renilla luciferase (rluc) and other aspects.Recommanded Product: 55779-48-1

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On June 7, 2019, Chaloupkova, Radka; Liskova, Veronika; Toul, Martin; Markova, Klara; Sebestova, Eva; Hernychova, Lenka; Marek, Martin; Pinto, Gaspar P.; Pluskal, Daniel; Waterman, Jitka; Prokop, Zbynek; Damborsky, Jiri published an article.Category: pyrazines The title of the article was Light-emitting dehalogenases: Reconstruction of multifunctional biocatalysts. And the article contained the following:

To obtain structural insights into the emergence of biol. functions from catalytically promiscuous enzymes, we reconstructed an ancestor of catalytically distinct, but evolutionarily related, haloalkane dehalogenases (EC 3.8.1.5) and Renilla luciferase (EC 1.13.12.5). This ancestor has both hydrolase and monooxygenase activities. Its crystal structure solved to 1.39 Å resolution revealed the presence of a catalytic pentad conserved in both dehalogenase and luciferase descendants and a mol. oxygen bound in between two residues typically stabilizing a halogen anion. The differences in the conformational dynamics of the specificity-determining cap domains between the ancestral and descendant enzymes were accessed by mol. dynamics and hydrogen-deuterium exchange mass spectrometry. Stopped-flow anal. revealed that the alkyl enzyme intermediate formed in the luciferase-catalyzed reaction is trapped by blockage of a hydrolytic reaction step. A single-point mutation (Ala54Pro) adjacent to one of the catalytic residues bestowed hydrolase activity on the modern luciferase by enabling cleavage of this intermediate. Thus, a single substitution next to the catalytic pentad may enable the emergence of promiscuous activity at the enzyme class level, and ancestral reconstruction has a clear potential for obtaining multifunctional catalysts. 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 light emitting dehalogenase hydrolase monooxygenase crystal structure conformation substrate, haloalkane dehalogenase luciferase ancestor hydrolase monooxygenase crystal structure conformation and other aspects.Category: pyrazines

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Magalhaes, Carla M.; Gonzalez-Berdullas, Patricia; Duarte, Diana; Correia, Ana Salome; Rodriguez-Borges, Jose E.; Vale, Nuno; Esteves da Silva, Joaquim C. G.; Pinto da Silva, Luis published an article in 2021, the title of the article was Target-Oriented Synthesis of Marine Coelenterazine Derivatives with Anticancer Activity by Applying the Heavy-Atom Effect.Computed Properties of 55779-48-1 And the article contains the following content:

Photodynamic therapy (PDT) is an anticancer therapeutic modality with remarkable advantages over more conventional approaches. However, PDT is greatly limited by its dependence on external light sources. Given this, PDT would benefit from new systems capable of a light-free and intracellular photodynamic effect. Herein, we evaluated the heavy-atom effect as a strategy to provide anticancer activity to derivatives of coelenterazine, a chemiluminescent single-mol. widespread in marine organisms. Our results indicate that the use of the heavy-atom effect allows these mols. to generate readily available triplet states in a chemiluminescent reaction triggered by a cancer marker. Cytotoxicity assays in different cancer cell lines showed a heavy-atom-dependent anticancer activity, which increased in the substituent order of hydroxyl < chlorine < bromine. Furthermore, it was found that the magnitude of this anticancer activity is also dependent on the tumor type, being more relevant toward breast and prostate cancer. The compounds also showed moderate activity toward neuroblastoma, while showing limited activity toward colon cancer. In conclusion, the present results indicate that the application of the heavy-atom effect to marine coelenterazine could be a promising approach for the future development of new and optimized self-activating and tumor-selective sensitizers for light-free PDT. 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 coelenterazine anticancer synthesis heavy atom, cancer, chemiluminescence, coelenterazine, heavy-atom effect, photodynamic therapy, self-activating photosensitizers, triplet chemiexcitation and other aspects.Computed Properties of 55779-48-1

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Nishihara, Ryo; Suzuki, Koji; Kim, Sung-Bae; Paulmurugan, Ramasamy published an article in 2021, the title of the article was Highly Bright NIR-BRET System for Imaging Molecular Events in Live Cells.COA of Formula: C26H21N3O3 And the article contains the following content:

The present protocol demonstrates a novel mammalian cell imaging platform exerting a bioluminescence resonance energy transfer (BRET) system. This platform achieves a ∼300 nm blue-to-near IR shift of the emission (NIR-BRET) with the development of a unique coelenterazine (CTZ) derivative named BBlue2.3 and a fusion reporter protein probe named iRFP-RLuc8.6-535SG. The best NIR-BRET shift was achieved by tuning the blue emission peak of BBlue2.3 to a Soret band of the iRFP. In mammalian cells, BBlue2.3 emits light that is ∼50-fold brighter than DeepBlueC in cell imaging when combined with RLuc8.6-535SG. This NIR-BRET platform is sufficiently brighter to be used for imaging live mammalian cells at single-cell level, and also for imaging metastases in deep tissues in live mice without generating considerable autoluminescence. This unique optical platform provides the brightest NIR-BLI template that can be used for imaging a diverse group of cellular events in living subjects. 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).COA of Formula: C26H21N3O3

The Article related to live cells imaging mol events nir bret, bioluminescence imaging (bli), bioluminescence resonance energy transfer (bret), blue-to-near infrared shift, coelenterazine derivatives, metastasis and other aspects.COA of Formula: C26H21N3O3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem