Category: Pyrazines

Nishihara, Ryo et al. published their research in Methods in Molecular Biology (New York, NY, United States) in 2021 |CAS: 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

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

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Chaloupkova, Radka et al. published their research in ACS Catalysis in 2019 |CAS: 55779-48-1

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

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

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Magalhaes, Carla M. et al. published their research in Biomedicines in 2021 |CAS: 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

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 et al. published their research in Methods in Molecular Biology (New York, NY, United States) in 2021 |CAS: 55779-48-1

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

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

Bai, Meng’s team published research in Chemistry of Natural Compounds in 2022-03-31 | 2873-36-1

Chemistry of Natural Compounds published new progress about Antibacterial agents. 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Quality Control of 2873-36-1.

Bai, Meng; He, Jia-Li; Gao, Cheng-Hai; Xiong, Fei-Xiang; Yang, Ya; Yang, Wei-Chan; Liu, Yong-Hong; Zhang, Wen-Fei published the artcile< Secondary Metabolites from Bacillus thuringiensis HS66>, Quality Control of 2873-36-1, the main research area is Bacillus Helicoverpa larva secondary metabolite.

In order to search for the bioactive chem. constituents from the B. thuringiensis, 12 compounds were isolated from the EtOAc extract of the B. thuringiensis. The isolated compoundswere identified as cyclo(L-Pro-L-Tyr) (1) [6], cyclo(Pro-Phe) (2) [7], cyclo(L-Pro-L-Phe) (3) [8], cyclo(Pro-Val) (4) [9], cyclo(L-Pro-L-Met) (5) [10], cyclo((S)-Pro-(R)-Ile) (6) [11], cyclo(L-Pro-L-Leu) (7) [12], N-(2-hydroxyphenyl)acetamide (8) [13], uracil (9) [13], 2-phenylacetamide (10) [14], anthranilic acid (11) [15], and S-(4-hydroxyphenyl)lactic acid (12) [16]. The growth inhibition activity against newly hatched larvae of Helicoverpa armigera Hubner was tested. Compounds 1-3, 6, 7, and 10 showed growth inhibition activity against newly hatched larvae of Helicoverpa armigera Hubner with IC 50 values ranging from 50 to 200 μg/mL. Azadirachtin was used as pos. control with the IC50 value of 25 μg/mL.

Chemistry of Natural Compounds published new progress about Antibacterial agents. 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Quality Control of 2873-36-1.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Liu, Rui’s team published research in Chemistry of Natural Compounds in 2020-05-31 | 2873-36-1

Chemistry of Natural Compounds published new progress about Antitumor agents. 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Safety of (3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione.

Liu, Rui; Li, Hui; Yang, Junxia published the artcile< A 2,5-Diketopiperazines from Aspergillus sp., the Endophytic Fungus of Astragalus membranaceus and their Anticancer Assay>, Safety of (3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione, the main research area is diketopiperazine anticancer Aspergillus endophytic fungus Astragalus cancer.

2,5-Diketopiperazines are cyclodipeptides obtained by the condensation of two α-amino acids. In our ongoing screening for biol. active secondary metabolites from endophytic fungi, we investigated metabolites produced by the endophytic fungus Aspergillus sp. isolated from roots of Astragalus membranaceus, a Chinese medicinal plant of the loess plateau of China. We have continued investigating endophytes from this biotope, since previous investigations have shown that a particularly high proportion of endophytes from plants from the Hengshan Mountains, China, were biol. active. This prompted us to carry out a secondary metabolites studies on this fungus, which resulted in the isolation of eight 2,5-diketopiperazines. We herein report on the isolation, structure, and anticancer properties of these compounds The fungal strain AR-17-2 was isolated from the roots of A. membranaceus collected in the Hengshan Mountains, China, on August, 2017. Subfraction B2 was further separated by HPLC with H2O-MeOH (2:5) to give compounds 1 (24.1 mg) and 2 (12.6 mg). Subfraction B3 was chromatographed on a Sephadex LH-20 column eluting with methanol to afford compound 3 (38 mg). Subfraction B4 was chromatographed over a silica gel column eluting with petroleum ether-Et acetate (50:1) and then subjected to PTLC to yield compound 4 (15.5 mg). The bioactive Fr. C was separated by column chromatog. on silica gel with a gradient of Et acetate in petroleum ether to give five subfractions (Subfrs. C1-5). Subfraction C2 that eluted with methanol was separated by semipreparative reversed-phase HPLC (H2O-MeOH, 1:4, 2.5 mL/min) to yield compounds 5 (9 mg), 6 (10.7 mg) and 7 (8.3 mg). Compound 8 (12 mg) were obtained from Subfr. C3 after separation with Sephadex LH-20 by MeOH-CHCl3 (1:1). These eight compounds were elucidated resp. as cyclo-(Pro-Gly) (1), cyclo-(Pro-Leu) (2), cyclo-(Pro-Ile) (3), cyclo-(Pro-Vla) (4), cyclo-(Phe-Gly) (5), cyclo-(Phe-Ala) (6), cyclo-(Phe-Tyr) (7), and cyclo-(Phe-Pro) (8) by comparison of their spectral data with the reported data in the literature.

Chemistry of Natural Compounds published new progress about Antitumor agents. 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Safety of (3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Jinendiran, Sekar’s team published research in Scientific Reports in 2020-12-31 | 2873-36-1

Scientific Reports published new progress about Apoptosis. 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, COA of Formula: C11H18N2O2.

Jinendiran, Sekar; Teng, Weilin; Dahms, Hans-Uwe; Liu, Wangta; Ponnusamy, Vinoth Kumar; Chiu, Charles Chien-Chih; Kumar, B. S. Dileep; Sivakumar, Natesan published the artcile< Induction of mitochondria-mediated apoptosis and suppression of tumor growth in zebrafish xenograft model by cyclic dipeptides identified from Exiguobacterium acetylicum>, COA of Formula: C11H18N2O2, the main research area is mitochondria apoptosis tumor growth zebrafish xenograft dipeptide Exiguobacterium acetylicum.

Colorectal cancer is the most common type of gastrointestinal cancers with poor survival and limited therapeutic options. In this study, four structurally different cyclic dipeptides (or diketopiperazine) were isolated and identified as cyclo (L-Pro-L-Leu), cyclo (L-Pro-L-Val), cyclo (L-Pro-L-Phe) and cyclo (L-Pro-L-Tyr) from the Et acetate extract in the cell-free filtrate of Exiguobacterium acetylicum S01. The anticancer potential of identified DKPs on colorectal cancer HT-29 cells in vitro and in vivo zebrafish xenograft model was evaluated. The MTT (3-(4, 5-dimethylthiazol-2yl)-2, 5-diphenyltetrazolium bromide) assay showed that four DKPs exhibited significant inhibition of HT-29 cells viability in a dose-dependent manner whereas there were no cytotoxic effects on normal mouse fibroblast 3T3 cells. Also, we observed that all DKPs induce early and late apoptotic cell death in HT-29 cells. Moreover, the expression levels of apoptotic (cytochrome-c, caspase-3 and Bid) and anti-apoptotic (Bcl-2) markers were up- and down-regulated in HT-29 cells in response to DKPs treatments. Furthermore, these four DKPs remarkably inhibited the tumor progression in a zebrafish xenograft model within a nonlethal dose range. Overall, our findings suggest that cyclic dipeptides derived from E. acetylicum S01 could be promising chemopreventive/ therapeutic candidates against cancer.

Scientific Reports published new progress about Apoptosis. 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, COA of Formula: C11H18N2O2.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Zhang, Hua’s team published research in Natural Product Research in 2020 | 2873-36-1

Natural Product Research published new progress about Diketopiperazines Role: BSU (Biological Study, Unclassified), NPO (Natural Product Occurrence), PAC (Pharmacological Activity), PRP (Properties), PUR (Purification or Recovery), BIOL (Biological Study), OCCU (Occurrence), PREP (Preparation). 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Safety of (3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione.

Zhang, Hua; Lai, Wei; Guan, Zhuo-Bin; Liao, Xiao-Jian; Zhao, Bing-Xin; Xu, Shi-Hai published the artcile< A new thiodiketopiperzaine from the marine sponge Tedania sp.>, Safety of (3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione, the main research area is diketopiperzaine isolation structure sponge; Sponge; Tedania sp.; thiodiketopiperzaine.

A new thiodiketopiperzaine, tedanizaine A (I), together with 6 known ones, were isolated from the marine sponge Tedania sp. Their structures were determined by spectroscopic analyses. The absolute configuration of I was established by ECD calculation I was the 2nd example of thiodiketopiperazine bearing a thiazolidine unit. Cytotoxic activities of I were also evaluated.

Natural Product Research published new progress about Diketopiperazines Role: BSU (Biological Study, Unclassified), NPO (Natural Product Occurrence), PAC (Pharmacological Activity), PRP (Properties), PUR (Purification or Recovery), BIOL (Biological Study), OCCU (Occurrence), PREP (Preparation). 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Safety of (3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Li, Yuan’s team published research in Journal of Functional Foods in 2020-09-30 | 2873-36-1

Journal of Functional Foods published new progress about Alcohols Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, HPLC of Formula: 2873-36-1.

Li, Yuan; Yuan, Siqi; Yong, Xihao; zhao, Ting; Liu, Jun published the artcile< Research progress on small peptides in Chinese Baijiu>, HPLC of Formula: 2873-36-1, the main research area is review peptide research progress Baijiu.

A review. Chinese Baijiu is a distilled spirit with >100 health promoting compounds produced by diverse microorganisms through the fermentation process. Compared with other distilled spirits in the world, various small peptide compounds in Chinese Baijiu endow it with unparalleled health benefits. In this review, we summarize the small peptides that have been found in Chinese Baijiu, and we provide the unique physiol. and pharmacol. activity of these small peptides by reviewing recent research papers. Existing problems in current research on small peptides in Chinese Baijiu, and the direction and significance of future research are also discussed.

Journal of Functional Foods published new progress about Alcohols Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, HPLC of Formula: 2873-36-1.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Wang, Fengwu’s team published research in Natural Product Research in 2021 | 2873-36-1

Natural Product Research published new progress about Alzheimer disease. 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Formula: C11H18N2O2.

Wang, Fengwu; Wang, Feng; Chen, Tiejun published the artcile< Secondary metabolites of Galactomyces geotrichum from Laminaria japonica ameliorate cognitive deficits and brain oxidative stress in D-galactose induced Alzheimer′s disease mouse model>, Formula: C11H18N2O2, the main research area is Alzheimer’s disease cognitive deficits brain oxidative stress Galactomyces Laminaria; Alzheimer’s disease; Galactomyces geotrichum; cognitive deficits; oxidative damages; secondary metabolites; toxicological evaluation.

Accumulating evidences have shown the beneficial effects of natural products for Alzheimer′s disease (AD) treatment. The present study was designed to investigate the neuroprotective effects of secondary metabolites of Galactomyces geotrichum (SMGG) on D-galactose induced AD mice. SMGG was extracted and its toxicol. evaluation was conducted. To explore the neuroprotective mechanism responsible for anti-AD activity of SMGG, spatial learning and memory behavioral, oxidative stress levels, acetylcholinesterase and choline acetyltransferase activity assays were employed. The AD mice received SMGG treatment exhibited significant improvement in cognitive performance, enhanced antioxidant capacity, decreased acetylcholinesterase activity and increased choline acetyltransferase activity. Meanwhile, SMGG had no toxicity and seven compounds were separated from it: 7,8-dimethyl-iso-alloxazine, 1-methyl-3-benzyl-6-(4-hydroxybenzyl)-2,5-piperzainedione, cyclo-(Phe-Pro), cyclo-(Leu-Pro), cyclo-(Pro-Gly), cyclo-(Gly-Leu) and uracil, resp. Overall, these data suggested that SMGG protects the brain against D-galactose induced cognitive impairment, oxidative damages and acetylcholine content decrease in AD mice.

Natural Product Research published new progress about Alzheimer disease. 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Formula: C11H18N2O2.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem