Category: 3066-84-0

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 3066-84-0, is researched, SMILESS is NC(N1)=NC(NC(Br)=N2)=C2C1=O, Molecular C5H4BrN5OJournal, Article, European Journal of Pharmaceutics and Biopharmaceutics called Scaffold hopping identifies 6,8-disubstituted purines as novel anaplastic lymphoma kinase inhibitors, Author is Schluetke, Laura; Immer, Markus; Preu, Lutz; Totzke, Frank; Schaechtele, Christoph; Kubbutat, Michael H. G.; Kunick, Conrad, the main research direction is purine derivative anaplastic lymphoma kinase inhibitor; Anaplastic lymphoma kinase, ALK; EML4-ALK fusion; Gatekeeper mutation; Protein kinase inhibitor; Purine; Scaffold hopping; Solubility; Thieno[3,2-d]pyrimidine; c-Met.Safety of 8-Bromoguanine.

Rearrangements of anaplastic lymphoma kinase (ALK) are associated with several cancer diseases. Due to resistance development against existing ALK-inhibitors, new, structurally unrelated inhibitors are required. By a scaffold hopping strategy, 6,8-disubstituted purines were designed as analogs of similar ALK-inhibiting thieno[3,2-d]pyrimidines. While the new title compounds indeed inhibited ALK and several ALK mutants in submicromolar concentrations, they retained poor water solubility

This compound(8-Bromoguanine)Safety of 8-Bromoguanine was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Alkylation of nucleic acids. I. Comparison study of the methylation of ribonucleic acids in aqueous and organic solutions》. Authors are Bollack, C.; Keith, G.; Ebel, J. P..The article about the compound:8-Bromoguaninecas:3066-84-0,SMILESS:NC(N1)=NC(NC(Br)=N2)=C2C1=O).Electric Literature of C5H4BrN5O. Through the article, more information about this compound (cas:3066-84-0) is conveyed.

Methylation of ribosomal and soluble RNA (from bakers’ yeast) by Me2SO4 in dimethylformamide (I) solution gives rise to the same derivatives as the methylation in aqueous solution, namely, 7-methylguanine, 1-methyladenine, and 1-methylcytosine. Uracil is not methylated. The percentages of methylated bases formed are lower in I medium than in water. Differences in the order of reactivity of the bases are observed according to the reaction carried out in I or in water. Methylation in aqueous solution does not affect the integrity of the RNA mols., even for high methylation percentages; but, methylation in I causes a degradation of the polynucleotide chains, especially for ribosomal RNA. Methylation causes some alteration of the secondary structure of soluble RNA and this alteration increases as the methylation percentage increases.

This compound(8-Bromoguanine)Electric Literature of C5H4BrN5O was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Quality Control of 8-Bromoguanine. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 8-Bromoguanine, is researched, Molecular C5H4BrN5O, CAS is 3066-84-0, about Prediction of Interaction Energies of Substituted Hydrogen-Bonded Watson-Crick Cytosine:Guanine8X Base Pairs. Author is Xue, Chunxia; Popelier, Paul L. A..

We investigated the variation in the interaction energy between the Watson-Crick hydrogen-bonded DNA base pairs guanine and cytosine (G8X:C), where guanine is substituted in the C8 position by 37 different functional groups. Base pairs were optimized at the B3LYP/6-311+G(2d,p) level. A base pair complex containing a more strongly electron-withdrawing group remarkably forms a more stable base pair with C. Multivariate linear regression provided a quant. relationship between the interaction energies and descriptors generated by the quantum chem. topol. (QCT) approach. The descriptors were sampled from the monomers only, not the supermol. base pair complexes. A model with r2 = 0.96 and a root-mean-square (rms) value of 0.6 kJ/mol was obtained for a training set of 28 base pair complexes. The model was tested by an external test set of 9 complexes, yielding r2 = 0.99 and an rms value of 0.2 kJ/mol. The results indicated that the bonds C6=O6 and N2-H2 at the hydrogen-bonded frontier of the guanine derivatives play an important role in transmitting the substituent effects. A linear correlation between substitution energies and Hammett constants (σm) was also obtained for all 37 substituents, yielding r2 = 0.82 and an rms value of 1.2 kJ/mol. The model based on QCT descriptors can therefore be used for the prediction of the interaction energy of the base pair G8X:C, strictly based on data for the G8X monomers only.

This compound(8-Bromoguanine)Quality Control of 8-Bromoguanine was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Name: 8-Bromoguanine. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 8-Bromoguanine, is researched, Molecular C5H4BrN5O, CAS is 3066-84-0, about Polarographic investigation of halogen atom mobility in the halosubstituted components of nucleic acids. Author is Kadysh, V. P.; Kaminskii, Yu. L.; Rumyantseva, L. N.; Efimova, V. L.; Stradinsh, J. P..

Reduction potentials for a series of bromo and iodo derivatives of nucleic acid components were determined in buffered solutions (pH 1.0, concentration 5 × 10-4 M/L) in an interval of -0.5…-1.8 V. Iodo derivatives were more easily reduced (500-800 MV) than the corresponding bromo derivatives

《Polarographic investigation of halogen atom mobility in the halosubstituted components of nucleic acids》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(8-Bromoguanine)Name: 8-Bromoguanine.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Manlove, Amelia H.; McKibbin, Paige L.; Doyle, Emily L.; Majumdar, Chandrima; Hamm, Michelle L.; David, Sheila S. researched the compound: 8-Bromoguanine( cas:3066-84-0 ).Application In Synthesis of 8-Bromoguanine.They published the article 《Structure-Activity Relationships Reveal Key Features of 8-Oxoguanine: A Mismatch Detection by the MutY Glycosylase》 about this compound( cas:3066-84-0 ) in ACS Chemical Biology. Keywords: oxoguanine adenine base pair mismatch recognition MutY DNA glycosylase. We’ll tell you more about this compound (cas:3066-84-0).

Base excision repair glycosylases locate and remove damaged based in DNA with remarkable specificity. The MutY glycosylases, unusual for their excision of undamaged adenines mispaired to the oxidized base 8-oxoguanine (OG), must recognize both bases of the mispair in order to prevent promutagenic activity. Moreover, MutY must effectively find OG:A mismatches within the context of highly abundant and structurally similar T:A base-pairs. Very little is known about the factors that initiate MutY’s interaction with the substrate when it first encounters an intrahelical OG:A mispair, or about the order of recognition checkpoints. Here we used structure-activity relationships (SAR) to investigate the features that influence the in vitro measured parameters of mismatch affinity and adenine base excision efficiency by E. coli MutY. We evaluated the impacts of the same substrate alterations on MutY-mediated repair in a cellular context. Our results show that MutY relies strongly on the presence of the OG base and recognizes multiple structural features at different stages of recognition and catalysis to insure that only inappropriately mispaired adenines are excised. Notably, some OG modifications resulted in more dramatic reductions in cellular repair than in the in vitro kinetic parameters, indicating their importance for initial recognition events needed to locate the mismatch within DNA. Indeed, the initial encounter of MutY with its target base pair may rely on specific interactions with the 2-amino group of OG in the major groove, a feature that distinguishes OG:A from T:A base-pairs. These results furthermore suggest that inefficient substrate location in human MutY homolog variants may prove predictive for the early-onset colorectal cancer phenotype known as MUTYH-Associated Polyposis, or MAP.

《Structure-Activity Relationships Reveal Key Features of 8-Oxoguanine: A Mismatch Detection by the MutY Glycosylase》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(8-Bromoguanine)Application In Synthesis of 8-Bromoguanine.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 8-Bromoguanine, is researched, Molecular C5H4BrN5O, CAS is 3066-84-0, about Electronic structure of nucleotide base antimetabolite-type possible anticarcinogens. II. Monosubstituted purines, adenines, and guanines, the main research direction is electronic structure purines; purines electronic structure; adenines electronic structure; guanines electronic structure.HPLC of Formula: 3066-84-0.

Charge distributions were calculated by the authors’ (1969) semiempirical SCF-LCAO-MO method for purine, substituted in the 2-, 6-, or 8-position by F, Cl, Br, I, OH, OMe, SH, NH2, Me, or CO2H; adenine similarly substituted in the 2- or 8-position; and guanine similarly substituted in the 8-position. Substitution of CO2H in the 2-position of adenine and the 8-position of guanine affected the charge distribution of the whole mol. Other substitutions in the 8-position had little effect on the charge d. of the 9-position.

《Electronic structure of nucleotide base antimetabolite-type possible anticarcinogens. II. Monosubstituted purines, adenines, and guanines》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(8-Bromoguanine)HPLC of Formula: 3066-84-0.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Quality Control of 8-Bromoguanine. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 8-Bromoguanine, is researched, Molecular C5H4BrN5O, CAS is 3066-84-0, about Structural Basis for Promutagenicity of 8-Halogenated Guanine. Author is Koag, Myong-Chul; Min, Kyungjin; Lee, Seongmin.

8-Halogenated guanine (haloG), a major DNA adduct formed by reactive halogen species during inflammation, is a promutagenic lesion that promotes misincorporation of G opposite the lesion by various DNA polymerases. Currently, the structural basis for such misincorporation is unknown. To gain insights into the mechanism of misincorporation across haloG by polymerase, the authors determined seven x-ray structures of human DNA polymerase β (polβ) bound to DNA bearing 8-bromoguanine (BrG). The authors determined two pre-catalytic ternary complex structures of polβ with an incoming nonhydrolyzable dGTP or dCTP analog paired with templating BrG. The authors also determined five binary complex structures of polβ in complex with DNA containing BrG·C/T at post-insertion and post-extension sites. In the BrG·dGTP ternary structure, BrG adopts syn conformation and forms Hoogsteen base pairing with the incoming dGTP analog. In the BrG·dCTP ternary structure, BrG adopts anti conformation and forms Watson-Crick base pairing with the incoming dCTP analog. In addition, the authors’ polβ binary post-extension structures show Hoogsteen BrG·G base pair and Watson-Crick BrG·C base pair. Taken together, the first structures of haloG-containing DNA bound to a protein indicate that both BrG·G and BrG·C base pairs are accommodated in the active site of polβ. The authors’ structures suggest that Hoogsteen-type base pairing between G and C8-modified G could be accommodated in the active site of a DNA polymerase, promoting G to C mutation.

《Structural Basis for Promutagenicity of 8-Halogenated Guanine》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(8-Bromoguanine)Quality Control of 8-Bromoguanine.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 8-Bromoguanine, is researched, Molecular C5H4BrN5O, CAS is 3066-84-0, about Effect of adsorption kinetics on dissociation of DNA-nucleobases on gold nanoparticles under pulsed laser illumination.Application In Synthesis of 8-Bromoguanine.

Photothermal therapy is a novel approach to destroy cancer cells by an increase of temperature due to laser illumination of gold nanoparticles (GNPs) that are incorporated into the cells. Here, the authors study the decomposition of DNA nucleobases via irradiation of gold nanoparticles with ns-laser pulses. The kinetics of the adsorption and decomposition process is described by a theor. model based on the Langmuir assumptions and correlated with exptl. determined reaction rates revealing a strong influence of the nucleobase specific adsorption. Beside the four nucleobases, their brominated analogs, which are potential radiosensitizers in cancer therapy, are also investigated and show a significant modification of the decomposition rates. The fastest decomposition rates are observed for adenine, 8-bromoadenine, 8-bromoguanine and 5-bromocytosine. These results are in good agreement with the relative adsorption rates that are determined from the aggregation kinetics of the GNPs taking the effect of an inhomogeneous surface into account. For adenine and its brominated analog, the decomposition products are further analyzed by surface enhanced Raman scattering (SERS) indicating a strong fragmentation of the mols. into their smallest subunits.

Different reactions of this compound(8-Bromoguanine)Application In Synthesis of 8-Bromoguanine require different conditions, so the reaction conditions are very important.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

HPLC of Formula: 3066-84-0. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 8-Bromoguanine, is researched, Molecular C5H4BrN5O, CAS is 3066-84-0, about Flipping duplex DNA inside out: A double base-flipping reaction mechanism by Escherichia coli MutY adenine glycosylase. Author is Bernards, Andrew S.; Miller, Jamie K.; Bao, Kogan K.; Wong, Isaac.

The Escherichia coli MutY adenine glycosylase plays a critical role in repairing mismatches in DNA between adenine and the oxidatively damaged guanine base 8-oxoguanine. Crystallog. studies of the catalytic core domain of MutY show that the scissile adenine is extruded from the DNA helix to be bound in the active site of the enzyme (Guan, Y., Manuel, R. C., Arvai, A. S., Parikh, S. S., Mol, C. D., Miller, J. H., Lloyd, S., and Tainer, J. A. (1998) Nat. Struct. Biol. 5, 1058-1064). However, the structural and mechanistic bases for the recognition of the 8-oxoguanine remain poorly understood. In experiments using a single-stranded 8-bromoguanine-containing synthetic oligodeoxyribonucleotide alone and in a duplex construct mismatched to an adenine, we observed UV crosslinking between MutY and the 8-bromoguanine probe. We further observed enhanced crosslinking in the single strand experiments, suggesting that neither the duplex context nor the mismatch with adenine is required for recognition of the 8-oxoguanine moiety. Stopped-flow fluorescence studies using 2-aminopurine-containing oligodeoxyribonucleotides further revealed the sequential extrusion of the 8-oxoguanine at 108 s-1 followed by the adenine at 16 s-1. A protein isomerization step following base flipping at 1.9 s-1 was also observed and is postulated to provide addnl. stabilization of the extruded adenine thereby facilitating its capture by the active site for excision.

Different reactions of this compound(8-Bromoguanine)HPLC of Formula: 3066-84-0 require different conditions, so the reaction conditions are very important.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 8-Bromoguanine, is researched, Molecular C5H4BrN5O, CAS is 3066-84-0, about Base-modified GDP-mannose derivatives and their substrate activity towards a yeast mannosyltransferase, the main research direction is nucleobase modification GDP mannose derivative recognition mannosyltransferase Kre2p; Donor analogue; Mannosyltransferase; NDP-mannose; Substrate.Product Details of 3066-84-0.

We have previously developed a new class of inhibitors and chem. probes for glycosyltransferases (GTs) through base-modification of the sugar-nucleotide donor. The key feature of these donor analogs is the presence of an addnl. substituent at the nucleobase. To date, the application of this general concept has been limited to UDP-sugars and UDP-sugar-dependent glycosyltransferases. Herein, we report for the first time the application of our approach to a GDP-mannose-dependent mannosyltransferase (ManT). We have prepared four GDP-mannose derivatives with an addnl. substituent at either position 6 or 8 of the nucleobase. These donor analogs were recognized as donor substrates by the mannosyltransferase Kre2p from yeast, albeit with significantly lower turnover rates than the natural donor GDP-mannose. The presence of the addnl. substituent also redirected enzyme activity from glycosyl transfer to donor hydrolysis. Taken together, our results suggest that modification of the donor nucleobase is, in principle, a viable strategy for probe and inhibitor development against GDP-mannose-dependent GTs.

The article 《Base-modified GDP-mannose derivatives and their substrate activity towards a yeast mannosyltransferase》 also mentions many details about this compound(3066-84-0)Product Details of 3066-84-0, you can pay attention to it or contacet with the author([email protected]) to get more information.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem