Category: 3066-84-0

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 Guanines are a quartet’s best friend: impact of base substitutions on the kinetics and stability of tetramolecular quadruplexes, the main research direction is DNA oligodeoxyribonucleotide guanine kinetics tetramol quadruplex.Product Details of 3066-84-0.

Parallel tetramol. quadruplexes may be formed with short oligodeoxynucleotides bearing a block of three or more guanines. We analyze the properties of sequence variants of parallel quadruplexes in which each guanine of the central block was systematically substituted with a different base. Twelve types of substitutions were assessed in more than 100 different sequences. We conducted a comparative kinetic anal. of all tetramers. Electrospray mass spectrometry was used to count the number of inner cations, which is an indicator of the number of effective tetrads. In general, the presence of a single substitution has a strong deleterious impact on quadruplex stability, resulting in reduced quadruplex lifetime/thermal stability and in decreased association rate constants We demonstrate extremely large differences in the association rate constants of these quadruplexes depending on modification position and type. These results demonstrate that most guanine substitutions are deleterious to tetramol. quadruplex structure. Despite the presence of well-defined non-guanine base quartets in a number of NMR and x-ray structures, our data suggest that most non-guanine quartets do not participate favorably in structural stability, and that these quartets are formed only by virtue of the docking platform provided by neighboring G-quartets. Two notable exceptions were found with 8-bromo-guanine (X) and 6-methyl-isoxanthopterin (P) substitutions, which accelerate quadruplex formation by a factor of 10 when present at the 5′ end. The thermodn. and kinetic data compiled here are highly valuable for the design of DNA quadruplex assemblies with tunable association/dissociation properties.

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

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, Research Support, Non-U.S. Gov’t, Research Support, U.S. Gov’t, Non-P.H.S., Research Support, U.S. Gov’t, P.H.S., Biochimica et Biophysica Acta, Gene Structure and Expression called Substrate and inhibitor specificity of tRNA-guanine ribosyltransferase, Author is Farkas, Walter R.; Jacobson, K. Bruce; Katze, Jon R., the main research direction is tRNA guanine ribosyltransferase specificity reticulocyte; structure activity tRNA guanine ribosyltransferase.Computed Properties of C5H4BrN5O.

A number of compounds, including derivatives of 7-deazaguanine, pteridines, purines, pyrimidines, and antimalarials were tested as inhibitors or substrates of tRNA-guanine ribosyltransferase (EC 2.4.2.29) (I). Virtually all purines and pteridines that were inhibitors or substrates of rabbit reticulocyte I had an amino N atom at the 2-position. In addition, the 9-position and the O atom at the 6-position may be important for recognition by the enzyme. Saturation of the double bond in the cyclopentenediol moiety of queuine (II) reduced the substrate activity and II analogs that lacked the cyclopentenediol moiety, such as 7-deazaguanine and 7-aminomethyl-7-deazaguanine, were relatively poor substrates for I. Adenosine was not an inhibitor of I and neoplanocin A (an adenosine analog in which a cyclopentenediol replaced the ribose moiety) was a poor inhibitor. The incorporation of 7-aminomethyl-7-deazaguanine into the tRNA of L-M cells resulted in a novel chromatog. form of tRNAAsp, indicating that L-M cells cannot modify this queuosone precursor (in Escherichia coli) to queuosine. The specific incorporation of 7-deazaguanine and 8-azaguanine into tRNA by L-M cells also resulted in novel chromatog. forms of tRNAAsp. With intact L-M cells, I-catalyzed insertion into tRNA of II, dihydro-II, 7-aminomethyl-7-deazaguanine, or 7-deazaguanine was irreversible, whereas guanine or 8-azaguanine incorporation was reversible, suggesting that it is the substitution of C-7 for N-7 which prevents the reversible incorporation of II into tRNA.

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

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, Research Support, U.S. Gov’t, P.H.S., Journal of Immunology called Role of salvage and phosphorylation in the immunostimulatory activity of C8-substituted guanine ribonucleosides, Author is Goodman, Michael G., the main research direction is C8 substituted guanine ribonucleoside immunostimulation; purine salvage phosphorylation guanine nucleoside immunostimulation.Synthetic Route of C5H4BrN5O.

Lymphokine-like activity and selective stimulation of B cell growth is exerted by a group of synthetic ribonucleosides derivatized at C8 and exemplified by 8-bromoguanosine (8BrGuo), 8-mercaptoguanosine, and 7-methyl-8-oxoguanosine. Here, it is demonstrated that, in contrast to naturally occurring nucleosides, 8BrGuo is not a substrate for salvage by purine nucleoside phosphorylase. The base that would be produced by putative phosphorolysis, 8-bromoguanine, is biol. inactive and is not a substrate for hypoxanthine-guanine phosphoribosyltransferase. Inhibitors of purine nucleoside phosphorylase-mediated salvage fail to inhibit nucleoside-induced immunostimulation selectively. There is no direct evidence that 8BrGuo is phosphorylated by B lymphocytes. Direct enzymic phosphorylation does not seem to be essential to the mechanism of action of the nucleoside insofar as competitive inhibition of deoxycytidine kinase (an enzyme that directly phosphorylates purines as well as pyrimidines) or of deoxyguanosine kinase fails to inhibit 8BrGuo stimulation selectively. Studies with synthetic nucleosides in which 3′ and/or 5′ hydroxyl groups were irreversibly blocked, precluding their phosphorylation, demonstrated that immunol. activity can occur in the absence of 3′ and/or 5′ phosphorylation. Experiments with radiolabeled nucleosides provide no evidence to support the hypothesis that they are incorporated into cellular nucleic acid. Apparently, it is the unmetabolized nucleoside that is active and, as such, is most likely to act in a regulatory capacity.

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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 《Viruses grown in the presence of base analogs. Specific alteration of susceptibility to inactivation by radiations, mutagens, and photodyes》. Authors are Thiry, Lise.The article about the compound:8-Bromoguaninecas:3066-84-0,SMILESS:NC(N1)=NC(NC(Br)=N2)=C2C1=O).Recommanded Product: 8-Bromoguanine. Through the article, more information about this compound (cas:3066-84-0) is conveyed.

Newcastle disease (NDV) and Western equine encephalomyelitis (WEE) viruses, were grown in the presence of various base analogs, and their sensitivity to inactivation by nitrous acid, dimethyl sulfate, hydroxylamine, uv and visible light, as well as to photosensitization by several dyes was examined The slopes of the inactivation curves were compared with those obtained with normal viruses. Viruses grown in the presence of 2,6-diaminopurine or 5-aminouridine were specifically hypersensitized to nitrous acid; those grown in the presence of 6-thiopurines became sensitive to visible light. Growth in the presence of 6-azauridine, dihydrouracil, and, to a lesser degree, 6-azacytidine plus deoxycytidine, induced an increased resistance to uv light. This was paralleled by increased resistance to photosensitization by toluidine blue, neutral red, proflavine, and ethidium chloride, but not by methylene blue. An increased susceptibility to the action of the first 4 dyes was observed with viruses grown in the presence of 5-fluorouracil and 2-thiouracil at concentrations of the analogs which did not modify the viral susceptibility to uv light. Viruses formed in the presence of 8-azaguanine and 8-bromoguanine were hypersusceptible to dimethyl sulfate and methylene blue, reagents known to react preferentially with guanine. When inosine plus an inhibitor of xanthine oxidase was added to the growth medium, the progeny of infective particles was hypersusceptible to dimethyl sulfate. The results show that infectious virus particles with a modified nucleic acid were produced in the presence of the base analogs cited above. The specificity of the modifications found suggests that the analogs were incorporated per se in the nucleic acid chain of the virus.

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

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called In vitro DNA synthesis. DNA activation necessary for the reaction by liver-homogenate supernatants in compensatory hypertrophy and hepatoma. Implicated enzymic mechanisms, published in 1964, which mentions a compound: 3066-84-0, mainly applied to , Reference of 8-Bromoguanine.

cf. CA 62, 3181g. The progressive transformation of native DNA into primer DNA in the presence of rat liver homogenate supernatants previously reported has been shown not to be due to action of the DNases I and II of these supernatants, but should probably be attributed to an enzyme of the type DNA-phosphatase-exonuclease, described by Richardson, et al. (CA 60, 5810f).

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

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 3066-84-0, is researched, Molecular C5H4BrN5O, about 8-Mercaptoguanine Derivatives as Inhibitors of Dihydropteroate Synthase, the main research direction is mercaptoguanine derivative inhibitor dihydropteroate synthase crystal structure; DHPS; antibiotics; drug discovery; inhibitors; pterin; substrate-envelope hypothesis.Category: tetrahydrofurans.

Dihydropteroate synthase (DHPS) is an enzyme of the folate biosynthesis pathway, which catalyzes the formation of 7,8-dihydropteroate (DHPt) from 6-hydroxymethyl-7,8-dihydropterin pyrophosphate (DHPPP) and para-aminobenzoic acid (pABA). DHPS is the long-standing target of the sulfonamide class of antibiotics that compete with pABA. In the wake of sulfa drug resistance, targeting the structurally rigid (and more conserved) pterin site has been proposed as an alternate strategy to inhibit DHPS in wild-type and sulfa drug resistant strains. Following the work on developing pterin-site inhibitors of the adjacent enzyme 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase (HPPK), we now present derivatives of 8-mercaptoguanine, a fragment that binds weakly within both enzymes, and quantify sub-μM binding using surface plasmon resonance (SPR) to Escherichia coli DHPS (EcDHPS). Eleven ligand-bound EcDHPS crystal structures delineate the structure-activity relationship observed providing a structural framework for the rational development of novel, substrate-envelope-compliant DHPS inhibitors.

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Tetrahydrofuran – Wikipedia,
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Mishra, S. K.; Mishra, P. C. published the article 《An ab initio study of electronic structure and spectra of 8-bromoguanine: a comparative study with guanine》. Keywords: bromoguanine tautomer ab initio electronic structure fluorescence; MP2 RHF electronic structure bromoguanine; isodensity surface polarized continuum electronic structure bromoguanine.They researched the compound: 8-Bromoguanine( cas:3066-84-0 ).Formula: C5H4BrN5O. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:3066-84-0) here.

Ground state geometries of the four tautomeric forms keto-N9H, keto-N7H, enol-N9H and enol-N7H of 8-bromoguanine (8BG) were optimized using the ab initio RHF procedure employing a mixed basis set consisting of the 6-311+G* basis set for the nitrogen atom of the amino group and the bromine atom, and the 4-31G basis set for all other atoms. These calculations were followed by correlation correction of the total energy at the MP2 level using the same basis set. The different tautomeric forms of 8BG in the ground state were solvated using the isodensity surface polarized continuum model (IPCM) of the SCRF theory both at the RHF and MP2 levels. Excited states were generated employing CI among singly excited configurations (CIS) obtained using a limited window of filled and empty MOs. Formation of hydrogen-bonded complexes between 8BG and three water mols. in the ground and excited states was considered in order to account for solvent effects approx. Excited state geometry was optimized in each case for the lowest singlet excited state which was found to be of π-π* type. Vibrational frequency anal. was performed in order to ensure that the stationary points located on the potential energy surfaces by geometry optimization were min. It is found that 8BG would occur in the ground state dominantly in the keto-N7H form both at the aqueous solution-air interface and inside the bulk liquid The observed absorption and fluorescence spectra of 8BG can be explained satisfactorily considering only the keto-N7H form of the mol. The enol tautomers of 8BG do not appear to be important from the point of view of ground state properties or electronic spectra. The observed differences between the behaviors of guanine and 8BG can be easily explained on the basis of the results obtained.

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

Safety of 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 Functional groups on ‘Z’ DNA recognized by monoclonal antibodies. Author is Lee, Jeremy S.; Woodsworth, Mary L.; Latimer, Laura J. P..

Both brominated poly[d(GC)] and poly[d(Gm5C), where m5C = 5-methylcytidylate] form stable left-handed Z-DNA structures at physiol. ionic strengths. These 2 antigens were used to prepare monoclonal antibodies from immunized mice. The specificity of the antibodies was studied in detail with a solid-phase radioimmune assay as well as by competition experiments Both immunogens produced several relatively nonspecific antibodies, but 2 types of very specific antibody were also distinguished. The 1st binds poly[d(Gm5C)] but not brominated poly[d(GC)], whereas the other has the opposite specificity and will only bind the brominated polymer. In these studies, monoclonal antibodies are used as model proteins for Z DNA functional group recognition.

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

Goodman, Michael G.; Weigle, William O. published an article about the compound: 8-Bromoguanine( cas:3066-84-0,SMILESS:NC(N1)=NC(NC(Br)=N2)=C2C1=O ).Quality Control of 8-Bromoguanine. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:3066-84-0) through the article.

8-Bromoguanosine (88rGuo), a low mol.weight nucleoside derivative that rapidly traverses the lymphocyte membrane to the interior of the cell, is an extremely potent inducer of Ig production by B lymphocytes. 88Br-cGMP and other cGMP analogs are at best weak inducers of Ig secretion, being >2 orders of magnitude less effective (per mol. taken up) then 8BrGuo. Incubation of lymphocytes with 88rGuo fails to elevate their intracellular concentrations of cGMP. Moreover, at equimolar concentrations, underivatized cGMP actually antagonizes the induction of antibody production by 8BrGuo. These data, in concert with observations that many lymphocyte activators fail to alter cGMP content, that many agents that elevate cGMP fail to induce Ig synthesis, and that some cGMP-elevating agents even inhibit it, suggest that the induction of proliferation in B cells, is not primarily dependent upon cGMP. A simple nucleoside derivative is described, the use of which should prove to be a powerful probe for investigating the triggering mechanisms underlying the proliferative and differentiative B lymphocyte pathways at the mol. level.

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

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 8-Bromoguanine( cas:3066-84-0 ) is researched.Computed Properties of C5H4BrN5O.Abdou, Ibrahim M.; Boone, Edna K.; Cao, Huachuan; Crummie, Cheryl; Schuster, Gary B. published the article 《Transport and reactions of radical cations in DNA: Steric and energetic control of reactivity》 about this compound( cas:3066-84-0 ) in Research on Chemical Intermediates. Keywords: radical cation transport reaction DNA. Let’s learn more about this compound (cas:3066-84-0).

A series of DNA oligomers was prepared that contain an anthraquinone group (AQ) linked to a 5′-terminus and have 8-methylguanine (MG) or 8-bromoguanine (BG) substituted for G at various positions. Irradiation of the AQ injects a radical cation into the oligonucleotide, which migrates through the DNA and reacts primarily at Gn sites where n = 2 or 3. Substitution with MG, which has an oxidation potential (EOX) slightly below G, traps the migrating radical cation, substitution with BG, which has an EOX above G, does not. However, both MG and BG affect the relative reactivity of the guanines in Gn steps. Moreover, a (G)3 sequence has a much smaller effect on the efficiency of radical cation migration than does MG, which demonstrates that the EOX of G in the (G)3 sequence is above that of MG. These findings show that the EOX of the base controls the efficiency of radical cation transport and that steric effects influence the relative reactivity of G in Gn sequences.

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