Category: 3066-84-0

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.Yoneyama, Toshie; Wilson, Lisa M.; Hatakeyama, Kazuyuki published the article 《GTP Cyclohydrolase I Feedback Regulatory Protein-Dependent and -Independent Inhibitors of GTP Cyclohydrolase I》 about this compound( cas:3066-84-0 ) in Archives of Biochemistry and Biophysics. Keywords: GTP cyclohydrolase I inhibitor GFRP protein guanine derivative; feedback regulatory protein inhibitor GTP cyclohydrolase I. Let’s learn more about this compound (cas:3066-84-0).

GTP cyclohydrolase I feedback regulatory protein (GFRP) mediates the feedback inhibition of GTP cyclohydrolase I activity by (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin (BH4) through protein complex formation. Since guanine and BH4 have a common pyrimidine ring structure, we examined the inhibitory effect of guanine and its analogs on the enzyme activity. Guanine, 8-hydroxyguanine, 8-methylguanine, and 8-bromoguanine inhibited the enzyme activity in a GFRP-dependent and pH-dependent manner and induced complex formation between GTP cyclohydrolase I and GFRP. The type of inhibition by this group is a mixed type. All these properties were shared with BH4. In striking contrast, inhibition by 8-azaguanine and 8-mercaptoguanine was GFRP-independent and pH-independent. The type of inhibition by 8-azaguanine and 8-mercaptoguanine was a competitive type. The two compounds did not induce complex formation between the enzyme and GFRP. These results demonstrate that guanine compounds of the first group bind to the BH4-binding site of the GTP cyclohydrolase I/GFRP complex, whereas 8-azaguanine and 8-mercaptoguanine bind to the active site of the enzyme. Finally, the possible implications in Lesch-Nyhan syndrome and Parkinson diseases of the inhibition of GTP cyclohydrolase I by guanine and 8-hydroxyguanine are discussed. (c) 2001 Academic Press.

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Category: tetrahydrofurans. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 8-Bromoguanine, is researched, Molecular C5H4BrN5O, CAS is 3066-84-0, about Exploring the chemical space around 8-mercaptoguanine as a route to new inhibitors of the folate biosynthesis enzyme HPPK. Author is Chhabra, Sandeep; Barlow, Nicholas; Dolezal, Olan; Hattarki, Meghan K.; Newman, Janet; Peat, Thomas S.; Graham, Bim; Swarbrick, James D..

As the second essential enzyme of the folate biosynthetic pathway, the potential antimicrobial target, HPPK (6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase), catalyzes the Mg2+-dependant transfer of pyrophosphate from the cofactor (ATP) to the substrate, 6-hydroxymethyl-7,8-dihydropterin. Recently, we showed that 8-mercaptoguanine (8-MG) bound at the substrate site (KD ∼ 13 μM), inhibited the S. aureus enzyme (SaHPPK) (IC50 ∼ 41 μM) and determined the structure of the SaHPPK/8-MG complex. Here we present the synthesis of a series of guanine derivatives, together with their HPPK binding affinities, as determined by SPR and ITC anal. The binding mode of the most potent was investigated using 2D NMR spectroscopy and x-ray crystallog. The results indicate, firstly, that the SH group of 8-MG makes a significant contribution to the free energy of binding. Secondly, direct N9 substitution, or tautomerization arising from N7 substitution in some cases, leads to a dramatic reduction in affinity due to loss of a critical N9-H···Val46 hydrogen bond, combined with the limited space available around the N9 position. The water-filled pocket under the N7 position is significantly more tolerant of substitution, with a hydroxyl Et 8-MG derivative attached to N7 (compound 21a) exhibiting an affinity for the apo enzyme comparable to the parent compound (KD ∼ 12 μM). In contrast to 8-MG, however, 21a displays competitive binding with the ATP cofactor, as judged by NMR and SPR anal. The 1.85 Å x-ray structure of the SaHPPK/21a complex confirms that extension from the N7 position towards the Mg2+-binding site, which affords the only tractable route out from the pterin-binding pocket. Promising strategies for the creation of more potent binders might therefore include the introduction of groups capable of interacting with the Mg2+ centers or Mg2+-binding residues, as well as the development of bitopic inhibitors featuring 8-MG linked to a moiety targeting the ATP cofactor binding site.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Nucleosides and nucleotides. XXX. Syntheses of 8-substituted guanosine derivatives》. Authors are Ikehara, Morio; Muneyama, Kei.The article about the compound:8-Bromoguaninecas:3066-84-0,SMILESS:NC(N1)=NC(NC(Br)=N2)=C2C1=O).Computed Properties of C5H4BrN5O. Through the article, more information about this compound (cas:3066-84-0) is conveyed.

cf. CA 64, 14255f. 8-Bromoguanosine (I) was converted to 8-mercaptoguanosine by the method of Holmes and Robins (CA 60, 14584c), and was methylated with methyl iodide to afford 8-methylthioguanosine (II). In addition, 8-ethylthioguanosine was obtained directly by reaction of I with ethyl mercaptide in ethanol. II was oxidized either with N-chlorosuccinimide or with H2O2 (H2O2, in limited amount, being preferable) to afford 8-(methylsulfonyl)guanosine (III). When III was heated at 80° in 0.1N HCl 4 hrs., 8-methylsulfonylguanine (IV) (but not an N-oxide derivative) was obtained. Treatment of III with 0.1N NaOH at 100° 3 hrs. also gave IV. When III was kept at 30° 40 hrs. in dimethyl sulfoxide with excess Na tert-butoxide, a substance having λ (H)+ 256, 284 mμ; λ(OH)- 286 mμ was obtained, accompanied by a small amount of IV. The former compound contained S and D-ribose moieties, and it was deduced from its uv properties that the guanosine ring in III had been cleaved. Its absorption could be explained if a bathochromic shift of approx. 10-20 mμ, which is generally observed by the substitution of a methyl sulfonyl group at the 8-position of guanosine, was added to the absorption spectra of 4-aminoimidazolecarboxamide 1-p-riboside (λ(H+) 267, 240 mμ; λ(OH-) 267 mμ). The pKa value of III (8.3) is much higher than that of guanosine (9.2-9.5). The easy dissociation of N’-H of III would render the pyrimidine ring more susceptible to the nucleophilic attack of tert-butoxide. Under similar reaction conditions guanosine did not react with tert-butoxide. When III was treated with Na methoxide in methanol at 130-50°, 8-methoxyguanosine was obtained, the structure of which was confirmed by comparison with a sample obtained from I. 8-Dimethylaminoguanosine was prepared by heating I with dimethylamine in methanol at 120-30° 5 hrs. It is concluded that nucleophilic substitution occurred smoothly in I, as expected in the case of aromatic halo compound activated by ο- or p-electron attracting groups. However, in the case of III the strong electron-attracting nature of the methylsulfonyl group at position 8 caused a nucleophilic attack on N1 or N3, and the subsequent cleavage of the pyrimidine ring. Moreover, acidic hydrolysis easily cleaved III at the glycosidic linkage, whereas 8-hydroxypurine D-ribonucleoside is resistant to such cleavage. 14 references.

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Quality Control of 8-Bromoguanine. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 8-Bromoguanine, is researched, Molecular C5H4BrN5O, CAS is 3066-84-0, about Electronic spectra of 8-bromoguanine and 8-bromoadenine. Author is Pandey, K. S.; Mishra, P. C..

Absorption and fluorescence spectra of oxygenated and UV-irradiated aqueous solutions of 8-bromoguanine (BG) and 8-bromoadenine (BA), and pH effect on the spectra were studied. Each of BG and BA seem to have an asym. double-well ground state, like the parent mols. guanine and adenine. A qual. comparison of BG and BA with guanine and adenine in these respects was made. BG is much less affected by oxygenation and UV irradiation than is guanine. BA is affected by such treatments, but to a smaller extent than adenine. The mechanism of interaction of oxygen with the mols. under UV irradiation and the possible significance of the results is discussed.

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Product Details of 3066-84-0. 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 Development of antischistosomal agents: inhibitors of hypoxanthine-guanine phosphoribosyltransferase. Author is Jadhav, Arun L.; Sirossian, Shahrokh.

Derivatives of purines and 5-phosphoribosyl 1-pyrophosphate (PRPP), substrates for purine salvage enzymes, were tested for their ability to inhibit hypoxanthine-guanine phosphoribosyltransferase (HPRT, E.C. 2.4.2.8) isolated from Schistosoma mansoni in vitro. The parasite enzyme exhibited different kinetic characteristics than the human enzyme. The C2- and C6-substituted purine derivatives, as well as PRPP-polyamine complexes, were found to be active against the enzyme. An intact purine ring appeared to be necessary for the activity against the hypoxanthine-dependent reactions mediated by the parasite enzyme, since benzimidazoles, quinolines, and triazoles were found to be inactive. Addnl., it appeared that PRPP-polyamine complexes which inhibit the PRPP-dependent reaction may provide a novel approach to new chemotherapeutics agents for schistosomiasis.

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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 The two faces of the guanyl radical: molecular context and behavior, published in 2021, which mentions a compound: 3066-84-0, mainly applied to review guanyl radical two face mol context behavior; DNA; G-quadruplex; guanine; guanine radical cation; guanyl radical; oligonucleotides; oxidation; reactive oxygen species (ROS); tautomerism; time-resolved spectroscopies, Safety of 8-Bromoguanine.

A review. The guanyl radical or neutral guanine radical G(-H)• results from the loss of a hydrogen atom (H•) or an electron/proton (e-/H+) couple from the guanine structures (G). The guanyl radical exists in two tautomeric forms. As the modes of formation of the two tautomers, their relationship and reactivity at the nucleoside level are subjects of intense research and are discussed in a holistic manner, including time-resolved spectroscopies, product studies, and relevant theor. calculations Particular attention is given to the one-electron oxidation of the GC pair and the complex mechanism of the deprotonation vs. hydration step of GC•+ pair. The role of the two G(-H)• tautomers in single- and double-stranded oligonucleotides and the G-quadruplex, the supramol. arrangement that attracts interest for its biol. consequences, are considered. The importance of biomarkers of guanine DNA damage is also addressed.

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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 Electronic structure of nucleotide-base antimetabolite-type potential anticarcinogens. II. Monosubstituted purines, adenines, and guanines, the main research direction is electron d purines pyrimidines; purines pyrimidines electron d; pyrimidines purines electron d.COA of Formula: C5H4BrN5O.

The π electron ds. of monosubstituted (F, Cl, Br, I, OH, OMe, SH, NH2, Me, CO2H) pyrimidines, uracils, thymines, and cytosines were calculated using the Pariser-Parr-Pople SCF-LCAO-MO method. The SCF electron d. of all the monosubstituted pyrimidines (the elements of the P(SCF) diagonal matrix) are given. While most substituents change the electron d. distribution of the mol. only at the substitution site or its immediate vicinity, the CO2H group causes change in the whole substituted mol. In some cases a correlation was established between the electronic structure of the compound and its anticarcinogenic activity.

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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 Structure-activity relationships for the binding of ligands to xanthine or guanine phosphoribosyltransferase from Toxoplasma gondii, the main research direction is phosphoribosyltransferase xanthine guanine structure activity Toxoplasma.Name: 8-Bromoguanine.

Preliminary characterization of Toxoplasma gondii phosphoribosyltransferase activity towards purine nucleobases indicates that there are at least two enzymes present in these parasites. One enzyme uses hypoxanthine, guanine, and xanthine as substrates, while a second enzyme uses only adenine. Furthermore, competition experiments using the four possible substrates suggest that there may be a third enzyme that uses xanthine. Therefore, sixty-eight purine analogs and thirteen related derivatives were evaluated as ligands of T. gondii phosphoribosyltransferase, using xanthine or guanine as substrates, by examining their ability to inhibit these reactions in vitro. Inhibition was quantified by determining apparent Ki values for compounds that inhibited these activities by greater than 10% at a concentration of 0.9 mM. On the basis of these data, a structure-activity relation for the binding of ligands to these enzymes was formulated using hypoxanthine (6-oxopurine) as a reference compound It was concluded that the following structural features of purine analogs are required or strongly preferred for binding to both enzymes: (1) a pyrrole-type nitrogen (lactam form) at the 1-position: (2) a methine (=CH-), a pyridine type nitrogen (=N-), or an exocyclic amine or oxo group at the 2-position; (3) no exocyclic substituents at the 3-position; (4) an exocyclic oxo or thio group in the one or thione tautomeric form at the 6-position; (5) a pyridine-type nitrogen (=N-) or a methine group at the 7-position; (6) a methine group at the 8-position; (7) a pyrrole-type nitrogen or a carbon at the 9-position; and (8) no exocyclic substituents at the 9-position. These findings provide the basis for the rational design of addnl. ligands of hypoxanthine, guanine, and xanthine phosphoribosyltransferase activities in T. gondii.

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Tetrahydrofuran – Wikipedia,
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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, Biochemistry called Guanine phosphoribosyltransferase from Escherichia coli. Specificity and properties, Author is Miller, Richard L.; Ramsey, Gwendolyn A.; Krenitsky, Thomas A.; Elion, Gertrude B., the main research direction is guanine phosphoribosyltransferase purine substrate; hypoxanthine guanine phosphoribosyltransferase.Name: 8-Bromoguanine.

The specificity and properties of a novel guanine phosphoribosyltransferase of E. coli were studied and compared to those of the hypoxanthine-guanine phosphoribosyltransferase from other sources. The structural requirements for binding of purines to this enzyme were explored by the determination of the Ki values for 100 purines and purine analogs. The most effective binding occurred when the purine contained an oxo or SH group in the 6 position and an NH2 or OH group in the 2 position. Unlike the hypoxanthine-guanine phosphoribosyltransferase from other sources, this enzyme bound hypoxanthine 67 times less effectively than guanine and 4 times less effectively than xanthine. Rates of nucleotide formation from a number of purines and purine analogs were also determined The enzyme had a pH optimum from 7.4 to 8.2. From secondary double-reciprocal plots derived from an initial velocity anal., the Km values were 0.037mM for guanine and 0.33mM for 5-phosphoribosyl 1-pyrophosphate. The enzyme was sensitive to inhibition by p-chloromercuribenzoate, and this inhibition could be reversed by either dithiothreitol or β-mercaptoethanol. The apparent activation energy with guanine as substrate was 12,800 cal/mole below 23° and 3370 cal/mole above 23°. Using isoelec. focusing, the guanine phosphoribosyltransferase had an apparent pI of 5.50, while the pI of a 2nd enzyme which was specific for hypoxanthine was 4.8.

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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.Lukina, Maria V.; Popov, Alexander V.; Koval, Vladimir V.; Vorobjev, Yuri N.; Fedorova, Olga S.; Zharkov, Dmitry O. researched the compound: 8-Bromoguanine( cas:3066-84-0 ).Electric Literature of C5H4BrN5O.They published the article 《DNA damage processing by human 8-oxoguanine-DNA glycosylase mutants with the occluded active site》 about this compound( cas:3066-84-0 ) in Journal of Biological Chemistry. Keywords: oxoguanineDNA glycosylase mutant DNA damage processing active site plasticity; 8-Oxoguanine; Abasic Site; DNA Damage; DNA Repair; Enzyme Kinetics; Enzyme Mutation; Molecular Modeling; OGG1; Presteady-state Kinetics; Substrate Recognition. We’ll tell you more about this compound (cas:3066-84-0).

8-Oxoguanine-DNA glycosylase (OGG1) removes pre-mutagenic lesion 8-oxoguanine (8-oxo-G) from DNA and then nicks the nascent abasic (apurinic/apyrimidinic) site by β-elimination. Although the structure of OGG1 bound to damaged DNA is known, the dynamic aspects of 8-oxo-G recognition are not well understood. To comprehend the mechanisms of substrate recognition and processing, the authors constructed OGG1 mutants with the active site occluded by replacement of Cys-253, which forms a wall of the base-binding pocket, with bulky Leu or Ile residues. The conformational dynamics of OGG1 mutants were characterized by single-turnover kinetics and stopped-flow kinetics with fluorescent detection. Addnl., the conformational mobility of wild-type and the mutant OGG1 substrate complex was assessed using mol. dynamics simulations. Although pocket occlusion distorted the active site and greatly decreased the catalytic activity of OGG1, it did not fully prevent processing of 8-oxo-G and apurinic/apyrimidinic sites. Both mutants were notably stimulated in the presence of free 8-bromoguanine, indicating that this base could bind to the distorted OGG1 and facilitate β-elimination. The results agreed with the concept of enzyme plasticity, suggesting that the active site of OGG1 is flexible enough to compensate partially for distortions caused by mutation.

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Tetrahydrofuran – Wikipedia,
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