Açúcares e Nucleobases da Espinha Dorsal

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6-Amino-2-iodopurine is a purine derivative that is used to study hypoxanthines. It can be converted to 2-chloroadenine, which has been shown to cause damage to cells in tissue culture. 6-Amino-2-iodopurine has also been shown to cause sarcomatous transformation of skin cells and the formation of 2-chloroadenosine and 2-aminoadenosine. These compounds are toxic and have been found in damaged DNA. 6-Amino-2-iodopurine also has substituents on the purines, which are damaged when they react with DNA.

Applications 6-Amino-5-nitrouracil (cas# 3346-22-3) is a compound useful in organic synthesis. References Graves, A., et al.: J. Mol. Biol., 377, 914 (2008),

Applications Used in the preparation of pyrrolotriazines.

6-Amino-1-benzyluracil is a triethyl orthoformate that reacts with an aldehyde to form an imine. This reaction is known as alkylation. The imine reacts with benzamidine to form an anticancer drug called lumazine, which has been shown to be effective against cancer cells. 6-Amino-1-benzyluracil had low solubility in water and was therefore refluxed with ethyl acetoacetate and elemental acetoacetate. 6-Amino-1-benzyluracil is insoluble in the organic phase and can be removed by filtration.

2'-Deoxy-5-fluoro-5'-o-[hydroxy(tetradecyloxy)phosphoryl]uridine is a pyrimidine nucleoside that is the active metabolite of 5-fluorouracil. It is an anticancer agent that inhibits tumor cells by blocking their ability to synthesize DNA. 2'-Deoxy-5-fluoro-5'-o-[hydroxy(tetradecyloxy)phosphoryl]uridine has been shown to be safe and effective in clinical trials in mice, but it has not yet been tested in humans. This drug may cause nausea and vomiting when administered intraperitoneally, which may limit its use as an anticancer agent.

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2’-C-Methyl-5-fluorouridine is a fine chemical that is used as a versatile building block for the synthesis of various complex compounds. It is also used as a reaction component in the synthesis of research chemicals and speciality chemicals. 2’-C-Methyl-5-fluorouridine is an important intermediate in organic chemistry and has many applications, such as being a reaction component in the synthesis of pharmaceuticals, agrochemicals, dyes, and perfumes.

Adenine phosphate is a molecule that acts as a regulator of endogenous adenosine. It has been shown to inhibit the growth of skin cells in tissue culture and to be effective against influenza virus and other viruses when used in combination with pyridoxine hydrochloride. The molecular weight of adenine phosphate is 314.2 g/mol, corresponding to two nitrogen atoms and four phosphorus atoms. Adenine phosphate is an oxidized form of adenosine triphosphate (ATP) with one phosphate group removed from the molecule. This irreversible oxidation occurs when ATP is exposed to the environment, for example, during tissue culture or viral infection. The effective dose for treating cancer has not yet been determined; however, doses of up to 5 mg/kg are not toxic to mice.

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Purine nucleobase; component of nucleic acids and coenzymes

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2-Bromopurine is an analog of the naturally occurring purine, adenine. It has been shown to be a potent inhibitor of DNA synthesis in both bacterial and mammalian cells. 2-Bromopurine has been shown to react with hydrophobic amino acids, such as methionine and tryptophan, in proteins to form crosslinks that inhibit protein synthesis. 2-Bromopurine is effective against tuberculosis and has been used for the treatment of this disease since the 1950s.

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Methyl Green: fluorescent dye, DNA stain, assesses cell viability via microscopy/flow cytometry, peaks at 633/677 nm, light-sensitive storage.

Sofosbuvir is a nucleotide analog that inhibits the hepatitis C virus (HCV) RNA-dependent RNA polymerase and prevents viral replication. Sofosbuvir is an inhibitor of HCV NS5B protein, which is essential for viral replication. Sofosbuvir has been shown to be effective against influenza A virus and picornaviruses in vitro, but not against other RNA viruses such as poliovirus and rhinovirus. It has also been shown to inhibit cancer cell growth in vitro and to inhibit the proliferation of replicating cells in culture. Sofosbuvir has been found to have good oral bioavailability, with a half-life of approximately 2 hours in humans, and can be taken with or without food.

8-Aza-2,6-diaminopurine sulfate (1:x) is a sulfate salt that is soluble in water. The molecular mass of the compound is 581.10 g/mol and it has a molecular formula of C5H7N3O4S. The crystal structure of the compound consists of an asymmetric unit containing one molecule. The 8-aza-2,6-diaminopurine monohydrate salt has a solubility of 1 g/100 mL in water at 25°C. It also has a melting point of 190°C and a boiling point of 340°C.

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5-Fluoro-1-(4-chlorobenzyl)-uracil is a prodrug that is metabolized to 5-fluorouracol (5FU) in the liver. The drug has been shown to be effective against sarcoma and tumors of mice. The drug was injected subcutaneously into the tumor site, which resulted in a significant reduction of tumor size. Injection of 5-fluoro-1-(4-chlorobenzyl)-uracil also inhibited the growth of tumors in mice by inhibiting DNA synthesis and cell division. It was found that the drug was not toxic to normal tissue cells, suggesting that it may be suitable for use as an anticancer agent.

Cy5 Tyramide, a red dye, amplifies signals in HRP-based immunoassays and nucleic acid hybridization.

CY3-SE: reactive dye for amino-groups in proteins, peptides, DNA. Excitation: 555 nm, Emission: 570 nm.

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6-n-Heptylmercaptopurine is a liquid crystal that has imbricated moieties and pyranosides. It can undergo phase transitions from the isotropic to the mesophase state. 6-n-Heptylmercaptopurine is thermotropic, which means it changes its temperature with respect to the temperature of its surroundings. 6-n-Heptylmercaptopurine is also a bilayer, long chain molecule and it has a monoclinic crystal structure. It is also intercalated in DNA, which may be due to its purine structure.

Purine analog; fluorescent probe; kinase inhibitor; mutagenic

Stability Unstable at Room Temperature Applications 7-Methyl-6-thioguanosine Chloride is a compound useful in organic synthesis.

5-Fluoro-2',3'-Dideoxy-3'-Fluorouridine (FdFO) is a nucleoside analog that inhibits the synthesis of thymine and leads to the production of uracil. FdFO is not metabolized by the liver and can be used for the treatment of hepatitis. FdFO has been shown to inhibit HIV replication in cell cultures. It binds to the noncompetitive site on DNA polymerase, preventing RNA synthesis and inhibiting DNA replication. 5-Fluoro-2',3'-Dideoxy-3'-Fluorouridine also acts as a competitive inhibitor against deoxyuridylate, which is needed in order to form thymidylate.

6-Fluorothymine is a fluorine-containing compound that is a structural analogue of thymine. It is an antiviral agent and a precursor to other drugs, such as benzoylated 6-fluoropurines. The chemical yields are high, with the use of refluxing conditions. 6-Fluorothymine has structural similarities to amines and can be synthesized by reacting primary amines with fluorine gas at elevated temperatures. 6-Fluorothymine also has vibrational frequencies in the range of infrared light, which can be used for identification purposes.

3-Methyladenine is a glycosylase that cleaves the glycosidic bond between the 3rd and 4th carbon of the ribose ring of the nucleotide 3-methyladenine. It also has synergistic effects with other agents that induce autophagy, such as rapamycin, and increases the expression of a response element in mouse monoclonal antibody. 3-Methyladenine inhibits growth factor-β1 and neuronal death by inducing apoptosis in cells overexpressing nuclear DNA polymerase. This drug is also used to study apoptosis by using a model system.

CY2-SE (Cyanine2 Succinimidyl Ester) is a dye for the labeling of amino-groups in oligonucleotides, peptides, and proteins (Excitation:492 nm, Emission: 510 nm

Cy3, a fluorescent dye, is used for labeling biomolecules and imaging in biological research.

1-(2,3-Dihydroxypropyl)-3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione (theophylline) is a bronchodilator and anti-inflammatory agent. It is used to treat asthma and other respiratory conditions. Theophylline is structurally similar to caffeine and theobromine and has been shown to have a similar effect on the heart and blood vessels as these stimulants. It also stimulates the central nervous system in a manner similar to that of theobromine. Theophylline has shown some benefit in congestive heart failure patients but has not been proven effective for treating high blood pressure or fibrillation.

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Applications Isotope labelled 5,6-Dihydrothymine is a derivative of Thymine, a nucleobase in the nucleic acid of DNA. 5,6-Dihydrothymine is a radiolysis product of DNA. References Hubbard, K. et al.: Biochemistry, 28, 4382 (1989); Cadet, J. et al.: Int. J. Rad. Biol. Rel. Stud. Phys. Chem. Med., 39, 119 (1981);

2-Chloro-9-methyl-9H-purine is an unmethylated, reactive molecule that can be synthesized through a reaction between piperidine and nucleophilic chloride. It has shown kinetic and kinetic properties, which are reversible reactions that depend on the concentration of reactants. 2-Chloro-9-methyl-9H-purine is able to produce anions such as hydroxide ions when it reacts with anions such as chloride or hydroxide ion. This compound is also able to form heterocycles with other molecules in the presence of methylsulphonyl hydroxide.

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1,3,6-Trimethyl-5-iodouracil (TMIU) is a nucleophile that reacts with electrophiles. It is used as a precursor to the synthesis of other compounds, such as 1,3,6-trimethyluracil. TMIU can be synthesized by chlorinating 6-methyluracil in the presence of a proton source. The reaction time for this synthesis is typically between 30 minutes and 3 hours. The yields are typically around 50%. Carbocations that form during this reaction are an analogous to methyl cations in nucleophilic substitutions. Bromination of TMIU has also been shown to produce bromo derivatives.

CY5-SE triethylamine salt (Fluorolink Cy5 triethanolamine salt) is a hydrophilic amine-reactive fluorescent probe (Ex=649 nm; Em=670 nm).

6-Chloro-9-benzylpurine is a purine derivative that has been shown to possess potential as an antiinflammatory agent. This compound reacts in a short time, with high efficiency and few byproducts, and has the potential for use in pharmaceuticals. 6-Chloro-9-benzylpurine is a potent inhibitor of histamine release from mast cells, which may be due to its ability to inhibit the production of inflammatory cytokines. It has also been shown to reduce the number of T cells which have infiltrated the skin in an animal model with psoriasis. 6-Chloro-9-benzylpurine is an anion that can be synthesized using acrylonitrile and butyl acrylate, and it has been found in nature. The reaction mechanism of 6-chloro 9-benzylpurine involves nucleophilic attack on the c-h bond followed by elimination of chloride ion and

Applications Used in therapy of mouse leukemia L1210 in combinations with Nebularin and Nitrobenzylthioinosine 5’-monophosphate. References Anderson, C., et al.: Neurosci. Lett., 219, 191 (1996), Allay, J., et al.: Nat. Med., 4, 1136 (1998),

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6-Azathymine is a compound that belongs to the group of amides. It has shown bacterial strain specificity and can be used for the treatment of infections caused by Group P2 bacteria. 6-Azathymine inhibits the enzyme activity of toll-like receptor, which is responsible for immune response and inflammation. It also has been shown to inhibit photosynthetic activity in plants. This drug may also be useful for eye disorders, such as retinitis pigmentosa and macular degeneration. 6-Azathymine is activated by hydroxyl groups, which leads to its toxicity at high concentrations.

8-Methoxymethyl-1-methyl-3-(2-methylpropyl) xanthine (8MMX) is an intracellular calcium ion chelator that inhibits enzyme activity in the cyclic nucleotide phosphodiesterase enzyme family. 8MMX has been shown to be a potent inhibitor of both cyclic nucleotide phosphodiesterases and cyclic nucleotide phosphodiesterase isoenzymes. 8MMX has been shown to inhibit bladder contractility and improve bladder function in animal models. It also reduces the incidence of papillary muscle rupture, which can lead to heart failure, and improves ventricular function by increasing the rate of relaxation of the left ventricle. 8MMX is a potential treatment for pulmonary hypertension, which is caused by increased concentrations of intracellular calcium ions.

Applications Labelled Guanine (G836000). Guanine is on one of the five nucleobases incorporated into biological nucleic acids. Guanine, along with adenine and cytosine, is present in both DNA and RNA, whereas thymine is usually seen only in DNA, and uracil only in RNA. References Geslain, R., et al.: J. Biol. Chem., 284, 27760 (2009), Manini, P., et al.: Toxicol. Lett., 190, 41 (2009), Gong, B., et al.: Biochem., 48, 11961 (2009), Sugimoto, M., et al.: J. Agric. Food Chem., 58, 374 (2010),