Açúcares e Nucleobases da Espinha Dorsal

Impurity Aciclovir EP Impurity B
Applications Guanine is 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. Aciclovir EP Impurity B.
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);

Applications Reagent used in the preparation of Antithyroid agents.
References Toropov, A., et al.: Eur. J. Med. Chem., 45, 3581 (2010), Daniels, C., et al>.: J. Bacteriol., 192, 2169 (2010), Castillo-Garit, J., et al.: Eur. J. Pharm. Sci., 39, 30 (2010),

Applications N-Succinyl-5-aminoimidazole-4-carboxamide Ribose 5’-Phosphate is a metabolite of Purine. Since adenosine is a potent inhibitor of neuronal function, depressing the release of several excitatory transmitters and causing direct hyperpolarization of neurons, it was possible that the symptoms seen in adenylosuccinate lyase (ASase) deficient patients could reflect an interference of succinylpurines with neurotransmission.
References Gollub, E.G., et al.: J. Bacteriol., 78, 320 (1959), Srivastava, P.C., et al.: J. Med. Chem., 17, 1207 (1974),

Applications Nucleoside derivatives of 5-substituted uracil have been explored for their potential application as anti-viral agents and in the treatment of tumors.
References Ressner, E.C., et al.: J. Med. Chem., 19, 1, 194 (1976)

Applications An intermediate in the preparation of thymidine derivatives
References el Kouni, M., et al.: Biochem. Pharmacol., 51, 1687 (1996),

Applications 4-Thiouracil is a derivative of Uracil (U801000), which is a nitrogenous base in RNA nucleic acid. 4-Thiouracil is used for tagging in cell type-specific RNA isolation from intact complex tissues.
References Miller, M., et al.: Nat. Methods, 6, 439 (2009); Seth, P., et al.: J. Med. Chem., 53, 8309 (2010); Cui, H., et al.: Eur. J. Med. Chem., 45, 5140 (2010);

Applications Modified nucleotide, essential for normal cell growth in some bacterial species. This compound is also able to chelate several metal ions.
References Ikeuchi, Y., et al.: Mol. Cell, 21, 97 (2006), Odani, A., et al.: J. Inorg. Biochem., 101, 727 (2007), Wohlgamuth-Benedum, J., et al.: J. Biol. Chem., 284, 23947 (2009),

Applications A useful intermediate in the synthesis of 1-substituted adenines.
References Laufer, S., et al.: J. Med. Chem., 48, 710 (2005), Lambertucci, C., et al.: Bioorg. Med. Chem., 17, 2812 (2009),

Applications 6-Benzyl-2-thiouracil (cas# 6336-50-1) is a useful research chemical.

Impurity Zidovudine EP Impurity C
Applications Thymine (Zidovudine EP Impurity C) is a nitrogenous base component in the nucleic acid of DNA.
References Keum, Y., et al.: App. Microbiol. Biotechnol., 80, 863 (2008); Redzic, Z., et al.: Neurochem. Res., 34, 566 (2009); Lanevskij, K., et al.: J. Pharm. Sci., 98, 122 (2009); Rajendar, B., et al.: Bioorg. Med. Chem., 17, 351 (2009);

Applications 9-(2-Propenyl)adenine is an N-substituted purine used in the preparation of mesityl dihydroisoxazolyl homo-N-nucleosides.
References Thalassitis, A. et al.: Bioorg. Med. Chem. Lett., 19, 6433 (2009); Chiacchio, U. et al.: Tetrahedron, 60, 441 (2004)

Applications N6-(2-Isopentenyl)adenine can be used in biological study for cytokinins stimulated expression of stress-related proteins and transcripts in Arabidopsis thaliana with isopentenyltransferase overexpression.
References Skalak, J., et al.: J. Exp. Bot., 67, 2861-2873 (2016)

Applications 1,3-Diethyl-5-nitroso-6-aminouracil (cas# 89073-60-9) is a compound useful in organic synthesis.

Stability Hygroscopic
Applications Adenine Hemisulfate can be one of the factors that influence in vitro growth and shoot multiplication of pomegranate. It can be used in biological study along with varied levels of sucrose, light intensity, and MS medium hydrogen ion concentration where those factors can all significantly influence multiplication and growth of Punica granatum shoots.
References Singh, P., & Patel, R., M.: Bioscan, 9, 1031-1035 (2014)

Applications 6-​Methyl-​2-​thiouracil is a derivative of methylthiouracil (M330710), a competitive inhibitor of Nitric Oxide Synthase (NOS). Potential anti-inflammatory agent.
References Palumbo, A. et al.: Biochem. Bioph. Res. Co. 282, 793(2001), Ku, S. et al.: Toxicol. App. Pharmacol., 288, 374 (2015);

Applications 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);

Applications 5-Hydroxymethyluracil (cas# 4433-40-3) is a compound useful in organic synthesis.

Stability Hygroscopic
Applications 5-Hydroxymethyl-2’-deoxyuridine acts as a biomarker for the diagnosis for oxidative stress in humans. Used as a diagnostic to for propensitiy for the development of breast cancer.
References McAnulty, L. et al.: App. Physiol. Nutr. Metab., 36, 976 (2011); Djuric Z. et al.: Cancer Epidemiol. Biomarkers. Prev., 10, 147 (2001); Frenkel, K. et al.: 7, 49, (1998);

Applications 5,6-Dimethylthiouracil is a heterocyclic building block.

Applications Protected guanine
References Tretyakova, N., et al.: Chem. Res. Toxicol., 20, 284 (2007), Rana, S., et al.: Bioorg. Med. Chem. Lett., 19, 670 (2009),

Applications Guanidinoacetic Acid is an important marker for renal failure, in kidney transplantation, and for the renal metabolic activity.
References Zugno, A., et al.: Neurochem. Res., 33, 1804 (2008), Debray, F., et al.: Neurol., 71, 44 (2008), da Silva, R., et al.: Am. J. Physiol., 296, E256 (2009),

5-Hydroxymethyluridine is a nucleoside that is synthesized from uridine. It has shown to be effective in the treatment of inflammatory diseases, such as rheumatoid arthritis, and also has antiviral activity against herpes simplex virus. 5-Hydroxymethyluridine has been shown to have a high affinity for hydrophilic interaction chromatography (HIC) and can be used to purify glycosylases. This compound can also inhibit the formation of cancer cells by inhibiting the transcriptional activity of RNA polymerase II. 5-Hydroxymethyluridine has been found to demethylate DNA while maintaining its ability to bind with DNA-dependent RNA polymerase II. This process is catalyzed by glycosylases and hydroxylases that are found in the body.

9-Deazaguanine is an analog of guanine, which has inhibitory properties. It reacts with the hydrogen bond of the enzyme and prevents its reaction with a substrate. 9-Deazaguanine binds to the target enzymes trifluoroacetic acid (TFA) and hydrogen bond interactions with water molecules. The reaction mechanism is based on the competitive inhibition of TFA, which is an important enzyme in DNA synthesis. 9-Deazaguanine inhibits the growth of k562 cells by inhibiting protein synthesis at specific sites in the ribosome. 9-Deazaguanine also shows inhibitory properties against autoimmune diseases and infectious diseases because it inhibits immune system reactions that are mediated by antibodies and T cells.

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.

5-Propyl-2-thiouracil (PTU) is a drug used in the treatment of various types of cancer. It is a chemical analogue of thiouracil, but has a different mechanism of action. PTU inhibits the production of tropomyosin, which leads to inhibition of transcriptional regulation and expression of protein genes. PTU also blocks the hydrogen bond between the amino acid glutamine and deoxyribose phosphate backbone, thereby inhibiting translation. Clinical studies have shown that PTU is effective in treating cardiac hypertrophy, renal proximal tubule cells and clinical nephropathy. The use of PTU as a chemotherapeutic agent for cancer treatment has been limited due to its toxicity to animals.

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Eniluracil is a prodrug of 5-fluorouracil, which is an anticancer drug. It is not active when taken orally and must be hydrolyzed by esterases in the stomach to produce 5-fluorouracil. The x-ray diffraction data for eniluracil was collected from untreated human serum samples. Eniluracil has been shown to have matrix effects on solid tumours in mice, leading to increased antitumor activity. This compound also inhibits the enzyme dihydropyrimidine dehydrogenase, which leads to decreased levels of diphosphate nucleotides and accumulation of dinucleotide phosphate. Enlargement of the tumor is also inhibited by this drug due to its ability to inhibit DNA replication and transcription.

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.

8-Bromoguanine is a nucleoside analog drug that is used as an antileukemic agent. It is a synthetic derivative of guanine and has been shown to inhibit the growth of leukemic cells by interfering with the synthesis of DNA. 8-Bromoguanine has also been shown to be reactive with eosinophil peroxidase and other electron-rich substances, which may be due to its hydroxyl group. The analytical method for 8-bromoguanine includes fluorescence spectroscopy, high pressure liquid chromatography (HPLC), and thin layer chromatography (TLC). Chemical diversity studies have shown that 8-bromoguanine can react with glycosylase or hydroxy groups, forming reaction products.