8-Azaguanine

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8-Azaguanine
8-azaguanine.png
Names
IUPAC names
5-amino-2,3-dihydrotriazolo[4,5-d]pyrimidin-7-one; [1]
5-amino-1,4-dihydro-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one; [2]
3-amino-2,4,7,8,9-pentazabicyclo[4.3.0]nona-1,3,6-trien-5-one [3]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.681 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-148-1
PubChem CID
RTECS number
  • XZ6157000
UNII
  • InChI=1S/C4H4N6O/c5-4-6-2-1(3(11)7-4)8-10-9-2/h(H4,5,6,7,8,9,10,11) Yes check.svgY
    Key: LPXQRXLUHJKZIE-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H4N6O/c5-4-6-2-1(3(11)7-4)8-10-9-2/h(H4,5,6,7,8,9,10,11)
    Key: LPXQRXLUHJKZIE-UHFFFAOYAO
  • C12=NNNC1=NC(=NC2=O)N
Properties
C4H4N6O
Molar mass 152.117 g·mol−1
Appearancewhite to off-white crystalline powder [4]
Density 2.64 g/cm3
Melting point > 300 °C (decomp.)
Insoluble
Hazards
Flash point 129.1 °C (264.4 °F; 402.2 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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8-Azaguanine is a purine analog with the chemical formula C4H4N6O. It has been widely studied for its biological activity. [5] It shows antineoplastic activity and has been used in the treatment of acute leukemia. [2]

Contents

Use in chemotherapy

The compound closely resembles guanine and appears to be competitive with it in the metabolism of living organisms. [6] It has been shown to cause retardation of some malignant neoplasms when administered to tumors in animals. [6] 8-Azaguanine was the first purine analogue discovered to inhibit experimental tumors in mice. [7]

Synonyms

* Sources: [3] [8] [9]

Related Research Articles

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A base pair (bp) is a fundamental unit of double-stranded nucleic acids consisting of two nucleobases bound to each other by hydrogen bonds. They form the building blocks of the DNA double helix and contribute to the folded structure of both DNA and RNA. Dictated by specific hydrogen bonding patterns, "Watson–Crick" base pairs allow the DNA helix to maintain a regular helical structure that is subtly dependent on its nucleotide sequence. The complementary nature of this based-paired structure provides a redundant copy of the genetic information encoded within each strand of DNA. The regular structure and data redundancy provided by the DNA double helix make DNA well suited to the storage of genetic information, while base-pairing between DNA and incoming nucleotides provides the mechanism through which DNA polymerase replicates DNA and RNA polymerase transcribes DNA into RNA. Many DNA-binding proteins can recognize specific base-pairing patterns that identify particular regulatory regions of genes.

<span class="mw-page-title-main">Guanine</span> Chemical compound of DNA and RNA

Guanine is one of the four main nucleobases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine. In DNA, guanine is paired with cytosine. The guanine nucleoside is called guanosine.

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Nucleotides are organic molecules composed of a nitrogenous base, a pentose sugar and a phosphate. They serve as monomeric units of the nucleic acid polymers – deoxyribonucleic acid (DNA) and ribonucleic acid (RNA), both of which are essential biomolecules within all life-forms on Earth. Nucleotides are obtained in the diet and are also synthesized from common nutrients by the liver.

<span class="mw-page-title-main">Purine</span> Heterocyclic aromatic organic compound

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Pyrimidine is an aromatic, heterocyclic, organic compound similar to pyridine. One of the three diazines, it has nitrogen atoms at positions 1 and 3 in the ring. The other diazines are pyrazine and pyridazine.

<span class="mw-page-title-main">Nucleobase</span> Nitrogen-containing biological compounds that form nucleosides

Nucleobases are nitrogen-containing biological compounds that form nucleosides, which, in turn, are components of nucleotides, with all of these monomers constituting the basic building blocks of nucleic acids. The ability of nucleobases to form base pairs and to stack one upon another leads directly to long-chain helical structures such as ribonucleic acid (RNA) and deoxyribonucleic acid (DNA). Five nucleobases—adenine (A), cytosine (C), guanine (G), thymine (T), and uracil (U)—are called primary or canonical. They function as the fundamental units of the genetic code, with the bases A, G, C, and T being found in DNA while A, G, C, and U are found in RNA. Thymine and uracil are distinguished by merely the presence or absence of a methyl group on the fifth carbon (C5) of these heterocyclic six-membered rings. In addition, some viruses have aminoadenine (Z) instead of adenine. It differs in having an extra amine group, creating a more stable bond to thymine.

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<span class="mw-page-title-main">2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine</span> Chemical compound

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2-Amino-5-formylamino-6-(5-phospho-<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-ribosylamino)pyrimidin-4(3<i>H</i>)-one Chemical compound

2-Amino-5-formylamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one is a metabolite in the riboflavin biosynthesis pathway. It is formed from GTP by the enzyme GTP cyclohydrolase IIa which catalyzes the hydrolysis of the 8,9 bond in the guanine group and loss of the beta and gamma phosphate groups. The molecule is deformylated by 2-amino-5-formylamino-6-ribosylaminopyrimidin-4(3H)-one 5'-monophosphate deformylase as the second step in the archaeal riboflavin biosynthetic pathway.

References

  1. "Azaguanine - Compound Summary (Descriptors)". National Center for Biotechnology Information. 27 March 2005. Retrieved 2009-03-03.
  2. 1 2 "8-azaguanine". Mondofacto. 12 December 1998. Archived from the original on 2010-02-15. Retrieved 2009-03-03.
  3. 1 2 "134-58-7, CAS Number: 3546-41-6". www.chemindustry.com. Archived from the original on 2011-07-16. Retrieved 2009-03-03.
  4. "8-AZAGUANINE". ChemicalLAND21.com. Retrieved 2009-03-03.
  5. Tong, George L.; Lee, William W.; Goodman, Leon; Frederiksen, Sune (1965). "Synthesis of some 2′-deoxyribosides of 8-azaadenine". Archives of Biochemistry and Biophysics. University of California: Elsevier. 112 (1): 76. doi:10.1016/0003-9861(65)90012-3.
  6. 1 2 Colsky, J.; Meiselas, E.L.; Rosen, J.S.; Schulman, I. (1955). "Response of patients with leukemia to 8-azaguanine" (PDF). Blood. 10 (5): 482–92. doi: 10.1182/blood.V10.5.482.482 . PMID   14363328.
  7. Timmis, G.M.; Williams, Donald Charles (1967). "Chemotherapy of Cancer: the Antimetabolite Approach". Butterworths. University of Michigan: 36.
  8. "MSDS 7H-v-Triazolo(4,5-d)pyrimidin-7-one,5-amino-1,6-dihydro- CAS 134-58-7 MSDS * 8 AG * 5-Amino-1,6-dihydro-7H-v-triazolo(4,5-d)pyrimidin-7-one * 5-Amino-1,4-dihydro-7H-1,2,3-triazolo(4,5-d)pyrimidin-7-one * 5-Amino-7-hydroxy-1H-v-triazolo(d)pyrimidine * 5-Amino-1H-v-triazolo(d)pyrimidin-7-ol * Azaguanine * Azaguanine-8 * 8-Azaguanine * Azan * AZG * B-28 * Guanazol * Guanazolo * NSC-749 * Pathocidin * Pathocidine * SF-337 * SK 1150 * Triazologuanine * v-Triazolo(4,5-d)pyrimidin-7-ol, 5-amino- * 7H-1,2,3-Triazolo(4,5-d)pyrimidin-7-one, 5-amino-1,4-dihydro-". www.chemcas.com. Retrieved 2009-03-03.
  9. "Azaguanine - Compound Summary (Synonyms)". National Center for Biotechnology Information. 27 March 2005. Retrieved 2009-03-03.