関: 8-azaguanine

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/05/20 16:47:01」(JST)

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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]

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

2-Amino-6-hydroxy-8-azapurine
2-Amino-6-oxy-8-azapurine
5-Amino-1,4-dihydro-7H-1,2,3-triazolo(4,5-d)pyrimidin-7-one
5-Amino-1,6-dihydro-7H-v-triazolo(4,5-d)pyrimidin-7-one
5-Amino-1H-triazolo(4,5-d)pyrimidin-7-ol
5-Amino-1H-v-triazolo(d)pyrimidin-7-ol
5-Amino-1H-(1,2,3)Triazolo(4,5-d)pyrimidin-7-ol
5-Amino-7-hydroxy-1H-v-triazolo(d)pyrimidine
7H-1,2,3-Triazolo(4,5-d)pyrimidin-7-one, 5-amino-1,4-dihydro- (9CI)
7H-1,2,3-Triazolo(4,5-d)pyrimidinone, 5-amino-1,4-dihydro-
7H-v-Triazolo(4,5-d)pyrimidin-7-one, 5-amino-1,6-dihydro-
8 AG
8azaG
Azaguanine

Azaguanine-8
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-

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

References

^ "Azaguanine - Compound Summary (Descriptors)". National Center for Biotechnology Information. 27 March 2005. Retrieved 2009-03-03.
^ ^a ^b "8-azaguanine". Mondofacto. 12 December 1998. Retrieved 2009-03-03.
^ ^a ^b http://www.chemindustry.com/chemicals/747854.html Retrieved on 2009-03-03.
^ "8-AZAGUANINE". ChemicalLAND21.com. Retrieved 2009-03-03.
^ 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.
^ ^a ^b 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. PMID 14363328.
^ Timmis, G.M.; Williams, Donald Charles (1967). "Chemotherapy of Cancer: the Antimetabolite Approach: The Antimetabolite Approach". University of Michigan: Butterworths: 36.
^ http://www.chemcas.com/msds/cas/msds137/134-58-7.asp Retrieved on 2009-03-03.
^ "Azaguanine - Compound Summary (Synonyms)". National Center for Biotechnology Information. 27 March 2005. Retrieved 2009-03-03.

External links

Digital renderings of the molecule
Some derivatives and similar molecules
Web-based 3D viewer with the molecule
"CAS: 134-58-7" on ChemCAS
"Azaguanine" on the Merck Index
"Azaguanine" (CID 8646) on PubChem

English Journal

Identification of Function and Mechanistic Insights of Guanine Deaminase from Nitrosomonas europaea: Role of the C-terminal Loop in Catalysis.

Bitra A, Hussain B, Tanwar AS, Anand R.AbstractABSTRACT. NE0047 from Nitrosomonas europaea has been annotated as a zinc dependent deaminase, however, the substrate specificity was unknown because of low structural similarity and sequence identity compared to other family members. In this study, the function of NE0047 was established as a guanine deaminase (catalytic efficiency 1.2 x 10<5> M<-1>sec<-1>), exhibiting secondary activity towards ammeline. The structure of NE0047 in presence of the substrate analog 8-azaguanine was also determined to a resolution of 1.9 Å. NE0047 crystallized with a homodimer in asymmetric unit. It was found that the extreme nine amino acid C-terminal loop forms an active site flap; in one monomer the flap is in the closed conformation and in the other in the open conformation with this loop region exposed to the solvent. Calorimetric data obtained using the full length version of the enzyme fits to a sequential binding model, thus supporting a cooperative mode of ligand occupancy. Whereas, the mutant form of the enzyme (∆C) with the deletion of extreme nine amino acids follows an independent model of ligand occupancy. In addition, the ∆C mutant also does not exhibit any enzyme activity. Therefore, we propose that the progress of the reaction is communicated via changes in conformation of the C-terminal flap and the closed form of the enzyme is the catalytically active form, while the open form allows for product release. The catalytic mechanism of deamination was also investigated and it was found that the mutagenesis of the highly conserved active site residues Glu79 and Glu143 resulted in complete loss of activity and it was concluded that they facilitate the reaction by serving as proton shuttles.
Biochemistry.Biochemistry.2013 Apr 4. [Epub ahead of print]
ABSTRACT. NE0047 from Nitrosomonas europaea has been annotated as a zinc dependent deaminase, however, the substrate specificity was unknown because of low structural similarity and sequence identity compared to other family members. In this study, the function of NE0047 was established as a guanine
PMID 23557066

Solution structures of purine base analogues 6-chloroguanine, 8-azaguanine and allopurinol.

Gogia S, Puranik M.Sourcea National Centre for Biological Sciences , GKVK Campus, Bellary Road , Bangalore , 560065 , India.
Journal of biomolecular structure & dynamics.J Biomol Struct Dyn.2013 Feb 5. [Epub ahead of print]
Analogues of purine bases are highly relevant in the biological context and have been implicated as drug molecules for therapy against a number of diseases. Additionally, these molecules have been implicated to have a role in the prebiotic RNA world. However, experimental data on the structures of t
PMID 23384120

Japanese Journal

The Achievement of Shuttle Vector Techniques in Mammalian Cell Mutation Research

Genes and environment : the official journal of the Japanese Environmental Mutagen Society 35(4), 93-98, 2013-11-20
NAID 10031196750

Design, synthesis and evaluation of antitumor and antiviral activities of 5-amino-1H-〔1,2,3〕triazolo〔 4,5-d〕pyrimidin-7(6H)-ones(8-azaguanines) and 7-amino-1H-〔1,2,3〕triazolo〔4,5-d〕-pyrimidin-5(4H)-ones (8-azaisoguanines)

Heterocycles 76(1), 605-616, 2008-09-03
NAID 40016208596

Synthesis and Antiviral and Antineoplastic Activities of Some Novel Carbocyclic Guanosine Analogues with a Cyclobutane Ring

Chemical & pharmaceutical bulletin 47(9), 1314-1317, 1999-09-15
NAID 110003617421

「アザグアニン」

8-Azaguanine
Names
	IUPAC names 5-amino-2,3-dihydrotriazolo[4,5-d]pyrimidin-7-one;; 5-amino-1,4-dihydro-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one;; 3-amino-2,4,7,8,9-pentazabicyclo[4.3.0]nona-1,3,6-trien-5-one
Identifiers
CAS Number	134-58-7 ;
3D model (Jmol)	Interactive image;
ChemSpider	8325 ;
ECHA InfoCard	100.004.681
PubChem CID	8646;
RTECS number	XZ6157000
UNII	Q150359I72 ;
	InChI 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) Key: LPXQRXLUHJKZIE-UHFFFAOYSA-N ; 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 ;
	SMILES O=C\2\N=C(/N=C1\C/2=N/NN1)N ;
Properties
Chemical formula	C4H4N6O
Molar mass	152.12 g·mol−1
Appearance	white to off-white crystalline powder
Density	2.64 g/cm³
Melting point	> 300 °C (decomp.)
Solubility in water	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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	Infobox references