関: azaguanine

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/03/01 22:07:29」(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. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8646#Descriptors. Retrieved 2009-03-03.
^ ^a ^b "8-azaguanine". Mondofacto. 12 December 1998. http://www.mondofacto.com/facts/dictionary?azaguanine. Retrieved 2009-03-03.
^ ^a ^b http://www.chemindustry.com/chemicals/747854.html Retrieved on 2009-03-03.
^ "8-AZAGUANINE". ChemicalLAND21.com. http://chemicalland21.com/lifescience/phar/8-AZAGUANINE.htm. 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". Blood 10 (5): 482–92. PMID 14363328. http://bloodjournal.hematologylibrary.org/cgi/reprint/10/5/482.pdf
^ Timmis, G.M.; Williams, Donald Charles (1967). Chemotherapy of Cancer: the Antimetabolite Approach: The Antimetabolite Approach. University of Michigan: Butterworths. p. 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. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8646&ncount=73#Synonyms. 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

Study of the interaction between 8-azaguanine and bovine serum albumin using optical spectroscopy and molecular modeling methods.

Gong QL, Hu XG, Fang GY, Li XH.SourceCollege of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 325035, China.
Journal of molecular modeling.2011 May 4. [Epub ahead of print]
The interaction between 8-azaguanine (8-Azan) and bovine serum albumin (BSA) in Tris-HCl buffer solutions at pH?7.4 was investigated by means of fluorescence and ultraviolet-visible (UV-Vis) spectroscopy. At 298?K and 310?K, at a wavelength of excitation (λ (ex)) of 282?nm, the fluorescence int
PMID 21541747

Metabolic engineering and classic selection of the yeast Candida famata (Candida flareri) for construction of strains with enhanced riboflavin production.

Dmytruk KV, Yatsyshyn VY, Sybirna NO, Fedorovych DV, Sibirny AA.SourceDepartment of Molecular Genetics and Biotechnology, Institute of Cell Biology, NAS of Ukraine, Drahomanov Street 14/16, Lviv 79005, Ukraine.
Metabolic engineering.2011 Jan;13(1):82-8. Epub 2010 Oct 30.
Currently, the mutant of the flavinogenic yeast Candida famata dep8 isolated by classic mutagenesis and selection is used for industrial riboflavin production. Here we report on construction of a riboflavin overproducing strain of C. famata using a combination of random mutagenesis based on the sele
PMID 21040798

Japanese Journal

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)

Islam Rafiqul,Ashida Noriyuki,Nagamatsu Tomohisa
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

BLANCO Jose M,CAAMANO Olga,FERNANDEZ Franco,GARCIA-MERA Xerardo,HERGUETA Antonio R,LOPEZ Carmen,RODRIGUEZ-BORGES Jose E,BALZARINI Jan,De CLERCQ Eric
Chemical & pharmaceutical bulletin 47(9), 1314-1317, 1999-09-15
… Cyclobutyl nucleoside analogues containing guanine and 8-azaguanine (compounds 5-10) were perpared from (1R, cis)-3-aminomethyl-2,2-dimethylcyclobutylmethanol (1). …
NAID 110003617421

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リンク元	「8-アザグアニン」
関連記事	「azaguanine」

「8-アザグアニン」

8-Azaguanine
	IUPAC name 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
PubChem	8646
ChemSpider	8325
UNII	Q150359I72
ChEMBL	CHEMBL374107
RTECS number	XZ6157000
Jmol-3D images	Image 1
	SMILES O=C\2\N=C(/N=C1\C/2=N/NN1)N ;
	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 ;
Properties
Molecular formula	C4H4N6O
Molar mass	152.11 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
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references