8-Azaguanine

Names

[ CAS No. ]:
134-58-7

[ Name ]:
8-Azaguanine

[Synonym ]:
2-Amino-6-hydroxy-8-azapurine,2-Amino-6-oxy-8-azapurine,8-AzaG
EINECS 205-148-1
8-Azaguanine
7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one, 3,4,5,6-tetrahydro-5-imino-
MFCD00056937
7H-1,2,3-Triazolo(4,5-d)pyrimidin-7-one, 5-amino-1,4-dihydro-
5-imino-3,4,5,6-tetrahydro-7H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
5-amino-2,3-dihydrotriazolo[4,5-d]pyrimidin-7-one
7H-1,2,3-Triazolo[4,5-d]pyrimidin-7-one, 5-amino-1,6-dihydro-
5-Amino-1H-[1,2,3]triazolo[4,5-d]pyrimidin-7(6H)-one
5-Amino-1,4-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one

Biological Activity

[Description]:

8-Azaguanine is a purine analogue which shows antineoplastic activity.

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

Research Areas >> Cancer

[In Vitro]

8-Azaguanine is a purine analogue which shows antineoplastic activity. The results show that cell viability decreases after incubation with 8-Azaguanine, in a dose and time dependent manner. After 24 h of treatment with 8-Azaguanine the IC50 for CEM cell line is about 100 μM while for MOLT3 cell line the IC50 is about 10 μM. CEM and MOLT3 cells surface expression of CD26 increases after treatment with 8-Azaguanine in a concentrations dependent manner[1].

[Cell Assay]

Detection of apoptosis and necrosis is analyzed by Annexin V and propidium iodide staining. After incubation in the absence or in the presence of 8-Azaguanine, cells are washed (centrifuged at 300×g during 5 min) and incubated for 10 min at 4°C in 440 μL Annexin buffer, containing 5 μL Annexin V and 5 μL propidium iodide. Then cells are washed and re-suspended in phosphate buffered saline (PBS) until analysis[1].

[References]

[1]. Dourado M, et al. CD26/DPPIV expression and 8-azaguanine response in T-acute lymphoblastic leukaemia cell lines in culture. Pathophysiology. 2007 May;14(1):3-10.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
2.6±0.1 g/cm3

[ Melting Point ]:
>300 °C(lit.)

[ Molecular Formula ]:
C₄H₄N₆O

[ Molecular Weight ]:
152.114

[ Flash Point ]:
129.1ºC

[ Exact Mass ]:
152.044662

[ PSA ]:
113.34000

[ LogP ]:
-0.71

[ Vapour Pressure ]:
0.00149mmHg at 25°C

[ Index of Refraction ]:
2.308

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XZ6157000

CHEMICAL NAME :: 7H-v-Triazolo(4,5-d)pyrimidin-7-one, 5-amino-1,6-dihydro-

CAS REGISTRY NUMBER :: 134-58-7

LAST UPDATED :: 199709

DATA ITEMS CITED :: 19

MOLECULAR FORMULA :: C4-H4-N6-O

MOLECULAR WEIGHT :: 152.14

WISWESSER LINE NOTATION :: T56 BNNM FVM INJ HZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 30 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD10 - Lethal Dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 90 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 50 mg/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 80 mg/kg

SEX/DURATION :: female 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 80 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

MUTATION DATA

TYPE OF TEST :: Mutation in mammalian somatic cells

TEST SYSTEM :: Rodent - hamster Lung

DOSE/DURATION :: 30 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 80,165,1981 *** REVIEWS *** TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 TOXICOLOGY REVIEW CRTXB2 CRC Critical Reviews in Toxicology. (CRC Press, Inc., 2000 Corporate Blvd., NW, Boca Raton, FL 33431) V.1- 1971- Volume(issue)/page/year: 2,159,1973

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
XZ6157000

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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