6-mercaptopurine-2'-deoxyriboside

Names

[ Name ]:
6-mercaptopurine-2'-deoxyriboside

[Synonym ]:
6-MERCAPTOPURINE-2'-DEOXYRIBONUCLEOSIDE
6-Mercaptopurine-2'-deoxyriboside
6-thio-2'-deoxyinosine
MFCD00056001
6-Mercapto-9-(2'-deoxy-b-D-ribofuranosyl)purine

Biological Activity

[Description]:

2′-Deoxy-6-thioinosine is a purine nucleoside analog. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc[1].

[Related Catalog]:

Research Areas >> Cancer

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

[References]

[1]. Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18(23):3373-88.

Chemical & Physical Properties

[ Density]:
1.87g/cm3

[ Boiling Point ]:
665.9ºC at 760mmHg

[ Molecular Formula ]:
C₁₀H₁₂N₄O₃S

[ Molecular Weight ]:
268.29

[ Flash Point ]:
356.5ºC

[ Exact Mass ]:
268.06300

[ PSA ]:
128.28000

[ LogP ]:
0.12960

[ Vapour Pressure ]:
1.23E-18mmHg at 25°C

[ Index of Refraction ]:
1.863

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UP0762000

CHEMICAL NAME :: 9H-Purine-6(1H)-thione, 9-(2-deoxy-beta-D-erythro-pentofuranosyl)-

CAS REGISTRY NUMBER :: 2239-64-7

LAST UPDATED :: 199206

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C10-H12-N4-O3-S

MOLECULAR WEIGHT :: 268.32

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1700 mg/kg

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

REFERENCE :: TDKNAF Takeda Kenkyusho Nempo. Annual Report of the Takeda Research Laboratories. (Osaka, Japan) V.1-28, 1936-69. For publisher information, see TAKHAA. Volume(issue)/page/year: 27,1,1968

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2100 mg/kg

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

REFERENCE :: TDKNAF Takeda Kenkyusho Nempo. Annual Report of the Takeda Research Laboratories. (Osaka, Japan) V.1-28, 1936-69. For publisher information, see TAKHAA. Volume(issue)/page/year: 27,1,1968

Safety Information

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
22

[ Safety Phrases ]:
36

[ WGK Germany ]:
3

[ RTECS ]:
UP0762000

Precursor & DownStream

Precursor

DownStream

Articles

Nucleosides of azathioprine and thiamiprine as antiarthritics.

J. Med. Chem. 32 , 1471-1475, (1989)

Azathioprine [Imuran; 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-1H-purine] is a widely used immunosuppressive and antiarthritic drug. For the sake of comparison, the riboside, the 2'-deoxyriboside, ...

Synthetic nucleosides and nucleotides. XIV. Facile synthesis and antitumor activities of 6-mercaptopurine 2'-deoxyriboside and related compounds.

J. Pharmacobiodyn. 3 , 105-110, (1980)

Convenient synthesis of oligodeoxynucleotides containing 2'-deoxy-6-thioinosine.

Nucleosides Nucleotides Nucleic Acids 22 , 635-639, (2003)

A facile synthesis of oligodeoxynucleotides (ODN) containing 2'-deoxy-6-thioinosine (dI6S) based on the convertible nucleoside O6-phenyl-2'-deoxyinosine is presented. After standard solid-phase DNA sy...