CAS 3868-32-4

2,8-diamino-9-pentofuranosyl-3,9-dihydro-6H-purin-6-one

Description:

2,8-Diamino-9-pentofuranosyl-3,9-dihydro-6H-purin-6-one, commonly known as a nucleoside analog, is characterized by its structural features that include a purine base and a sugar moiety. This compound contains two amino groups at the 2 and 8 positions of the purine ring, which can influence its biological activity and interaction with nucleic acid synthesis. The presence of the pentofuranosyl sugar indicates that it is a ribonucleoside, which is essential for its role in biological systems, particularly in the synthesis of RNA. The dihydro form of the purine ring suggests that it may exhibit different reactivity and stability compared to its fully aromatic counterparts. This compound is of interest in medicinal chemistry and biochemistry due to its potential applications in antiviral and anticancer therapies, as it may interfere with nucleic acid metabolism. Overall, its unique structural characteristics contribute to its function and potential therapeutic uses in various biological contexts.

Formula: C₁₀H₁₄N₆O₅

InChI: InChI=1/C10H14N6O5/c11-9-14-6-3(7(20)15-9)13-10(12)16(6)8-5(19)4(18)2(1-17)21-8/h2,4-5,8,17-19H,1H2,(H2,12,13)(H3,11,14,15,20)

SMILES: C(C1C(C(C(n2c3c(c(nc(=N)[nH]3)O)[nH]c2=N)O1)O)O)O

Synonyms:

• 2,8-diamino-9-pentofuranosyl-1,9-dihydro-6H-purin-6-one
• 6H-purin-6-one, 2,8-diamino-1,9-dihydro-9-pentofuranosyl-
• 8-Aminoguanosine
• Guanosine, 8-Amino-

8-Aminoguanosine

CAS: 3868-32-4

Formula: C₁₀H₁₄N₆O₅

Purity: ≥ 95.0%

Color and Shape: Light beige to light brown solid

Molecular weight: 298.26

Ref: 7W-GN1689

8-Aminoguanosine

Controlled Product

CAS: 3868-32-4

Applications A potent inhibitor of purine nucleoside phosphorylase
References Kazmers, I.S., et al.: Science, 214, 1137 (1981), Chern, J-W., et al.: J. Med. Chem., 36, 1024 (1993)

Formula: C₁₀H₁₄N₆O₅

Color and Shape: Neat

Molecular weight: 298.26

Ref: TR-A609875

8-Aminoguanosine-13C2,15N

Controlled Product

CAS: 3868-32-4

Formula: C₂C₈H₁₄₁₅NN₅O₅

Color and Shape: Neat

Molecular weight: 301.234

Ref: TR-A609877

8-Aminoguanosine

CAS: 3868-32-4

8-Aminoguanosine is a synthetic purine nucleoside that inhibits DNA synthesis. It has been shown to inhibit the proliferation of HL-60 cells, which are a model for human monocytes and neutrophils. 8-Aminoguanosine has been shown to bind to the template strand of DNA and inhibit the incorporation of deoxyribonucleotide triphosphates into the newly synthesized strand. This binding prevents DNA replication by preventing access to the template strand of DNA. 8-Aminoguanosine inhibits cyclin D2, an enzyme required for cell division, at concentrations as low as 0.1 mM, and it also inhibits microtubule assembly. 8-Aminoguanosine has shown in vitro activity against various tumor cell lines including Molt-4 and MCF7 cells, and in vivo activity in a mouse model against C3H/HeJ mice transplanted with Lewis lung carcinoma cells.

Formula: C₁₀H₁₄N₆O₅

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 298.26 g/mol

Ref: 3D-NA04479