5375-85-9

Basic information

• Product Name: (2-amino-7H-purin-6-yl)selanyl
• CAS NO: 5375-85-9
• Molecular Formula: C₅H₅N₅Se
• Molecular Weight: 213.0788
• Mol File: 5375-85-9.mol

Chemical Properties

• CAS DataBase Reference: (2-amino-7H-purin-6-yl)selanyl(CAS DataBase Reference)
• NIST Chemistry Reference: (2-amino-7H-purin-6-yl)selanyl(5375-85-9)
• EPA Substance Registry System: (2-amino-7H-purin-6-yl)selanyl(5375-85-9)

Safety Data

• Hazardous Substances Data: 5375-85-9(Hazardous Substances Data)

Upstream product

• 630-10-4 selenourea 
• 10310-21-1 2-Amino-6-chloropurin 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 

Relevant articles and documents

Seleno-nucleobases and their water-soluble ruthenium- Arene half-sandwich complexes: Chemistry and biological activity

Half-sandwich organometallic ruthenium complexes of seleno- nucleobases, 3 and 4, were synthesized and characterized. The structures of both complexes were determined by X-ray crystallography and are the first crystal structures of ruthenium complexes with seleno-nucleobases. Interestingly, 3 self-assembles aided by adventitious water in DMF to give a tetranuclear square 3a.6H2O. Complex 4 is active against Jurkat and Molt-4 cell lines but inactive against the K562 cell line, whereas 3 is completely inactive against all three cell lines. The free ligand 6-selenopurine (1) and 6-selenoguanine (2) are highly active against these cell lines. Compound 2, like its thio analogue, is unstable under UVA light, whereas 4 is stable under similar conditions, which suggests that the ruthenium complex could reduce problems associated with the instability of the free ligand, 2, under irradiation.

Heavy-Atom-Substituted Nucleobases in Photodynamic Applications: Substitution of Sulfur with Selenium in 6-Thioguanine Induces a Remarkable Increase in the Rate of Triplet Decay in 6-Selenoguanine

Sulfur substitution of carbonyl oxygen atoms of DNA/RNA nucleobases promotes ultrafast intersystem crossing and near-unity triplet yields that are being used for photodynamic therapy and structural-biology applications. Replacement of sulfur with selenium or tellurium should significantly red-shift the absorption spectra of the nucleobases without sacrificing the high triplet yields. Consequently, selenium/tellurium-substituted nucleobases are thought to facilitate treatment of deeper tissue carcinomas relative to the sulfur-substituted analogues, but their photodynamics are yet unexplored. In this contribution, the photochemical relaxation mechanism of 6-selenoguanine is elucidated and compared to that of the 6-thioguanine prodrug. Selenium substitution leads to a remarkable enhancement of the intersystem crossing lifetime both to and from the triplet manifold, resulting in an efficiently populated, yet short-lived triplet state. Surprisingly, the rate of triplet decay in 6-selenoguanine increases by 835-fold compared to that in 6-thioguanine. This appears to be an extreme manifestation of the classical heavy-atom effect in organic photochemistry, which challenges conventional wisdom.

A nucleoside compound synthesis method (by machine translation)

The invention relates to a method for synthesis of nucleoside compound, in particular of formula I and II shown in the preparation method of the compound, in the formula I and II, R1 And R2 Respectively is independently an hydroxy protecting group, preferably benzoyl, trityl, disubstituted phenyl, ethyl or tertiary butyl dimethyl silyl group; R3 And R4 Is alkyl (preferably C1 - C10 Alkyl, more preferably methyl, ethyl) or halogen (such as F, Cl or Br); B is the following arbitrary group wherein R5 Hydrogen or alkyl (preferably C1 - C10 Alkyl, more preferably methyl); X is hydroxyl or amino; Y is sulfur. (by machine translation)