126788-73-6

Basic information

• Product Name: Guanosine, 2'-deoxy-8-[(4-methylphenyl)amino]-
• CAS NO: 126788-73-6
• Molecular Formula: C17H20N6O4
• Molecular Weight: 372.384
• Mol File: 126788-73-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Guanosine, 2'-deoxy-8-[(4-methylphenyl)amino]-(CAS DataBase Reference)
• NIST Chemistry Reference: Guanosine, 2'-deoxy-8-[(4-methylphenyl)amino]-(126788-73-6)
• EPA Substance Registry System: Guanosine, 2'-deoxy-8-[(4-methylphenyl)amino]-(126788-73-6)

Safety Data

• Hazardous Substances Data: 126788-73-6(Hazardous Substances Data)

Upstream product

• 1124321-44-3 8N-(4-methylphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine 
• 1124321-44-3 C₂₉H₄₈N₆O₄Si₂ 
• 623-10-9 N-(4-methylphenyl)hydroxylamine 
• 369651-29-6 N-(acetyloxy)-N-(4-methylphenyl)-benzamide 
• 19064-77-8 C-phenyl-N-p-tolyl-nitrone 
• 769141-97-1 O⁶-benzyl-8-(4-methylphenylamino)-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine 
• 328394-26-9 O⁶-benzyl-8-bromo-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine 
• 769141-88-0 8-bromo-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine 
• 13389-03-2 8-bromo-2'-deoxyguanosine 
• 369651-31-0 N-(Benzoyl)-N-(deoxyguanosin-8-yl)-4-methylaniline 
• 961-07-9 2'-Deoxyguanosine 
• 132540-70-6 C₁₂H₁₇NO₂ 
• 126901-21-1 (N^α-Benzylalanin)-N-(4-methylphenyl)hydroxamsaeure 
• 126875-83-0 N-acetoxy-4-methylaniline 

Downstream Products

• 1125587-06-5 N₂-formamidino-8N-(4-methylphenylamino)-2'-deoxyguanosine 

Relevant articles and documents

Synthesis of DNA strands site-specifically damaged by C8-arylamine purine adducts and effects on various DNA polymerases

C8-Arylamine-dG and C8-arylamine-dA adducts have been prepared using palladium cross-coupling chemistry. These adducts were subsequently converted into the corresponding 5′-O-DMTr-C8-arylamine-3′-O-phosphoramidites and then used for the automated synthesi

Site-specific synthesis and properties of oligonucleotides containing C8-deoxyguanosine adducts of the dietary mutagen IQ

The site-specific synthesis of oligonucleotides containing the C8-deoxyguanosine adduct of the highly mutagenic heterocyclic amine 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) has been achieved, and the oligonucleotides were characterized by UV melting te

Synthesis, characterization, and conformational analysis of DNA adducts from methylated anilines present in tobacco smoke

The ability of a series of aromatic amines present in tobacco smoke (2-, 3-, and 4-methylaniline, 2,3- and 2,4-dimethylaniline) to bind to DNA has been investigated by reacting N-(acyloxy)arylamines with dG, dG nucleotides, and DNA. The predominant products from reactions with dG and the nucleotides were characterized as N-(deoxyguanosin-8-yl)arylamines by spectroscopic and HPLC methods. HPLC and spectroscopic analyses of the modified DNA indicated the same adducts. Analyses of the 1H and 13C NMR spectra suggested that the adducts containing a methyl substituent ortho to the arylamine nitrogen had a higher percentage of syn conformers. This observation was supported by theoretical simulation studies that indicated substantial percentages of low energy syn conformers, increasing with the substitution pattern in the order para meta ortho ortho,para ortho,meta. The results demonstrate that, although single-ring arylamines are considered weak carcinogens, their electrophilic N-acetoxy derivatives, which are plausible metabolic intermediates, react with DNA to yield covalent adducts structurally identical to those derived from carcinogenic polyarylamines, such as 2- aminofluorene and 4-aminobiphenyl. Furthermore, the conformational perturbation induced in DNA by the formation of the monoarylamine-DNA adducts, especially those with an ortho substituent, may contribute to the biological activities of these compounds.