23662-75-1

Basic information

• Product Name: 8-METHYLGUANINE
• Synonyms: 8-METHYLGUANINE;6H-Purin-6-one, 2-aMino-1,7-dihydro-8-Methyl-
• CAS NO: 23662-75-1
• Molecular Formula: C₆H₇N₅O
• Molecular Weight: 165.15
• Mol File: 23662-75-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 574.1 °C at 760 mmHg
• Flash Point: 301 °C
• Appearance: /
• Density: 1.96 g/cm³
• Vapor Pressure: 3.47E-13mmHg at 25°C
• Refractive Index: 1.925
• CAS DataBase Reference: 8-METHYLGUANINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-METHYLGUANINE(23662-75-1)
• EPA Substance Registry System: 8-METHYLGUANINE(23662-75-1)

Safety Data

• Hazardous Substances Data: 23662-75-1(Hazardous Substances Data)

Usage

General Description

8-Methylguanine is a derivative of the purine base guanine, which is a component of DNA and RNA. It is a modified nucleobase formed by adding a methyl group to the 8th position of the guanine molecule. This modification can occur through exposure to certain mutagenic agents, such as alkylating agents or oxidative stress. 8-Methylguanine is known to cause mutations in DNA and is associated with the development of cancer. It is also involved in the repair of damaged DNA through the process of base excision repair. Additionally, 8-methylguanine has been studied for its potential use in cancer therapy through the inhibition of DNA repair processes.

InChI:InChI=1/C6H7N5O/c1-2-8-3-4(9-2)10-6(7)11-5(3)12/h1H3,(H4,7,8,9,10,11,12)

Upstream product

• 85819-69-8 8-methyl-2'-deoxyguanosine 
• 3149-34-6 7-methoxypterin 
• 113193-93-4 7-isopropoxypterin 
• 113230-79-8 7-ethoxypterin 
• 113193-94-5 7-(methylthio)pterin 
• 75-91-2 tert.-butylhydroperoxide 
• 961-07-9 2'-Deoxyguanosine 

Downstream Products

• 160948-27-6 O⁶-benzyl-8-methylguanine 

Relevant articles and documents

Stability of N-glycosidic bond of (5′ S)-8,5′-Cyclo-2′- deoxyguanosine

8,5′-Cyclopurine deoxynucleosides are unique tandem lesions containing an additional covalent bond between the base and the sugar. These mutagenic and genotoxic lesions are repaired only by nucleotide excision repair. The N-glycosidic (or C1′-N9) bond of 2′-deoxyguanosine (dG) derivatives is usually susceptible to acid hydrolysis, but even after cleavage of this bond of the cyclopurine lesions, the base would remain attached to the sugar. Here, the stability of the N-glycosidic bond and the products formed by formic acid hydrolysis of (5′S)-8,5′-cyclo-2′-deoxyguanosine (S-cdG) were investigated. For comparison, the stability of the N-glycosidic bond of 8,5′-cyclo-2′,5′-dideoxyguanosine (ddcdG), 8-methyl-2′-deoxyguanosine (8-Me-dG), 7,8-dihydro-8-oxo-2′- deoxyguanosine (8-Oxo-dG), and dG was also studied. In various acid conditions, S-cdG and ddcdG exhibited similar stability to hydrolysis. Likewise, 8-Me-dG and dG showed comparable stability, but the half-lives of the cyclic dG lesions were at least 5-fold higher than those of dG or 8-Me-dG. NMR studies were carried out to investigate the products formed after the cleavage of the C1′-N9 bond. 2-Deoxyribose generated α and β anomers of deoxyribopyranose and deoxyribopyranose oligomers following acid treatment. S-cdG gave α- and β-deoxyribopyranose linked guanine as the major products, but α and β anomers of deoxyribofuranose linked guanine and other products were also detected. The N-glycosidic bond of 8-Oxo-dG was found exceptionally stable in acid. Computational studies determined that both the protonation of the N7 atom and the rate constant in the bond breaking step control the overall kinetics of hydrolysis, but both varied for the molecules studied indicating a delicate balance between the two steps. Nevertheless, the computational approach successfully predicted the trend observed experimentally. For 8-Oxo-dG, the low pKa of O8 and N3 prevented appreciable protonation, making the free energy for N-glycosidic bond cleavage in the subsequent step very high.

RING TRANSFORMATION OF PTERINS TO GUANINES

7-Alkoxypterins undergo a ring contraction into guanine derivatives and demethoxylation by activated aluminum.