7057-53-6

Basic information

• Product Name: 8-methoxyguanosine
• Synonyms: 8-methoxyguanosine
• CAS NO: 7057-53-6
• Molecular Formula: C11H15N5O6
• Molecular Weight: 313.2667
• Mol File: 7057-53-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 715.4°Cat760mmHg
• Flash Point: 386.4°C
• Appearance: /
• Density: 2.12g/cm³
• Vapor Pressure: 1.77E-21mmHg at 25°C
• Refractive Index: 1.866
• PKA: 9.36±0.20(Predicted)
• CAS DataBase Reference: 8-methoxyguanosine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-methoxyguanosine(7057-53-6)
• EPA Substance Registry System: 8-methoxyguanosine(7057-53-6)

Safety Data

• Hazardous Substances Data: 7057-53-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H15N5O6/c1-21-11-13-4-7(14-10(12)15-8(4)20)16(11)9-6(19)5(18)3(2-17)22-9/h3,5-6,9,17-19H,2H2,1H3,(H3,12,14,15,20)

Upstream product

• 67-56-1 methanol 
• 4016-63-1 8-bromoguanosine 
• 945933-52-8 8-fluoro-2',3',5'-tri-O-acetylguanosine 

Relevant articles and documents

Structure-based design of guanosine analogue inhibitors targeting GTP cyclohydrolase IB towards a new class of antibiotics

GTP cyclohydrolase (GCYH-I) is an enzyme in the folate biosynthesis pathway that has not been previously exploited as an antibiotic target, although several pathogens including N. gonorrhoeae use a form of the enzyme GCYH-IB that is structurally distinct from the human homologue GCYH-IA. A comparison of the crystal structures of GCYH-IA and -IB with the nM inhibitor 8-oxo-GTP bound shows that the active site of GCYH-IB is larger and differently shaped. Based on this structural information, we designed and synthesized a small set of 8-oxo-G derivatives with ether linkages at O6 and O8 expected to displace water molecules from the expanded active site of GCYH-IB. The most potent of these compounds, G3, is selective for GCYH-IB, supporting the premise that potent and selective inhibitors of GCYH-IB could constitute a new class of small molecule antibiotics.

8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells

A variety of 8-substituted guanosine and 2'-deoxyguanosine derivatives were synthesized and tested as inducers of the differentiation of Friend murine erythroleukemia cells in culture. The most active agents in the guanosine series were 8-substituted -N(CH3)2, -NHCH3, -NH2, -OH, and -SO2CH3, which caused 68, 42, 34, 33, and 30% of erythroleukemia cells to attain benzidine positivity, a functional measure of maturation, at concentrations of 5, 1, 0.4, 5, and 5 mM, respectively. The 8-OH derivative of the 2'-deoxyguanosine series produced comparable activity, causing 62% benzidine-positive cells at a level of 0.2 mM. These findings indicate that 8-substituted analogues of guanosine and 2'-deoxyguanosine have the potential to terminate leukemia cell proliferation through conversion to end-stage differentiated cells.