62462-38-8

Basic information

• Product Name: 1,N(2)-ethenoguanosine
• Synonyms: 1,N(2)-ethenoguanosine
• CAS NO: 62462-38-8
• Molecular Formula: C12H13N5O5
• Molecular Weight: 307.26
• Mol File: 62462-38-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 897.7°C at 760 mmHg
• Flash Point: 496.7°C
• Appearance: /
• Density: 2.14g/cm³
• Vapor Pressure: 1.16E-34mmHg at 25°C
• Refractive Index: 1.958
• CAS DataBase Reference: 1,N(2)-ethenoguanosine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,N(2)-ethenoguanosine(62462-38-8)
• EPA Substance Registry System: 1,N(2)-ethenoguanosine(62462-38-8)

Safety Data

• Hazardous Substances Data: 62462-38-8(Hazardous Substances Data)

Usage

Type

Modified nucleoside

Formation

Result of the reaction between guanine and lipid peroxidation products

Mutagenic

Yes, it is mutagenic

Carcinogenic

Yes, it is carcinogenic

Implication

Involved in the development of various types of cancers

Presence

Found in environmental pollutants such as tobacco smoke, charred foods, and polluted air

DNA Damage

Causes DNA damage

Genetic Mutations

Induces genetic mutations

Cancer Risk

Associated with an increased risk of cancer development

Neurodegenerative Diseases

May play a role in the pathogenesis of neurodegenerative diseases

Hazardous Substance

Considered a hazardous substance with potential health implications

InChI:InChI=1/C12H13N5O5/c18-3-5-7(19)8(20)11(22-5)17-4-14-6-9(17)15-12-13-1-2-16(12)10(6)21/h1-2,4-5,7-8,11,18-20H,3H2,(H,13,15)/t5-,7-,8-,11?/m1/s1

Upstream product

• 118-00-3 G 
• 2004-07-1 2-Amino-6-chloropurine riboside 
• 17157-48-1 bromoacetaldehyde 
• 2065-75-0 2-Bromo-malonaldehyde 
• 765-34-4 Glycidaldehyde 
• 3209-33-4 3-methyloxirane-2-carbaldehyde 

Downstream Products

• 56287-13-9 3H,5H,9H-imidazo[1,2-a]purin-9-one 

Relevant articles and documents

Ring-Extended Products from the Reaction of Epoxy Carbonyl Compounds and Nucleic Acid Bases

Purine and pyrimidine bases react with epoxy carbonyl compounds in aqueous solution to yield ring-extended adducts.These products include etheno-modified bases as well as adducts in which the modification involves the formation of an additional six-membered ring.The latter examples are among the first known cases of this type of modification of pyrimidine bases.Plausible mechanisms for the formation of these adducts are discussed.

CYCLIC DINUCLEOTIDES AS ANTICANCER AGENTS

The present invention is directed to compounds of the formula (I), wherein all substituents are defined herein, as well as pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

Mechanisms of formation of adducts from reactions of glycidaldehyde with 2′-deoxyguanosine and/or guanosine

Convenient syntheses of rac-glycidaldehyde from rac-but-3-ene-1,2-diol and (R)-glycidaldehyde from D-mannitol are described. (R)-Glycidaldehyde (1) reacts with guanosine in water (pH 4-11, faster reaction at higher pH) to give initially 6(S)-hydroxy-7(S)-(hydroxymethyl)-3-(β-D-ribofuranosyl)-5,6,7- trihydroimidazo[1,2-a]purin-9(3H)-one (7a) and 6(S),7(R)-dihydroxy-3-(β-D-ribofuranosyl)-5,6,73-tetrahydropyrimido[1,2-a] purin-10(3H)-one (8a). The former decomposes to 7-(hydroxymethyl)-5,9-dihydro-9-oxo-3-(β-D-ribofuranosyl)imidazo[1,2-a] purine (3a), 5,9-dihydro-9-oxo-3-(β-D-ribofuranosyl)imidazo[1,2-a]purine (5a, 1,N2-ethenoguanosine), and formaldehyde, while the latter adduct is relatively stable. The position of the hydroxymethyl group on the imidazo ring of 7-(hydroxymethyl)-5,9-dihydro-9-oxo-3-(β-D-ribofuranosyl)imidazo-[1,2-a] purine was proved by 13C NMR analysis of adducts derived from [1-15N]guanosine and [amino-15N]guanosine. At longer reaction times, the adduct 7,7′-methylenebis[5,9-dihydro-9-oxo-3-(β-D-ribofuranosyl)imidazo[1,2- a]purine[ (4a) is formed from guanosine and glycidaldehyde. The structure analysis of this adduct was also aided by 13C NMR analysis of the 15N-labeled adduct derived from [1-15N]guanosine. Analogous adducts were obtained from the reaction between glycidaldehyde and deoxyguanosine. Mechanisms of formation of the adducts from glycidaldehyde and guanosine/deoxyguanosine are proposed and supported by model studies with simple amines. The formaldehyde produced in the reactions described reacts with guanosine to give the known adduct N2-(hydroxymethyl)guanosine (9).