132014-87-0

Basic information

• Product Name: α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine (Mixture of DiastereoMers)
• Synonyms: α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine (Mixture of DiastereoMers);3-(2-Deoxy-β-D-erythro-pentofuranosyl)-4,6,7,8-tetrahydro-8-hydroxy-6-MethylpyriMido[1,2-a]purin-10(3H)-one
• CAS NO: 132014-87-0
• Molecular Formula: C₁₄H₁₉N₅O₅
• Molecular Weight: 337.33116
• Product Categories: Carbohydrates & Derivatives;Heterocycles;Mutagenesis Research Chemicals
• Mol File: 132014-87-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 135-137°C
• Boiling Point: 724.7±70.0 °C(Predicted)
• Appearance: /
• Density: 1.93±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 11.80±0.40(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine (Mixture of DiastereoMers)(CAS DataBase Reference)
• NIST Chemistry Reference: α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine (Mixture of DiastereoMers)(132014-87-0)
• EPA Substance Registry System: α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine (Mixture of DiastereoMers)(132014-87-0)

Safety Data

• Hazardous Substances Data: 132014-87-0(Hazardous Substances Data)

Usage

Description

α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine (Mixture of DiastereoMers) is a genotoxic cyclic adduct of 2'-deoxyguanosine with crotonaldehyde. It is formed by the reaction of the primary metabolite of alcohol and the carcinogenic crotonaldehyde with DNA. α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine
(Mixture of DiastereoMers) is a white solid and has significant implications in the study of DNA damage and repair mechanisms.

Uses

Used in Research Applications:
α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine (Mixture of DiastereoMers) is used as a research tool for studying the formation and effects of DNA adducts, particularly in the context of alcohol metabolism and carcinogen exposure. It helps researchers understand the molecular mechanisms underlying genotoxicity and the role of histones in accelerating the formation of cyclic 1,N2-propanoguanine adducts.
Used in Pharmaceutical Industry:
α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine (Mixture of DiastereoMers) is used as a reference compound in the development of drugs and therapies targeting DNA repair mechanisms and cancer prevention. Its unique properties make it a valuable tool for evaluating the efficacy of potential treatments and understanding the molecular pathways involved in DNA damage and repair.
Used in Environmental and Occupational Health:
α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine (Mixture of DiastereoMers) is used in the assessment of environmental and occupational exposure to genotoxic agents, such as crotonaldehyde. By studying the presence and levels of this adduct in biological samples, researchers can gain insights into the potential health risks associated with exposure to these harmful substances.

Upstream product

• 75-07-0 acetaldehyde 
• 961-07-9 2'-Deoxyguanosine 
• 123-73-9 trans-Crotonaldehyde 
• 123-73-9 crotonaldehyde 
• 117706-97-5 (R)-3-Hydroxybutanal 

Downstream Products

• 961-07-9 2'-Deoxyguanosine 

Relevant articles and documents

A schiff base is a major DNA adduct of crotonaldehyde

Previous studies have demonstrated that the reaction of crotonaldehyde with DNA produces Michael addition products, and these have been detected in human tissues as well as tissues of untreated laboratory animals. A second class of crotonaldehyde - DNA ad

(E)-2-hexenal-induced DNA damage and formation of cyclic 1,N2-(1,3- propano)-2'-deoxyguanosine adducts in mammalian cells

(E)-2-Hexenal (hexenal), a natural flavor compound, acts as directly genotoxic agent and forms cyclic 1,N2-propano adducts with deoxyguanosine. Formation of this adduct in isolated DNA and in cells was studied with a modified 32P-postlabeling procedure including HPLC separation, nuclease P1 enrichment, two-dimensional TLC of adducted nucleotide bisphosphates on PEI- cellulose, and quantification of adduct spots by liquid scintillation counting. Adduct formation with the more reactive crotonaldehyde was included for comparison. Synthesized adducted dG-3'-phosphates served as external standards for identification and quantification. In calf thymus DNA, hexenal (0.2 mM) shows a time dependent formation of adducts, yielding 1.55 pmol/μmol of DNA at 5 h incubation. With crotonaldehyde (0.2 mM) the adduct rate was about 10-fold higher. Hexenal also generated 1,N2-propano-dG adducts in the human lymphoblastoid Namalva cell line (0.2 mM, 1 h, 86 fmol/μmol of DNA) and in primary rat colon mucosa cells (0.4 mM, 30 min, 50 fmol/μmol of DNA). In primary colon mucosa cells from rats and humans, hexenal and crotonaldehyde (0.4 mM, 30 min) induced DNA damage, detected by single cell microgel electrophoresis (comet assay). In primary rat gastric mucosa cells, hexenal was only weakly active, inducing detectable DNA damage in 20% of cells at 0.8 mM concentration. In contrast, primary mucosa cells from rat esophagus were as sensitive as colon cells. After single oral application of hexenal to rats (up to 320 mg/kg body wt) DNA damage was not detectable in gastrointestinal mucosa. Analysis of hexenal in selected flavored foods revealed concentrations up to 14 ppm (0.14 mM) that are comparable to its natural occurrence in some fruits and vegetables (up to 30 ppm). Thus, the concentration range selected for the toxicological studies described here clearly is relevant: Hexenal, at concentrations found in food, exerts genotoxic effects in cells from rat and human gastrointestinal tract.

Identification of DNA adducts of acetaldehyde

Acetaldehyde is a mutagen and carcinogen which occurs widely in the human environment, sometimes in considerable amounts, but little is known about its reactions with DNA. In this study, we identified three new types of stable acetaldehyde DNA adducts, including an interstrand cross-link. These were formed in addition to the previously characterized N2-ethylidenedeoxyguanosine. Acetaldehyde was allowed to react with calf thymus DNA or deoxyguanosine. The DNA was isolated and hydrolyzed enzymatically; in some cases, the DNA was first treated with NaBH3CN. Reaction mixtures were analyzed by HPLC, and adducts were isolated and characterized by UV, 1H NMR, and MS. The major adduct was N2-ethylidenedeoxyguanosine (1), which was identified as N2-ethyldeoxyguanosine (7) after treatment of the DNA with NaBH3CN. The new acetaldehyde adducts were 3-(2-deoxyribos-1-yl)-5,6,7,8-tetrahydro-8-hydroxy-6-methylpyrimido[1,2-α]pu rine-10(3H)one (9), 3-(2-deoxyribos-1-yl)-5,6,7,8-tetrahydro-8-(N2-deoxyguanosyl)- 6-methylpyrimido[1,2-α]purine-10(3H)one (12), and N2-(2,6-dimethyl-1,3-dioxan-4-yl)deoxyguanosine (11). Adduct 9 has been previously identified in reactions of crotonaldehyde with DNA. However, the distribution of diastereomers was different in the acetaldehyde and crotonaldehyde reactions, indicating that the formation of 9 from acetaldehyde does not proceed through crotonaldehyde. Adduct 12 is an interstrand cross-link. Although previous evidence indicates the formation of cross-links in DNA reacted with acetaldehyde, this is the first reported structural characterization of such an adduct. This adduct is also found in crotonaldehyde-deoxyguanosine reactions, but in a diastereomeric ratio different than that observed here. A common intermediate, N2-(4-oxobut-2-yl)deoxyguanosine (6), is proposed to be involved in formation of adducts 9 and 12. Adduct 11 is produced ultimately from 3-hydroxybutanal, the major aldol condensation product of acetaldehyde. Levels of adducts 9, 11, and 12 were less than 10% of those of N2-ethylidenedeoxyguanosine (1) in reactions of acetaldehyde with DNA. As nucleosides, adducts 9, 11, and 12 were stable, whereas N2-ethylidenedeoxyguanosine (1) had a half-life of 5 min. These new stable adducts of acetaldehyde may be involved in determination of its mutagenic and carcinogenic properties.