structure of S-[2-(N7-Guanyl)ethyl]glutathione

S-[2-(N7-Guanyl)ethyl]glutathione

CAS No.: 100840-34-4
M. Wt: 484.48700
M. Fa: C17H24N8O7S
InChI Key: -

Names and Identifiers of S-[2-(N7-Guanyl)ethyl]glutathione

CAS Number

100840-34-4

IUPAC Name

(2S)-2-azanyl-5-[[(2R)-3-[2-(2-azanyl-6-oxidanylidene-1H-purin-7-yl)ethylsulfanyl]-1-(2-hydroxy-2-oxoethylamino)-1-oxidanylidene-propan-2-yl]amino]-5-oxidanylidene-pentanoic acid

Canonical SMILES

C1=NC2=C(N1CCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)C(=O)NC(=N2)N

Physical and chemical properties of S-[2-(N7-Guanyl)ethyl]glutathione

Density

1.77g/cm3

Exact Mass

484.14900

Index of Refraction

1.765

LogP

0.03600

Molecular Formula

C17H24N8O7S

Molecular Weight

484.48700

PSA

281.68000

Storage condition

Hygroscopic, -20°C Freezer, Under inert atmosphere

Applications of S-[2-(N7-Guanyl)ethyl]glutathione

S-[2-(N7-Guanyl)ethyl]glutathione serves several important applications in research:

  • Cancer Research: It is studied extensively as a biomarker for exposure to alkylating agents and their potential role in cancer development.
  • Toxicology: Understanding its formation helps in assessing the risks associated with various environmental toxins.
  • Analytical Chemistry: Used as an internal standard in assays to quantify DNA adducts formed from different carcinogens.

Interaction Studies of S-[2-(N7-Guanyl)ethyl]glutathione

Studies have shown that S-[2-(N7-Guanyl)ethyl]glutathione interacts primarily with DNA, leading to the formation of stable adducts that can persist within cells. These interactions are crucial for understanding how chemical exposure leads to genetic alterations. The binding affinity and kinetics of these interactions are often evaluated using various biochemical assays, which help elucidate the mechanisms behind mutagenesis.

Biological Activity of S-[2-(N7-Guanyl)ethyl]glutathione

S-[2-(N7-Guanyl)ethyl]glutathione has been implicated in several biological activities primarily related to its role as a DNA adduct. The formation of this compound signifies a potential pathway for genotoxicity where it can lead to mutations during DNA replication. Studies have shown that this adduct may interfere with normal cellular processes and contribute to carcinogenesis by causing mispairing during DNA synthesis.

Additionally, its formation is often associated with oxidative stress conditions where elevated levels of reactive oxygen species can enhance the reactivity of electrophiles with cellular components.

Retrosynthesis analysis of S-[2-(N7-Guanyl)ethyl]glutathione

  • Route#1

    Cas:26578-09-6
    Cas:100840-34-4