100840-34-4 Usage
Uses
Used in Research and Development:
S-[2-(N7-guanyl)ethyl]GSH is used as a biomarker for [detecting the presence of ethylene dibromide (EDB) exposure and its potential carcinogenic effects]. It serves as a valuable tool in understanding the molecular mechanisms of DNA damage and repair, as well as the role of GSH in these processes.
Used in Environmental Monitoring:
S-[2-(N7-guanyl)ethyl]GSH is used as an indicator for [assessing the level of ethylene dibromide (EDB) contamination in the environment]. This can help in identifying areas with potential health risks and implementing necessary safety measures to reduce exposure to this carcinogen.
Used in Pharmaceutical Industry:
S-[2-(N7-guanyl)ethyl]GSH is used as a target for [developing new drugs or therapies to counteract the harmful effects of ethylene dibromide (EDB) exposure]. By understanding the molecular interactions between GSH and EDB, researchers can potentially design drugs that can either prevent the formation of this DNA adduct or promote its repair, thereby reducing the risk of cancer development.
Used in Toxicology Studies:
S-[2-(N7-guanyl)ethyl]GSH is used as a model compound for [studying the toxicological effects of ethylene dibromide (EDB) and other similar carcinogens]. This can provide insights into the mechanisms of carcinogenesis and help in the development of strategies to mitigate the harmful effects of these compounds on human health.
Check Digit Verification of cas no
The CAS Registry Mumber 100840-34-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,0,8,4 and 0 respectively; the second part has 2 digits, 3 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 100840-34:
(8*1)+(7*0)+(6*0)+(5*8)+(4*4)+(3*0)+(2*3)+(1*4)=74
74 % 10 = 4
So 100840-34-4 is a valid CAS Registry Number.
InChI:InChI=1/C17H24N8O7S/c18-8(16(31)32)1-2-10(26)22-9(14(29)20-5-11(27)28)6-33-4-3-25-7-21-13-12(25)15(30)24-17(19)23-13/h7-9H,1-6,18H2,(H,20,29)(H,22,26)(H,27,28)(H,31,32)(H3,19,23,24,30)/t8-,9-/m0/s1
100840-34-4Relevant academic research and scientific papers
Peterson,Harris,Guengerich
, p. 3284 - 3291 (1988)
The carcinogen ethylene dibromide (EDB) is bioactivated via a pathway involving initial conjugation with the tripeptide glutathione (GSH) in a reaction catalyzed by GSH S-transferase. The conjugate then reacts preferentially with DNA guanyl residues to generate S-[2-(N7-guanyl)ethyl]glutathione. Rates of hydrolysis and alkylation of 4-(p-nitrobenzyl)pyridine with several cysteinyl and homocysteinyl analogues of S-(2-haloethyl)glutathione at pHs 2.2, 6.4, and 8.5 are consistent with the hypothesis that an episulfonium ion is a common intermediate in both the hydrolysis and alkylation reactions. Consistently, 2-amino-6-chlorohexanoic acid failed to react with 4-(p-nitrobenzyl)pyridine. The stereochemical course of the overall reaction was studied with [threo-1,2-2H2]EDB and [erythro-1,2-2H2]EDB, which were incubated with GSH, rat liver cytosol, and DNA; the resulting DNA N7-guanyl adducts were isolated and analyzed by NMR techniques in order to determine the stereochemical course of the reaction. Two-dimensional correlated (COSY) NMR indicated that the reaction had occurred by a single stereochemical course. The magnitude of nuclear Overhauser effects between the ethylene protons suggests that the reaction occurs with net inversion of configuration of the methylene protons. This conclusion was confirmed upon comparison of the COSY NMR spectra of the biologically generated adducts with those that were synthetically prepared from the deuteriated EDB diastereomers via a known stereochemical route. This observation, combined with the kinetic data, supports a reaction mechanism where the EDB-GSH conjugate forms an episulfonium ion prior to reaction with DNA guanyl residues.
