I6125
Iodoacetamide
≥99% (NMR), crystalline
Synonym(s):
α-Iodoacetamide, 2-Iodoacetamide
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All Photos(5)
About This Item
Linear Formula:
ICH2CONH2
CAS Number:
Molecular Weight:
184.96
Beilstein:
1739080
EC Number:
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
biological source
synthetic (organic)
Quality Level
Assay
≥99% (NMR)
form
crystalline
mp
92-95 °C (lit.)
solubility
H2O: soluble 0.5 M, clear, colorless
storage temp.
2-8°C
SMILES string
NC(=O)CI
InChI
1S/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5)
InChI key
PGLTVOMIXTUURA-UHFFFAOYSA-N
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Application
- A Mass Spectrometry Strategy for Protein Quantification Based on the Differential Alkylation of Cysteines Using Iodoacetamide and Acrylamide.: This study presents a novel mass spectrometry method for quantifying proteins by differentially alkylating cysteines with iodoacetamide and acrylamide, enhancing the accuracy of protein quantification in complex samples. (Virág et al., 2024).
- Laminarin ameliorates iodoacetamide-induced functional dyspepsia via modulation of 5-HT(3) receptors and the gut microbiota.: Research demonstrates that laminarin can mitigate functional dyspepsia induced by iodoacetamide through modulating 5-HT(3) receptors and altering gut microbiota composition, offering potential therapeutic benefits. (Liu et al., 2024).
- Redox proteomics in melanoma cells: An optimized protocol.: This paper describes an optimized redox proteomics protocol using iodoacetamide, which facilitates the identification of redox-sensitive proteins in melanoma cells, aiding in the understanding of redox regulation in cancer. (Cunha et al., 2024).
- Molecular targets of cisplatin in HeLa cells explored through competitive activity-based protein profiling strategy.: Utilizing iodoacetamide in competitive activity-based protein profiling, this study identifies molecular targets of cisplatin in HeLa cells, providing insights into the drug′s mechanisms. (Chen et al., 2024).
- Development and Comparison of 4-Thiouridine to Cytidine Base Conversion Reaction.: This research compares base conversion reactions involving 4-thiouridine and cytidine, with iodoacetamide playing a crucial role in the reaction mechanism, contributing to advancements in nucleotide chemistry. (Ohashi et al., 2024).
Biochem/physiol Actions
Iodoacetamide acts as an alkylating reagent for cysteine residues in peptide sequencing. It is an irreversible inhibitor of enzymes with cysteine at the active site. It reacts much more slowly with histidine residues, but that activity is responsible for inhibiting ribonuclease.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 3 Oral - Aquatic Chronic 4 - Resp. Sens. 1 - Skin Sens. 1
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Mirko Zaffagnini et al.
Antioxidants & redox signaling, 16(1), 17-32 (2011-06-29)
Cysteines (Cys) made acidic by the protein environment are generally sensitive to pro-oxidant molecules. Glutathionylation is a post-translational modification that can occur by spontaneous reaction of reduced glutathione (GSH) with oxidized Cys as sulfenic acids (-SOH). The reverse reaction (deglutathionylation)
Chiara Francavilla et al.
The Journal of cell biology, 187(7), 1101-1116 (2009-12-30)
Neural cell adhesion molecule (NCAM) associates with fibroblast growth factor (FGF) receptor-1 (FGFR1). However, the biological significance of this interaction remains largely elusive. In this study, we show that NCAM induces a specific, FGFR1-mediated cellular response that is remarkably different
Valentina R Minciacchi et al.
Oncotarget, 6(13), 11327-11341 (2015-04-11)
Large oncosomes (LO) are atypically large (1-10 µm diameter) cancer-derived extracellular vesicles (EVs), originating from the shedding of membrane blebs and associated with advanced disease. We report that 25% of the proteins, identified by a quantitative proteomics analysis, are differentially
Elena B Lugli et al.
Arthritis research & therapy, 17, 9-9 (2015-01-21)
Smoking is a well-established risk factor for rheumatoid arthritis (RA), and it has been proposed that smoking-induced citrullination renders autoantigens immunogenic. To investigate this mechanism, we examined human lung tissue from 40 subjects with defined smoking status, with or without
Gabriela Venturini et al.
American journal of physiology. Cell physiology, 317(2), C326-C338 (2019-05-09)
Atherosclerotic plaque development is closely associated with the hemodynamic forces applied to endothelial cells (ECs). Among these, shear stress (SS) plays a key role in disease development since changes in flow intensity and direction could stimulate an atheroprone or atheroprotective
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