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I6125

Sigma-Aldrich

Iodoacetamide

≥99% (NMR), crystalline

Synonym(s):

α-Iodoacetamide, 2-Iodoacetamide

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About This Item

Linear Formula:
ICH2CONH2
CAS Number:
Molecular Weight:
184.96
Beilstein/REAXYS Number:
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.

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 4 - Resp. Sens. 1 - Skin Sens. 1

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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
Helen R Stagg et al.
The Journal of cell biology, 186(5), 685-692 (2009-09-02)
The US2 and US11 gene products of human cytomegalovirus promote viral evasion by hijacking the endoplasmic reticulum (ER)-associated degradation (ERAD) pathway. US2 and US11 initiate dislocation of newly translocated major histocompatibility complex class I (MHC I) from the ER to
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
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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