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| Targets |
2-Iodoacetamide targets cysteine residues in proteins. As an electrophile, it covalently modifies nucleophilic residues such as cysteine, methionine, and histidine. Its primary mechanism of action is the alkylation of the thiol group of cysteine, which prevents the formation of disulfide bonds. This modification is commonly used in proteomics to block cysteines and prevent unwanted disulfide bond formation during sample preparation.
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| ln Vitro |
The production of viral structural proteins involves a partial cleavage cascade mechanism. The largest virally induced protein found in infected cells has a molecular weight of 144,000. Two polypeptides with molecular weights of 205,000 and 180,000 emerge when the infected cells are pretreated with iodoacetamide before being pulsed with 35S-methionine. When iodoacetamide is present, additional modifications take place in the viral protein precursors.[2]
In vitro, 2-Iodoacetamide is used as a reagent for protein modification. It alkylates cysteine residues, preventing disulfide bond formation. This activity is assessed by measuring the extent of cysteine alkylation in proteins using mass spectrometry or other analytical techniques. It is a standard reagent in proteomics workflows for protein digestion and peptide mapping. |
| ln Vivo |
2-Iodoacetamide (2.0–10 mg; 20–93 days; drinking; daily) In the secretory portion of the rat stomach, feeding invariably results in long-term, deep ulcers[2].
In vivo, 2-Iodoacetamide can be used to construct animal models of functional dyspepsia. Its mechanism in this context may involve the modification of specific proteins or enzymes in the gastrointestinal tract, leading to altered function. However, its primary use is as a research reagent for in vitro applications. |
| Enzyme Assay |
For protein modification studies, 2-Iodoacetamide is incubated with proteins or peptides at various concentrations. The reaction typically occurs at a basic pH to deprotonate the thiol group of cysteine. The extent of alkylation is assessed by mass spectrometry or by measuring the loss of free thiols using Ellman's reagent. The compound is typically dissolved in water or buffer.
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| Cell Assay |
After being pretreated for 15 minutes with 2 mM iodoaeetamide, infected cells were pulsed for 30 minutes with 500 μCi of 35S-methionine. By directly comparing the corresponding autoradiogram and the stained dried slab gel, the molecular weights are determined.
For cellular studies, 2-Iodoacetamide can be used to modify proteins in cell lysates. Cells are lysed, and the lysate is treated with the compound to alkylate cysteine residues. This is a common step in proteomic sample preparation to prevent disulfide bond formation and to stabilize proteins for analysis. |
| Animal Protocol |
Animal/Disease Models: SD (Sprague-Dawley) rats[2]
Doses: 2.0-10 mg Route of Administration: Drinking water, daily, for periods of 20 to 93 days Experimental Results: Produced gastritis which was further complicated by chronic ulceration in many of the test rats . For in vivo animal studies, 2-Iodoacetamide is used to construct models of functional dyspepsia. The compound is administered to rodents via an appropriate route, and the animals are monitored for symptoms of functional dyspepsia, such as delayed gastric emptying or visceral hypersensitivity. |
| ADME/Pharmacokinetics |
Pharmacokinetic properties of 2-Iodoacetamide are not extensively detailed in the provided sources. It has a molecular weight of 184.96 and is a white to light brown crystalline solid. It has a melting point of 92-95°C and is soluble in water (0.5 M at 20°C) and ethanol. It should be stored at room temperature.
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| Toxicity/Toxicokinetics |
2-Iodoacetamide is toxic and should be handled with caution. It is an alkylating agent and can be hazardous if inhaled, ingested, or absorbed through the skin. Standard laboratory safety precautions, including the use of personal protective equipment, should be followed when handling this compound. It is intended for research use only and is not for human therapeutic applications.
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| References | |
| Additional Infomation |
Iodoacetamide is a thiol alkylating agent that forms a covalent bond with the thiol group of cysteine, thereby preventing the formation of disulfide bonds in proteins or peptide chains. It is a thiol alkylating agent, and its function is similar to that of iodoacetic acid.
2-Iodoacetamide is a thiol-alkylating agent with a molecular formula of C2H4INO and a molecular weight of 184.96. It is used to alkylate cysteine residues in proteins, preventing disulfide bond formation. It is a standard reagent in proteomics for protein digestion and peptide mapping. This research compound is for laboratory use only and has not been approved for clinical applications. |
| Molecular Formula |
C2H4INO
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| Molecular Weight |
184.96
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| Exact Mass |
184.933
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| CAS # |
144-48-9
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| Related CAS # |
2-Iodoacetamide-d4;1219802-64-8
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| PubChem CID |
3727
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| Appearance |
White to yellow solid powder
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| Density |
2.3±0.1 g/cm3
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| Boiling Point |
297.1±23.0 °C at 760 mmHg
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| Melting Point |
92-95 °C(lit.)
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| Flash Point |
133.5±22.6 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.602
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| LogP |
-0.19
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
5
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| Complexity |
44.9
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
PGLTVOMIXTUURA-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5)
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| Chemical Name |
2-iodoacetamide
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| Synonyms |
Iodoacetamide; 2-Iodoacetamide
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : 40~100 mg/mL (216.3~540.7 mM)
H2O : ~100 mg/mL (~540.7 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.52 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (13.52 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (13.52 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 100 mg/mL (540.66 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.4066 mL | 27.0329 mL | 54.0657 mL | |
| 5 mM | 1.0813 mL | 5.4066 mL | 10.8131 mL | |
| 10 mM | 0.5407 mL | 2.7033 mL | 5.4066 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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