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2-iodoacetamide, also known as iodoacetamide or IAM, is a multifunctional organic compound belonging to the acetamide class. Molecular formula C2H4INO, CAS 144-48-9, this colorless to yellow liquid has a unique odor and is widely used in various scientific and industrial applications due to its unique reactivity. One of the primary applications lies in proteomics research, where it serves as an alkylating agent for cysteine residues in proteins. This reaction, known as carbamidomethylation, prevents disulfide bond reformation during sample preparation steps for proteomic analysis, enabling better preservation of protein structure and facilitating mass spectrometry-based protein identification and quantification.
In addition to its use in proteomics, it has found applications in the synthesis of bioactive compounds, owing to its ability to serve as a building block for introducing iodine, a biologically essential halogen, into organic molecules. It can also participate in click chemistry reactions, broadening its synthetic utility in the field of organic chemistry.
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| Chemical Formula | C2H4INO |
| Exact Mass | 184.93 |
| Molecular Weight | 184.96 |
| m/z | 184.93 (100.0%), 185.94 (2.2%) |
| Elemental Analysis | C, 12.99; H, 2.18; I, 68.61; N, 7.57; O, 8.65 |
1. Alkylation of cysteine
2-iodoacetamide is a commonly used cysteine alkylating reagent in proteomics. During the sample preparation process, it undergoes an irreversible reaction with the thiol group (- SH) of protein cysteine residues to form covalent carbon sulfur bonds (R-S-CH ₂ CONH ₂), thereby modifying the protein structure. This reaction can effectively prevent the protein from re forming disulfide bonds in subsequent processing, ensuring complete denaturation of the sample and maintaining a reduced state.
Application scenarios: Peptide sequencing, protein structure analysis, protein interaction research.
Experimental advantages: Rapid reaction (can be completed in 20 minutes at room temperature), strong specificity, and minimal impact on other amino acid residues in the protein.
Case: Using 2-iodoacetamid to treat protein samples before mass spectrometry analysis can significantly improve peptide identification rate and reduce missed detection rate.
2. Histidine modification
It can also react with the imidazole ring of histidine, but the reaction rate is slow and is commonly used in the study of specific enzyme activity inhibition. For example, by modifying the histidine residue at the active site of ribonuclease, the enzyme catalytic mechanism can be explored.
3. Enzyme inhibitor development
It can be used as an irreversible enzyme inhibitor to block enzyme function through thiol or imidazole groups in the active center of alkylating enzymes.
Target enzyme types: enzymes with thiol groups as the active center (such as alcohol dehydrogenase, succinate dehydrogenase, 3-phosphoglyceraldehyde dehydrogenase), as well as histidine dependent enzymes (such as certain proteases).
Mechanism of action: The reaction generates stable covalent adducts (R-S-CH ₂ CONH ₂ or R-N-CH ₂ CONH ₂), which permanently inactivate the enzyme.
Application value: In drug development, 2-iodoacetamid derivatives can serve as lead compounds for designing specific enzyme inhibitors.
Organic synthesis: multifunctional intermediates and reaction reagents
1. Synthesis of bioactive molecules
Its iodine atom has excellent departure properties, making it an ideal intermediate for synthesizing functional compounds containing thiols, amines, and other groups.
Reaction type:
Alkylation reaction: reacts with thiols to form disulfide bonds, used to modify peptides or proteins.
Substitution reaction: As an electrophilic reagent, it undergoes substitution with heteroatoms containing lone pair electrons (such as oxygen and nitrogen).
Addition reaction: Participate in Michael addition and other reactions to construct carbon carbon bonds.
Application example: When synthesizing anticancer drugs containing thiol groups, they can react with thiol groups in the target molecule to form stable disulfide bonds, thereby improving drug stability.
2. Ubiquitin research
In the study of the ubiquitin proteasome system, the activity of deubiquitinases (DUBs) can be inhibited. By binding to the cysteine residue of the DUB active site, it blocks its cleavage of the ubiquitin chain, thereby maintaining the stability of ubiquitinated proteins.
Experimental method: Adding 2-iodoacetamide to cell lysate can effectively inhibit endogenous DUBs, facilitating subsequent enrichment and analysis of ubiquitinated proteins.
3. Peptide sequencing auxiliary reagents
In peptide sequencing, alkylating cysteine residues can prevent the reformation of disulfide bonds during the sequencing process, thereby improving sequencing accuracy. In addition, the modified peptides can generate characteristic fragment ions in mass spectrometry analysis to assist in structural analysis.
1. Construction of animal models
Can be used to induce animal digestive system disease models, study their pathogenesis and drug efficacy.
Functional dyspepsia (FD) model in rats: Administration of 2-iodoacetamid (2.0-10 mg/d, lasting 20-93 days) via gavage can induce chronic deep ulcers in the antrum of the stomach, simulating human FD symptoms.
Ulcerative colitis model: Combined with tail clamping stress, it can exacerbate intestinal inflammatory response and is used for screening anti-inflammatory drugs.
Model advantages: Easy to operate, good repeatability, suitable for drug screening and pathological mechanism research.
2. Cell level research
In cell experiments, inhibition of enzymes containing thiol groups can interfere with cellular metabolic processes.
Glycolysis inhibition: By inhibiting glyceraldehyde-3-phosphate dehydrogenase, blocking the glycolysis pathway, and studying the regulation of cellular energy metabolism.
Muscle contraction research: Inhibiting thiol groups in myosin light chain kinase to explore the molecular mechanism of muscle contraction.
3. Application of photosensitive properties
Easy to decompose under light, it needs to be stored away from light (brown bottle, 4 ℃ refrigerator). This characteristic makes it potentially applicable in light controlled release systems, such as achieving precise spatiotemporal regulation by inducing the release of active molecules through light.
Other application areas
1. Research on disinfection by-products
As a byproduct of disinfection in drinking water, the study of its generation mechanism and toxicity is of great significance for ensuring drinking water safety.
2. Industrial Chemistry
2-iodoacetamid can be used for the synthesis of polymer materials, surfactants, etc., but its industrial application scale is relatively small and mainly focused on laboratory research.
It is an important chemical reagent that is widely used in many fields such as proteomics, peptide sequencing, and enzyme inhibitors. Its synthesis is mainly carried out by the reaction of chloroacetamide and sodium iodide. The following is a detailed synthesis and preparation method:
principle
The synthesis of 2-Iodoacetamide is based on a halogen exchange reaction, where the chlorine atom in chloroacetamide is replaced by an iodine atom.
Reactants & Reagents
1
as the main raw material of the reaction.
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as the reaction solvent, it helps the reactants to mix and react fully.
3
provides iodine atoms to exchange with the chlorine atoms in chloroacetamide.
4
used for subsequent treatment and purification steps.
steps
Mixing reactants: Chloroacetamide, anhydrous acetone and anhydrous sodium iodide are mixed in a reaction vessel in a certain proportion.
Heating and reflux: The mixture is refluxed under heating conditions for a period of time (usually 15 hours) to ensure that the reaction is fully carried out.
Cooling and filtering: After the reaction is completed, the mixture is cooled to room temperature and the generated sodium chloride solid is filtered out.
Recovering the solvent: Recover and treat the reaction solvent acetone for reuse or safe disposal.
Neutralization and crystallization: After the filtrate is cooled slightly, it is poured into ice water of sodium bisulfate and then neutralized to pH 6 with a saturated sodium sulfate solution. Then cool and crystallize, and filter to obtain a crude product.
Recrystallization: The crude product is recrystallized with water to further purify the product and finally obtain high-purity product.
In vivo studies, the toxic effects have been explored in detail, especially in long-term exposure experiments conducted in animal models. These studies usually use rats as experimental subjects to evaluate the potential effects of the compound on organisms.
Experimental models and conditions
Animal model: Sprague-Dawley rats
Dosage: 2.0-10 mg
Administration: Daily administration through drinking water
Duration: 20 to 93 days
Experimental results
In these experiments, the main results observed were:
Gastritis production: Many experimental rats developed inflammation of the stomach (gastritis) after exposure to it.
Chronic ulcers: Further studies found that these gastritis further complicated with chronic deep ulcers in many rats, mainly in the secretory part of the stomach.
Safety and toxicity assessment
These in vivo findings highlight the potential toxicity in organisms, especially in the case of long-term exposure.
Therefore, when using this compound for biological research, it is necessary to be cautious and strictly control the experimental conditions to ensure the safety of experimental animals and the reliability of experimental results.
Since it is sensitive to light and moisture, its storage conditions are also particularly important. It is generally recommended to store it in a sealed container at 2-8°C, away from light sources and moisture. In addition, when handling this compound, appropriate protective equipment, such as protective gloves and respiratory protective equipment, should be worn to avoid inhalation of dust or vapor.
English Translation Iodoacetamide has no documented independent "natural discovery" process and is a halogenated alkylamide derivative produced via targeted artificial synthesis.
After synthetic frameworks for haloacetic acid derivatives took shape in the late 19th century, researchers prepared this compound through halogen exchange between chloroacetamide and sodium iodide. In its early days, it served only as a niche intermediate in organic synthesis, with no systematic characterization of its physicochemical properties. Groundbreaking discoveries regarding its biological activity emerged in biochemistry during the 1930s.
A landmark study in 1937 revealed that this compound interacts specifically with protein thiol groups. Around 1940, multiple papers published in the *Journal of Biological Chemistry* systematically described its alkylation reactions with cysteine thiol groups present in urease and ovalbumin, clearly establishing its capacity for thiol capping and thiol enzyme inhibition.
Over the subsequent decades, its synthetic procedures underwent continuous optimization, and purification via aqueous recrystallization became standardized.
With advances in proteomics and mass spectrometry, from the late 20th century to the early 21st century, iodoacetamide evolved into a standard alkylating reagent for protein sample pretreatment, completing its transformation from an obscure organic raw material to an essential biochemical tool reagent.
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