Iodoacetamide
From ToxBankWiki
Executive Summary Information
Compound | Iodoacetamide |
Toxicities | Cytotoxicity |
Mechanisms | Iodoacetamide is representative of alkylating reagents that are selective for thiols. Enzymes that use cysteine as a catalytic nucleophile may be 2-3 orders of magnitude more sensitive to alkylation by this reagent than is GSH. Glyceraldehyde phosphate dehydrogenase is rapidly inactivated, and blockage of glycolysis is a major mechanism of toxicity. Iodoacetamide rapidly increases the GSSG/GSH ratio, which is inferred to result from an increase in the NAD/NADH ratio associated with inhibition of glycolysis. Caspases are also known to be sensitive, and enzymes that transfer the CoASH cofactor in fatty acid synthesis and oxidation are expected to be sensitive. Tagged derivatives of iodoacetamide are used in proteomic analysis of protein redox states. |
Comments | Iodoacetamide is selected based on its chemical reactivity, representing thiol alkylating agents without accompanying redox activity. |
Feedback Contact | Gold Compound Working Group (GCWG) |
Iodoacetamide | |
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Identifiers | |
Leadscope Id | LS-7458 |
CAS | 144-48-9 |
ChemSpider | 3596 |
UNII | ZRH8M27S79 |
Pathway DBs | |
Assay DBs | |
PubChem CID | 3727 |
ChEMBL | 276727 |
Omics DBs | |
Properties | |
ToxCast Accepted | yes |
ToxBank Accepted | yes |
Target | MOA standard for thiol alkylation |
Toxicities | Cytotoxicity |
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PubMed references
The following resource link will perform a PubMed query for the terms " Iodoacetamide " and "liver toxicity".
Iodoacetamide Search
The following resource link will perform a PubMed query for the terms " Iodoacetamide " and "cardio toxicity".
Iodoacetamide Search
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The recommended source is Sigma Aldrich, product number I1149.
Iodoacetamide | |
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Source | Sigma Aldrich |
Product ID | I1149 |
Mol Weight | 184.96 |
Purity | ≥99 % |
Brand | Sigma BioUltra |
Quantity | 5 g |
Cost | 51.3 |
Storage | Store at +2-8 °C |
Stability | All solutions are sensitive to light and should be freshly prepared. Store with desiccant. Product is sensitive to light and moisture |