The reaction of halogenacetic acids with glutathione and cysteine. , Several studies have shown iodoacetate has anti-tumor effects. It reacts with cysteine residues in proteins. Iodoacetamide is an irreversible inhibitor of all cysteine peptidases, with the mechanism of inhibition occurring from alkylation of the catalytic cysteine residue (see schematic). , Iodide is a naturally occurring ion that can be found in many source waters and it is easily oxidized by wastewater disinfectants. It is an irreversible inhibitor of all cysteine proteases by alkylation of the catalytic cysteine residue, including deubiquitinating enzymes (DUBs), Cathepsin B, and beta-Amylase. This observation appears contradictory to standard chemical reactivity, however the presence of a favourable interaction between the positive imidazolium ion of the catalytic histidine and the negatively charged carboxyl-group of the i… One of the products of iodide oxidation is hypoiodous acid (HOI or OI−) which is capable of reacting with background organic materials to generate iodinated disinfection by-products (DBPs) including iodoacetic acid.
Iodoacetic acid is a derivative of acetic acid. The nature of active-site functional groups and comparisons with the native enzyme", "Interaction of halogenacetates and SH compounds. It is a toxic compound, because, like many alkyl halides, it is an alkylating agent. Commonly used small molecules such as iodoacetamide or N-ethyl maleimide (NEM) inhibit the activity of Cys deubiquitinating enzymes in cell lysates [3,5]. Iodoacetamide is an alkylation agent by reacting with histidine, methionine and sulfhydryl groups of proteins. Iodoacetate is an irreversible inhibitor of all cysteine peptidases, with the mechanism of inhibition occurring from alkylation of the catalytic cysteine residue (see schematic). This observation appears contradictory to standard chemical reactivity, however the presence of a favourable interaction between the positive imidazolium ion of the catalytic histidine and the negatively charged carboxyl-group of the iodoacetate i… Iodoacetic acid is more toxic than bromoacetic acid and much more toxic than chloroacetic acid. In 2002 Dr. Fawzia Fahim showed that "a single IAA treatment of tumor-bearing mice significantly increased the levels of plasma lactate dehydrogenase (LDH) activity, while it also significantly decreased the levels of plasma glucose and liver total protein, RNA and DNA, compared to normal controls. The mechanism of iodoacetate poisoning of glyoxalase", https://en.wikipedia.org/w/index.php?title=Iodoacetic_acid&oldid=978485160, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Articles with dead external links from April 2017, Articles with permanently dead external links, Creative Commons Attribution-ShareAlike License, This page was last edited on 15 September 2020, at 06:00. It is often used to modify SH-groups to prevent the re-formation of disulfide bonds after the reduction of cystine residues to cysteine during protein sequencing. By virtue of its reaction with cysteine, iodoacetamide is an irreversible inhibitor of enzymes with cysteine at the active site.  Iodoacetic acid has exhibited traits indicating it as a potential carcinogen, however, it has not been proven to be carcinogenic. α-Iodoacetamide, CAS 144-48-9, is an irreversible inhibitor of several cysteine proteases. However, all these compounds lack specificity.  In 1966 Charles A. Apffel, Barry G. Arnason & John H. Peters showed anti-tumor activity for iodoacetate. , Except where otherwise noted, data are given for materials in their, "Antitumor Activities of Iodoacetate and Dimethylsulphoxide Against Solid Ehrlich Carcinoma Growth in Mice", "Effect of Iodoacetate on the Bone Marrow Immunocompetence of AKR Mice", 10.1002/(SICI)1096-9926(199606)53:6<352::AID-TERA6>3.0.CO;2-1, "Inactivation of the RTEM-1 cysteine beta-lactamase by iodoacetate. This observation appears contradictory to standard chemical reactivity, however the presence of a favourable interaction between the positive imidazolium ion of the catalytic histidine and the negatively charged carboxyl-group of the iodoacetic acid is the reason for the increased activity of iodoacetamide. Iodoacetate is an irreversible inhibitor of all cysteine peptidases, with the mechanism of inhibition occurring from alkylation of the catalytic cysteine residue (see schematic). Inhibitor. In comparison with its amide derivative, iodoacetamide, iodoacetate reacts substantially slower. In a study performed by Plewa, et al., IAA was determined to be one of the most cytotoxic of those studied, with a median lethal dose on the order of magnitude of 10−5 M. It was the most genotoxic of more than 60 DBPs studied and is the most genotoxic DBP identified thus far. α-Iodoacetamide - CAS 144-48-9 - Calbiochem MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.  Monohaloacetic acids are the most toxic, with toxicity increasing with halogen size. It reacts much more slowly with histidine residues, but that activity is responsible for inhibition of ribonuclease. In comparison with its acid derivative, iodoacetate, iodoacetamide reacts substantially faster. " In 1975 Melvin S. Rhein, Joyce A. Filppi and Victor S. Moore showed that iodoacetate improved the immune response of bone marrow.
Ubiquitin-based inhibitors have been developed that target Cys-based DUBs.  Its toxicity correlates to its ability as an alkylating agent, which will modify cysteine residues in proteins.  The trend continues in teratogenicity, with iodoacetic acid’s potency surpassing that of its brominated and chlorinated analogs.
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