iodoacetamide

Summary

Summary: An alkylating sulfhydryl reagent. Its actions are similar to those of iodoacetate.

Top Publications

  1. Boja E, Fales H. Overalkylation of a protein digest with iodoacetamide. Anal Chem. 2001;73:3576-82 pubmed
    ..After reduction, the sulfhydryls are usually reacted with iodoacetamide (IAM), iodoacetic acid (IAA), or another electrophile to prevent reformation of disulfide linkages in a random ..
  2. Ozaki N, Bielefeldt K, Sengupta J, Gebhart G. Models of gastric hyperalgesia in the rat. Am J Physiol Gastrointest Liver Physiol. 2002;283:G666-76 pubmed
    ..Rats received either 20% acetic acid (HAc) or saline injections into the stomach wall or 0.1% iodoacetamide (IA) in drinking water...
  3. Ren J, Davidoff A, Ingwall J. Creatine kinase inhibitor iodoacetamide antagonizes calcium-stimulated inotropy in cardiomyocytes. Clin Exp Pharmacol Physiol. 2009;36:141-5 pubmed publisher
    ..Adult rat cardiomyocytes were perfused with the creatine kinase inhibitor iodoacetamide (90 micromol/L) for 90 min...
  4. Nielsen M, Vermeulen M, Bonaldi T, Cox J, Moroder L, Mann M. Iodoacetamide-induced artifact mimics ubiquitination in mass spectrometry. Nat Methods. 2008;5:459-60 pubmed publisher
  5. Painsipp E, Wultsch T, Shahbazian A, Edelsbrunner M, Kreissl M, Schirbel A, et al. Experimental gastritis in mice enhances anxiety in a gender-related manner. Neuroscience. 2007;150:522-36 pubmed
    ..Gastritis was induced by adding iodoacetamide (0.1%) to the drinking water for at least 7 days...
  6. Xu Y, Wu X, Liu W, Lin X, Chen J, He R. A convenient assay of glycoserum by nitroblue tetrazolium with iodoacetamide. Clin Chim Acta. 2002;325:127-31 pubmed
    ..To determine glycoserum, the nitroblue tetrazolium (NBT) assay is quick, economical, convenient and easily automated. This method, however, is vulnerable to interference by thiol group, which should not be ignored during the analysis...
  7. Person M, Mason D, Liebler D, Monks T, Lau S. Alkylation of cytochrome c by (glutathion-S-yl)-1,4-benzoquinone and iodoacetamide demonstrates compound-dependent site specificity. Chem Res Toxicol. 2005;18:41-50 pubmed
    The reaction of cytochrome c with the electrophilic compounds (glutathion-S-yl)-1,4-benzoquinone (GSBQ) and iodoacetamide was studied using mass spectrometry...
  8. Adachi Y, Chen W, Shang W, Kamata T. Development of a direct and sensitive detection method for DNA-binding proteins based on electrophoretic mobility shift assay and iodoacetamide derivative labeling. Anal Biochem. 2005;342:348-51 pubmed
  9. Ceruti M, Balliano G, Rocco F, Lenhart A, Schulz G, Castelli F, et al. Synthesis and biological activity of new iodoacetamide derivatives on mutants of squalene-hopene cyclase. Lipids. 2005;40:729-35 pubmed
    New iodoacetamide derivatives, containing a dodecyl or a squalenyl moiety, were synthesized...

More Information

Publications62

  1. NELSON K, Day A, Zeng B, King S, Poole L. Isotope-coded, iodoacetamide-based reagent to determine individual cysteine pK(a) values by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Anal Biochem. 2008;375:187-95 pubmed
    ..value of cysteine residues through quantitative mass spectrometry following chemical modification with an iodoacetamide-based reagent over a range of pH buffers...
  2. Williams D, Meadows C, Bori I, Hawkridge A, Comins D, Muddiman D. Synthesis, characterization, and application of iodoacetamide derivatives utilized for the ALiPHAT strategy. J Am Chem Soc. 2008;130:2122-3 pubmed publisher
  3. Sun M, Chen C, Huang Y, Wu Z, Ho Y. Matrix-assisted laser desorption/ionization-MS-based relative quantification of peptides and proteins using iodoacetamide and N-methyliodoacetamide as labeling reagents. J Sep Sci. 2008;31:538-47 pubmed publisher
    The use of iodoacetamide (IAA) and N-methyliodoacetamide (MIAA) as labeling agents for the relative measurements of proteins using MALDI-MS is described herein...
  4. Criddle A, Geeves M, Jeffries T. The use of actin labelled with N-(1-pyrenyl)iodoacetamide to study the interaction of actin with myosin subfragments and troponin/tropomyosin. Biochem J. 1985;232:343-9 pubmed
    ..Thin filiments reconstituted from pyrene-labelled actin show a 5% increase in pyrene fluorescence on binding Ca2+...
  5. Eliakim R, Karmeli F, Cohen P, Heyman S, Rachmilewitz D. Dual effect of chronic nicotine administration: augmentation of jejunitis and amelioration of colitis induced by iodoacetamide in rats. Int J Colorectal Dis. 2001;16:14-21 pubmed
    ..We investigated the effect of chronic nicotine administration on the small and large bowel in iodoacetamide-induced jejunitis and colitis...
  6. Schwarz G, Beck S, Weller M, Linscheid M. MeCAT--new iodoacetamide reagents for metal labeling of proteins and peptides. Anal Bioanal Chem. 2011;401:1203-9 pubmed publisher
    ..In the current study, we developed a new labeling approach utilizing an iodoacetamide MeCAT reagent (MeCAT-IA)...
  7. Gabler W, Tsukuda N. The influence of divalent cations and doxycycline on iodoacetamide-inhibitable leukocyte adherence. Res Commun Chem Pathol Pharmacol. 1991;74:131-40 pubmed
    ..To account for nonspecific leukocyte-substrata interactions the OD's of iodoacetamide-inhibited adherent cell systems were subtracted from the OD values of adherent cells of noninhibited systems...
  8. Piqueras L, Corpa J, Martinez J, Martinez V. Gastric hypersecretion associated to iodoacetamide-induced mild gastritis in mice. Naunyn Schmiedebergs Arch Pharmacol. 2003;367:140-50 pubmed
    ..Mild gastritis was induced with 0.1% iodoacetamide administered intragastrically and added to the drinking water for a 6 days period...
  9. Nishio H, Hayashi Y, Terashima S, Takeuchi K. Role of endogenous nitric oxide in mucosal defense of inflamed rat stomach following iodoacetamide treatment. Life Sci. 2006;79:1523-30 pubmed
    ..inhibitors on gastric ulcerogenic and acid secretory responses following daily exposure of the stomach to iodoacetamide and investigated the role of each NOS isozyme in gastric protection from subchronic mucosal irritation...
  10. Joliot P, Alric J. Inhibition of CO2 fixation by iodoacetamide stimulates cyclic electron flow and non-photochemical quenching upon far-red illumination. Photosynth Res. 2013;115:55-63 pubmed publisher
    ..b>Iodoacetamide reacts irreversibly with free -SH groups of cysteine residues and inhibits the enzymes responsible for CO2 ..
  11. McLeish M, Caine J. Chemical modification of PABA synthase. Biochem Int. 1991;24:1033-42 pubmed
    ..Results indicate that cysteine, histidine, arginine and tyrosine residues are important for enzyme activity. Attempts were made to determine the subunits upon which these residues were located...
  12. Eggler A, Luo Y, van Breemen R, Mesecar A. Identification of the highly reactive cysteine 151 in the chemopreventive agent-sensor Keap1 protein is method-dependent. Chem Res Toxicol. 2007;20:1878-84 pubmed
    ..The electrophilic agent biotinylated iodoacetamide (BIA) has been used by different laboratories to determine the most reactive cysteines in human Keap1, and the ..
  13. Jurjus A, Barada K, Khoury N, Assef M, Foltzer C, Reimund J, et al. Morphological and biochemical alterations in the jejunum following iodoacetamide-induced colitis in rats. Can J Physiol Pharmacol. 2006;84:1191-203 pubmed
    ..small and large intestines as well as the expression of some enterocyte enzymes and carriers in a rat model of iodoacetamide-induced colitis...
  14. Tolstanova G, Deng X, French S, Lungo W, Paunovic B, Khomenko T, et al. Early endothelial damage and increased colonic vascular permeability in the development of experimental ulcerative colitis in rats and mice. Lab Invest. 2012;92:9-21 pubmed publisher
    ..We showed that in rats with iodoacetamide (IA)-induced UC increased colonic VP occurs early (ie, 2.6-fold increase at 15 min, P<0...
  15. Barua B, Winkelmann D, White H, Hitchcock Degregori S. Regulation of actin-myosin interaction by conserved periodic sites of tropomyosin. Proc Natl Acad Sci U S A. 2012;109:18425-30 pubmed publisher
    ..The evolutionarily conserved residues are important for actomyosin regulation, a universal function of Tm that has a common structural basis and mechanism...
  16. Jiang J, Denner L, Ling Y, Li J, Davis A, Wang Y, et al. Double blockade of cell cycle at g(1)-s transition and m phase by 3-iodoacetamido benzoyl ethyl ester, a new type of tubulin ligand. Cancer Res. 2002;62:6080-8 pubmed
    ..Besides being a novel lead for the design of new anticancer tubulin ligands, the activity of 3-IAABE in the cell cycle may also help us to understand the molecular pharmacology of microtubule-active drugs...
  17. Thurston R, Korn N, Froman D, Bodine A. Proteolytic enzymes in seminal plasma of domestic turkey (Meleagris gallopavo). Biol Reprod. 1993;48:393-402 pubmed
    ..95 x 10(-4) M (n = 6), respectively. TSPE, like acrosin and trypsin, was inhibited by benzamidine but not iodoacetamide. While all natural trypsin inhibitors tested inhibited acrosin, TSPE was not inhibited by ovomucoid from ..
  18. Tian R, Christe M, Spindler M, Hopkins J, Halow J, Camacho S, et al. Role of MgADP in the development of diastolic dysfunction in the intact beating rat heart. J Clin Invest. 1997;99:745-51 pubmed
    ..This was achieved by applying a low dose of iodoacetamide to selectively inhibit the creatine kinase activity in isolated perfused rat hearts...
  19. Rajkarnikar A, Strankman A, Duran S, Vargas D, Roberts A, Barretto K, et al. Analysis of mutants disrupted in bacillithiol metabolism in Staphylococcus aureus. Biochem Biophys Res Commun. 2013;436:128-33 pubmed publisher
    ..aureus USA 300 LAC 2626 as a BSH-S-transferase, which is able to conjugate chlorodinitrobenzene, cerulenin, and rifamycin to BSH. ..
  20. Lavis L, Rutkoski T, Raines R. Tuning the pK(a) of fluorescein to optimize binding assays. Anal Chem. 2007;79:6775-82 pubmed
    ..12 increased the Z'-factor from -0.17 to 0.69. We propose that synthetic "tuning" of the pKa of fluorescein and other pH-sensitive fluorophores provides a general means to optimize binding assays...
  21. Teigelkamp S, Bhardwaj R, Roth J, Meinardus Hager G, Karas M, Sorg C. Calcium-dependent complex assembly of the myeloic differentiation proteins MRP-8 and MRP-14. J Biol Chem. 1991;266:13462-7 pubmed
    ..5 kDa) were identified as [MRP-8)2.(MRP-14] trimer and [MRP-8)2.(MRP-14)2) tetramer, respectively. All complexes could be shown to be noncovalently associated in vivo. Furthermore, the association of MRPs was shown to be Ca2+ dependent...
  22. Dotan I, Hershkoviz R, Karmeli F, Brazowski E, Peled Y, Rachmilewitz D, et al. Heparin and low-molecular-weight heparin (enoxaparin) significantly ameliorate experimental colitis in rats. Aliment Pharmacol Ther. 2001;15:1687-97 pubmed
    ..We investigated whether a low dose of low-molecular-weight heparin-enoxaparin (Clexane, Rhône-Poulenc Rorer, France)-ameliorates the inflammatory response in two models of experimental colitis...
  23. Kumar S, Kayastha A. Soybean (Glycine max) urease: significance of sulfhydryl groups in urea catalysis. Plant Physiol Biochem. 2010;48:746-50 pubmed publisher
    ..time-dependent inactivation of urease with DTNB, p-chloromercuribenzoate (p-CMB), N-ethylmaleimide (NEM) and iodoacetamide (IAM) showed biphasic kinetics, where half of the enzyme activity was lost more rapidly than the other half...
  24. Muruganandan S, Cribb A. Calpain-induced endoplasmic reticulum stress and cell death following cytotoxic damage to renal cells. Toxicol Sci. 2006;94:118-28 pubmed
    ..we explored the link between ER stress, calpain, and cell death in renal cell injury due to model RCTs (iodoacetamide, menadione, tert-butyl hydroperoxide) and ER stress inducers (tunicamycin [TUN], thapsigargin [THAPS])...
  25. Martin H, Dean M. Identification of a thioredoxin-related protein associated with plasma membranes. Biochem Biophys Res Commun. 1991;175:123-8 pubmed
    ..weight membrane associated sulphydryl protein was detected on a wide range of nucleated cells when [14C]-iodoacetamide was used as a probe...
  26. Holyoak T, Nowak T. pH Dependence of the reaction catalyzed by avian mitochondrial phosphoenolpyruvate carboxykinase. Biochemistry. 2004;43:7054-65 pubmed
    ..1. One of the basic ionizations is attributed to the P-loop lysine (K275) and the other to C273...
  27. Yuan C, Ault Riché D, Borchardt R. Chemical modification and site-directed mutagenesis of cysteine residues in human placental S-adenosylhomocysteine hydrolase. J Biol Chem. 1996;271:28009-16 pubmed
    ..identified as Cys113, Cys195, and Cys421, respectively, by protein sequencing after modification with [1-14C]iodoacetamide. Of the three modifiable cysteines, Cys113 and Cys195 could be protected from modification in the presence of ..
  28. Landar A, Oh J, Giles N, Isom A, Kirk M, Barnes S, et al. A sensitive method for the quantitative measurement of protein thiol modification in response to oxidative stress. Free Radic Biol Med. 2006;40:459-68 pubmed
    ..used as quantitative standards in electrophoretic separation of protein samples labeled with biotin-conjugated iodoacetamide. The utility of the approach was assessed by measuring modification of thiols in response to exposure to thiol ..
  29. Günther Sillero M, de Diego A, Silles E, Sillero A. Synthesis of (di)nucleoside polyphosphates by the ubiquitin activating enzyme E1. FEBS Lett. 2005;579:6223-9 pubmed
    ..Previous treatment of the enzyme (E1) with iodoacetamide inhibited only partially the synthesis of p4A...
  30. Di Luccio E, Azulay D, Regaya I, Fajloun Z, Sandoz G, Mansuelle P, et al. Parameters affecting in vitro oxidation/folding of maurotoxin, a four-disulphide-bridged scorpion toxin. Biochem J. 2001;358:681-92 pubmed
    ..During the oxidation/folding of reduced L-sMTX, the oxidation intermediates were blocked by iodoacetamide alkylation of free cysteine residues, and analysed by MS...
  31. Gentile M, Blanch H. Physiology and xanthophyll cycle activity of Nannochloropsis gaditana. Biotechnol Bioeng. 2001;75:1-12 pubmed
    ..Addition of iodoacetamide dramatically affected the xanthophyll cycle activity: 50% of the violaxanthin was replaced by zeaxanthin (90%) ..
  32. Stone E, Costello A, Tierney D, Fast W. Substrate-assisted cysteine deprotonation in the mechanism of dimethylargininase (DDAH) from Pseudomonas aeruginosa. Biochemistry. 2006;45:5618-30 pubmed
    ..These results support a proposed substrate-assisted mechanism for Pa DDAH in which ligand binding modulates the reactivity of the active-site cysteine...
  33. Bingle W, Le K, Smit J. The extreme N-terminus of the Caulobacter crescentus surface-layer protein directs export of passenger proteins from the cytoplasm but is not required for secretion of the native protein. Can J Microbiol. 1996;42:672-84 pubmed
  34. Rosa R, Calvin M. Comparative effects of two sulfhydryl reagents on the activities of a multifunctional red cell enzyme: bisphosphoglycerate mutase. Biochem Biophys Res Commun. 1988;153:945-51 pubmed
    ..With iodoacetamide the mutase and the stimulated-phosphatase activities were completely inhibited whereas the non-stimulated ..
  35. Yang L, Lin G, Nelson R, Jian Y, Telser J, Li L. Mechanistic studies of the spore photoproduct lyase via a single cysteine mutation. Biochemistry. 2012;51:7173-88 pubmed
    ..Here we show that C141 can be readily alkylated in the native SPL by an iodoacetamide treatment, suggesting that it is accessible to the TpT radical...
  36. Xue H, Xue Y, DOUBLIE S, Carter C. Chemical modifications of Bacillus subtilis tryptophanyl-tRNA synthetase. Biochem Cell Biol. 1997;75:709-15 pubmed
    ..By comparison, modification of sulfhydryl groups by means of iodoacetamide did not reduce TrpRS activity...
  37. Cordero J, Rodríguez P, Romero P. Differences in intramembrane particle distribution in young and old human erythrocytes. Cell Biol Int. 2004;28:423-31 pubmed
    ..The results suggest that their low ATP content may account for the increased particle density of senescent cells...
  38. Zalkin H, Truitt C. Characterization of the glutamine site of Escherichia coli guanosine 5'-monophosphate synthetase. J Biol Chem. 1977;252:5431-6 pubmed
    ..GMP synthetase exhibits glutaminase activity when ATP is replaced by adenosine plus PPi. Iodoacetamide inactivates glutaminase concomitant with glutamine-dependent GMP synthetase...
  39. Horigome T, Ogata F, Golding T, Korach K. Estradiol-stimulated proteolytic cleavage of the estrogen receptor in mouse uterus. Endocrinology. 1988;123:2540-8 pubmed
    ..5 mM p-chloromercuribenzoic acid and 2.5 mM p-chloromercuriphenylsulfonate and partially inhibited by 2.5 mM iodoacetamide but not by 1 mg/ml leupeptin, 0.1 mg/ml antipain, 0.1 mg/ml chymostatin, 0.1 mg/ml pepstatin, 0...
  40. Krolczyk G, Gil K, Zurowski D, Jung A, Thor P. The vagal afferents discharge and myoelectrical activity in the gastric hyperalgesia model in rats. J Physiol Pharmacol. 2008;59:707-16 pubmed
    ..The gastric mucosal inflammation was induced by addition iodoacetamide to drinking water for 5 days...
  41. Miller R, Sies H, Park E, Thomas J. Phosphorylase and creatine kinase modification by thiol-disulfide exchange and by xanthine oxidase-initiated S-thiolation. Arch Biochem Biophys. 1990;276:355-63 pubmed
    ..For proteins typified by phosphorylase b, the accumulation of S-thiolated forms may be more independent of GSH...
  42. Pretzer E, Wiktorowicz J. Saturation fluorescence labeling of proteins for proteomic analyses. Anal Biochem. 2008;374:250-62 pubmed publisher
    ..We also showed that the dye exhibits little to no effect on the two-dimensional mobilities of labeled proteins derived from cells...
  43. Cebi M, Koert U. Reactivity recognition by TRPA1 channels. Chembiochem. 2007;8:979-80 pubmed
  44. Galvani M, Rovatti L, Hamdan M, Herbert B, Righetti P. Protein alkylation in the presence/absence of thiourea in proteome analysis: a matrix assisted laser desorption/ionization-time of flight-mass spectrometry investigation. Electrophoresis. 2001;22:2066-74 pubmed
    ..adopted recently (namely thiourea) strongly quenches such alkylation process (as typically carried out with iodoacetamide, IAA)...
  45. Rawat M, Uppal M, Newton G, Steffek M, Fahey R, Av Gay Y. Targeted mutagenesis of the Mycobacterium smegmatis mca gene, encoding a mycothiol-dependent detoxification protein. J Bacteriol. 2004;186:6050-8 pubmed publisher
    ..mutation in mca renders the mutant strain more susceptible to electrophilic toxins, such as N-ethylmalemide, iodoacetamide, and chlorodinitrobenzene, and to several oxidants, such as menadione and plumbagin...
  46. Vardhana P, Illsley N. Transepithelial glucose transport and metabolism in BeWo choriocarcinoma cells. Placenta. 2002;23:653-60 pubmed
    ..Experiments involving stimulation and inhibition of cellular glucose consumption demonstrated that there is a single intracellular glucose pool in BeWo cells, supplying both metabolism and transcellular transport...
  47. Nagababu E, Chrest F, Rifkind J. Hydrogen-peroxide-induced heme degradation in red blood cells: the protective roles of catalase and glutathione peroxidase. Biochim Biophys Acta. 2003;1620:211-7 pubmed
    ..is reduced to at least 40% of its initial value as a result of incubation or by reacting the glutathione with iodoacetamide. Reactive catalase only slows down the depletion of glutathione, but does not directly prevent the formation ..
  48. Liu L, Winston J, Shenoy M, Song G, Chen J, Pasricha P. A rat model of chronic gastric sensorimotor dysfunction resulting from transient neonatal gastric irritation. Gastroenterology. 2008;134:2070-9 pubmed publisher
  49. San Blas G, Sorais F, Niño Vega G, Mendez C, San Blas F. Cytosolic neutral proteinases of Paracoccidioides brasiliensis. Curr Microbiol. 1998;37:141-3 pubmed
    ..inhibition of the mycelial enzymes by ethylene diamine tetraacetic acid (EDTA), 1,10-phenanthroline, and iodoacetamide, also suggested the presence of cysteine- and metallo-proteinases...
  50. Balmer Y, Vensel W, Hurkman W, Buchanan B. Thioredoxin target proteins in chloroplast thylakoid membranes. Antioxid Redox Signal. 2006;8:1829-34 pubmed
  51. Wolf J, Lachmann I, Wagner U, Osman A, Mothes T. Immunoassay of in vitro activated human tissue transglutaminase. Anal Biochem. 2011;411:10-5 pubmed publisher
    ..The new assay represents a promising tool for the study of tTG in normal cell physiology and under pathological conditions...
  52. Hagman C, Ramström M, Håkansson P, Bergquist J. Quantitative analysis of tryptic protein mixtures using electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry. J Proteome Res. 2004;3:587-94 pubmed
    ..This method can be used for observing protein dynamics in a specific cell type, tissue, or in body fluids...
  53. Geoghegan K, Hoth L, Tan D, Borzilleri K, Withka J, Boyd J. Cyclization of N-terminal S-carbamoylmethylcysteine causing loss of 17 Da from peptides and extra peaks in peptide maps. J Proteome Res. 2002;1:181-7 pubmed
    Enzymatic digests of proteins S-alkylated with iodoacetamide may contain peptides with N-terminal S-carbamoylmethylcysteine. These can be partly converted to a form with 17 Da lower mass and increased HPLC retention...