SML4172
Iodoacetamide Alkyne-C3
≥95% (HPLC), powder, acysteine-reactive ABPP benchmark probe
Synonym(s):
IPM, IA-Alkyne-C3, IAM-Alkyne-C3, IAA-C3, N-Propynyliodoacetamide, 2-Iodo-N-(prop-2-yn-1-yl)acetamide, 2-Iodo-N-2-propyn-1-ylacetamide, N-Propargyl-2-iodoacetamide
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About This Item
Empirical Formula (Hill Notation):
C5H6INO
CAS Number:
Molecular Weight:
223.01
MDL number:
Quality Level
Assay
≥95% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
-10 to -25°C
SMILES string
O=C(CI)NCC#C
General description
Iodoacetamide alkyne-C3 (IPM, IAA-C3, IA-alkyne-C3, IAM-alkyne-C3) is abifunctional, thiol-reactive probe engineered for activity-based proteinprofiling (ABPP) of reactive cysteine residues in live cells, tissuehomogenates,and tissues. This probe combines an iodoacetamide group, functioning as acovalent warhead for selective cysteine labeling, with a C3 alkyne moiety thatacts as a click-chemistry handle. This alkyne allows for the subsequentconjugation of fluorophores or biotin-linked azido reporters, facilitatingeither the visualization or enrichment of labeled proteins. The IAA-C3 probe,the gold standard in the cysteinomics field, facilitates site-specific analysisof cysteine accessibility, reactivity, redox modification status, and covalentengagement in biological samples by allowing researchers to treat cellhomogenates with varying concentrations of IA-alkyne C3, identifying highly reactivecysteines-suchas those in enzyme active sites or redox-sensitive regions-thatremain reactive despite dilution effects.
Application
IodoacetamideAlkyne-C3 is suitable for use in isotopic tagging strategies for quantitativecysteine-reactivity profiling in various biological samples.
Biochem/physiol Actions
Acysteine-reactive ABPP (activity-based protein profiling) benchmark probe enabling live-cell labeling, visualization, and enrichment of thiol-containing proteins.
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Masahiro Abo et al.
Molecular pharmaceutics, 15(3), 743-749 (2017-11-28)
Cysteine residues on proteins serve a variety of catalytic and regulatory functions due to the high nucleophilicity and redox activity of the thiol group. Quantitative proteomic platforms for profiling cysteine reactivity can provide valuable information related to the post-translational modification
John S Coukos et al.
ACS chemical biology, 18(1), 91-101 (2022-12-24)
Methylglyoxal (MGO), a reactive metabolite byproduct of glucose metabolism, is known to form a variety of posttranslational modifications (PTMs) on nucleophilic amino acids. For example, cysteine, the most nucleophilic proteinogenic amino acid, forms reversible hemithioacetal and stable mercaptomethylimidazole adducts with
Romain Tessier et al.
Angewandte Chemie (International ed. in English), 59(27), 10961-10970 (2020-04-02)
Current approaches to introduce terminal alkynes for bioorthogonal reactions into biomolecules still present limitations in terms of either reactivity, selectivity, or adduct stability. We present a method for the ethynylation of cysteine residues based on the use of ethynylbenziodoxolone (EBX)
Ling Fu et al.
Nature protocols, 15(9), 2891-2919 (2020-07-22)
Cysteine is unique among all protein-coding amino acids, owing to its intrinsically high nucleophilicity. The cysteinyl thiol group can be covalently modified by a broad range of redox mechanisms or by various electrophiles derived from exogenous or endogenous sources. Measuring
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