Itaconate-alkyne

• CAT Number: I045754
• CAS Number: 2454181-83-8
• Molecular Formula: C13H18O4
• Molecular Weight: 238.28
• Purity: ≥95%
• Synonyms: 2-methylidene-4-oct-7-ynoxy-4-oxobutanoic acid
• InChI: InChI=1S/C13H18O4/c1-3-4-5-6-7-8-9-17-12(14)10-11(2)13(15)16/h1H,2,4-10H2,(H,15,16)
• InChIKey: NPWMZOZWVAFQMP-UHFFFAOYSA-N
• SMILES: C=C(CC(=O)OCCCCCCC#C)C(=O)O

Itaconate-alkyne (ITalk) is a specific bioorthogonal probe for quantitative and site-specific chemoproteomic profiling of Itaconation in living cells. Itaconate-alkyne, a functional analogue of Itaconate, exhibits comparable antiinflammatory effect with Itaconate and enables the labeling of bona fide targets of Itaconate[1]. Itaconate-alkyne is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
Itaconate-alkyne (ITalk; 0.005, 0.01, 0.05, 0.1, 0.5, 1, 5, 10 mM; 0-4 hours) has the concentration- and time-dependent labeling in the lysates of Raw264.7 cells[1].
Itaconate-alkyne (100 μM; for 4 hours) significantly increases the protein level of NRF-2 in LPS (100 ng/mL)-stimulated Raw264.7 cells and significantly inhibits lactate production in LPS-stimulated Raw264.7 cells. Itaconate-alkyne significantly inhibits the secretion of interlukin-1β (IL-1β) in LPS-timulated Raw264.7 cells[1].
Itaconate-alkyne (100 μM; for 12 hours) does not affect the cell viability of Raw264.7 cells[1].
Itaconate-alkyne can capture itaconate targets including DNA damage-binding protein 1 (DDB1), Gelsolin (GSN), ATP-citrate synthase (ACLY) and Adenylate kinase 2 (AK2) in inflammatory macrophages[1].

Reference

[1]. Wei Qin, et al. Chemoproteomic Profiling of Itaconation by Bioorthogonal Probes in Inflammatory Macrophages. J Am Chem Soc . 2020 Jun 24;142(25):10894-10898.
 [Content Brief]