A chemical probe for sulfenic acid detection
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DAz-2

Item No. 13382

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-(3-azidopropyl)-1,3-cyclohexanedione
CAS Number
1176905-54-6
Synonyms
  • DCP-N3
Molecular Formula
C9H13N3O2
Formula Weight
195.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 14 mg/mlEthanol: 25 mg/mlEthanol:PBS (pH 7.2) (1:10): 0.1 mg/ml
λmax
253 nm
SMILES
O=C(C1)C(CCCN=[N+]=[N-])CCC1=O
InChi Code
InChI=1S/C9H13N3O2/c10-12-11-5-1-2-7-3-4-8(13)6-9(7)14/h7H,1-6H2
InChi Key
GQYUHTIXSZXDBD-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $69

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    5 mg

    $229

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    10 mg

    $426

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    Product Description

    DAz-2 is a cell-permeable chemical probe used to detect cysteine oxidation in proteins. Redox-sensitive cysteine residues in proteins may function as sensors of reactive oxygen species (ROS) and also serve as molecular switches, activating or deactivating proteins, following a change in oxidation state. Modification of protein function through the reversible oxidation of cysteine is emerging as a biologically relevant signal transduction mechanism. Sulfenic acid is the initial oxidation product of cysteine by relatively mild oxidizing agents such as hydrogen peroxide. Sulfenic acid can be reduced back to the free thiol or be further oxidized to sulfinic and sulfonic acids.1 DAz-2 is a cell-permeable chemical probe that reacts specifically with sulfenic acid-modified proteins.2 The azido group of DAz-2 provides a method for selective conjugation to phosphine- or alkynyl- derivatized reagents, such as biotin or various fluorophores, for subsequent analysis of the labeled proteins. Use of DAz-2 in HeLa cells followed by Staudinger ligation to biotin and subsequent LC-MS/MS analysis, led to the identification of 193 sulfenic acid-modified proteins having a diverse range of functions.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Reddie, K.G., and Carroll, K.S. Expanding the functional diversity of proteins through cysteine oxidation. Curr. Opin. Chem. Biol. 12(6), 746-754 (2008).

    2. Leonard, S.E., Reddie, K.G., and Carroll, K.S. Mining the thiol proteome for sulfenic acid modifications reveals new targets for oxidation in cells. ACS Chem. Biol. 4(9), 783-799 (2009).

    Product Citations

    Zhang, H., Lv, B., Liu, K., et al. Sulfur dioxide controls M1 macrophage polarization by sulphenylation of prolyl hydroxylase 2 at cysteine 260. Free Radic. Biol. Med. 230, 33-47 (2025).

    Qiu, B., Zhang, S., Ge, S., et al. Vascular smooth muscle cell-derived SO2 sulphenylated interferon regulatory factor 1 to inhibit VSMC senescence. Front. Pharmacol. 16, 1516885 (2025).

    Zhang, S., Qiu, B., Lv, B., et al. Endogenous sulfur dioxide deficiency as a driver of cardiomyocyte senescence through abolishing sulphenylation of STAT3 at cysteine 259. Redox Biol. 71, 103124 (2024).