DCP-Bio1

DCP-Bio1 is dimedone based and contains a biotin tag making it compatible with several techniques and forms of analysis.

Features:

  • Contains cleavable biotin tag
  • Stable, reproducible binding to cysteine sulfenic acid (-SOH) at pH 6.0 - 8.0
  • Ester linkage allows for efficient hydrolysis using NH4OH
    (Doesn't hydrolyse under physiological conditions)
  • Great for In vitro and In vivo applications
  • Compatible with WB, ELISA, and Affinity Isolation

Redox-sensitive cysteine residues in proteins may serve as important components of oxidative signaling or sensors of oxidative stress. Cysteine sulfenic acid modification is an emerging area of interest for those studying biological signal transduction within the cell.

Cysteine sulfenic acid formation in proteins results from the oxidative modification of susceptible cysteine residues by mild oxidizing agents such as hydrogen peroxide, alkyl hydroperoxides, and peroxynitrite. These sulfenic acid modified proteins can be identified by their ability to form adducts with dimedone, but this reagent provides no spectral or affinity tag to such adduct to allow for later analysis. DCP-Bio1 can be used to effectively detect the formation of cysteine sulfenic acid in the redox regulation of proteins, and with the presence of a biotin label, DCP-Bio1 is compatible with several techniques and forms of analysis post-labeling.

From the laboratories of Leslie B. Poole, PhD and S. Bruce King, PhD, Wake Forest School of Medicine.

Catalog Number Product Size AVAILABILITY Price Qty
EE0028
DCP-Bio1 - 2mg
2mg In stock
Price: $205.00
Specifications
Product Type: Small Molecule
Name: DCP-Bio1; 3-(2,4-dioxocyclohexyl)propyl 5-((3aR,6S,6aS)-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-6-yl)pentanoate
Chemical Formula: C19H28N2O5S
Molecular Weight: 396.5 g/mol
Format: solid
Purity: >98% pure, see Poole, et al., 2007
Solubility: At least 500 mM in DMSO, at least 5 mg/ml in acetonitrile
Stability: stable > 6 months at -20 degC
Source: synthetic
Spectral Information: No visible absorbance; NMR data, etc. in Poole et al., 2007
Storage: room temperature for short term, -20 degC for long term
Provider
From the laboratories of Leslie B. Poole, PhD and S. Bruce King, PhD, Wake Forest School of Medicine.
Comments

Stock solution in DMSO can be added to cell lysis buffer, preferrably keeping final [DMSO] < 2% for labeling proteins. Can be dissolved in acetonitrile to prepare aliquots and redry.

References
  1. Poole, L.B., Klomsiri, C., Knaggs, S.A., Furdui, C.M., Nelson, K.J., Thomas, M.J., Fetrow, J.S., Daniel, L.W. & King, S.B. Fluorescent and affinity-based tools to detect cysteine sulfenic acid formation in proteins. Bioconjug Chem 18, 2004-17 (2007). PMC2526167
  2. Klomsiri, C., Nelson, K.J., Bechtold, E., Soito, L., Johnson, L.C., Lowther, W.T., Ryu, S.E., King, S.B., Furdui, C.M. & Poole, L.B. Use of dimedone-based chemical probes for sulfenic acid detection: evaluation of conditions affecting probe incorporation into redox-sensitive proteins. Methods Enzymol 473, 77-94 (2010)
  3. Nelson, K.J., Klomsiri, C., Codreanu, S.G., Soito, L., Liebler, D.C., Rogers, L.C., Daniel, L.W. & Poole, L.B. Use of dimedone-based chemical probes for sulfenic acid detection; methods to visualize and identify labeled proteins. Methods Enzymol 473, 95-115 (2010).

DCP-Bio1 Application References

  1. Oshikawa, J., Urao, N., Kim, H.W., Kaplan, N., Razvi, M., McKinney, R., Poole, L.B., Fukai, T. & Ushio-Fukai, M. Extracellular SOD-derived H2O2 promotes VEGF signaling in caveolae/lipid rafts and post-ischemic angiogenesis in mice. PLoS One 5, e10189 (2010). PMC2858087
  2. Kaplan, N., Urao, N., Furuta, E., Kim, S.J., Razvi, M., Nakamura, Y., McKinney, R.D., Poole, L.B., Fukai, T. & Ushio-Fukai, M. Localized cysteine sulfenic acid formation by vascular endothelial growth factor:role in endothelial cell migration and angiogenesis. Free Radic Res 45, 1124-35 (2011).
  3. Wani, R., Qian, J., Yin, L., Bechtold, E., King, S.B., Poole, L.B., Paek, E., Tsang, A.W. & Furdui, C.M. Isoform-specific regulation of Akt by PDGF-induced reactive oxygen species. Proc Natl Acad Sci U S A 108, 10550-5 (2011).
  4. Oger, E., et al. (2012). "Sulfenylated proteins in the Medicago truncatula-Sinorhizobium meliloti symbiosis." J Proteomics 75(13): 4102-4113.
  5. Wang L, Zhang L, Niu Y, Sitia R, Wang CC. Glutathione peroxidase 7 utilizes hydrogen peroxide generated by Ero1? to promote oxidative protein folding. Antioxid Redox Signal. 2014 Feb 1;20(4):545-56.
  6. Hristova M, Habibovic A, Veith C, Janssen-Heininger YM, Dixon AE, Geiszt M, van der Vliet A. Airway epithelial dual oxidase 1 mediates allergen-induced IL-33 secretion and activation of type 2 immune responses. J Allergy Clin Immunol. 2015 Nov 17. pii: S0091-6749(15)01428-1.
  7. Cook NL, Moeke CH, Fantoni LI, Pattison DI, Davies MJ. The myeloperoxidase-derived oxidant hypothiocyanous acid inhibits protein tyrosine phosphatases via oxidation of key cysteine residues. Free Radic Biol Med. 2015 Nov 23. pii: S0891-5849(15)01123-5. doi: 10.1016/ j.freeradbiomed.2015.11.025. [Epub ahead of print] PubMed PMID: 26616646.
  8. Luanpitpong S, Chanvorachote P, Stehlik C, Tse W, Callery PS, Wang L,Rojanasakul Y. Regulation of apoptosis by Bcl-2 cysteine oxidation in human lung epithelial cells. Mol Biol Cell. 2013 Mar;24(6):858-69. View Article
  9. Hourihan JM, Moronetti Mazzeo LE, Fernández-Cárdenas LP, Blackwell TK.Cysteine Sulfenylation Directs IRE-1 to Activate the SKN-1/Nrf2 AntioxidantResponse. Mol Cell. 2016 Aug 18;63(4):553-66. View Article
  10. Heppner DE, Hristova M, Dustin CM, Danyal K, Habibovic A, van der Vliet A. TheNADPH oxidases DUOX1 and NOX2 Play Distinct Roles in Redox Regulation ofEpidermal Growth Factor Receptor Signaling. J Biol Chem. 2016 Sep 20. pii:jbc.M116.749028. View Article
  11. Pan L, Zhu B, Hao W, Zeng X, Vlahopoulos SA, Hazra TK, Hegde ML, Radak Z, Bacsi A, Brasier AR, Ba X, Boldogh I. Oxidized Guanine Base Lesions Function in 8-Oxoguanine DNA Glycosylase-1-mediated Epigenetic Regulation of Nuclear Factor κB-driven Gene Expression. J Biol Chem. 2016 Dec 2;291(49):25553-25566. PubMed PMID: 27756845; PubMed Central PMCID: PMC5207254.View Article
  12. Kenche H, Ye ZW, Vedagiri K, Richards DM, Gao XH, Tew KD, Townsend DM, Blumental-Perry A. Adverse Outcomes Associated with Cigarette Smoke Radicals Related to Damage to Protein-disulfide Isomerase. J Biol Chem. 2016 Feb 26;291(9):4763-78. doi: 10.1074/jbc.M115.712331. PubMed PMID: 26728460; PubMed Central PMCID: PMC4813498.View Article
  13. Habibovic A, Hristova M, Heppner DE, Danyal K, Ather JL, Janssen-Heininger YM, Irvin CG, Poynter ME, Lundblad LK, Dixon AE, Geiszt M, van der Vliet A. DUOX1 mediates persistent epithelial EGFR activation, mucous cell metaplasia, and airway remodeling during allergic asthma.JCI Insight. 2016 Nov 3;1(18):e88811. View Article
  14. DOI: 10.1007/978-3-319-06710-0_7 In book: Nitric Oxide in Plants: Metabolism and Role in Stress Physiology, Edition: http://link.springer.com/chapter/10.1007%2F978-3-319-06710-0_7, Chapter: Nitric oxide synthesis, detection methods and possible roles during jasmonate-regulated stress response., Publisher: Springer International, Switzerland, Editors: Khan N., Mobin M., Mohammad F., Corpas F.J., pp.127-138 View Article
  15. Wood ST, Long DL, Reisz JA, Yammani RR, Burke EA, Klomsiri C, Poole LB, Furdui CM, Loeser RF. Cysteine-Mediated Redox Regulation of Cell Signaling in Chondrocytes Stimulated With Fibronectin Fragments. Arthritis Rheumatol. 2016 Jan;68(1):117-26. doi: 10.1002/art.39326. PubMed PMID: 26314228; PubMed Central PMCID: PMC4849859. View Article
  16. Ba X, Bacsi A, Luo J, Aguilera-Aguirre L, Zeng X, Radak Z, Brasier AR, Boldogh I. 8-oxoguanine DNA glycosylase-1 augments proinflammatory gene expression by facilitating the recruitment of site-specific transcription factors. J Immunol. 2014 Mar 1;192(5):2384-94. View Article
  17. Heppner DE, Hristova M, Ida T, Mijuskovic A, Dustin CM, Bogdándi V, Fukuto JM, Dick TP, Nagy P, Li J, Akaike T, van der Vliet A. Cysteine perthiosulfenic acid (Cys-SSOH): A novel intermediate in thiol-based redox signaling? Redox Biol. 2017 Oct 9;14:379-385. View Article

If you publish research with this product, please let us know so we can cite your paper.

 
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