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Bis-sulfone Amine (CCT-1148)

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Description

Bis-sulfone Amine is a bis-alkylating labeling reagent that is selective for the cysteine sulfur atoms from a native disulfide. These reagents undergo bis-alkylation to conjugate both thiols derived from the two cysteine residues of a reduced native disulfide bond such as the interchain disulfide bonds of an antibody. The reaction results in covalent rebridging of the disulfide bond via a three carbon bridge leaving the protein structurally intact.

The covalent, site-specific conjugation of PEG to a polyhistidine tag (His-tag) on a protein with bis-alkylating reagents was also reported in literature (see Selected References section).

Specifications

Unit Size1000 mg, 5 g
Molecular weight593.15 (HCl salt)
Chemical compositionC28H33ClN2O6S2
CASN/A
SolubilityDMSO, DMF, DCM, THF, Chloroform
Purity>95% (HPLC)
AppearanceGrey amorphous solid
Storage Conditions-20°C. Desiccate
Shipping ConditionsAmbient temperature

Selected References

    1. Khalili, H., et al. (2012). Comparative Binding of Disulfide-Bridged PEG-Fabs. Bioconjug. Chem., 23(11), 2262-77. [PubMed]
    2. Badescu, G., et al. (2014). Bridging Disulfides for Stable and Defined Antibody Drug Conjugates. Bioconjug. Chem., 25(6), 1124-36. [PubMed]
    3. Brocchini, S., et al. (2008). Disulfide bridge based PEGylation of proteins. Adv Drug Deliv Rev., 60, 3-12. [PubMed]
    4. Balan, S., et al. (2007). Site-Specific PEGylation of Protein Disulfide Bonds Using a Three-Carbon Bridge. Bioconjugate Chem.,18, 61-76. [PubMed]
    5. Wang, T., et al. (2014). Bis-sulfide bioconjugates for glutathione triggered tumor responsive drug release. ChemComm.,50, 1116-1118. [PubMed]
    6. Wilbur, T., et al. (1994). Monoclonal antibody Fab’ fragment cross-linking using equilibrium transfer alkylation reagents. A strategy for site-specific conjugation of diagnostic and therapeutic agents with F(ab’)2 fragments. Bioconjugate Chem.,5, 220-235. [PubMed]
Site specific conjugation to a polyhistidine tag (His-tag).
  1. Cong, Y., et al. (2012). Site-Specific PEGylation at Histidine Tags. Bioconjugate Chem.,23, 148-263. [PubMed]

Applicable patents and legal notices are available at legal notices.

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