A protein cross-linking reagent
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Product Categories

Product Type

Biochemicals

Research Area

Cancer
Immunology
Immunology & Inflammation
Adaptive Immunity

Application

SMCC

Item No. 28955

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)methyl]-cyclohexanecarboxylic acid, 2,5-dioxo-1-pyrrolidinyl ester
CAS Number
64987-85-5
Synonyms
  • NSC 344483
  • Succinimidyl 4-(N-maleimidomethyl)cyclohexan-1-carboxylate
Molecular Formula
C16H18N2O6
Formula Weight
334.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 15mg/mlDMF:PBS (pH 7.2) (1:4): 0.2mg/mlDMSO: 10mg/ml
λmax
217 nm
SMILES
O=C(ON1C(CCC1=O)=O)C(CC2)CCC2CN(C(C=C3)=O)C3=O
InChi Code
InChI=1S/C16H18N2O6/c19-12-5-6-13(20)17(12)9-10-1-3-11(4-2-10)16(23)24-18-14(21)7-8-15(18)22/h5-6,10-11H,1-4,7-9H2
InChi Key
JJAHTWIKCUJRDK-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    SMCC is a heterobifunctional cross-linking reagent that contains an amine-reactive N-hydroxysuccinimide ester and a sulfhydryl-reactive maleimide group that can be used in the conjugation of proteins.1,2,3 It has been used to cross-link the anticancer agent DM1 (mertansine; Item No. 22483) to an IgG1 monoclonal antibody to form the antibody-drug conjugate DM1-SMCC (Item No. 23926).4 Immunization of mice with SMCC-coupled keyhole limpet hemocyanin (KLH) antigen and syngeneic splenocytes increases the percentage of proliferating T cells in isolated splenocytes from recipient mice compared to mice immunized with KLH and the adjuvant LPS.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bieniarz, C., Husain, M., Barnes, G., et al. Extended length heterobifunctional coupling agents for protein conjugations. Bioconjug. Chem. 7(1), 88-95 (1996).

    2. Hermanson, G.T. The reactions of bioconjugation. Bioconjugate Techniques (2013).

    3. Guo, Y., Werbel, T., Wan, S., et al. Potent antigen-specific immune response induced by infusion of spleen cells coupled with succinimidyl-4-(N-maleimidomethyl cyclohexane)-1-carboxylate (SMCC) conjugated antigens. Int. Immunopharmacol. 31, 158-168 (2019).

    4. Luo, Q., Chung, H.H., Borths, C., et al. Structural characterization of a monoclonal antibody-maytansinoid immunoconjugate. Anal. Chem. 88(1), 695-702 (2016).