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SMCC


An amine-to-sulfhydryl crosslinker with a medium-length cyclohexane-stabilized spacer arm (8.3 angstroms).

Pierce SMCC

Thermo Scientific Pierce SMCC is an amine-to-sulfhydryl crosslinker that contains NHS-ester and maleimide reactive groups at opposite ends of a medium-length cyclohexane-stabilized spacer arm (8.3 angstroms).

Succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate (SMCC) is a non-cleavable and membrane permeable crosslinker. It contains an amine-reactive N -hydroxysuccinimide (NHS ester) and a sulfhydryl-reactive maleimide group. NHS esters react with primary amines at pH 7-9 to form stable amide bonds. Maleimides react with sulfhydryl groups at pH 6.5-7.5 to form stable thioether bonds. The maleimide groups of SMCC and Sulfo-SMCC and are unusually stable up to pH 7.5 because of the cyclohexane bridge in the spacer arm.

Highlights:

  • Reactive groups: NHS ester and maleimide
  • Reactive toward: amino and sulfhydryl groups
  • Non-cleavable
  • Water-insoluble (dissolve first in DMF or DMSO); compare to Sulfo-SMCC
  • High purity, crystalline reagent can be used to create high-purity maleimide-activated derivatives
  • Cyclohexane bridge confers added stability to the maleimide group making SMCC an ideal crosslinking agent for maleimide activation of proteins. Maleimide groups are stable for 64 hours in 0.1 M sodium phosphate buffer, pH 7 at 4°C.

Applications:

  • Enzyme labeling of antibodies - both enzyme and antibody specificity can be preserved
  • Create specific bioconjugates via one- or two-step crosslinking reactions
  • Create sulfhydryl-reactive, maleimide-activated carrier proteins for coupling haptens

Product Details:

Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate; SMCC
 
Chemical structure of SMCC crosslinking reagent.

 

Antibody-enzyme conjugation with Sulfo-SMCC
 
Antibody-enzyme conjugation with SMCC. [This example shows Sulfo-SMCC]. This conjugation method enables preparation of maleimide-activated protein (step 1), which can be stably stored for later conjugation to a sulfhydryl-containing protein (step 2). Depending upon the availability of amines and sulfhydryls on respective proteins, the approach can be used in either direction (e.g., enzyme-to-antibody or antibody-to-enzyme). A very popular application for SMCC is activation of immunogenic carrier proteins for conjugation to cysteine-terminated peptides for use in antibody production (e.g., Part No. 77606).

 

Properties of SMCC.
Molecular formula C16H18N2O6
Molecular weight 334.32
Spacer arm length 8.3 Å (9 atoms)
CAS Number 64987-85-5
Storage conditions 4°C, protect from moisture, use only fresh solution
Reactive groups: NHS ester, reacts with primary amines at pH 7.0-9.0
  Maleimide, reacts with sulfhydryls at pH 6.5-7.5

Specifications:

We manufacture SMCC to the highest specifications to produce the most specific bioconjugates and maleimide-activated proteins, ensure the integrity of your data and to provide you with the highest degree of crosslinking consistency. Each lot of SMCC is tested to meet the following minimum specifications.

  • Identity: IR scan shows only peaks characteristic of the structure and functional groups of SMCC cross linker
  • Purity: ≥ 92% by NMR

References:

  1. Uto, I., et al. (1991). J. Immunol. Methods 138, 87-94.
  2. Bieniarz, C., et al. (1996). Extended Length Heterobifunctional Coupling Agents for Protein Conjugations. Bioconjug. Chem. 7, 88-95.
  3. Chrisey, L.A., et al. (1996). Nucleic Acids Res. 24(15), 3031-3039.
  4. Kuijpers, W.H., et al. (1993). Bioconjug. Chem. 4(1), 94-102.
  5. Brinkley, M.A. (1992). A survey of methods for preparing protein conjugates with dyes, haptens and crosslinking reagents. Bioconjugate Chem. 3, 2-13.
  6. Hashida, S., et al. (1984). More useful maleimide compounds for the conjugation of Fab to horseradish peroxidase through thiol groups in the hinge. J. Appl. Biochem. 6, 56-63.
  7. Mattson, G., et al. (1993). A practical approach to crosslinking. Molecular Biology Reports 17, 167-183.
  8. Partis, M.D., et al. (1983). Crosslinking of proteins by omega-maleimido alkanoyl N-hydroxysuccinimide esters. J. Protein. Chem. 2, 263-277.
  9. Samoszuk, M.K., et al. (1989). A peroxide-generating immunoconjugate directed to eosinophil peroxidase is cytotoxic to Hodgkin’s disease cells in vitro. Antibody, Immunoconjugates and Radiopharmaceuticals 2, 37-45.
  10. Yoshitake, S., et al. (1982). Mild and efficient conjugation of rabbit Fab and horseradish peroxidase using a maleimide compound and its use for enzyme immunoassay. J. Biochem. 92, 1413-1424.

Product References:

Crosslinker Application Guide -- search for recent literature references for this product

Related Resources:

Overview of crosslinking
Chemistry of crosslinking

Related Products:

Crosslinkers at a glance (selection guide)
Sulfo-SMCC
Bioconjugate Techniques (book)
Maleimide Activated Carrier Proteins and Kits


Ordering Information
 
Product # Description Pkg. Size Instructions MSDS CofA Price
22360 SMCC
Formulation: Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate; powder solid
Sufficient For: 150mL of typical 1X (1mM) reaction solution, or approx. 25 uses at 2mg reagent per use
50mg Product Instructions for product #22360 SMCC MSDS for product #22360 SMCC Certificate of Analysis for product #22360 SMCC $90.00

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22360B SMCC
Formulation: Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate; powder solid
Custom MSDS for product #22360B SMCC Certificate of Analysis for product #22360B SMCC

Instructions | MSDS | CofA
Product Instructions | MSDS | CofA  

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