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Sulfo-SMCC


A water-soluble amine-to-sulfhydryl crosslinker with a medium-length cyclohexane spacer arm (8.3 angstroms).

Pierce Sulfo-SMCC

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

Sulfosuccinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate (Sulfo-SMCC) is a water-soluble, non-cleavable and membrane impermeable 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 Sulfo-SMCC and SMCC are unusually stable up to pH 7.5 because of the cyclohexane bridge in the spacer arm. Because it contains the hydrophilic sulfonyl moiety, Sulfo-SMCC is soluble up to ~10 mM in water and many commonly used buffers, thus avoiding the use of organic solvents which may perturb protein structure.

Highlights:

  • Reactive groups: sulfo-NHS ester and maleimide
  • Reactive towards: amino and sulfhydryl groups
  • Water-soluble (compare to SMCC), so crosslinking can be done in physiologic solutions
  • High purity, crystalline reagent can be used to create high-purity maleimide-activated derivatives
  • Cyclohexane bridge confers added stability to the maleimide group making Sulfo-SMCC the 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:

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

 

Antibody-enzyme conjugation with Sulfo-SMCC
 
Antibody-enzyme conjugation with 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 Sulfo-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 Sulfo-SMCC.
Molecular formula C16H17N2O9SNa
Molecular weight 436.37
Spacer arm length 8.3 Å (9 atom)
CAS Number 92921-24-9
Storage conditions -20°C, protect from moisture, use only fresh solutions
Reactive groups: Sulfo-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 Sulfo-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 Sulfo-SMCC is tested to meet the following minimum specifications.

  • Identity: IR scan shows only peaks characteristic of the structure and functional groups of Sulfo-SMCC crosslinker
  • Purity: ≥ 90% by quantitative NMR (the highest standard for crosslinker purity)
  • Solubility: ≥ 10mg/mL in DI water

References:

  1. Muller L. et al. (2010) Evolutionary gain of function for the ER membrane protein Sec62 from yeast to humans. Mol. Biol. Cell. 21, 691-703.
  2. Dickgreber N. et al. (2009) Targeting antigen to MHC class II molecules promotes efficient cross-presentation and enhances immunotherapy. J. Immunol. 182, 1260-9.
  3. Kersemans V. et al. (2008) Drug-resistant aml cells and primary aml specimens are killed by 111In-anti-CD33 monoclonal antibodies modified with nuclear localizing peptide sequences. J. Nucl. Med. 49, 1546-54.
  4. Duval M. et al. (2008) A bispecific antibody composed of a nonneutralizing antibody to the gp41 immunodominant region and an anti-CD89 antibody directs broad human immunodeficiency virus destruction by neutrophils. J. Virol. 82, 4671-4.
  5. Costantini D. L. et al. (2008) Trastuzumab-resistant breast cancer cells remain sensitive to the auger electron-emitting radiotherapeutic agent 111In-NLS-Trastuzumab and are radiosensitized by methotrexate. J. Nucl. Med. 49, 1498-505.
  6. Brinkmann M. M. et al. (2007) The interaction between the ER membrane protein UNC93b and TLR3, 7, and 9 is crucial for TLR signaling. J. Cell Biol. 177, 265-75.
  7. Kehoe J. W. et al. (2006) Using phage display to select antibodies recognizing post-translational modifications independently of sequence context. Mol. Cell. Proteomics. 5, 2350-63.

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)
SMCC
Bioconjugate Techniques (book)
Maleimide Activated Carrier Proteins and Kits


Ordering Information
 
Product # Description Pkg. Size Instructions MSDS CofA Price
22122 Sulfo-SMCC
Formulation: Sulfosuccinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate; powder solid
Sufficient For: 2292mL of typical 1X (1mM) reaction solution, or approx. 500 uses at 2mg reagent per use
1g Product Instructions for product #22122 Sulfo-SMCC MSDS for product #22122 Sulfo-SMCC Certificate of Analysis for product #22122 Sulfo-SMCC $2,040.00

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22322 Sulfo-SMCC
Formulation: Sulfosuccinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate; powder solid
Sufficient For: 115mL of typical 1X (1mM) reaction solution, or approx. 25 uses at 2mg reagent per use
50mg Product Instructions for product #22322 Sulfo-SMCC MSDS for product #22322 Sulfo-SMCC Certificate of Analysis for product #22322 Sulfo-SMCC $158.00

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22322B Sulfo-SMCC
Formulation: Sulfosuccinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate; powder solid
Custom MSDS for product #22322B Sulfo-SMCC
22622 Sulfo-SMCC, No-Weigh Format
Formulation: Sulfosuccinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate; solid
Sufficient For: 37mL of typical 1X (1mM) reaction solution (total), or 8 separate uses
8 x 2mg Product Instructions for product #22622 Sulfo-SMCC, No-Weigh Format MSDS for product #22622 Sulfo-SMCC, No-Weigh Format Certificate of Analysis for product #22622 Sulfo-SMCC, No-Weigh Format $153.00

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Instructions | MSDS | CofA
Product Instructions | MSDS | CofA  

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