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LC-SMCC


An amine-to-sulfhydryl crosslinker with a long cyclohexane-stabilized spacer arm (16.2 angstroms).

Pierce LC-SMCC

Thermo Scientific Pierce LC-SMCC is an amine-to-sulfhydryl crosslinker that contains NHS-ester and maleimide reactive groups at opposite ends of a long cyclohexane-stabilized spacer arm (16.2 angstroms).

LC-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 LC-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
  • Long-chain variety of SMCC
  • High purity, crystalline reagent can be used to create high-purity maleimide-activated derivatives
  • Non-cleavable
  • Water-insoluble (dissolve first in DMF or DMSO)
  • Cyclohexane bridge confers added stability to the maleimide group making LC-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:

  • Ideal reagent for enzyme labeling of antibodies, both enzyme activity 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-carboxy-(6-amidocaproate); LC-SMCC
 
Chemical structure of LC-SMCC crosslinking reagent.

LC-SMCC is often used for the preparation of antibody-enzyme and hapten-carrier conjugates. In this type of conjugation, the NHS ester is reacted first with the antibody, excess crosslinking reagent removed and then the sulfhydryl-containing enzyme molecule is added. This two-step reaction scheme results in formation of specific antibody-enzyme conjugates.

LC-SMCC is a reagent of choice for creating stable maleimide-activated carrier proteins that will spontaneously react with sulfhydryls. In this application, the NHS ester of LC-SMCC is reacted with lysine residues on the carrier protein, converting them to reactive maleimides. These relatively stable maleimide-activated intermediates may be lyophilized and stored for later conjugation to a hapten.

Properties of LC-SMCC.
Molecular formula C22H29N3O7
Molecular weight 447.48
Spacer arm length 16.1Å (16 atoms)
CAS Number 64987-85-5
Storage conditions 4°C, protect from moisture, use only fresh solutions
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 LC-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 LC-SMCC is tested to meet the following minimum specifications.

  • Identity: IR scan shows only peaks characteristic of the structure and functional groups of LC-SMCC crosslinker
  • Purity: ≥ 90% by NMR

References:

  1. Bieniarz, C., et al. (1996). Extended length Heterobifunctional Coupling Agents for Protein Conjugations. Bioconjug. Chem. 7, 88-95.
  2. Kuijpers, W.H., et al. (1993). Bioconjug. Chem. 4(1), 94-102.
  3. Mattson, G., et al. (1993). A practical approach to crosslinking. Molecular Biology Reports 17, 167-183.
  4. Brinkley, M.A. (1992). A survey of methods for preparing protein conjugates with dyes, haptens and crosslinking reagents. Bioconjugate Chem. 3, 2-13.
  5. Uto, I., Ishimatsu, T., Hirayama, H., Ueda, S., Tsuruta, J. and Kambara, T. (1991). Determination of urinary Tamm-Horsfall protein by ELISA using a maleimide method for enzyme-antibody conjugation. J. Immunol. Methods 138, 87-94.
  6. Partis, M.D., et al. (1983). Crosslinking of proteins by omega-maleimido alkanoyl N-hydroxysuccinimide esters. J. Protein. Chem. 2, 263-277.
  7. 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
22362 LC-SMCC
Formulation: Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxy-(6-amidocaproate); solid
Sufficient For: 112mL of typical 1X (1mM) reaction solution, or approx. 25 uses at 2mg reagent per use
50mg Product Instructions for product #22362 LC-SMCC MSDS for product #22362 LC-SMCC Certificate of Analysis for product #22362 LC-SMCC $137.00

Add to cart
22362B LC-SMCC
Formulation: Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxy-(6-amidocaproate); solid
Custom MSDS for product #22362B LC-SMCC Certificate of Analysis for product #22362B LC-SMCC

Instructions | MSDS | CofA
Product Instructions | MSDS | CofA  

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