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Pierce™ SMCC
Pierce™ SMCC
Thermo Scientific™

Pierce™ SMCC

Thermo Scientific Pierce SMCC is a hetero-bifunctional crosslinker that contain N-hydroxysuccinimide (NHS) ester and maleimide groups that allow covalent conjugationRead more
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Catalog NumberQuantity
2236050 mg
A3539410 x 1 mg
Catalog number 22360
Price (USD)
153.00
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50 mg
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Price (USD)
153.00
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Thermo Scientific Pierce SMCC is a hetero-bifunctional crosslinker that contain N-hydroxysuccinimide (NHS) ester and maleimide groups that allow covalent conjugation of amine- and sulfhydryl-containing molecules. NHS esters react with primary amines at pH 7–9 to form amide bonds, while maleimides react with sulfhydryl groups at pH 6.5–7.5 to form stable thioether bonds. In aqueous solutions, NHS ester hydrolytic degradation is a competing reaction whose rate increases with pH. The maleimide group is more stable than the NHS-ester group, but will slowly hydrolyze and lose its reaction specificity for sulfhydryls at pH values > 7.5. For these reasons, conjugations with these crosslinkers are usually performed at pH 7.2–7.5, with the NHS ester (amine-targeted) reacted before or simultaneous with the maleimide (sulfhydryl-targeted) reaction.

The cyclohexane ring in the spacer arm of this reagent decreases the rate of hydrolysis of the maleimide group compared to similar reagents that do not contain this ring. This feature enables proteins that have been maleimide-activated with SMCC to be lyophilized and stored for later conjugation to a sulfhydryl-containing molecule. Many maleimide-activated protein products are produced in this manner.

Thermo Scientific No-Weigh products are specialty reagents provided in a pre-aliquoted format. The pre-weighed packaging prevents the loss of reagent reactivity and contamination over time by eliminating the repetitive opening and closing of the vial. The format enables use of a fresh vial of reagent each time, eliminating the hassle of weighing small amounts of reagents and reducing concerns over reagent stability.

Features of SMCC:

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.

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.

Applications:
• Enzyme labelling 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

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

Product References:
Crosslinker Application Guide -- search for recent literature references for this product
For Research Use Only. Not for use in diagnostic procedures.
Specifications
Cell PermeabilityYes
FormPowder
Labeling MethodChemical Labeling
Molecular Weight (g/mol)334.32
PEGylatedNo
Product LinePierce™
Quantity50 mg
Reactive MoietyMaleimide, NHS Ester
Shipping ConditionAmbient
SolubilityDMF, DMSO
Spacer Arm Length8.3 Å
Water SolubleNo
Chemical ReactivityAmine-Sulfhydryl
CleavableBy Thiols
Crosslinker TypeHeterobifunctional
FormatStandard, Single-use
Product TypeCrosslinker
SpacerShort (<10 Å)
Unit SizeEach
Contents & Storage
Upon receipt store desiccated at 4°C.
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Frequently asked questions (FAQs)

Can you provide the shelf-life for SMCC (succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate)?

SMCC (succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate) is covered under our general 1-year warranty and is guaranteed to be fully functional for 12 months from the date of shipment, if stored as recommended. Please see section 8.1 of our Terms & Conditions of Sale (https://www.thermofisher.com/content/dam/LifeTech/Documents/PDFs/Terms-and-Conditions-of-Sale.pdf) for more details.

Find additional tips, troubleshooting help, and resources within our Protein Purification and Isolation Support Center.

What is the difference between SMCC and Sulfo-SMCC?

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). Sulfo-SMCC is a similar compound but it has a sulfonate group on the NHS ring which makes it water-soluble whereas SMCC is water-insoluble and needs to be dissolved first in an organic solvent like DMF or DMSO. Subsequent dilution into aqueous reaction buffer is generally possible, and most protein reactants will remain soluble if the final concentration of organic solvent is less than 10%.

Find additional tips, troubleshooting help, and resources within our Protein Purification and Isolation Support Center.

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Lot #Certificate TypeDateCatalog Number(s)
3215154Certificate of AnalysisJun 10, 202522360
AC404162Certificate of AnalysisApr 07, 202522360
AC404161Certificate of AnalysisApr 02, 202522360
ZL404023Certificate of AnalysisFeb 12, 202522360, DNU-22360
ZL402964Certificate of AnalysisFeb 12, 202522360, DNU-22360
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Citations & References (7)

Citations & References
Abstract
Solid phase DNA amplification: characterisation of primer attachment and amplification mechanisms.
Authors:Adessi C, Matton G, Ayala G, Turcatti G, Mermod JJ, Mayer P, Kawashima E
Journal:Nucleic Acids Res
PubMed ID:11024189
Different chemical methods used to attach oligonucleotides by their 5'-end on a glass surface were tested in the framework of solid phase PCR where surface-bound instead of freely-diffusing primers are used to amplify DNA. Each method was first evaluated for its capacity to provide a high surface coverage of oligonucleotides ... More
Covalent attachment of synthetic DNA to self-assembled monolayer films.
Authors:Chrisey LA, Lee GU, O'Ferrall CE
Journal:Nucleic Acids Res
PubMed ID:8760890
'The covalent attachment of thiol-modified DNA oligomers; to self-assembled monolayer silane films on fused silica and oxidized silicon substrates is described. A heterobifunctional crosslinking molecule bearing both thiol- and amino-reactive moieties was used to tether a DNA oligomer (modified at its terminus with a thiol group) to an aminosilane film ... More
Protein/oligonucleotide conjugates as a cell specific PNA carrier.
Authors:Obara K, Ishihara T, Akaike T, Maruyama A
Journal:Nucleic Acids Res Suppl
PubMed ID:12836342
'We have focused on proteineus ligand conjugate with oligonucleotides (ODNs) as a cell-specific delivery vector for peptide nucleic acids (PNAs). Asialofetuin (AF), a hepatocyte-specific proteineus ligand, was conjugated with ODNs that served as binding sites for PNAs. Succinimidyl-transe-4(N-maleimidylmethyl)-cyclohexane-1-carboxylate (SMCC) modified AF was coupled with 5''-thiolated oligodeoxynucleotide (HS-ODN). The resulting conjugate ... More
Antibody-maytansinoid conjugates designed to bypass multidrug resistance.
Authors:Kovtun YV, Audette CA, Mayo MF, Jones GE, Doherty H, Maloney EK, Erickson HK, Sun X, Wilhelm S, Ab O, Lai KC, Widdison WC, Kellogg B, Johnson H, Pinkas J, Lutz RJ, Singh R, Goldmacher VS, Chari RV
Journal:Cancer Res
PubMed ID:20197459
'Conjugation of cytotoxic compounds to antibodies that bind to cancer-specific antigens makes these drugs selective in killing cancer cells. However, many of the compounds used in such antibody-drug conjugates (ADC) are substrates for the multidrug transporter MDR1. To evade the MDR1-mediated resistance, we conjugated the highly cytotoxic maytansinoid DM1 to ... More
Surface modification, functionalization and bioconjugation of colloidal inorganic nanoparticles.
Authors:Sperling RA, Parak WJ
Journal:Philos Trans A Math Phys Eng Sci
PubMed ID:20156828
Inorganic colloidal nanoparticles are very small, nanoscale objects with inorganic cores that are dispersed in a solvent. Depending on the material they consist of, nanoparticles can possess a number of different properties such as high electron density and strong optical absorption (e.g. metal particles, in particular Au), photoluminescence in the ... More
7 total citations

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