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MedKoo Cat#: 610311 | Name: SMCC crosslinker
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

SMCC, also known as succinimidyl-4-[N-maleimidomethyl]cyclohexane-1-carboxylate, is a heterobifunctional protein crosslinker. 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). SMCC conjugation occurs via a maleimide group that is sulfhydryl (thiol; -SH) reactive and a NHS ester group that is amine reactive and forms stable, covalent protein crosslinks.

Chemical Structure

SMCC crosslinker
SMCC crosslinker
CAS#64987-85-5

Theoretical Analysis

MedKoo Cat#: 610311

Name: SMCC crosslinker

CAS#: 64987-85-5

Chemical Formula: C16H18N2O6

Exact Mass: 334.1165

Molecular Weight: 334.33

Elemental Analysis: C, 57.48; H, 5.43; N, 8.38; O, 28.71

Price and Availability

Size Price Availability Quantity
100mg USD 45.00 Ready to ship
200mg USD 60.00 Ready to ship
500mg USD 110.00 Ready to ship
1g USD 150.00 Ready to ship
2g USD 225.00 Ready to ship
5g USD 450.00 Ready to ship
10g USD 750.00 Ready to ship
20g USD 1,250.00 2 Weeks
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Related CAS #
No Data
Synonym
SMCC, heterobifunctional cross-linker; SMCC crosslinker;
IUPAC/Chemical Name
N-Succinimidyl 4-(N-Maleimidomethyl)cyclohexanecarboxylate
InChi Key
JJAHTWIKCUJRDK-UHFFFAOYSA-N
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
SMILES Code
O=C(C1CCC(CN2C(C=CC2=O)=O)CC1)ON3C(CCC3=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO and DMF
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
SMCC crosslinker must be dissolved in an organic solvent, such as DMSO or DMF, and then can be added to an aqueous crosslinking reaction. SMCC crosslinking reagent is permeable across the lipid bilayer of the cell membrane and can be used to crosslink intracellular proteins and peptides. 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
Biological target:
SMCC is a protein crosslinker.
In vitro activity:
To be determined
In vivo activity:
To be determined
Solvent mg/mL mM
Solubility
DMSO 17.5 52.34
DMF 15.0 44.87
DMF:PBS (pH 7.2) (1:4) 0.2 0.60
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 334.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
To be determined
In vitro protocol:
To be determined
In vivo protocol:
To be determined
Palacios M, Tampe R, Del Campo M, Zhong TY, López MN, Salazar-Onfray F, Becker MI. Antitumor activity and carrier properties of novel hemocyanins coupled to a mimotope of GD2 ganglioside. Eur J Med Chem. 2018 Apr 25;150:74-86. doi: 10.1016/j.ejmech.2018.02.082. Epub 2018 Feb 27. PMID: 29524730.