SMCC crosslinker

Alias: SMCC, heterobifunctional cross-linker SMCC crosslinker
Cat No.:V11269 Purity: = 99.62%
SMCC, formerly known as succinimidyl-4-[N-maleimidomethyl]cyclohexane-1-carboxylate, is a heterobifunctional protein crosslinker.
SMCC crosslinker Chemical Structure CAS No.: 64987-85-5
Product category: ADC Linker
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: = 99.62%

Product Description

SMCC, formerly 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.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
OVA and keyhole limpet hemocyanin (KLH) can be conjugated using SMCC or sulfo-SMCC. 300 μl KLH or OVA (3 mg) and 30 μl SMCC or Sulfo-SMCC (final concentration of 0.1 mM) are added in PBS with a final volume of 3 ml to the conjugation system. [1]
ln Vivo
The SMCC-conjugation technique allows antigen-coupled syngeneic splenic mononuclear cells to be injected into mice, eliciting strong immune responses to whole protein or peptide antigens[1].
References

[1]. Potent antigen-specific immune response induced by infusion of spleen cells coupled with succinimidyl-4-(N-maleimidomethyl cyclohexane)-1-carboxylate (SMCC) conjugated antigens. Int Immunopharmacol. 2016 Feb;31:158-68.

[2]. Li F, Wang Z, Huang Y, Xu H, He L, Deng Yan, Zeng X, He N. Delivery of PUMA Apoptosis Gene Using Polyethyleneimine-SMCC-TAT/DNA Nanoparticles: Biophysical Characterization and In Vitro Transfection Into Malignant Melanoma Cells. J Biomed Nanotechnol. 2015 Oct;11(10):1776-82. PubMed PMID: 26502640.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H18N2O6
Molecular Weight
334.328
Exact Mass
334.1165
Elemental Analysis
C, 57.48; H, 5.43; N, 8.38; O, 28.71
CAS #
64987-85-5
Appearance
Solid powder
SMILES
O(C(C1([H])C([H])([H])C([H])([H])C([H])(C([H])([H])N2C(C([H])=C([H])C2=O)=O)C([H])([H])C1([H])[H])=O)N1C(C([H])([H])C([H])([H])C1=O)=O
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
Chemical Name
N-Succinimidyl 4-(N-Maleimidomethyl)cyclohexanecarboxylate
Synonyms
SMCC, heterobifunctional cross-linker SMCC crosslinker
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : 25 mg/mL (~74.78 mM ) H2O : < 0.1 mg/mL
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.9911 mL 14.9553 mL 29.9106 mL
5 mM 0.5982 mL 2.9911 mL 5.9821 mL
10 mM 0.2991 mL 1.4955 mL 2.9911 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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