SMCC crosslinker
Synonym(s):N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate;SMCC;Succinimidyl- trans-4-(N-maleimidylmethyl)cyclohexane-1-carboxylate;Succinimidyl-trans-4-(N-maleimidylmethyl)cyclohexane-1-carboxylate
- CAS NO.:64987-85-5
- Empirical Formula: C16H18N2O6
- Molecular Weight: 334.32
- MDL number: MFCD00009634
- EINECS: 1592732-453-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-20 11:41:24
What is SMCC crosslinker?
Description
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.
Chemical properties
White Crystalline Solid
The Uses of SMCC crosslinker
A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. It conjugates anti-digoxin F(abTaIII)2 fragments to l-B-galactosidase. Conjugates hIgG to alkaline phosphatase.Spacer Arm: 11.6 Angstroms.
The Uses of SMCC crosslinker
A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. It conjugates anti-digoxin F(ab’)2 fragments to ?-galactosidase. Conjugates hIgG to alkaline phosphatase. Spacer Arm: 11.6 Angstroms
Definition
ChEBI: Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate is an N-hydroxysuccinimide ester derived from 4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid. It is a member of maleimides and a N-hydroxysuccinimide ester.
What are the applications of Application
SMCC is a heterobifunctional sulfhydryl- and amine- reactive crosslinker, 11.6 Angstrom spacer arm
General Description
4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester (SMCC) is a heterobifunctional cross-linking reagent incorporating an extended spacer with amine and sulfhydryl reactivity. It is typically coupled initially to molecules containing primary amine by amide bond buffered at pH 7.5 (6.5-8.5). The second coupling is specific for molecules containing free sulfhydryl by thioether linkage buffered at pH 6.8 (6.5-7.0). SMCC contains nine atom linker. An extended aliphatic spacer stabilizes the maleimide prior to coupling compared to aromatic spacers.
Chemical Reactivity
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.
Properties of SMCC crosslinker
Melting point: | 180-182 °C (lit.) |
Boiling point: | 501.7±42.0 °C(Predicted) |
Density | 1.42±0.1 g/cm3(Predicted) |
storage temp. | -20°C |
solubility | chloroform: 50 mg/mL |
form | powder |
pka | -2.24±0.20(Predicted) |
color | White to Off-White |
Sensitive | Moisture & Light Sensitive |
BRN | 1555271 |
InChI | 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 |
CAS DataBase Reference | 64987-85-5(CAS DataBase Reference) |
Safety information for SMCC crosslinker
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up. |
Computed Descriptors for SMCC crosslinker
InChIKey | JJAHTWIKCUJRDK-UHFFFAOYSA-N |
SMILES | C1(C(ON2C(=O)CCC2=O)=O)CCC(CN2C(=O)C=CC2=O)CC1 |
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