Basic information Safety Supplier Related

SMCC crosslinker

Basic information Safety Supplier Related

SMCC crosslinker Basic information

Product Name:
SMCC crosslinker
Synonyms:
  • N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate, SMCC
  • SMCC [4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester]
  • trans-4-(Maleimidomethyl)-cyclohexane carboxylic acid-NHS ester
  • N-SucciniMidyl 4-(N-MaleiMidoMethyl)cyclohexanecarboxylate
  • 4-(N-MaleiMidoMethyl)cyclohexane-1-carboxylic acid N-hydroxysucciniMide ester, 98+%
  • NSC 344483
  • 4-(N-Maleimidomethyl)cyclohexanecarboxylic Acid N-Succinimidyl Ester SMCC
  • 25MG/100MG/10G
CAS:
64987-85-5
MF:
C16H18N2O6
MW:
334.32
EINECS:
1592732-453-0
Product Categories:
  • heteroXlink
  • Heterobifunctional Crosslinker
  • Maleimide Derivatives
  • Cross Linking Reagents
  • MTS & Sulfhydryl Active Reagents
  • ADC LINKER
Mol File:
64987-85-5.mol
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SMCC crosslinker Chemical Properties

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
InChIKey
JJAHTWIKCUJRDK-UHFFFAOYSA-N
SMILES
C1(C(ON2C(=O)CCC2=O)=O)CCC(CN2C(=O)C=CC2=O)CC1
CAS DataBase Reference
64987-85-5(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-60-37
WGK Germany 
3
10-21
HS Code 
29280000

MSDS

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SMCC crosslinker Usage And Synthesis

Description

SMCC crosslinker is a hetero-bifunctional crosslinker that contain N-hydroxysuccinimide (NHS) ester and maleimide groups that allow covalent conjugation of amine- and sulfhydryl-containing molecules. 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.

Chemical Properties

White Crystalline Solid

Uses

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.

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.

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.

SMCC crosslinkerSupplier

Suzhou Highfine Biotech Co., Ltd Gold
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0512-69209928 18306209922
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Hygeia (Chengdu) pharmaceutical technique Co., Ltd Gold
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028-84502008 13568869383
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Suzhouhongxiong Gold
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Shandong utilizing biological technology co., LTD Gold
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15966937598
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Shanghai Bolu Biotechnology Co., Ltd Gold
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13062875887 13062875887
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3662942976@QQ.com