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SMCC crosslinker

SMCC crosslinker structure

CAS No:
64987-85-5
Formula:
C16H18N2O6
Chemical 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
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

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.

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.

White Crystalline Solid

4-(N-Maleimidomethyl)cyclohexanecarboxylic acidN-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.

SMCC crosslinker Basic Attributes

Molecular Weight：

334.32

Exact Mass：

334.32

BRN：

1555271

EC Number：

1592732-453-0

UNII：

B357P1G1IF

NSC Number：

344483

DSSTox ID：

DTXSID30215307

Color/Form：

White to Off-White

HScode：

29280000

Characteristics

Chemical Properties：

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.

Density：

1.42±0.1 g/cm3(Predicted)

Melting Point：

180-182 °C (lit.)

Boiling Point：

501.7±42.0 °C(Predicted)

PKA：

-2.24±0.20(Predicted)

Critical Temperature & Pressure：

-20°C

Safety Information

wgk germany：

hazard class code：

safety instructions：

26-36-60-37

Hazard Statements：

36/37/38

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 82 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Drug Information

MeSH Entry Terms：

N-(4-carboxycyclohexylmethyl)maleimide N-hydroxysuccinimide ester

SMCC crosslinker Use and Manufacturing

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.

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