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SMCC [4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester] *CAS 64987-85-5*

SMCC is a non-cleavable and membrane permeable crosslinker with a spacer arm of 8.3Å. It contains an amine-reactive succinimidyl ester (SE) 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 SE group of SMCC is reacted with lysine residues on the carrier protein, converting them to reactive maleimides. SMCC is a reagent that is widely used for generating stable maleimide-activated carrier proteins that can spontaneously react with sulfhydryls. Alternatively these relatively stable maleimide-activated intermediates may be lyophilized and stored for later conjugation to a hapten.

Calculators

Common stock solution preparation

Table 1. Volume of DMSO needed to reconstitute specific mass of SMCC [4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester] *CAS 64987-85-5* to given concentration. Note that volume is only for preparing stock solution. Refer to sample experimental protocol for appropriate experimental/physiological buffers.

0.1 mg0.5 mg1 mg5 mg10 mg
1 mM299.115 µL1.496 mL2.991 mL14.956 mL29.911 mL
5 mM59.823 µL299.115 µL598.229 µL2.991 mL5.982 mL
10 mM29.911 µL149.557 µL299.115 µL1.496 mL2.991 mL

Molarity calculator

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Citations

View all 2 citations: Citation Explorer
Identification and functional characterization of potential oncofetal targets in human hepatocellular carcinoma
Authors: Li, Mei-Mei and Kong, Fan-En and Li, Guang-Meng and He, Yi-Ti and Zhang, Xiao-Feng and Zhang, Cheng-Yang and Liang, Jie-Kai and Guan, Xin-Yuan and Ma, Ning-Fang and Xie, Mao-Bin and others,
Journal: STAR Protocols (2022): 101921
N-glycan targeted gene delivery to the dendritic cell SIGN receptor
Authors: Anderson, Kevin and Fern, undefined and ez, Christian and Rice, Kevin G
Journal: Bioconjugate chemistry (2010): 1479--1485

References

View all 25 references: Citation Explorer
Time-resolved FRET method for typing polymorphic alleles of the human leukocyte antigen system by using a single DNA probe
Authors: Andreoni A, Bondani M, Nardo L.
Journal: Photochem Photobiol Sci (2009): 1202
Tumor-specific detection of an optically targeted antibody combined with a quencher-conjugated neutravidin "quencher-chaser": a dual "quench and chase" strategy to improve target to nontarget ratios for molecular imaging of cancer
Authors: Ogawa M, Kosaka N, Choyke PL, Kobayashi H.
Journal: Bioconjug Chem (2009): 147
The detection of platelet derived growth factor using decoupling of quencher-oligonucleotide from aptamer/quantum dot bioconjugates
Authors: Kim GI, Kim KW, Oh MK, Sung YM.
Journal: Nanotechnology (2009): 175503
Development of a cell-based hepatitis C virus infection fluorescent resonance energy transfer assay for high-throughput antiviral compound screening
Authors: Yu X, Sainz B, Jr., Uprichard SL.
Journal: Antimicrob Agents Chemother (2009): 4311
An improved cell-penetrating, caspase-activatable, near-infrared fluorescent peptide for apoptosis imaging
Authors: Maxwell D, Chang Q, Zhang X, Barnett EM, Piwnica-Worms D.
Journal: Bioconjug Chem (2009): 702
Page updated on December 6, 2024

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25 mg
1 g
Catalog Number
45014502
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Physical properties

Molecular weight

334.32

Solvent

DMSO

Storage, safety and handling

H-phraseH303, H313, H333
Hazard symbolXN
Intended useResearch Use Only (RUO)
R-phraseR20, R21, R22

Storage

Freeze (< -15 °C)
UNSPSC12352200

CAS

64987-85-5
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