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SMCC [4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester] *CAS 64987-85-5*
Ordering information
| Price | |
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Additional ordering information
| Telephone | 1-800-990-8053 |
| Fax | 1-800-609-2943 |
| sales@aatbio.com | |
| International | See distributors |
| Bulk request | Inquire |
| Custom size | Inquire |
| Shipping | Standard overnight for United States, inquire for international |
Physical properties
| Molecular weight | 334.32 |
| Solvent | DMSO |
Storage, safety and handling
| H-phrase | H303, H313, H333 |
| Hazard symbol | XN |
| Intended use | Research Use Only (RUO) |
| R-phrase | R20, R21, R22 |
| Storage | Freeze (< -15 °C) |
| UNSPSC | 12352200 |
| Overview |  SDSProtocol |
See also: Crosslinkers
CAS 64987-85-5 | Molecular weight 334.32 |
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 mg | 0.5 mg | 1 mg | 5 mg | 10 mg | |
| 1 mM | 299.115 µL | 1.496 mL | 2.991 mL | 14.956 mL | 29.911 mL |
| 5 mM | 59.823 µL | 299.115 µL | 598.229 µL | 2.991 mL | 5.982 mL |
| 10 mM | 29.911 µL | 149.557 µL | 299.115 µL | 1.496 mL | 2.991 mL |
Molarity calculator
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Images
Figure 1. Chemical structure for SMCC [4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester] *CAS 64987-85-5*
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
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
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
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
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
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
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
Authors: Maxwell D, Chang Q, Zhang X, Barnett EM, Piwnica-Worms D.
Journal: Bioconjug Chem (2009): 702
Feasibility of single nucleotide polymorphism genotyping with a single-probe by time-resolved Forster resonance energy transfer
Authors: Andreoni A, Bondani M, Nardo L.
Journal: Mol Cell Probes (2009): 119
Authors: Andreoni A, Bondani M, Nardo L.
Journal: Mol Cell Probes (2009): 119
Photodynamic molecular beacon triggered by fibroblast activation protein on cancer-associated fibroblasts for diagnosis and treatment of epithelial cancers
Authors: Lo PC, Chen J, Stefflova K, Warren MS, Navab R, B and archi B, Mullins S, Tsao M, Cheng JD, Zheng G.
Journal: J Med Chem (2009): 358
Authors: Lo PC, Chen J, Stefflova K, Warren MS, Navab R, B and archi B, Mullins S, Tsao M, Cheng JD, Zheng G.
Journal: J Med Chem (2009): 358
Rapid detection and quantification of Propionibacteriaceae
Authors: Goldschmidt P, Ferreira CC, Degorge S, Benallaoua D, Boutboul S, Laroche L, Batellier L, Chaumeil C.
Journal: Br J Ophthalmol (2009): 258
Authors: Goldschmidt P, Ferreira CC, Degorge S, Benallaoua D, Boutboul S, Laroche L, Batellier L, Chaumeil C.
Journal: Br J Ophthalmol (2009): 258
Evaluation of tetramethylrhodamine and black hole quencher 1 labeled probes and five commercial amplification mixes in TaqMan real-time RT-PCR assays for respiratory pathogens
Authors: Yang GP, Erdman DD, Tondella ML, Fields BS.
Journal: J Virol Methods (2009): 288
Authors: Yang GP, Erdman DD, Tondella ML, Fields BS.
Journal: J Virol Methods (2009): 288
Design of FRET-TaqMan probes for multiplex real-time PCR using an internal positive control
Authors: Jothikumar P, Hill V, Narayanan J.
Journal: Biotechniques (2009): 519
Authors: Jothikumar P, Hill V, Narayanan J.
Journal: Biotechniques (2009): 519
Application notes
Buccutite™ Bioconjugation Technology
SMCC and SMCC Plus™ Protein Crosslinkers
A New Protein Crosslinking Method for Labeling and Modifying Antibodies
A New Robust No-Wash FLIPR Calcium Assay Kit for Screening GPCR and Calcium Channel Targets
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SMCC and SMCC Plus™ Protein Crosslinkers
A New Protein Crosslinking Method for Labeling and Modifying Antibodies
A New Robust No-Wash FLIPR Calcium Assay Kit for Screening GPCR and Calcium Channel Targets
A Novel NO Wash Probeniceid-Free Calcium Assay for Functional Analysis of GPCR and Calcium Channel Targets
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