64987-85-5

Basic information

• Product Name: N-Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate
• Synonyms: N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate, SMCC;SMCC [4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester];trans-4-(Maleimidomethyl)-cyclohexane carboxylic acid-NHS ester;SMCC N-SucciniMidyl 4-(N-MaleiMidoMethyl)cyclohexane-1-carboxylate;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
• CAS NO: 64987-85-5
• Molecular Formula: C₁₆H₁₈N₂O₆
• Molecular Weight: 334.32
• EINECS: 1592732-453-0
• Product Categories: Heterobifunctional Crosslinker;heteroXlink;Maleimide Derivatives;Cross Linking Reagents;MTS & Sulfhydryl Active Reagents
• Mol File: 64987-85-5.mol

Chemical Properties

• Melting Point: 180-182 °C(lit.)
• Boiling Point: 501.7 °C at 760 mmHg
• Flash Point: 257.2 °C
• Appearance: /powder
• Density: 1.42 g/cm³
• Vapor Pressure: 3.38E-10mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: 2-8°C
• Solubility: chloroform: 50 mg/mL
• PKA: -2.24±0.20(Predicted)
• Sensitive: Moisture & Light Sensitive
• BRN: 1555271
• CAS DataBase Reference: N-Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: N-Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate(64987-85-5)
• EPA Substance Registry System: N-Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate(64987-85-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-60-37
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 64987-85-5(Hazardous Substances Data)

Usage

Uses

Used in Bioconjugation:
SMCC is used as a sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent for the covalent attachment of amineand sulfhydryl-containing molecules, such as proteins, peptides, and other biomolecules.
Used in Enzyme Conjugation:
In the enzyme industry, SMCC is used as a crosslinking agent to conjugate anti-digoxin F(ab’)2 fragments to β-galactosidase, facilitating the development of immunoassays and other diagnostic tools.
Used in Immunoassays:
SMCC is employed in the conjugation of hIgG (human immunoglobulin G) to alkaline phosphatase, which is crucial for the development of various immunoassay techniques, such as enzyme-linked immunosorbent assays (ELISA), providing enhanced sensitivity and specificity in detecting target antigens.
Overall, SMCC is a versatile crosslinking agent widely used in the fields of bioconjugation, enzyme conjugation, and immunoassays, due to its ability to form stable covalent bonds between amineand sulfhydryl-containing molecules, and its spacer arm that allows for greater flexibility and stability in the resulting conjugates.

InChI:InChI=1/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

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 108-31-6 maleic anhydride 
• 1197-17-7 4-aminomethyl-cyclohexanecarboxylic acid 
• 64987-82-2 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexane-1-carboxylic acid 

Downstream Products

• 400647-59-8 doxorubicin-succinimidyl 4-[N-maleimidomethyl]cyclohexane-1-carboxylate 
• 172100-40-2 6-(4-((2,5-dioxo-2,5-di hydro-1 H-pyrrol-1-yl)methyl)cyclohexanecarboxamido)hexanoic acid 
• 909023-85-4 RBI 1032 
• 1036847-90-1 4-(N-maleimidomethyl)-N-(2-propynyl)cyclohexane-1-carboxamide 
• 1374847-68-3 {[(2R,5R)-5-(6-amino-9H-purin-9-yl)-4-[({[(2R,5R)-5-(6-amino-9H-purin-9-yl)-4-[({[(2R,5R)-5-(6-amino-9H-purin-9-yl)-4-[({[6-({4-[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl]cyclohexyl}formamido)hexyl]oxy}(hydroxy)phosphoryl)-oxy]-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid 
• 1374847-87-6 2-[3-(2-{1-[4-(6-{[2-(6-aminopurin-9-yl)-4-hydroxy-5-thiophosphonooxymethyltetrahydrofuran-3-yloxy]hydroxythiophosphoryloxy}hexylcarbamoyl)cyclohexylmethyl]-2,5-dioxopyrrolidin-3-ylsulfanyl}-1-carboxyethyl)ureido]pentanedioic acid 
• 1374847-75-2 2-(3-{1-carboxy-2-[1-(4-{[(4-fluoro-benzylamino)methyl]carbamoyl}cyclohexyl)-2,5-dioxopyrrolidin-3-ylsulfanyl]ethyl}ureido)pentanedioic acid 
• 1374847-77-4 2-[3-(2-{1-[4-(6-tert-butoxycarbonylaminohexylcarbamoyl)cyclohexyl]-2,5-dioxopyrrolidin-3-ylsulfanyl}-1-carboxyethyl)ureido]pentanedioic acid 
• 1374847-79-6 6-{[4-(3-{2-carboxy-2-[3-(1,3-dicarboxypropyl)ureido]ethylsulfanyl}-2,5-dioxo-pyrrolidin-1-yl)cyclohexanecarbonyl]amino}hexylammonium chloride 
• 1374847-89-8 2-[({2-[(1-{[4-({6-[({[(2R,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(4-fluorophenyl)methyl]carbamoyl}methyl)sulfanyl](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}(hydroxy)sulfanylidenephosphanyl)oxy]hexyl} carbamoyl)cyclohexyl]methyl}-2,5-dioxopyrrolidin-3-yl)sulfanyl]-1-carboxyethyl} carbamoyl)amino]pentanedioic acid 
• 1374847-70-7 C₂₅H₃₂N₄O₁₃S 

Relevant articles and documents

Enzyme immunoassay for captopril

A simple enzyme immunoassay for the determination of captopril was developed. A specific antibody for captopril was produced in rabbits that were immunized with a hapten-bovine immunoglobulin G conjugate, which was prepared by using 4-(maleimidomethyl)cyclohexane carboxylic acid as a spacer group. The limit of detection in plasma is 0.5 ng/mL. The assay has an adequate specificity, so isolation of captopril is unnecessary.

Synthesis, characterization, and targeted chemotherapy of SCT200-linker-monomethyl auristatin E conjugates

Antibody-drug conjugates (ADCs) are currently among the most successful and important strategies for treating patients with solid tumors. ADCs are composed of a monoclonal antibody and warhead, which are conjugated via a linker. Currently, monomethyl auristatin E (MMAE) is the most widely applied warhead in the development of ADCs. However, MMAE-based ADCs are generally constructed using the MC-VC-PABC linker, and this design has limited structural diversity and some disadvantages. Accordingly, in this study, we generated three types of novel linker-MMAE (with alterations in the spacer, catabolizing area, and self-immolative compared with MC-VC-PABC-MMAE) in ADCs, termed SCT200-linker-MMAE conjugates, and then evaluated the linker-drug plasma stability and the rate of drug release by cathepsin B. The binding ability, internalization rates, and efficacy of all SCT200-linker-MMAE ADCs were systematically studied, and the expression of apoptosis-associated proteins and the therapeutic efficacies of SCT200-M-2, -C-2, and -C-4 were evaluated. The results showed that the activities of some of these ADCs were increased for epidermal growth factor receptor-positive tumors. Moreover, the novel linkers designed in this study can be linked with other antibodies to treat other types of cancer. Overall, these findings provide important insights into the application of SCT200-based linkers in ADCs.

Biocompatible organic coatings based on bisphosphonic acid RGD‐derivatives for PEO‐modified titanium implants

Currently, significant attention is attracted to the problem of the development of the specific architecture and composition of the surface layer in order to control the biocompatibility of implants made of titanium and its alloys. The titanium surface properties can be tuned both by creating an inorganic sublayer with the desired morphology and by organic top coating contributing to bioactivity. In this work, we developed a composite biologically active coatings based on hybrid molecules obtained by chemical crosslinking of amino acid bisphosphonates with a linear tripeptide RGD, in combination with inorganic porous sublayer created on titanium by plasma electrolytic oxidation (PEO). After the addition of organic molecules, the PEO coated surface gets nobler, but corrosion currents increase. In vitro studies on proliferation and viability of fibroblasts, mesenchymal stem cells and osteoblastlike cells showed the significant dependence of the molecule bioactivity on the structure of bisphosphonate anchor and the linker. Several RGDmodified bisphosphonates of β–alanine, γ–aminobutyric and ε–aminocaproic acids with BMPS or SMCC linkers can be recommended as promising candidates for further in vivo research.