| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| 10mg |
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| 50mg |
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| Other Sizes |
| Targets |
Thiol groups (cysteine residues) and primary amine groups (lysine residues) on proteins, peptides, or antibodies.
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|---|---|
| ln Vitro |
One ligand is for an E3 ubiquitin ligase, and the other is for the target protein; these two ligands are joined by a linker to form PROTACs. To specifically destroy target proteins, PROTACs take advantage of the intracellular ubiquitin-proteasome system.[1]
The maleimide group reacts specifically with thiols at pH 6.5-7.5 to form stable thioether bonds. The sulfo-NHS ester reacts with primary amines at pH 7-9 to form amide bonds. The sulfonate group confers water solubility, eliminating the need for organic solvents. The 6-carbon caproic acid spacer provides flexibility and reduces steric hindrance. Crosslinking efficiency is typically 60-90% under optimized conditions. |
| ln Vivo |
Sulfo-EMCS is used to prepare antibody-drug conjugates (ADCs), protein-protein conjugates, and immobilized affinity matrices. In vivo, conjugates prepared with Sulfo-EMCS show improved stability compared to non-sulfo analogs due to reduced aggregation. The water solubility minimizes non-specific protein precipitation. It is not administered alone but as a crosslinking reagent.
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| Enzyme Assay |
In a cell-free conjugation assay, the sulfo-NHS ester is incubated with a model protein containing lysine residues (e.g., BSA, 1-10 mg/mL) in PBS pH 7.2-7.5 for 30-60 minutes at room temperature. The reaction is quenched with Tris or glycine. The maleimide group is then reacted with a thiol-containing molecule (e.g., cysteine or reduced antibody) at pH 6.5-7.0 for 1-2 hours. Conjugation efficiency is assessed by SDS-PAGE or MALDI-TOF.
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| Cell Assay |
Sulfo-EMCS is used to conjugate antibodies to drugs, enzymes, or fluorescent probes on cell surfaces. Cells expressing surface thiols (e.g., engineered cells) are incubated with Sulfo-EMCS (0.1-1 mM) in PBS for 30 minutes at 4degC, washed, then incubated with an amine-containing cargo. Flow cytometry measures conjugation efficiency. Cytotoxicity of the resulting conjugates is evaluated by MTT assay.
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| Animal Protocol |
Animals are injected with antibody-drug conjugates prepared using Sulfo-EMCS. For efficacy studies, xenograft mice receive the ADC (1-10 mg/kg, IV) once weekly. Blood samples are collected to measure ADC stability and drug release. Tumor growth inhibition is monitored. The crosslinker itself is not administered alone. Toxicity of the ADC is assessed by body weight loss, serum chemistry, and histopathology.
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| ADME/Pharmacokinetics |
The molecular weight is 452.37 g/mol. The sulfo-NHS ester hydrolyzes rapidly in aqueous solution (half-life ~1-2 hours at pH 7.5), so reactions must be performed immediately. The maleimide group is stable for several hours at pH 6.5-7.0 but hydrolyzes slowly at alkaline pH. The compound is stored desiccated at -20degC.
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| Toxicity/Toxicokinetics |
Sulfo-EMCS has low acute toxicity (LD50 > 2000 mg/kg). Upon hydrolysis, it releases N-hydroxysulfosuccinimide and maleimidocaproic acid, which are generally non-toxic. However, the reactive ester can cause skin and eye irritation. Standard PPE is required. Not for human use.
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| References |
[1]. An S, et al. Small-molecule PROTACs: An emerging and promising approach for the development of targeted therapy drugs. EBioMedicine. 2018 Oct;36:553-562
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| Additional Infomation |
Sulfo-EMCS is a research reagent, not a drug. It is widely used for ADC synthesis, protein immobilization, and biotinylation. Compared to non-sulfo EMCS, it offers improved water solubility, avoiding DMSO or DMF. The maleimide-thiol bond is stable in circulation but can undergo retro-Michael exchange with serum albumin; therefore, more stable maleimide derivatives are sometimes preferred. No clinical approval as a therapeutic.
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| Molecular Formula |
C14H15N2NAO9S
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|---|---|
| Molecular Weight |
410.33
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| Exact Mass |
410.04
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| CAS # |
215312-86-0
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| Related CAS # |
6-Maleimidocaproic acid sulfo-NHS;103848-61-9
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| PubChem CID |
4229287
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| Appearance |
Typically exists as solid at room temperature
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| Melting Point |
158-165 °C
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
27
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| Complexity |
769
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1C(C(=O)N(C1=O)OC(=O)CCCCCN2C(=O)C=CC2=O)S(=O)(=O)[O-].[Na+]
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| InChi Key |
MIDXXTLMKGZDPV-UHFFFAOYSA-M
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| InChi Code |
InChI=1S/C14H16N2O9S.Na/c17-10-5-6-11(18)15(10)7-3-1-2-4-13(20)25-16-12(19)8-9(14(16)21)26(22,23)24;/h5-6,9H,1-4,7-8H2,(H,22,23,24);/q;+1/p-1
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| Chemical Name |
sodium;1-[6-(2,5-dioxopyrrol-1-yl)hexanoyloxy]-2,5-dioxopyrrolidine-3-sulfonate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO :~125 mg/mL (~304.63 mM)
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4371 mL | 12.1853 mL | 24.3706 mL | |
| 5 mM | 0.4874 mL | 2.4371 mL | 4.8741 mL | |
| 10 mM | 0.2437 mL | 1.2185 mL | 2.4371 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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