| Size | Price | Stock | Qty |
|---|---|---|---|
| 25mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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Purity: ≥98%
| Targets |
Sulfo-SMCC targets primary amines and sulfhydryl groups on proteins. The NHS ester group reacts with primary amines to form stable amide bonds, while the maleimide group reacts with sulfhydryl groups to form stable thioether bonds. This dual reactivity makes sulfo-SMCC a valuable tool for conjugating two different proteins or for attaching a drug to an antibody (as in antibody-drug conjugates, ADCs).
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| ln Vitro |
Maleimide and N-hydroxysuccinimide ester groups are coupled with sulfhydryl groups and primary amines, respectively, to form the cross-linking agent Sulfo-SMCC. Stable microtubule (MT) end-to-end annealing is inhibited by sulfo-SMCC. After being incubated for 0, 6, and 24 hours, MTs were photographed following treatment with 250 μM Sulfo-SMCC. Sulfo-SMCC-treated MTs have a consistent average length that is unaffected by incubation duration [1].
Sulfo-SMCC is used in vitro for protein crosslinking and conjugation. It is commonly used to conjugate antibodies to drugs for the development of ADCs. It has been used to conjugate anti-programmed death-ligand 1 (PD-L1) antibodies to drugs. Its water solubility makes it suitable for use in aqueous environments. |
| ln Vivo |
Sulfo-SMCC is not used in vivo as a therapeutic agent itself; it is a research reagent used for protein conjugation. It is used to create ADCs, which are then administered in vivo for targeted cancer therapy.
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| Enzyme Assay |
Sulfo-SMCC is a chemical reagent that reacts with primary amines and sulfhydryl groups. In a typical assay, a protein containing primary amines is incubated with sulfo-SMCC. The NHS ester reacts with the amines, forming a stable amide bond and introducing a maleimide group. The maleimide-modified protein can then react with a second protein or drug containing a sulfhydryl group. The efficiency of conjugation is assessed by SDS-PAGE or mass spectrometry.
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| Cell Assay |
Sulfo-SMCC is dissolved in aqueous buffers and applied to proteins. The reaction with primary amines is carried out at pH 7-9. After incubation, the maleimide-modified protein is purified, and then reacted with a sulfhydryl-containing molecule. The conjugated product is then analyzed.
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| ADME/Pharmacokinetics |
Sulfo-SMCC Sodium has a molecular weight of 436.37 g/mol and a molecular formula of C16H17N2O9SNa. It is a water-soluble compound. The compound is typically stored as a powder at -20°C for long-term stability. Sulfo-SMCC is also known as 4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid 3-sulfo-N-hydroxysuccinimide ester sodium salt.
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| Toxicity/Toxicokinetics |
Sulfo-SMCC is considered to have low toxicity for research use. It is a chemical reagent that should be handled with appropriate safety precautions. It may cause skin and eye irritation. Inhalation and ingestion should be avoided.
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| References | |
| Additional Infomation |
Sulfo-SMCC Sodium is a commonly used hetero-bifunctional, noncleavable ADC crosslinker bearing N-hydroxysuccinimide (NHS) ester and maleimide groups to react with primary amines and sulfhydryl groups, respectively. It is a water-soluble protein cross-linking reagent. Sulfo-SMCC sodium is a widely used heterobifunctional cross-linker. It is a non-degradable ADC linker. The NHS ester group reacts with primary amines, while the maleimide group reacts with sulfhydryl groups.
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| Molecular Formula |
C16H17N2NAO9S
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|---|---|
| Molecular Weight |
436.3690
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| Exact Mass |
436.055
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| CAS # |
92921-24-9
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| Related CAS # |
103708-09-4 (free acid);92921-24-9 (sodium);
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| PubChem CID |
4618794
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| Appearance |
White to off-white solid powder
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| Melting Point |
>270ºC (dec.)
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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 |
6
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| Heavy Atom Count |
29
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| Complexity |
853
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
VUFNRPJNRFOTGK-UHFFFAOYSA-M
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| InChi Code |
InChI=1S/C16H18N2O9S.Na/c19-12-5-6-13(20)17(12)8-9-1-3-10(4-2-9)16(23)27-18-14(21)7-11(15(18)22)28(24,25)26;/h5-6,9-11H,1-4,7-8H2,(H,24,25,26);/q;+1/p-1
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| Chemical Name |
sodium;1-[4-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexanecarbonyl]oxy-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 (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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 (~286.45 mM)
H2O : ~5 mg/mL (~11.46 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.77 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (4.77 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (4.77 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 4.17 mg/mL (9.56 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C). |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2916 mL | 11.4582 mL | 22.9163 mL | |
| 5 mM | 0.4583 mL | 2.2916 mL | 4.5833 mL | |
| 10 mM | 0.2292 mL | 1.1458 mL | 2.2916 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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