803472

SMPT (4-succinimidyloxycarbonyl-alpha-methyl-alpha(2-pyridyldithio)toluene)

• Synonym(s): 2,5-Dioxo-1-pyrrolidinyl 4-[1-(2-pyridinyldithio)ethyl]benzoate, SMPT
• Empirical Formula (Hill Notation): C₁₈H₂₀N₂O₂S₂
• CAS Number: 112241-19-7
• Molecular Weight: 360.49
• MDL number: MFCD00083161
• UNSPSC Code: 12352106
• PubChem Substance ID: 329768810
• NACRES: NA.22

Properties

• Assay: ≥90%
• Quality Level: 100
• form: powder
• mol wt: 388.46
• reaction suitability: reagent type: cross-linking reagent
• storage condition: desiccated
• solubility: DMSO or DMF: soluble
• functional group: NHS ester
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: O=C(ON1C(CCC1=O)=O)C2=CC=C(C(SSC3=CC=CC=N3)C)C=C2
• InChI: 1S/C18H16N2O4S2/c1-12(25-26-15-4-2-3-11-19-15)13-5-7-14(8-6-13)18(23)24-20-16(21)9-10-17(20)22/h2-8,11-12H,9-10H2,1H3
• InChI key: GKSPIZSKQWTXQG-UHFFFAOYSA-N

Description

General description

SMPT is a heterobifunctional sulfhydryl- and amine-reactive cross-linker. SMPT is used often for conjugating a toxin molecule to a monoclonal antibody directed against a cell-surface antigen. These immunotoxins produced with SMPT are highly potent as the cleavable disulfide imparts increased cytotoxicity compared to conjugates without a cleavable bond, such as those produced with SPDP. Also, next to the pyridine-2-thione in the spacer arm are a benzene ring and a methyl group adjacent to a carbon that hinders the disulfide bond, allowing exceptional conjugate stability in vivo. SMPT has the added benefit of being more stable to hydrolysis in aqueous solutions than other NHS cross-linkers.

Features and Benefits

• Reactive groups: NHS ester and pyridyldithiol
• Reactive towards: amino and sulfhydryl groups
• Cleavable with disulfide reducing agents
• Water-insoluble (dissolve first in DMF or DMSO)
• Contains a hindered disulfide bond; has formed immunotoxins with improved stability
• In vitro, an SMPT conjugate was as effective as conjugates formed with SPDP and 2-IT
• Compare to other varieties of SPDP-type reagents, including pegylated forms

Caution

This product is sensitive to moisture. The vial is packaged in a resealable bag with a desiccant to reduce exposure to moisture. After cold storage, equilibrate the vial to room temperature before opening to reduce condensation inside the vial. Make fresh solutions. Storage of stock solutions is not recommended. After use, return the vial to the resealable bag. Close the bag and store the product at the recommended temperature.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable