Skip to Content
Merck
CN
All Photos(1)

Documents

Safety Information

803472

Sigma-Aldrich

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

Synonym(s):

2,5-Dioxo-1-pyrrolidinyl 4-[1-(2-pyridinyldithio)ethyl]benzoate, SMPT

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

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

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

Related Categories

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

新产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Y V van Oosterhout et al.
Blood, 95(12), 3693-3701 (2000-06-14)
This study evaluated the anti-graft versus host disease (GVHD) potential of a combination of immunotoxins (IT), consisting of a murine CD3 (SPV-T3a) and CD7 (WT1) monoclonal antibody both conjugated to deglycosylated ricin A. In vitro efficacy data demonstrated that these
D H Na et al.
Bioconjugate chemistry, 10(2), 306-310 (1999-03-17)
Determination of the introduced moieties into derivatized proteins is an essential step in the preparation and quality control of chemically defined immunoconjugates. For the derivatized proteins using pyridyl disulfide-containing cross-linkers such as N-succinimidyl 3-(2-pyridyldithio)propionate (SPDP) and 4-succinimidyloxycarbonyl-alpha-methyl-alpha-(2-pyridyldithio)tolu ene (SMPT), the
H Shaw Warren et al.
The Journal of infectious diseases, 188(9), 1382-1393 (2003-11-01)
Naturally present antibacterial proteins play an important role in innate host defense. A synthetic peptide mimicking the C-terminal lipopolysaccharide (LPS)-binding domain of rabbit cathelicidin CAP18 was coupled to immunoglobulin (Ig) G to create CAP18(106-138)-IgG, a construct that, in concentrations equimolar

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service