803472
SMPT (4-succinimidyloxycarbonyl-alpha-methyl-alpha(2-pyridyldithio)toluene)
Synonym(s):
2,5-Dioxo-1-pyrrolidinyl 4-[1-(2-pyridinyldithio)ethyl]benzoate, SMPT
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About This Item
Empirical Formula (Hill Notation):
C18H20N2O2S2
CAS Number:
Molecular Weight:
360.49
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352106
MDL number:
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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
SMILES string
O=C(ON1C(CCC1=O)=O)C2=CC=C(C(SSC3=CC=CC=N3)C)C=C2
InChI key
GKSPIZSKQWTXQG-UHFFFAOYSA-N
assay
≥90%
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
Quality Level
Related Categories
Disclaimer
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.
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
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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
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
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
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