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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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Size/SKUAvailabilityPrice
50 mg
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$506.00
$379.50

About This Item

Empirical Formula (Hill Notation):
C18H20N2O2S2
CAS Number:
112241-19-7
Molecular Weight:
360.49
NACRES:
NA.22
PubChem Substance ID:
329768810
UNSPSC Code:
12352106
MDL number:
MFCD00083161
Assay:
≥90%
Form:
powder

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assay

≥90%

Quality Segment

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

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

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.

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This Item
803316803642P3415
SMPT (4-succinimidyloxycarbonyl-alpha-methyl-alpha(2-pyridyldithio)toluene)

Sigma-Aldrich

803472

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

Sulfo-LC-SPDP (sulfosuccinimidyl 6-[3′-(2-pyridyldithio)propionamido]hexanoate)

Sigma-Aldrich

803316

Sulfo-LC-SPDP (sulfosuccinimidyl 6-[3′-(2-pyridyldithio)propionamido]hexanoate)

LC-SPDP (succinimidyl 6-[3(2-pyridyldithio)propionamido]hexanoate)

Sigma-Aldrich

803642

LC-SPDP (succinimidyl 6-[3(2-pyridyldithio)propionamido]hexanoate)

3-(2-Pyridyldithio)propionic acid N-hydroxysuccinimide ester ≥95%, powder

Sigma-Aldrich

P3415

3-(2-Pyridyldithio)propionic acid N-hydroxysuccinimide ester

assay

≥90%

assay

≥90%

assay

≥95%

assay

≥95%

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

200

reaction suitability

reagent type: cross-linking reagent

reaction suitability

reagent type: cross-linking reagent

reaction suitability

reagent type: cross-linking reagent

reaction suitability

reagent type: cross-linking reagent

solubility

DMSO or DMF: soluble

solubility

soluble (>95 mg/ml in water)

solubility

DMSO or DMF: soluble

solubility

acetone: 50 mg/mL, DMF: soluble

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

form

powder

form

powder

form

powder

form

powder

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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