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

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Synonym(s):
2,5-Dioxo-3-sulfo-1-pyrrolidinyl 6-[[1-oxo-3-(2-pyridinyldithio)propyl]amino]hexanoate, Sulfo-LC SPDP, Sulfosuccinimidyl 6-(3′-(2-pyridyldithio)propionamido)hexanoate
Empirical Formula (Hill Notation):
C14H16N3NaO8S3
Molecular Weight:
473.48
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

≥90%

Quality Level

form

powder

mol wt

527.57

reaction suitability

reagent type: cross-linking reagent

storage condition

desiccated

solubility

soluble (>95 mg/ml in water)

shipped in

ambient

storage temp.

−20°C

SMILES string

O=C1CC(S(=O)([O-])=O)C(N1OC(CCCCCNC(CCSSC2=CC=CC=N2)=O)=O)=O.[Na+]

InChI

1S/C18H23N3O8S3.Na/c22-14(8-11-30-31-15-6-3-5-10-20-15)19-9-4-1-2-7-17(24)29-21-16(23)12-13(18(21)25)32(26,27)28;/h3,5-6,10,13H,1-2,4,7-9,11-12H2,(H,19,22)(H,26,27,28);/q;+1/p-1

InChI key

ZAPNXDUFCQIHFS-UHFFFAOYSA-M

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This Item
P3415803359803340
Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

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

soluble (>95 mg/ml in water)

solubility

acetone: 50 mg/mL, DMF: soluble

solubility

water: soluble

solubility

water: soluble

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

form

powder

form

powder

form

powder

form

powder

General description

The SPDP reagents are a unique group of amine- and sulfhydryl-reactive heterobifunctional crosslinkers. Whether they are used to form amine-to-amine or amine-to-sulfhydryl crosslinks among molecules, the SPDP reagents produce disulfide-containing linkages that can be cleaved later with reducing agents such as dithiothreitol (DTT).

Features and Benefits

  • Reactive groups: NHS ester and pyridyldithiol
  • Reactive towards: amino and sulfhydryl groups
  • Releases a detectable by-product when reacted with a free sulfhydryl group; by measuring the release of pyridine-2-thione at 343 nm, the reaction can be easily followed
  • Water soluble, sulfo-NHS ester reacts rapidly with any primary amine-containing molecule
  • Disulfide bond in the spacer arm is readily cleaved by 10-50 mM DTT or TCEP at pH 8.5
  • Spacer arm is also easily cleaved using reducing SDS-PAGE sample loading buffer
  • Cleavable crosslinker allows separation of crosslinked products
  • Sulfo-LC-SPDP crosslinker is not membrane permeable, allowing cell surface labeling
  • 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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Neurath, A. R. and Strick, N.
J. Virol. Methods, 3, 155-165 (1981)
Preparation of antibody-toxin conjugates.
A J Cumber et al.
Methods in enzymology, 112, 207-225 (1985-01-01)
J Carlsson et al.
The Biochemical journal, 173(3), 723-737 (1978-09-01)
A heterobifunctional reagent, N-succinimidyl 3-(2-pyridyldithio)propionate, was synthesized. Its N-hydroxysuccinimide ester group reacts with amino groups and the 2-pyridyl disulphide structure reacts with aliphatic thiols. A new thiolation procedure for proteins is based on this reagent. The procedure involves two steps.

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