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SPDP and LC-SPDP


Short- and long-chain disulfide crosslinkers for reversible amine-to-sulfhydryl conjugation.

Pierce SPDP

Thermo Scientific Pierce SPDP is a short-chain crosslinker for amine-to-sulfhydryl conjugation via NHS-ester and pyridyldithiol reactive groups that form cleavable (reducible) disulfide bonds with cysteine sulfhydryls.

Thermo Scientific Pierce LC-SPDP is a long-chain crosslinker for amine-to-sulfhydryl conjugation via NHS-ester and pyridyldithiol reactive groups that form cleavable (reducible) disulfide bonds with cysteine sulfhydryls.

We offer three analogs of SPDP: the standard version (SPDP), a derivative with a longer spacer arm (LC-SPDP), and a sulfonated water-soluble variety (Sulfo-LC-SPDP). SPDP (N-Succinimidyl 3-(2-pyridyldithio)-propionate) and LC-SPDP (Succinimidyl 6-(3-[2-pyridyldithio]-propionamido)hexanoate) are heterobifunctional, thiol-cleavable and membrane permeable crosslinkers. They each contain an amine-reactive N-hydroxysuccinimide (NHS) ester that will react with lysine residues to form a stable amide bond. The other end of the spacer arm is terminated in the pyridyl disulfide group that will react with sulfhydryls to form a reversible disulfide bond.

Highlights:

  • 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
  • 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
  • Water-insoluble (dissolve first in DMF or DMSO)
  • SPDP crosslinker is membrane permeable, so crosslinking can be done inside the cells
  • Compare to other varieties of SPDP-type reagents, including pegylated forms

Applications:

  • Reversible crosslinking of proteins
  • Adding sulfhydryl groups to proteins by attachment to lysine residues
  • Protein crosslinking to create antibody-enzyme and other bioconjugates via a two-step reaction
  • Attaching haptens to carrier proteins for antibody production
  • Preparing immunotoxin conjugates

Product Details:

Succinimidyl 3-(2-pyridyldithio)propionate; SPDP
 
Succinimidyl 6-[3(2-pyridyldithio) propionamido] hexanoate; LC-SPDP
 
Chemical structure of SPDP and LC-SPDP crosslinking reagents.

 

Properties of SPDP and LC-SPDP.
  SPDP LC-SPDP
Molecular formula C12H12O4N2S2 C18H23O5N3S4
Molecular weight 312.37 425.52
Spacer arm length 6.8 Å 15.7 Å
CAS Number 68181-17-9 N/A
Storage conditions -20°C, protect from moisture, use only fresh solutions
Reactive groups: NHS ester, reacts with primary amines
  Pyridyl disulfide, reacts with sulfhydryls

Specifications:

We manufacture SPDP and LC-SPDP to the highest specifications to produce the most specific bioconjugates, ensure the integrity of your data and to provide you with the highest degree of consistency. Each lot of SPDP and LC-SPDP is tested to ensure it is >95% pure by quantitative NMR (the highest standard for crosslinker purity).

References:

  1. Carlsson, J., et al. (1978) Protein thiolation and reversible protein-protein conjugation. N-succinimidyl-3-(2-pyridyldithio)propionate, a new heterobifunctional reagent. Biochem. J. 173, 723-737.
  2. Cumber, A.J., et al. (1985) Preparation of antibody-toxin conjugates. Meth. Enzymol., New York: Academic Press, 112, 207-225.
  3. Engstler, M., et al. (2004) J. Cell Sci.117, 1105-1115.
  4. Itoh, Y., et al. (2001) Proc. Natl. Acad. Sci. USA98, 4883-4887.
  5. Wang, D., et al. (1997) Bioconjug. Chem. 8 , 878-884.

Product References:

Crosslinker Application Guide -- search for recent literature references for this product

Related Resources:

Overview of crosslinking
Chemistry of crosslinking

Related Products:

Crosslinkers at a glance (selection guide)

Related Products:

Crosslinkers at a glance (selection guide)
Other SPDP-type Reagents


Ordering Information
 
Product # Description Pkg. Size Instructions MSDS CofA Price
21651 LC-SPDP
Formulation: Succinimidyl 6-[3(2-pyridyldithio) propionamido] hexanoate; powder solid
Sufficient For: 118mL of typical 1X (1mM) reaction solution, or approx. 25 uses at 2mg reagent per use
50mg Product Instructions for product #21651 LC-SPDP MSDS for product #21651 LC-SPDP Certificate of Analysis for product #21651 LC-SPDP $355.00

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21857 SPDP
Formulation: Succinimidyl 3-(2-pyridyldithio)propionate; powder solid
Sufficient For: 160mL of typical 1X (1mM) reaction solution, or approx. 25 uses at 2mg reagent per use
50mg Product Instructions for product #21857 SPDP MSDS for product #21857 SPDP Certificate of Analysis for product #21857 SPDP $133.00

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21857B SPDP
Formulation: Succinimidyl 3-(2-pyridyldithio)propionate; powder solid
Custom MSDS for product #21857B SPDP Certificate of Analysis for product #21857B SPDP

Instructions | MSDS | CofA
Product Instructions | MSDS | CofA  

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