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P3415

Sigma-Aldrich

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

≥95%, powder

Synonym(s):

N-Succinimidyl 3-(2-pyridyldithio)propionate, SPDP

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About This Item

Empirical Formula (Hill Notation):
C12H12N2O4S2
CAS Number:
Molecular Weight:
312.36
Beilstein:
1548137
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NC.07

Quality Level

Assay

≥95%

form

powder

reaction suitability

reagent type: cross-linking reagent

mp

84-86 °C (lit.)

solubility

acetone: 50 mg/mL
DMF: soluble

functional group

NHS ester

storage temp.

−20°C

SMILES string

O=C(CCSSC1=NC=CC=C1)ON2C(CCC2=O)=O

InChI

1S/C12H12N2O4S2/c15-10-4-5-11(16)14(10)18-12(17)6-8-19-20-9-3-1-2-7-13-9/h1-3,7H,4-6,8H2

InChI key

JWDFQMWEFLOOED-UHFFFAOYSA-N

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General description

3-(2-Pyridyldithio)propionic acid N-hydroxysuccinimide ester (SPDP) is a heterobifunctional cross-linking reagent with amine and sulfhydryl reactivity. It is typically coupled initially to molecules containing primary amines by amide bonds buffered at pH 7.5 (6.5-8.5). Second coupling specific for molecules containing free sulfhydryl by thiol-disulfide exchange buffered at pH 8.0 (7.5-8.5). Alternately, this reagent may be used as a protected thiolating reagent following initial coupling and reduction of linker. It incorporates four atom linker.

Application

3-(2-Pyridyldithio)propionic acid N-hydroxysuccinimide ester (SPDP) is useful for the preparation of enzyme immunoconjugates and hapten carrier molecule conjugates.
It has been used for antibody conjugation and as a protein cross-linker.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

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Peter R Berthold et al.
Bioconjugate chemistry, 21(10), 1933-1938 (2010-09-30)
Peptide nucleic acid (PNA) is potentially an attractive antisense and antigene agent for which more efficient cellular delivery systems are still warranted. The cationic polymer polyethylenimine (PEI) is commonly used for cellular transfection of DNA and RNA complexes, but is
Shima Gholizadeh et al.
International journal of pharmaceutics, 548(2), 747-758 (2017-10-19)
Dactolisib (NVP-BEZ235, also referred to as: 'BEZ235' or 'BEZ') is a dual mTOR/PI3K inhibitor that is of potential interest in the treatment of inflammatory disorders. This work focuses on formulation of BEZ-loaded polymeric nanoparticles composed of a blend of poly(D,L-lactide-co-glycolide)
Anita C Thomas et al.
Journal of controlled release : official journal of the Controlled Release Society, 100(3), 357-377 (2004-11-30)
There is an urgent need to treat restenosis, a major complication of the treatment of arteries blocked by atherosclerotic plaque, using local delivery techniques. We observed that cross-linked fibrin (XLF) is deposited at the site of surgical injury of arteries.
Integrin-independent tyrosine phosphorylation of p125fak in human platelets stimulated by collagen.
Achison M
The Journal of Biological Chemistry, 276, 3167-3174 (2001)
Bispecific Antibodies (2011)

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Kanjiro Miyata (The University of Tokyo, Japan) provides insights on the rational design of polymeric materials for “smart” oligonucleotide delivery.

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