68181-17-9

Basic information

• Product Name: SPDP
• Synonyms: 3-(PYRIDIN-2-YLDISULFANYL)-PROPIONIC ACID-OSU;3-(2-PYRIDYLDITHIO)PROPIONIC ACID N-HYDROXY-SUCCINIMIDE ESTER;3-(2-PYRIDYLDITHIO)PROPIONIC ACID N-SUCCINIMIDYL ESTER;3-(2-PYRIDYLDITHIO)-PROPIONIC ACID-OSU;succinimidyl3-(2-pyridyldithio)propionate(spdp);SUCCINIMIDYL 3-(2-PYRIDYLDITHIO)PROPIONATE;SPDP;N-SUCCINIMIDYL-3-(2-PYRIDYLDITHIO)PROPIONANATE
• CAS NO: 68181-17-9
• Molecular Formula: C₁₂H₁₂N₂O₄S₂
• Molecular Weight: 312.36
• EINECS: 269-034-3
• Product Categories: Nitric Oxide Reagents;Cross Linking Reagents;Heterobifunctional Crosslinker;heteroXlink
• Mol File: 68181-17-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 84-86 °C(lit.)
• Boiling Point: 465.9 °C at 760 mmHg
• Flash Point: 235.5 °C
• Appearance: /powder
• Density: 1.48 g/cm³
• Vapor Pressure: 7.42E-09mmHg at 25°C
• Refractive Index: 1.649
• Storage Temp.: −20°C
• Solubility: acetone: 50 mg/mL
• PKA: 1.76±0.19(Predicted)
• Stability: Hygroscopic, Moisture Sensitive
• BRN: 1548137
• CAS DataBase Reference: SPDP(CAS DataBase Reference)
• NIST Chemistry Reference: SPDP(68181-17-9)
• EPA Substance Registry System: SPDP(68181-17-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 1-10
• Hazardous Substances Data: 68181-17-9(Hazardous Substances Data)

Usage

Description

SPDP NHS ester is a heterobiofunctional crosslinker which can react with amine and sulfhydryl groups. SPDP NHS esters are membrane permeable therefore allowing them to funtion inside of cells.

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 68181-17-9 differently. You can refer to the following data:
1. Important crosslinking reagent for the preparation of protein-protein and peptide-protein conjugates linked by disulfide bonds.
2. 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.
3. A heterobifunctional cross-linker

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.

InChI:InChI=1/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

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 2127-03-9 2,2'-dipyridyldisulphide 
• 107-96-0 3-mercaptopropionic acid 
• 68617-64-1 3-(2-pyridyldithio)propionic acid 
• 2637-34-5 pyridine-2-thione 
• 119023-07-3 3-(2-pyridylthio)propionic acid methyl ester 
• 59089-57-5 pyridin-2-yl sulfenyl chloride 
• 119023-08-4 3-(2-pyridylthio)propionic acid hydrochloride 

Downstream Products

• 221209-20-7 5-<3-<<<<2-<2-pyridyldithio>ethyl>amino>ethyl>amino>-3-oxopropyl>-5'-O-DMT-2'-deoxyuridine 
• 115616-51-8 3-(2-pyridinyldithio)propanoic acid hydrazide 
• 1226778-21-7 cyclo(RGDyK)SH 

Relevant articles and documents

A new biomimetic route to engineer enzymatically active mechano-responsive materials

Using modified β-galactosidase covalently linked to cross-linked polyelectrolyte multilayers (PEM), catalytically active materials have been designed. Their enzymatic activity can be modulated, partially in a reversible way, simply by stretching. This strategy, based on enzyme conformational changes, constitutes a new tool for the development of biocatalytic mechano-responsive materials.

Nanoscale protein pores modified with PAMAM dendrimers

We describe nanoscale protein pores modified with a single hyperbranched dendrimer molecule inside the channel lumen. Sulfhydryl-reactive polyamido amine (PAMAM) dendrimers of generations 2, 3 and 5 were synthesized, chemically characterized, and reacted with engineered cysteine residues in the transmembrane pore α-hemolysin. Successful coupling was monitored using an electrophoretic mobility shift assay. The results indicate that G2 and G3 but not G5 dendrimers permeated through the 2.9 nm cis entrance to couple inside the pore. The defined molecular weight cutoff for the passage of hyperbranched PAMAM polymers is in contrast to the less restricted accessibility of flexible linear poly(ethylene glycol) polymers of comparable hydrodynamic volume. Their higher compactness makes sulfhydryl-reactive PAMAM dendrimers promising research reagents to probe the structure of porous membrane proteins with wide internal diameters. The conductance properties of PAMAM-modified proteins pores were characterized with single-channel current recordings. A G3 dendrimer molecule in the channel lumen reduced the ionic current by 45%, indicating that the hyperbranched and positively charged polymer blocked the passage of ions through the pore. In line with expectations, a smaller and less dense G2 dendrimer led to a less pronounced current reduction of 25%. Comparisons to recordings of PEG-modified pores revealed striking dissimilarities, suggesting that differences in the structural dynamics of flexible linear polymers vs compact dendrimers can be observed at the single-molecule level. Current recordings also revealed that dendrimers functioned as ion-selectivity filters and molecular sieves for the controlled passage of molecules. The alteration of pore properties with charged and hyperbranched dendrimers is a new approach and might be extended to inorganic nanopores with applications in sensing and separation technology.

With deficiency oxygen target tropism of polyvalent ligand drug conjugates (by machine translation)

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A Programmable Signaling Molecular Recognition Nanocavity Prepared by Molecular Imprinting and Post-Imprinting Modifications

Inspired by biosystems, a process is proposed for preparing next-generation artificial polymer receptors with molecular recognition abilities capable of programmable site-directed modification following construction of nanocavities to provide multi-functionality. The proposed strategy involves strictly regulated multi-step chemical modifications: 1) fabrication of scaffolds by molecular imprinting for use as molecular recognition fields possessing reactive sites for further modifications at pre-determined positions, and 2) conjugation of appropriate functional groups with the reactive sites by post-imprinting modifications to develop programmed functionalizations designed prior to polymerization, allowing independent introduction of multiple functional groups. The proposed strategy holds promise as a reliable, affordable, and versatile approach, facilitating the emergence of polymer-based artificial antibodies bearing desirable functions that are beyond those of natural antibodies.