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, or 3-(2-Pyridyldithio)propionic acid N-hydroxysuccinimide ester, is a heterobifunctional cross-linking reagent with amine and sulfhydryl reactivity. It is a white solid that is membrane permeable, allowing it to function inside of cells. SPDP is typically coupled initially to molecules containing primary amines by amide bonds and then specifically for molecules containing free sulfhydryl by thiol-disulfide exchange. It can also be used as a protected thiolating reagent following initial coupling and reduction of the linker. SPDP incorporates a four-atom linker.

Uses

Used in Bioconjugation:
SPDP is used as an important crosslinking reagent for the preparation of protein-protein and peptide-protein conjugates linked by disulfide bonds. It is particularly useful for antibody conjugation and as a protein cross-linker.
Used in Enzyme Immunoconjugates and Hapten Carrier Molecule Conjugates:
SPDP is used as a heterobifunctional cross-linker for the preparation of enzyme immunoconjugates and hapten carrier molecule conjugates. This application takes advantage of its ability to form stable bonds with both amine and sulfhydryl groups, creating stable and functional conjugates for various biological applications.
Used in Pharmaceutical and Biomedical Research:
SPDP's ability to form stable bonds with amine and sulfhydryl groups makes it a valuable tool in pharmaceutical and biomedical research. It can be used to create novel drug delivery systems, develop new therapeutic agents, and study protein interactions and functions.
Used in Diagnostic Applications:
Due to its reactivity with amine and sulfhydryl groups, SPDP can be employed in the development of diagnostic tools and assays, where the formation of stable conjugates is crucial for accurate detection and measurement of specific biomolecules.
Used in Material Science:
SPDP's cross-linking properties can be utilized in material science to create novel materials with specific properties, such as improved stability or functionality, by forming covalent bonds between different components or molecules within a material.

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 
• 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 
• 68617-64-1 3-(2-pyridyldithio)propionic acid 

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)

The invention discloses a deficiency oxygen target tropism of polyvalent ligand drug conjugates, through containing mercapto homeotropic deficiency oxygen target drug derivative molecule ligand and with the maleimide derivatized dextran of connected, can realize the corresponding drug molecules on tumor tissues to [...], has good anti-tumor activity. . (by machine translation)

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.