N-Succinimidyl 3-(2-pyridyldithio)propionate (HCID 100682)

Overview

heterobifunctional reagent

Names & identifiers

Preferred name: N-Succinimidyl 3-(2-pyridyldithio)propionate
IUPAC: (2,5-dioxopyrrolidin-1-yl) 3-(pyridin-2-yldisulfanyl)propanoate
English name: SPDP
Molecular formula: C12H12N2O4S2
Molecular weight: 312.36

Names & synonyms

SPDP68181-17-9N-Succinimidyl 3-(2-pyridyldithio)propionate2OHG8V08NLNSC-3444851-(1-Oxo-3-(2-pyridyldithio)propoxy)pyrrolidine-2,5-dione2,5-Pyrrolidinedione, 1-(1-oxo-3-(2-pyridinyldithio)propoxy)-DTXSID60218366N-SUCCINIMIDYL 3-[2-PYRIDYLDITHIO]PROPIONATESIPDTPRefChem:164199DTXCID80140857

Show more names

SUCCINIMIDYL 3-(2-PYRIDYLDITHIO)PROPIONATE2,5-dioxopyrrolidin-1-yl 3-(pyridin-2-yldisulfaneyl)propanoatePDPH,SPDPSPDP (SPDP Crosslinker)3-(2-PYRIDYLDITHIO)-PROPIONIC ACID-OSU3-(Pyridin-2-yldisulfanyl)-propionic acid-OS

N-succinilimidyl 3-(2-pyridylthio)propionate269-034-33-(2-Pyridyldithio)propionic acid N-hydroxysuccinimide esterSPDP NHS ester2,5-dioxopyrrolidin-1-yl 3-(pyridin-2-yldisulfanyl)propanoateSPDP Crosslinker3-(2-Pyridyldithio)propionic Acid N-Succinimidyl EsterMFCD00009636

Database identifiers

CAS: 68181-17-9
PubChem CID: 100682
DTXSID: DTXSID60218366
UNII: 2OHG8V08NL
EC Number: 269-034-3
Nikkaji: J317.385B

Properties

Computed structural properties

XLogP: 0.7
Topological polar surface area: 127 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 7
Rotatable bonds: 7
Heavy atoms: 20
Formal charge: 0
Complexity: 376

Physicochemical properties

Melting point: 84 · 84-86 °C(lit.)
Boiling point: 465.9 · 465.9±55.0 °C(Predicted)
Density: 1.48 · 1.48±0.1 g/cm3(Predicted)
storage temp.: -20 °C · -20°C
solubility: 50 mg/mL · acetone: 50 mg/mL
form: powder
pka: 1.76 · 1.76±0.19(Predicted)
color: White to Light Yellow
BRN: 1548137 · 1548137
Stability: Hygroscopic, Moisture Sensitive
InChI: 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
InChIKey: JWDFQMWEFLOOED-UHFFFAOYSA-N
SMILES: C(ON1C(=O)CCC1=O)(=O)CCSSC1=NC=CC=C1
CAS DataBase Reference: 68181 · 68181-17-9(CAS DataBase Reference)
FDA UNII: 2 OHG8V08NL · 2OHG8V08NL
UNSPSC Code: 12352106 · 12352106
NACRES: 7 · NC.07
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H317
Precautionary statements: 280 · P280
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 3 · 3
F: 1 · 1-10
HS Code: 29333990 · 29333990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information2,5-Pyrrolidinedione, 1-1-oxo-3-(2-pyridinyldithio)propoxy-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

F: 1-10
PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
hs_code: 29333990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H317
Precautionary statements: P280

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 1 item

Reagents with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between side chains of amino acids in proteins; the locations of naturally reactive areas within proteins can thereby be identified; may also be used for other macromolecules, like glycoproteins, nucleic acids, or other.

Applications · 5 items

DescriptionSPDP 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.

UsesImportant crosslinking reagent for the preparation of protein-protein and peptide-protein conjugates linked by disulfide bonds.

Uses3-(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.

UsesA heterobifunctional cross-linker

General Description3-(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.