IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER Chemical Properties

Melting point:

148°C

Boiling point:

315.6±44.0 °C(Predicted)

Density 

2.11±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMF: 50 mg/mL

form 

powder

color 

White to Off-White

InChI

InChI=1S/C6H6INO4/c7-3-6(11)12-8-4(9)1-2-5(8)10/h1-3H2

InChIKey

VRDGQQTWSGDXCU-UHFFFAOYSA-N

SMILES

C(ON1C(=O)CCC1=O)(=O)CI

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29251900

MSDS

• Language:English Provider:SigmaAldrich

IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER Usage And Synthesis

Description

SIA Crosslinker is a non-cleavable, water-soluble crosslinker containig an NHS ester and an iodine group. The NHS ester is reactive toward amines while the iodine reacts with thiol groups.

Chemical Properties

White Solid

Uses

A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. Spacer Arm: 1.5 Angstroms

Uses

forms water soluble carboxylate derivatives

Uses

A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. Spacer Arm: 1.5 Angstroms

reaction suitability

reagent type: cross-linking reagent

Biological Activity

SIA Crosslinker is a non-cleavable ADC linker that can be used to synthesize antibody drug conjugates (ADCs).

Synthesis

N-hydroxysuccinimide (12.6 mmol) and dicyclohexylcarbodiimide (20.3 mmol) were dissolved in an appropriate amount of solvent at 0 °C, followed by the addition of iodoacetic acid (6 mmol). The reaction mixture was gradually warmed up to room temperature with continuous stirring for 4 hours. For the synthesis of compound VIa, maleic anhydride (10 mmol) was pre-reacted with β-alanine in N,N-dimethylformamide for 1 hour. After completion of the reaction, the solvent was removed by distillation under reduced pressure and the crude product was dissolved in dichloromethane and washed with water. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated to dryness. The residue was purified by recrystallization to afford the target product succinimidyl iodoacetate (VIb) in 30% yield. The structure of the product was confirmed by 1H NMR (CDCl3) and 13C NMR (CDCl3): 1H NMR (CDCl3) δppm: 2.87 (2H, s), 3.96 (1H, s); 13C NMR (CDCl3) δppm: -12.47 (1C, s) 25.85 (2C, s) 164.78 (1C, s) 168.78 (2C, s).

in vitro

ADCs are comprised of an antibody to which is attached an ADC cytotoxin through an ADC linker.

References

[1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 32, p. 7777 - 7791
[2] Patent: US2013/273581, 2013, A1. Location in patent: Page/Page column 0092; 0111-0112; 0114
[3] Farmaco, 1992, vol. 47, # 11, p. 1367 - 1383

IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER(39028-27-8)Related Product Information

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• IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER