| Identification | Back Directory | [Name]
IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER | [CAS]
39028-27-8 | [Synonyms]
SIA
NHS IODOACETATE
SIA Crosslinker
Succinimidyl iodoacetate
N-IodoacetoxysucciniMide
N-SUCCINIMIDYL IODOACETATE
N-SucciniMidyl iodoacetate(SIA)
N-HYDROXYSUCCINIMIDYL IODOACETATE
2,5-Dioxopyrrolidin-1-yl 2-iodoacetate
2,5-Pyrrolidinedione, 1-[(iodoacetyl)oxy]-
IODOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER
N-HydroxysucciniMide Iodoacetic Acid Ester
Iodoacetic acid N-hydroxysuccinimide ester powder
Iodoacetic Acid N-Succinimidyl Ester
N-(Iodoacetoxy)succinimide | [Molecular Formula]
C6H6INO4 | [MDL Number]
MFCD00058451 | [MOL File]
39028-27-8.mol | [Molecular Weight]
283.02 |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [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 |
| Hazard Information | Back Directory | [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 | [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. | [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 |
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