Iodoacetic acid N-hydroxysuccinimide ester

SIA Crosslinker is a non-cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs)[1].

On a solution of N-hydroxysuccinimide (12.6 mmol) and dicyclohexylcarbodiimide (20.3 mmol) at 0° C., corresponding acid (6 mmol) was added and allowed to react for 4 hours at room temperature. In the case of compound VIa, a solution of maleic anhydride (10 mmol) and β-alanine was added in N, N-dimethylformamide, which has been previously made react for 1 hour. After 4 hours, mixture was evaporated at reduced pressure and the crude was dissolved in dichloromethane and washed with water. Organic extracts were dried with anhydrous magnesium sulfate, filtered and evaporated to dryness. Resulting residue was recrystallized to give desired compound. [0112] Using this methodology, and corresponding acid, the following compounds were prepared: Succinimidyl iodoacetate (VIb, 30percent yield).

forms water soluble carboxylate derivatives

Molecular Weight:283.02
XLogP3:-0.1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:282.93416
Monoisotopic Mass:282.93416
Topological Polar Surface Area:63.7
Heavy Atom Count:12
Complexity:224
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes