All Photos(1)
Synonym(s):
3-(4-formylphenyl)propiolonitrile, APN-aldehyde
Empirical Formula (Hill Notation):
C10H5NO
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form
powder
reaction suitability
reagent type: cross-linking reagent
functional group
carbonyl
storage temp.
2-8°C
SMILES string
N#CC#CC1=CC=C(C=O)C=C1
InChI
1S/C10H5NO/c11-7-1-2-9-3-5-10(8-12)6-4-9/h3-6,8H
InChI key
LYISHMGQKXLBHI-UHFFFAOYSA-N
Application
APN-Aldehyde is a bifunctional crosslinker for introduction of aldehyde into biomolecules. The coupling can be performed with high selectivity in biological medium using mild reaction conditions.
Preparation Note
Standard protein labeling procedure (cysteine labeling).
- Dissolve the protein in the appropriate buffer with pH 6.5-9.0 (e.g. PBS) at 1-10 mg/mL concentration.
- Apply the appropriate amount of the stock solution of the reagent (1-5 molar eq. per free cysteine residue).
- Incubate at room temperature for 2 hours.
- If necessary, purify the protein-aldehyde conjugate using size exclusion chromatography or ultrafiltration.
- The conjugate can be readily coupled with hydrazides/hydrazones/hydroxylamines using standard protocols.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Sergii Kolodych et al.
Bioconjugate chemistry, 26(2), 197-200 (2015-01-24)
Amine-to-thiol coupling is the most common route for the preparation of antibody-drug conjugates (ADC). It is usually achieved by using heterobifunctional reagents possessing an activated ester at one end and a maleimide group at the other. However, maleimide-based conjugates were
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