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806021

Sigma-Aldrich

APN-CHO

Synonym(s):

3-(4-formylphenyl)propiolonitrile, APN-aldehyde

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About This Item

Empirical Formula (Hill Notation):
C10H5NO
Molecular Weight:
155.15
UNSPSC Code:
12352101
PubChem Substance ID:
329768984
NACRES:
NA.22

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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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