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807745

Sigma-Aldrich

APN-COCI

Synonym(s):

4-(cyanoethynyl)benzoyl chloride

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About This Item

Empirical Formula (Hill Notation):
C10H4ClNO
Molecular Weight:
189.60
UNSPSC Code:
12352101
PubChem Substance ID:
329768747
NACRES:
NA.22

form

powder

Quality Level

100

reaction suitability

reagent type: cross-linking reagent

storage temp.

2-8°C

SMILES string

N#CC#CC1=CC=C(C(Cl)=O)C=C1

InChI

1S/C10H4ClNO/c11-10(13)9-5-3-8(4-6-9)2-1-7-12/h3-6H

InChI key

OWNJCJKKKZXTIX-UHFFFAOYSA-N

Application

APN-COCl is a bifunctional reagent appropriate for the introduction of APN function.

Other Notes

The coupling between an amine and APN-COCl should be performed in dry organic solvents (e.g. THF) in the presence of a base (e.g. TEA). The resulting conjugate can be readily coupled with thiol-containing biomolecules using the following protocol:

  • 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 APN-labeled molecule (1-5 molar eq. per free cysteine residue).
  • Incubate at room temperature for 2 hours.
If necessary, purify the protein conjugate using size exclusion chromatography or ultrafiltration.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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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