807745
APN-COCI
Synonym(s):
4-(cyanoethynyl)benzoyl chloride
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About This Item
Empirical Formula (Hill Notation):
C10H4ClNO
Molecular Weight:
189.60
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22
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
form
powder
reaction suitability
reagent type: cross-linking reagent
storage temp.
2-8°C
Quality Level
Related Categories
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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B
Storage Class
8A - Combustible corrosive hazardous materials
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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