806013
APN-BCN
95%
Synonym(s):
Bicyclo[6.1.0]non-4-yn-9-ylmethyl (4-(cyanoethynyl)phenyl)carbamate
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About This Item
Empirical Formula (Hill Notation):
C20H18N2O2
Molecular Weight:
318.37
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22
SMILES string
N#CC#CC1=CC=C(NC(OCC2C3CCC#CCCC23)=O)C=C1
InChI
1S/C19H16N2O2/c20-13-5-6-14-9-11-15(12-10-14)21-19(22)23-18-16-7-3-1-2-4-8-17(16)18/h9-12,16-18H,3-4,7-8H2,(H,21,22)
InChI key
LVFLVSUFJDGHRN-UHFFFAOYSA-N
assay
95%
form
powder
reaction suitability
reagent type: cross-linking reagent
storage temp.
−20°C
Application
APN-BCN is a bifunctional crosslinker for thiol-to-azide coupling. 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-BCN conjugate using size exclusion chromatography or ultrafiltration.
- The conjugate can be readily coupled with azide-containing molecules by incubating the components in an aqueous buffer.
signalword
Warning
hcodes
pcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
13 - Non Combustible Solids
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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