806595
APN-Azide
95%
Synonym(s):
3-(4-Azidophenyl)propiolonitrile, APN-N3
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About This Item
Empirical Formula (Hill Notation):
C9H4N4
CAS Number:
Molecular Weight:
168.15
UNSPSC Code:
12352125
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
assay
95%
form
powder
reaction suitability
reagent type: cross-linking reagent
mp
100 °C
functional group
azide
storage temp.
2-8°C
SMILES string
N#CC#CC1=CC=C(N=[N+]=[N-])C=C1
InChI
1S/C9H4N4/c10-7-1-2-8-3-5-9(6-4-8)12-13-11/h3-6H
InChI key
BDLXITYEYYHQNK-UHFFFAOYSA-N
Application
APN-Azide is a bifunctional crosslinker for thiol-to-alkyne coupling. This coupling can be performed with high selectivity in biological medium using mild reaction conditions.
Standard protein labeling procedure (cysteine labeling)
1. Dissolve the protein in the appropriate buffer* with pH 6.5-9.0 (e.g. PBS) at 1-10 mg/mL concentration.
2. Apply the appropriate amount of the stock solution of the reagent (1-5 molar eq. per free cysteine residue).
3. Incubate at room temperature for 2 hours.
4. If necessary, purify the protein-azide conjugate using size exclusion chromatography or ultrafiltration.
5. The conjugate can be readily coupled with alkyne-containing using standard click-chemistry protocols.
*Note: avoid thiol-containing buffers.
Standard protein labeling procedure (cysteine labeling)
1. Dissolve the protein in the appropriate buffer* with pH 6.5-9.0 (e.g. PBS) at 1-10 mg/mL concentration.
2. Apply the appropriate amount of the stock solution of the reagent (1-5 molar eq. per free cysteine residue).
3. Incubate at room temperature for 2 hours.
4. If necessary, purify the protein-azide conjugate using size exclusion chromatography or ultrafiltration.
5. The conjugate can be readily coupled with alkyne-containing using standard click-chemistry protocols.
*Note: avoid thiol-containing buffers.
signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Sol. 1 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
4.1B - Flammable solid hazardous materials
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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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