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806595

Sigma-Aldrich

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:
1643841-88-6
Molecular Weight:
168.15
MDL number:
MFCD29059836
UNSPSC Code:
12352125
PubChem Substance ID:
329769021
NACRES:
NA.22

Quality Level

100

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.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H228,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Sol. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

JAN Code

806595-BULK:
806595-VAR:
806595-50MG:4548173921037

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT4305
MKCS2830
MKCP2466
MKCL6097
MKCC4442

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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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