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806536

Sigma-Aldrich

APN-Maleimide

Synonym(s):

3-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl)propiolonitrile, MAPN

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About This Item

Empirical Formula (Hill Notation):
C13H6N2O2
Molecular Weight:
222.20
UNSPSC Code:
12352111
PubChem Substance ID:
329769017
NACRES:
NA.22

form

powder

Quality Level

100

storage temp.

2-8°C

SMILES string

N#CC#CC1=CC=C(N2C(C=CC2=O)=O)C=C1

InChI

1S/C13H6N2O2/c14-9-1-2-10-3-5-11(6-4-10)15-12(16)7-8-13(15)17/h3-8H

InChI key

CHKKXKRQICWZFF-UHFFFAOYSA-N

Application

APN-Maleimide is a bifunctional crosslinker for thiol-to-thiol coupling. The coupling can be performed with high selectivity in biological medium using mild reaction conditions. Due to kinetic resolution the first thiol reacts exclusively with the maleimide residue producing the protein-APN conjugate. This conjugate can be readily coupled with thiol-containing molecules.

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 10 minutes.
  • If necessary, purify the protein-APN conjugate using size exclusion chromatography or ultrafiltration.
  • The conjugate can be readily coupled with thiol-containing substrates by incubating the components in aqueous buffer (pH 6.5-9.0) at ambient temperature for 2 hours.
*Note: avoid thiol-containing buffers.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Oleksandr Koniev et al.
Bioconjugate chemistry, 26(9), 1863-1867 (2015-09-04)
Thiols are among the most frequently used functional groups in the field of bioconjugation. While there exists a variety of heterobifunctional reagents that allow for coupling thiols to other functions (e.g., amines, carboxylic acids), there is no specific reagent for
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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