All Photos(1)
Synonym(s):
3-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl)propiolonitrile, MAPN
Empirical Formula (Hill Notation):
C13H6N2O2
Recommended Products
form
powder
Quality Level
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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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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