806536
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
MDL number:
UNSPSC Code:
12352111
PubChem Substance ID:
NACRES:
NA.22
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
form
powder
storage temp.
2-8°C
Quality Level
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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
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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