MAPN: First-in-Class Reagent for Kinetically Resolved Thiol-to-Thiol Conjugation.
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 creating heteroconjugates using two different thiols. In response to the ever-increasing demand for bioconjugation tools, we have developed p-(maleimide)-phenylpropionitrile (MAPN)-an efficient reagent for kinetically resolved thiol-to-thiol coupling. In a comparative study with its closest commercially available analogue, p-phenylenedimaleimide, MAPN has shown substantial advantages for the preparation of thiol-thiol heteroconjugates. Namely, an antibody-drug conjugate (ADC) with mertansine (DM1), conjugated to the cysteine residues of Trastuzumab, was prepared for the first time.
Laboratory of Functional ChemoSystems (UMR 7199), Labex Medalis, University of Strasbourg , 74 route du Rhin, 67401 Illkirch-Graffenstaden, France.|Syndivia SAS , 4 Rue Boussingault, 67000 Strasbourg, France.
Oleksandr
O
Koniev
Laboratory of Functional ChemoSystems (UMR 7199), Labex Medalis, University of Strasbourg , 74 route du Rhin, 67401 Illkirch-Graffenstaden, France.|Syndivia SAS , 4 Rue Boussingault, 67000 Strasbourg, France.
Sergii
S
Kolodych
Laboratory of Functional ChemoSystems (UMR 7199), Labex Medalis, University of Strasbourg , 74 route du Rhin, 67401 Illkirch-Graffenstaden, France.
Zoljargal
Z
Baatarkhuu
BioOrganic Mass Spectrometry Laboratory (LSMBO), IPHC, University of Strasbourg , 25 rue Becquerel, 67087 Strasbourg, France.|IPHC, CNRS, UMR7178, 25 rue Becquerel, 67087 Strasbourg, France.
Johann
J
Stojko
Laboratory of Functional ChemoSystems (UMR 7199), Labex Medalis, University of Strasbourg , 74 route du Rhin, 67401 Illkirch-Graffenstaden, France.
Jitka
J
Eberova
Syndivia SAS , 4 Rue Boussingault, 67000 Strasbourg, France.
Jean-Yves
JY
Bonnefoy
BioOrganic Mass Spectrometry Laboratory (LSMBO), IPHC, University of Strasbourg , 25 rue Becquerel, 67087 Strasbourg, France.|IPHC, CNRS, UMR7178, 25 rue Becquerel, 67087 Strasbourg, France.
Sarah
S
Cianférani
BioOrganic Mass Spectrometry Laboratory (LSMBO), IPHC, University of Strasbourg , 25 rue Becquerel, 67087 Strasbourg, France.|IPHC, CNRS, UMR7178, 25 rue Becquerel, 67087 Strasbourg, France.
Alain
A
Van Dorsselaer
Laboratory of Functional ChemoSystems (UMR 7199), Labex Medalis, University of Strasbourg , 74 route du Rhin, 67401 Illkirch-Graffenstaden, France.
Alain
A
Wagner
D000480:Alkynes / Q000737:chemistry*; D045744:Cell Line, Tumor; D006801:Humans; D018796:Immunoconjugates / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D007700:Kinetics; D008301:Maleimides / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D000480:Alkynes; D018796:Immunoconjugates; D007202:Indicators and Reagents; D008301:Maleimides; D013438:Sulfhydryl Compounds; C000608414:p-(maleimide)phenylpropionitrile; C043592:maleimide