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Life sciences · Journal article
Bioconjugate Chemistry · August 10, 2026
Raises a question worth testing. It does not answer one.
This is an exploratory chemical study comparing the chemoselectivity of monovalent and bivalent maleimide linkers using virus-like particles as a model substrate. The authors report that bivalent maleimides exhibit broader reactivity (cross-reactivity toward lysine and cysteine) compared to the cysteine selectivity of monovalent maleimides, suggesting that linker valency influences reaction specificity. The finding is mechanistic and raises questions about how multivalent linker design affects bioconjugation selectivity, but does not establish clinical utility or validate the approach in therapeutic contexts.
In vitro chemical characterization study. Physalis mottle virus-like particles as a model substrate; no biological or clinical population.. Intervention: Bivalent maleimide linker (mal-PEG11-mal) and monovalent maleimide linker (mPEG12-mal). Compared with: Comparison of mono- versus bivalent maleimide chemoselectivity.
Monovalent maleimides (mPEG12-mal) are highly selective for cysteine modifications Bivalent maleimides (mal-PEG11-mal) exhibit cross-reactivity toward both lysine and cysteine residues Linker valency influences chemoselectivity of maleimide-based conjugation chemistry
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An exploratory chemical characterization study demonstrating differential reactivity patterns of maleimide reagents; raises mechanistic questions about linker valency but does not test clinical or therapeutic outcomes.
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Abstract Maleimides are widely utilized in bioconjugation because they efficiently and selectively react with thiols. Owing to their favorable reaction kinetics, maleimides have found broad applications in bioconjugate chemistry, including the synthesis of antibody-drug conjugates for cancer therapy, fluorescence labeling of proteins, or functionalization of materials. As increasingly complex platforms are developed, multivalent linkers are being incorporated more frequently into synthetic strategies. Although the chemistry of monovalent maleimides is well understood, the chemoselectivity of multivalent maleimide linkers has not been fully established. To investigate differences in the chemoselectivity of mono- and bivalent maleimides, we performed bioconjugation of mal-PEG11-mal or mPEG12-mal with the physalis mottle virus-like particle. Through a series of chemical assays and characterization studies, we demonstrate that while monovalent maleimides are highly selective for cysteine modifications, bivalent maleimides exhibit cross-reactivity toward both lysine and cysteine residues. Overall, this study highlights how linker valency can influence the chemoselectivity of maleimide-based conjugation chemistry.
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