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MECHANOCHEMISTRY

Pulling together to improve stability

Maleimide–thiol adducts are popular in both bioconjugation and materials chemistry, however, they are unstable under physiological conditions. Now, a mechanochemical approach uses pulling forces to stabilize maleimide–thiol adducts and improve the stability of polymer–protein conjugates.

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References

  1. 1.

    Chalker, J. M., Bernardes, G. J., Lin, Y. A. & Davis, B. G. Chem. Asian J. 4, 630–640 (2009).

  2. 2.

    Huang, W. et al. Nat. Chem. https://doi.org/10.1038/s41557-018-0209-2 (2019).

  3. 3.

    Ryan, C. P. et al. Chem. Comm. 47, 5452–5454 (2011).

  4. 4.

    Kalia, J. & Raines, R. T. Bioorg. Med. Chem. Lett. 17, 6286–6289 (2007).

  5. 5.

    Fontaine, S. D., Reid, R., Robinson, L., Ashley, G. W. & Santi, D. V. Bioconjugate Chem. 26, 145–152 (2015).

  6. 6.

    Lyon, R. P. et al. Nat. Biotechnol. 32, 1059–1062 (2014).

  7. 7.

    Shen, B.-Q. et al. Nat. Biotechnol. 30, 184–189 (2012).

  8. 8.

    Beyer, M. K. & Clausen-Schaumann, H. Chem. Rev. 105, 2921–2948 (2005).

  9. 9.

    Beck, A., Goetsch, L., Dumontet, C. & Corvaïa, N. Nat. Rev. Drug Discov. 16, 315–337 (2017).

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Correspondence to Phillip B. Messersmith.

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Fig. 1: Mechanochemical acceleration of hydrolysis of thiol-maleimide adducts.