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Revisiting Boronate/Diol Complexation as a Double Stimulus-Responsive Bioconjugation.

Arianna Gennari1, Chirag Gujral1, Erwin Hohn1

  • 1NorthWest Centre of Advanced Drug Delivery (NoWCADD), School of Health Sciences, University of Manchester , Oxford Road, Manchester, M13 9PT, United Kingdom.

Bioconjugate Chemistry
|April 7, 2017
PubMed
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Boronate/catechol complexation offers a reversible, dual-responsive bioconjugation strategy. This reaction, sensitive to oxidation and pH changes, shows promise for advanced bioconjugation applications.

Area of Science:

  • Bioconjugation Chemistry
  • Chemical Biology
  • Materials Science

Background:

  • Developing reversible and stimuli-responsive bioconjugation reactions is crucial for advanced biological applications.
  • Boronic acids and diols form reversible covalent bonds, but their responsiveness and efficiency vary.
  • Catechol derivatives offer enhanced binding affinity compared to aliphatic diols.

Purpose of the Study:

  • To quantitatively assess the complexation between boronic acids and various diols, including catechols.
  • To evaluate the double-stimulus responsiveness (oxidation and acidification) of boronate/diol complexation for bioconjugation.
  • To explore the application of this reaction in enzyme kinetics and functionalized biomaterials.

Main Methods:

  • Competition assays were used to determine equilibrium constants for 34 boronate/diol pairs.

Related Experiment Videos

  • Enzymatic reactions were employed to generate diols in situ for complexation studies.
  • Michaelis-Menten parameters were calculated for catechol-producing enzymatic reactions.
  • Phenylboronic acid-functionalized hyaluronic acid was synthesized and characterized for pH and H2O2 responsiveness.

    • Main Results:

    • Catechol-based diols exhibited equilibrium constants approximately three orders of magnitude higher than aliphatic diols.
    • The boronate/catechol complexation was successfully demonstrated with in situ generated diols.
    • Phenylboronic acid-functionalized hyaluronic acid showed pH and hydrogen peroxide-responsive complexation with Alizarin Red S.

    Conclusions:

    • The boronate/catechol reaction is a highly versatile and selective bioconjugation strategy.
    • Its reversible nature and responsiveness to oxidation and acidification make it suitable for various biological applications.
    • This reaction holds significant potential for developing novel bioconjugates and drug delivery systems.