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Advances in Proximity-Assisted Bioconjugation.

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Proximity-induced chemistry (PIC) enables proximity-assisted bioconjugation (PAB) for precise modification of biomolecules. This approach enhances antibody-drug conjugate stability and enables regioselective modification of challenging targets like histone H3.

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Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Biotechnology

Background:

  • Proximity-induced chemistry (PIC) describes transient reactivity between molecules in close proximity, crucial for biological processes.
  • PIC is utilized in chemical biology for degrading biomolecules and creating protein therapeutics, including antibody-drug conjugates (ADCs).
  • Existing site-specific bioconjugation methods often face challenges with yield, stability, and regioselectivity.

Purpose of the Study:

  • To develop and showcase proximity-assisted bioconjugation (PAB) strategies for precise and regioselective modification of biomolecules.
  • To address limitations of current bioconjugation techniques by leveraging PIC principles.
  • To explore PAB applications in antibody-drug conjugate (ADC) development and modification of challenging biomolecules.

Main Methods:

  • Investigated maleic acid derivatives for cysteine bioconjugation, discovering unexpected lysine participation.
  • Developed PAB strategies by harnessing proximal lysine residues (e.g., K207 in Trastuzumab) to tune ADC stability.
  • Created regioselective lysine acetylation of histone H3 and phage display-compatible peptide cyclization using PAB.

Main Results:

  • Discovered that proximal lysines on THIOMAB antibodies influence bioconjugate product formation.
  • Demonstrated that specific lysine residues can be engineered to precisely control ADC stability.
  • Successfully implemented PAB for regioselective modification of histone H3 and peptide cyclization.

Conclusions:

  • PAB strategies effectively overcome limitations of traditional bioconjugation, enabling precise and regioselective biomolecule modification.
  • The findings provide insights into the chemical landscape of antibodies, informing future ADC design.
  • PAB methodologies offer versatile tools for chemical biologists, expanding applications in bioconjugation and beyond.