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Engineering an Affinity-Enhanced Peptide through Optimization of Cyclization Chemistry.

Chayanon Ngambenjawong1, Julio Marco B Pineda1, Suzie H Pun1

  • 1Department of Bioengineering and Molecular Engineering and Sciences Institute, University of Washington , Seattle, Washington 98195, United States.

Bioconjugate Chemistry
|October 26, 2016
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Summary

Peptide cyclization strategies significantly enhance M2 macrophage-binding peptide (M2pep) affinity. The decafluorobiphenyl (DFBP)-cyclized M2pep(RY) analog showed the highest binding activity, demonstrating optimized peptide therapeutics.

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Area of Science:

  • Medicinal Chemistry
  • Peptide Chemistry
  • Immunology

Background:

  • Peptide cyclization improves stability and activity, with disulfide bridges being common.
  • Alternative cyclization chemistries offer enhanced efficiency and stability.
  • Fine-tuning peptide activity through diverse cyclization linkers is an underappreciated strategy.

Purpose of the Study:

  • To investigate how different peptide cyclization strategies impact the binding affinity of an M2 macrophage-binding peptide (M2pep).
  • To synthesize and evaluate M2pep(RY) analogs using various cyclization methods, including amide, triazole, decafluorobiphenyl (DFBP), and decafluorobiphenyl sulfone (DFS).
  • To compare the binding activity and selectivity of these analogs to M1 and M2 macrophages.

Main Methods:

  • Synthesis of four cyclic M2pep(RY) analogs utilizing distinct cyclization strategies: Asp-[amide]-Lys, azido-Lys-[triazole(CuAAC)]-propargyl-Gly, Cys-[DFBP]-Cys, and Cys-[DFS]-Cys.
  • Comparative analysis of binding affinity (KD) to M2 macrophages against a previously reported disulfide-cyclized analog and the linear M2pep.
  • Evaluation of binding selectivity towards M2 macrophages over M1 macrophages.

Main Results:

  • The DFBP-cyclized M2pep(RY) analog exhibited the highest binding activity to M2 macrophages, with an apparent dissociation constant (KD) of approximately 2.03 μM.
  • This represents a significant enhancement compared to the disulfide-cyclized analog (36.3 μM) and the linear peptide (220 μM).
  • DFS-cyclized M2pep(RY) also showed improved binding, while amide- and triazole-cyclized analogs displayed weaker binding.

Conclusions:

  • Diverse peptide cyclization strategies can be employed to optimize the binding affinity of M2 macrophage-targeting peptides.
  • DFBP-cyclized M2pep(RY) demonstrates superior M2 macrophage-binding activity, highlighting the potential of this approach for developing targeted therapeutics.
  • While DFBP cyclization enhances binding, considerations for solubility and toxicity, as seen with diphenylalanine incorporation, are important.