2. Academic Validation
  3. Highly Efficient Thiol-Michael Addition Post-Modification toward Potent Degradable Antibacterial Polyesters with Guanidine Moiety

Highly Efficient Thiol-Michael Addition Post-Modification toward Potent Degradable Antibacterial Polyesters with Guanidine Moiety

  • Biomacromolecules. 2025 Jun 9;26(6):3852-3867. doi: 10.1021/acs.biomac.5c00461.
Yilin Qian 1,  Wei Li 2,  Yang Cheng 3,  Xiao-Tuan Zhang 4,  Fu-Sheng Du 1,  Zi-Chen Li 1
Affiliations

Affiliations

  • 1 Beijing National Laboratory for Molecular Sciences, Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center for Soft Matter Science and Engineering, College of Chemistry & Molecular Engineering, Peking University, Beijing 100871, China.
  • 2 Department of Breast and Thyroid Surgery, The Second Affiliated Hospital of University of South China, Hengyang 421001, Hunan Province, China.
  • 3 Department of Anesthesiology, The Second Affiliated Hospital of University of South China, Hengyang 421001, Hunan Province, China.
  • 4 Department of Clinical Laboratory, The Second Affiliated Hospital of University of South China, Hengyang 421001, Hunan Province, China.
PMID: 40335887 DOI: 10.1021/acs.biomac.5c00461
Abstract

We have previously synthesized poly(3-methylene-1,5-dioxepan-2-one) (PMDXO) that could be modified through the thiol-Michael addition reaction to afford versatile degradable Polymers. Herein, we find that the γ-oxa in PMDXO exerts a dramatically accelerating effect on the thiol-Michael addition post-modification, which makes PMDXO a promising platform polymer for synthesizing guanidinium-functionalized aliphatic polyesters under mild and approximately stoichiometric conditions. The relationship between polymer structure and Antibacterial performance was investigated. A promising cationic polyester, P20-2C, which shows extremely low hemolytic activity, moderate cytotoxicity, and broad-spectrum potent bactericidal capability against 214 clinically isolated ESKAPE strains, is obtained. The good biocompatibility and potent in vivo Antibacterial efficacy of P20-2C have been demonstrated in mice using three Bacterial infection models, including MDR E. coli-infected peritonitis and MRSA-infected subcutaneous abscess and skin wound. Finally, a multimodal bactericidal mechanism of membrane disruption plus Reactive Oxygen Species upregulation is proposed for P20-2C against E. coli and S. aureus.

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