Engineering an Artificial Myxopyronin Derivative with Enhanced Metabolic Stability via Mutasynthesis
Alexander F Kiefer1,2,3,4, Alexander Voltz1,2,3,4,5, Domen Scherzer1,2,3,4,5
1Helmholtz Institute for Pharmaceutical Research Saarland (HIPS), Campus E8.1, 66123 Saarbrücken, Germany.
Abstract:
The rise of multidrug-resistant pathogens, such as Staphylococcus aureus and Mycobacterium tuberculosis, underscores an urgent need for therapeutic innovation. The antibiotic development pipeline targeting these bacteria is critically limited, with most discovered candidates exhibiting structurally similar features of prominent chemical entities and with well-established molecular targets or binding modes. The myxobacterial α-pyrone antibiotics, myxopyronins, represent a highly promising compound class due to their ability to inhibit RNA polymerase by binding to the "switch region", a distinct binding site to that of standard-of-care antibiotics. Mutasynthesis, leveraging engineered microorganisms and tailored precursors, provides a viable alternative to total synthesis for generating novel derivatives. This study utilized a heterologous expression system in Myxococcus xanthus DK1622 to generate analogs. Two carrier protein domain mutants were engineered to facilitate mutasynthesis-based production of structurally diverse derivatives. A trifluoromethyl-modified analog, once accessible only through total synthesis but now obtained via mutasynthesis, exhibits potent antimicrobial activity against Gram-positive pathogens including Mycobacterium tuberculosis and favorable in vitro absorption, distribution, metabolism, excretion and toxicity properties. These findings highlight a promising pathway for developing optimized α-pyrone antibiotics to address the global antimicrobial-resistance crisis.
Insights
Novel antibiotic precursors, myxopyronins, were generated using mutasynthesis. A new trifluoromethyl-modified analog shows potent activity against drug-resistant bacteria like Mycobacterium tuberculosis, offering hope against antimicrobial resistance.
Area of Science:
- Microbiology
- Medicinal Chemistry
- Drug Discovery
Background:
- Multidrug-resistant pathogens pose a significant global health threat.
- Existing antibiotic development faces limitations in novelty and pipeline.
- Myxopyronins, myxobacterial α-pyrone antibiotics, offer a novel mechanism by inhibiting RNA polymerase at a distinct site.
Purpose of the Study:
- To explore mutasynthesis for generating novel myxopyronin derivatives.
- To engineer a heterologous expression system for analog production.
- To develop optimized α-pyrone antibiotics to combat antimicrobial resistance.
Main Methods:
- Utilized a heterologous expression system in Myxococcus xanthus DK1622.
- Engineered two carrier protein domain mutants to facilitate mutasynthesis.
- Produced and characterized novel myxopyronin analogs, including a trifluoromethyl-modified derivative.
Main Results:
- Successfully generated structurally diverse myxopyronin analogs via mutasynthesis.
- A novel trifluoromethyl-modified analog, previously requiring total synthesis, was produced.
- This analog demonstrated potent antimicrobial activity against Mycobacterium tuberculosis and Gram-positive pathogens.
- The analog exhibited favorable in vitro ADMET properties.
Conclusions:
- Mutasynthesis is a viable strategy for producing novel α-pyrone antibiotic derivatives.
- The engineered system enables efficient generation of compounds with potential therapeutic value.
- Optimized α-pyrone antibiotics show promise in addressing the urgent need for new treatments against antimicrobial resistance.
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