دورية أكاديمية
أعرض في EDS

Minimalist Tetrazine N -Acetyl Muramic Acid Probes for Rapid and Efficient Labeling of Commensal and Pathogenic Peptidoglycans in Living Bacterial Culture and During Macrophage Invasion.

التفاصيل البيبلوغرافية
العنوان: Minimalist Tetrazine N -Acetyl Muramic Acid Probes for Rapid and Efficient Labeling of Commensal and Pathogenic Peptidoglycans in Living Bacterial Culture and During Macrophage Invasion.
المؤلفون: Hillman AS; Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States., Hyland SN; Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States., Wodzanowski KA; Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States., Moore DL; Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States., Ratna S; Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States., Jemas A; Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States., Sandles LD; Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States., Chaya T; Department of Plant and Soil Sciences, University of Delaware, Newark, Delaware 19716, United States., Ghosh A; Delaware Biotechnology Institute, UDEL Flow Cytometry Core, University of Delaware, Newark, Delaware 19716, United States., Fox JM; Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States.; Department of Materials Science and Engineering, University of Delaware, Newark, Delaware 19716, United States., Grimes CL; Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States.; Department of Biological Sciences, University of Delaware, Newark, Delaware 19716, United States.
المصدر: Journal of the American Chemical Society [J Am Chem Soc] 2024 Mar 13; Vol. 146 (10), pp. 6817-6829. Date of Electronic Publication: 2024 Mar 01.
نوع المنشور: Journal Article; Research Support, Non-U.S. Gov't; Research Support, N.I.H., Extramural
اللغة: English
بيانات الدورية: Publisher: American Chemical Society Country of Publication: United States NLM ID: 7503056 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-5126 (Electronic) Linking ISSN: 00027863 NLM ISO Abbreviation: J Am Chem Soc Subsets: MEDLINE
أسماء مطبوعة: Publication: Washington, DC : American Chemical Society
Original Publication: Easton, Pa. [etc.]
مواضيع طبية MeSH: Peptidoglycan* , Heterocyclic Compounds*, Humans ; Azides ; Muramic Acids ; Cycloaddition Reaction ; Alkynes
مستخلص: N -Acetyl muramic acid (NAM) probes containing alkyne or azide groups are commonly used to investigate aspects of cell wall synthesis because of their small size and ability to incorporate into bacterial peptidoglycan (PG). However, copper-catalyzed alkyne-azide cycloaddition (CuAAC) reactions are not compatible with live cells, and strain-promoted alkyne-azide cycloaddition (SPAAC) reaction rates are modest and, therefore, not as desirable for tracking the temporal alterations of bacterial cell growth, remodeling, and division. Alternatively, the tetrazine- trans -cyclooctene ligation (Tz-TCO), which is the fastest known bioorthogonal reaction and not cytotoxic, allows for rapid live-cell labeling of PG at biologically relevant time scales and concentrations. Previous work to increase reaction kinetics on the PG surface by using tetrazine probes was limited because of low incorporation of the probe. Described here are new approaches to construct a minimalist tetrazine (Tz)-NAM probe utilizing recent advancements in asymmetric tetrazine synthesis. This minimalist Tz-NAM probe was successfully incorporated into pathogenic and commensal bacterial PG where fixed and rapid live-cell, no-wash labeling was successful in both free bacterial cultures and in coculture with human macrophages. Overall, this probe allows for expeditious labeling of bacterial PG, thereby making it an exceptional tool for monitoring PG biosynthesis for the development of new antibiotic screens. The versatility and selectivity of this probe will allow for real-time interrogation of the interactions of bacterial pathogens in a human host and will serve a broader utility for studying glycans in multiple complex biological systems.
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معلومات مُعتمدة: T32 GM133395 United States GM NIGMS NIH HHS; U01 CA221230 United States CA NCI NIH HHS; P20 GM103446 United States GM NIGMS NIH HHS; S10 OD030321 United States OD NIH HHS; R01 GM138599 United States GM NIGMS NIH HHS; P20 GM139760 United States GM NIGMS NIH HHS; R21 AI163949 United States AI NIAID NIH HHS; P20 GM104316 United States GM NIGMS NIH HHS; R01 GM132460 United States GM NIGMS NIH HHS; P30 GM110758 United States GM NIGMS NIH HHS
المشرفين على المادة: 0 (Peptidoglycan)
0 (Azides)
246FXU111L (N-acetylmuramic acid)
0 (Muramic Acids)
0 (Heterocyclic Compounds)
0 (Alkynes)
تواريخ الأحداث: Date Created: 20240301 Date Completed: 20240314 Latest Revision: 20240710
رمز التحديث: 20240710
مُعرف محوري في PubMed: PMC10941766
DOI: 10.1021/jacs.3c13644
PMID: 38427023
قاعدة البيانات: MEDLINE
الوصف
تدمد:1520-5126
DOI:10.1021/jacs.3c13644