ArticleOrganic & biomolecular chemistry2016
Deoxyfluoro-d-trehalose (FDTre) analogues as potential PET probes for imaging mycobacterial infection.
Article in Organic & biomolecular chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 33 papers.
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Who cites it
33 citing papers in PubMed, 62 citations in OpenAlex.
- Fluorescence-Quenched Mycoloyl-Arabinofuranoside Analogs: Fluorogenic Probes for Mycobacterial Outer Membrane-Degrading Enzymes.Chembiochem : a European journal of chemical biology · 2026Article
- Tre-DST: A Drug Susceptibility Test forACS infectious diseases · 2026Article
- Stereospecific Synthesis of 2-Deoxy-2-fluoroglycosides via SCCS chemistry · 2026Article
- Synthesis and evaluation of Trehalose-Pks13 inhibitor conjugates targeting mycobacteria.Carbohydrate research · 2025Article
- Overview of Small Molecules as Fluorescent Probes ofACS omega · 2024Review
- Distributable, metabolic PET reporting of tuberculosis.Nature communications · 2024Article
- Classification of early tuberculosis states to guide research for improved care and prevention: an international Delphi consensus exercise.The Lancet. Respiratory medicine · 2024Review
- Pathogenicity and virulence ofVirulence · 2023Review
- The Promise of Molecular Imaging: Focus on Central Nervous System Infections.The Journal of infectious diseases · 2023Review
- Immune Targeting of Mycobacteria through Cell Surface Glycan Engineering.ACS chemical biology · 2023Article
- Fluorinated carbohydrates forChemical Society reviews · 2023Review
- Article
- Azido Inositol Probes Enable Metabolic Labeling of Inositol-Containing Glycans and Reveal an Inositol Importer in Mycobacteria.ACS chemical biology · 2023Article
- A Far-Red Molecular Rotor Fluorogenic Trehalose Probe for Live Mycobacteria Detection and Drug-Susceptibility Testing.Angewandte Chemie (International ed. in English) · 2023Article
- Interrogation of the Pathogen Box reveals small molecule ligands against the mycobacterial trehalose transporter LpqY-SugABC.RSC medicinal chemistry · 2022Article
- Chemical Reporters for Bacterial Glycans: Development and Applications.Chemical reviews · 2022Review
- Toward Point-of-Care Detection ofJACS Au · 2021Article
- The role of chemoenzymatic synthesis in advancing trehalose analogues as tools for combatting bacterial pathogens.Chemical communications (Cambridge, England) · 2020Article
- Small Molecule Sensors Targeting the Bacterial Cell Wall.ACS infectious diseases · 2020Review
- Recent Developments in the Application of Flow Cytometry to Advance our Understanding of Mycobacterium tuberculosis Physiology and Pathogenesis.Cytometry. Part A : the journal of the International Society for Analytical Cytology · 2020Review
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Authors and funding
10 authors at 3 institutions in 1 country.
Funding
Abstract
Mycobacterium tuberculosis, the etiological agent of human tuberculosis, requires the non-mammalian disaccharide trehalose for growth and virulence. Recently, detectable trehalose analogues have gained attention as probes for studying trehalose metabolism and as potential diagnostic imaging agents for mycobacterial infections. Of particular interest are deoxy-[(18)F]fluoro-d-trehalose ((18)F-FDTre) analogues, which have been suggested as possible positron emission tomography (PET) probes for in vivo imaging of M. tuberculosis infection. Here, we report progress toward this objective, including the synthesis and conformational analysis of four non-radioactive deoxy-[(19)F]fluoro-d-trehalose ((19)F-FDTre) analogues, as well as evaluation of their uptake by M. smegmatis. The rapid synthesis and purification of several (19)F-FDTre analogues was accomplished in high yield using a one-step chemoenzymatic method. Conformational analysis of the (19)F-FDTre analogues using NMR and molecular modeling methods showed that fluorine substitution had a negligible effect on the conformation of the native disaccharide, suggesting that fluorinated analogues may be successfully recognized and processed by trehalose metabolic machinery in mycobacteria. To test this hypothesis and to evaluate a possible route for delivery of FDTre probes specifically to mycobacteria, we showed that (19)F-FDTre analogues are actively imported into M. smegmatis via the trehalose-specific transporter SugABC-LpqY. Finally, to demonstrate the applicability of these results to the efficient preparation and use of short-lived (18)F-FDTre PET radiotracers, we carried out (19)F-FDTre synthesis, purification, and administration to M. smegmatis in 1 hour.
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