Literature DB >> 32222086

Arabinofuranose-derived positron-emission tomography radiotracers for detection of pathogenic microorganisms.

Mausam Kalita1, Matthew F L Parker1, Justin M Luu1, Megan N Stewart1, Joseph E Blecha1, Henry F VanBrocklin1, Michael J Evans1, Robert R Flavell1, Oren S Rosenberg2, Michael A Ohliger1,3, David M Wilson1.   

Abstract

PURPOSE: Detection of bacteria-specific metabolism via positron emission tomography (PET) is an emerging strategy to image human pathogens, with dramatic implications for clinical practice. In silico and in vitro screening tools have recently been applied to this problem, with several monosaccharides including l-arabinose showing rapid accumulation in Escherichia coli and other organisms. Our goal for this study was to evaluate several synthetically viable arabinofuranose-derived 18 F analogs for their incorporation into pathogenic bacteria. PROCEDURES: We synthesized four radiolabeled arabinofuranose-derived sugars: 2-deoxy-2-[18 F]fluoro-arabinofuranoses (d-2-18 F-AF and l-2-18 F-AF) and 5-deoxy-5-[18 F]fluoro-arabinofuranoses (d-5-18 F-AF and l-5-18 F-AF). The arabinofuranoses were synthesized from 18 F- via triflated, peracetylated precursors analogous to the most common radiosynthesis of 2-deoxy-2-[18 F]fluoro-d-glucose ([18 F]FDG). These radiotracers were screened for their uptake into E. coli and Staphylococcus aureus. Subsequently, the sensitivity of d-2-18 F-AF and l-2-18 F-AF to key human pathogens was investigated in vitro.
RESULTS: All 18 F radiotracer targets were synthesized in high radiochemical purity. In the screening study, d-2-18 F-AF and l-2-18 F-AF showed greater accumulation in E. coli than in S. aureus. When evaluated in a panel of pathologic microorganisms, both d-2-18 F-AF and l-2-18 F-AF demonstrated sensitivity to most gram-positive and gram-negative bacteria.
CONCLUSIONS: Arabinofuranose-derived 18 F PET radiotracers can be synthesized with high radiochemical purity. Our study showed absence of bacterial accumulation for 5-substitued analogs, a finding that may have mechanistic implications for related tracers. Both d-2-18 F-AF and l-2-18 F-AF showed sensitivity to most gram-negative and gram-positive organisms. Future in vivo studies will evaluate the diagnostic accuracy of these radiotracers in animal models of infection.
© 2020 John Wiley & Sons, Ltd.

Entities:  

Keywords:  arabinofuranose; imaging; infection; positron emission tomography; sugars

Year:  2020        PMID: 32222086      PMCID: PMC7364301          DOI: 10.1002/jlcr.3835

Source DB:  PubMed          Journal:  J Labelled Comp Radiopharm        ISSN: 0362-4803            Impact factor:   1.921


  36 in total

1.  A Systematic Approach for Developing Bacteria-Specific Imaging Tracers.

Authors:  Alvaro A Ordonez; Edward A Weinstein; Lauren E Bambarger; Vikram Saini; Yong S Chang; Vincent P DeMarco; Mariah H Klunk; Michael E Urbanowski; Kimberly L Moulton; Allison M Murawski; Supriya Pokkali; Alvin S Kalinda; Sanjay K Jain
Journal:  J Nucl Med       Date:  2016-09-15       Impact factor: 10.057

Review 2.  Atomic structure and specificity of bacterial periplasmic receptors for active transport and chemotaxis: variation of common themes.

Authors:  F A Quiocho; P S Ledvina
Journal:  Mol Microbiol       Date:  1996-04       Impact factor: 3.501

3.  High Enantiomeric Excess In-Loop Synthesis of d-[methyl-11C]Methionine for Use as a Diagnostic Positron Emission Tomography Radiotracer in Bacterial Infection.

Authors:  Megan N Stewart; Matthew F L Parker; Salma Jivan; Justin M Luu; Tony L Huynh; Brailee Schulte; Youngho Seo; Joseph E Blecha; Javier E Villanueva-Meyer; Robert R Flavell; Henry F VanBrocklin; Michael A Ohliger; Oren Rosenberg; David M Wilson
Journal:  ACS Infect Dis       Date:  2019-11-21       Impact factor: 5.084

4.  Crystallization and characterization of the L-arabinose-binding protein of Escherichia coli B-r.

Authors:  R G Parsons; R W Hogg
Journal:  J Biol Chem       Date:  1974-06-10       Impact factor: 5.157

5.  D-arabinose metabolism in Escherichia coli B: induction and cotransductional mapping of the L-fucose-D-arabinose pathway enzymes.

Authors:  E A Elsinghorst; R P Mortlock
Journal:  J Bacteriol       Date:  1988-12       Impact factor: 3.490

6.  Escherichia coli from urine of female patients with urinary tract infections is competent for intracellular bacterial community formation.

Authors:  Corinne K Garofalo; Thomas M Hooton; Steven M Martin; Walter E Stamm; Joseph J Palermo; Jeffrey I Gordon; Scott J Hultgren
Journal:  Infect Immun       Date:  2006-10-30       Impact factor: 3.441

7.  Comparison of the periplasmic receptors for L-arabinose, D-glucose/D-galactose, and D-ribose. Structural and Functional Similarity.

Authors:  N K Vyas; M N Vyas; F A Quiocho
Journal:  J Biol Chem       Date:  1991-03-15       Impact factor: 5.157

8.  Synthesis of putative chain terminators of mycobacterial arabinan biosynthesis.

Authors:  Iain A Smellie; Sanjib Bhakta; Edith Sim; Antony J Fairbanks
Journal:  Org Biomol Chem       Date:  2007-06-08       Impact factor: 3.876

9.  Staphylococcus aureus-associated skin and soft tissue infections in ambulatory care.

Authors:  Linda F McCaig; L Clifford McDonald; Sanjay Mandal; Daniel B Jernigan
Journal:  Emerg Infect Dis       Date:  2006-11       Impact factor: 6.883

10.  Investigation of 6-[¹⁸F]-fluoromaltose as a novel PET tracer for imaging bacterial infection.

Authors:  Gayatri Gowrishankar; Mohammad Namavari; Erwan Benjamin Jouannot; Aileen Hoehne; Robert Reeves; Jonathan Hardy; Sanjiv Sam Gambhir
Journal:  PLoS One       Date:  2014-09-22       Impact factor: 3.240

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  1 in total

Review 1.  Small Molecule Sensors Targeting the Bacterial Cell Wall.

Authors:  Matthew F L Parker; Robert R Flavell; Justin M Luu; Oren S Rosenberg; Michael A Ohliger; David M Wilson
Journal:  ACS Infect Dis       Date:  2020-06-09       Impact factor: 5.084

  1 in total

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