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Peptidoglycan-Targeted [ 18 F]3,3,3-Trifluoro-d-alanine Tracer for Imaging Bacterial Infection.

التفاصيل البيبلوغرافية
العنوان: Peptidoglycan-Targeted [ 18 F]3,3,3-Trifluoro-d-alanine Tracer for Imaging Bacterial Infection.
المؤلفون: Sorlin AM; Department of Radiology, Biomedical Imaging University of California, San Francisco, San Francisco, California 94158, United States., López-Álvarez M; Department of Radiology, Biomedical Imaging University of California, San Francisco, San Francisco, California 94158, United States., Biboy J; The Centre for Bacterial Cell Biology, Newcastle University Newcastle, Newcastle upon Tyne NE2 4AX, United Kingdom., Gray J; The Centre for Bacterial Cell Biology, Newcastle University Newcastle, Newcastle upon Tyne NE2 4AX, United Kingdom., Rabbitt SJ; Department of Radiology, Biomedical Imaging University of California, San Francisco, San Francisco, California 94158, United States., Rahim JU; Department of Radiology, Biomedical Imaging University of California, San Francisco, San Francisco, California 94158, United States., Lee SH; Department of Radiology, Biomedical Imaging University of California, San Francisco, San Francisco, California 94158, United States., Bobba KN; Department of Radiology, Biomedical Imaging University of California, San Francisco, San Francisco, California 94158, United States., Blecha J; Department of Radiology, Biomedical Imaging University of California, San Francisco, San Francisco, California 94158, United States., Parker MFL; Department of Radiology, Biomedical Imaging University of California, San Francisco, San Francisco, California 94158, United States.; Department of Psychiatry, Renaissance School of Medicine at Stony Brook University, Stony Brook, New York 11794, United States., Flavell RR; Department of Radiology, Biomedical Imaging University of California, San Francisco, San Francisco, California 94158, United States.; UCSF Helen Diller Family Comprehensive Cancer Center, University of California, San Francisco, San Francisco, California 94158, United States.; Department of Pharmaceutical Chemistry, University of California, San Francisco, San Francisco, California 94158, United States., Engel J; Department of Medicine, University of California, San Francisco, San Francisco, California 94158, United States.; Department of Microbiology and Immunology, University of California, San Francisco, San Francisco, California 94158, United States., Ohliger M; Department of Radiology, Biomedical Imaging University of California, San Francisco, San Francisco, California 94158, United States.; Department of Radiology, Zuckerberg San Francisco General Hospital, San Francisco, California 94110, United States., Vollmer W; The Centre for Bacterial Cell Biology, Newcastle University Newcastle, Newcastle upon Tyne NE2 4AX, United Kingdom.; Institute for Molecular Bioscience, The University of Queensland, Brisbane 4072, Australia., Wilson DM; Department of Radiology, Biomedical Imaging University of California, San Francisco, San Francisco, California 94158, United States.
المصدر: JACS Au [JACS Au] 2024 Feb 26; Vol. 4 (3), pp. 1039-1047. Date of Electronic Publication: 2024 Feb 26 (Print Publication: 2024).
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: American Chemical Society Country of Publication: United States NLM ID: 101775714 Publication Model: eCollection Cited Medium: Internet ISSN: 2691-3704 (Electronic) Linking ISSN: 26913704 NLM ISO Abbreviation: JACS Au Subsets: PubMed not MEDLINE
أسماء مطبوعة: Original Publication: Washington, DC : American Chemical Society, [2021]-
مستخلص: Imaging is increasingly used to detect and monitor bacterial infection. Both anatomic (X-rays, computed tomography, ultrasound, and MRI) and nuclear medicine ([ 111 In]-WBC SPECT, [ 18 F]FDG PET) techniques are used in clinical practice but lack specificity for the causative microorganisms themselves. To meet this challenge, many groups have developed imaging methods that target pathogen-specific metabolism, including PET tracers integrated into the bacterial cell wall. We have previously reported the d-amino acid derived PET radiotracers d-methyl-[ 11 C]-methionine, d-[3- 11 C]-alanine, and d-[3- 11 C]-alanine-d-alanine, which showed robust bacterial accumulation in vitro and in vivo . Given the clinical importance of radionuclide half-life, in the current study, we developed [ 18 F]3,3,3-trifluoro-d-alanine (d-[ 18 F]-CF 3 -ala), a fluorine-18 labeled tracer. We tested the hypothesis that d-[ 18 F]-CF 3 -ala would be incorporated into bacterial peptidoglycan given its structural similarity to d-alanine itself. NMR analysis showed that the fluorine-19 parent amino acid d-[ 19 F]-CF 3 -ala was stable in human and mouse serum. d-[ 19 F]-CF 3 -ala was also a poor substrate for d-amino acid oxidase, the enzyme largely responsible for mammalian d-amino acid metabolism and a likely contributor to background signals using d-amino acid derived PET tracers. In addition, d-[ 19 F]-CF 3 -ala showed robust incorporation into Escherichia coli peptidoglycan, as detected by HPLC/mass spectrometry. Based on these promising results, we developed a radiosynthesis of d-[ 18 F]-CF 3 -ala via displacement of a bromo-precursor with [ 18 F]fluoride followed by chiral stationary phase HPLC. Unexpectedly, the accumulation of d-[ 18 F]-CF 3 -ala by bacteria in vitro was highest for Gram-negative pathogens in particular E. coli . In a murine model of acute bacterial infection, d-[ 18 F]-CF 3 -ala could distinguish live from heat-killed E. coli , with low background signals. These results indicate the viability of [ 18 F]-modified d-amino acids for infection imaging and indicate that improved specificity for bacterial metabolism can improve tracer performance.
Competing Interests: The authors declare no competing financial interest.
(© 2024 The Authors. Published by American Chemical Society.)
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تواريخ الأحداث: Date Created: 20240401 Latest Revision: 20240403
رمز التحديث: 20240403
مُعرف محوري في PubMed: PMC10976610
DOI: 10.1021/jacsau.3c00776
PMID: 38559735
قاعدة البيانات: MEDLINE
الوصف
تدمد:2691-3704
DOI:10.1021/jacsau.3c00776