A 99mTc-Labelled Tetrazine for Bioorthogonal Chemistry. Synthesis and Biodistribution Studies with Small Molecule trans-Cyclooctene Derivatives

Vito, Alyssa; Alarabi, Hussain; Czorny, Shannon; Beiraghi, Omid; Kent, Jeff; Janzen, Nancy; Genady, Afaf R.; Al-Karmi, Salma; Rathmann, Stephanie; Naperstkow, Zoya; Blacker, Megan; Llano, Lisset; Berti, Paul J.; Valliant, John F.

doi:10.1371/journal.pone.0167425

Cited by 22 publications

(20 citation statements)

References 32 publications

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“…99m Tc-labelled vancomycin and 99m Tc-HYNIC-vancomycin (Scheme 2; coordination chemistry unknown) were also studied for their potential to image bacterial infections [42,43]. Vancomycin, to date the first line antibiotic treatment for methicillin-resistant S. aureus (MRSA), is a natural antibiotic that inhibits the bacterial cell wall synthesis of Gram-positive bacteria by binding to a peptidoglycan precursor and subsequent accumulation on the bacterial cell wall [44].…”

Section: Bacterial Infection Imaging Agents Based On Antibioticsmentioning

confidence: 99%

An update on radiotracer development for molecular imaging of bacterial infections

Welling

Hensbergen

Bunschoten

et al. 2019

Clin Transl Imaging

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Background Bacterial infections are still a major global healthcare problem. To combat the increasing antimicrobial resistance, early diagnosis of bacterial infections-including the identification of bacterial species-is needed to improve antibiotic stewardship and to help reduce the use of broad-spectrum antibiotics. To aid successful targeted antibiotic treatment, specific detection and localisation of infectious organisms is warranted. Nuclear medicine imaging approaches have been successfully used to diagnose bacterial infections and to differentiate between pathogen induced infections and sterile inflammatory processes. Aim In this comprehensive review we present an overview of recent developments in radiolabelled bacterial imaging tracers. Methods The PubMed/MEDLINE and Embase (OvidSP) literature databases were systematically searched for publications on SPECT and PET on specific imaging of bacterial using specific guidelines with MeSH-terms, truncations, and completion using cross-references. Tracers in literature that was extensively reviewed before 2016 were not included in this update. Where possible, the chemical structure of the radiolabelled compounds and clinical images were shown. Results In 219 original articles pre-clinical and clinical imaging of bacterial infection with new tracers were included. In our view, the highest translational potential lies with tracers that are specific to target the pathogens: e.g., 99m Tc-and 68 Galabelled UBI 29-41 , 99m Tc-vancomycin, m-[ 18 F]-fluoro-PABA, [methyl-11 C]-D-methionine, [ 18 F]-FDS, [ 18 F]-maltohexaose and [ 18 F]-maltotriose. An encouraging note is that some of these tracers have already been successfully evaluated in clinical settings. Conclusion This review summarises updates in tracer development for specific (pre-clinical and clinical) imaging of bacterial infections. We propsed some promising tracers that are likely to become innovative standards in the clinical setting in the near feature.

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Section: Bacterial Infection Imaging Agents Based On Antibioticsmentioning

confidence: 99%

An update on radiotracer development for molecular imaging of bacterial infections

Welling

Hensbergen

Bunschoten

et al. 2019

Clin Transl Imaging

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“…Vancomycin was also labeled through [ 99m Tc]Tc-HYNIC tetrazine click chemistry. A 3-fold uptake at the S. aureus infection site compared to control was found [82].…”

Section: Radiolabeled Vancomycinmentioning

confidence: 89%

New Imaging Tracers for the Infected Diabetic Foot (Nuclear and Optical Imaging)

Ankrah

Klein

Elsinga

2018

CPD

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Diabetic Foot Infections (DFIs) are associated with increased morbidity, an economic burden on patients, their families and healthcare systems and increased mortality. Early diagnosis with prompt, appropriate and adequate treatment of the infected diabetic foot is crucial. The determination of DFIs, however, may be quite perplexing and invasive. Imaging is useful in the evaluation of certain cases of DFIs, especially in suspected instances with no overt clinical features, or in the diagnosis of osteomyelitis. Nuclear medicine imaging is currently used in the evaluation of DFIs; however, like all the imaging techniques now available, it has its limitations. Several radiopharmaceuticals presently available play useful roles in the management of DFIs, while new ones are being evaluated. Optical imaging techniques have recently demonstrated promising results in the evaluation of many infections including DFIs. Using the same molecule, a tracer can be labeled with a radioisotope or an optical imaging dye. This enables infections to be evaluated both pre- and intra-operatively when surgery is required in their management. In some cases, tracers have been simultaneously labeled with both a radioisotope and an optical imaging dye to produce a hybrid tracer. These new tracers potentially provide powerful and new opportunities in the management of DFIs. In this review, we briefly examine tracers that have been used in the evaluation of the infected diabetic foot. We then explore the potential of new imaging tracers currently under development for infection that may be useful in the management of DFIs.

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“…TCO functionalized alendronate (4) was selected as the first targeting vector ( Figure 2). It binds to exposed hydroxyapatite surfaces in bone [23] and has been used in pretargeting experiments to evaluate tetrazines bearing the short-lived radioisotopes, technetium-99m, (t 1/2 = 6 h) and scandium-44 (t 1/2 = 4 h) [21][22][23][24][25][26]. The second agent was based on the mAb CC49, which targets the TAG-72 antigen in human colorectal cancer cells.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of a 68Ga-Labeled DOTA-Tetrazine as a PET Alternative to 111In-SPECT Pretargeted Imaging

et al. 2020

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The bioorthogonal reaction between a tetrazine and strained trans-cyclooctene (TCO) has garnered success in pretargeted imaging. This reaction was first validated in nuclear imaging using an 111In-labeled 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA)-linked bispyridyl tetrazine (Tz) ([111In]In-DOTA-PEG11-Tz) and a TCO functionalized CC49 antibody. Given the initial success of this Tz, it has been paired with TCO functionalized small molecules, diabodies, and affibodies for in vivo pretargeted studies. Furthermore, the single photon emission tomography (SPECT) radionuclide, 111In, has been replaced with the β-emitter, 177Lu and α-emitter, 212Pb, both yielding the opportunity for targeted radiotherapy. Despite use of the ‘universal chelator’, DOTA, there is yet to be an analogue suitable for positron emission tomography (PET) using a widely available radionuclide. Here, a 68Ga-labeled variant ([68Ga]Ga-DOTA-PEG11-Tz) was developed and evaluated using two different in vivo pretargeting systems (Aln-TCO and TCO-CC49). Small animal imaging and ex vivo biodistribution studies were performed and revealed target specific uptake of [68Ga]Ga-DOTA-PEG11-Tz in the bone (3.7 %ID/g, knee) in mice pretreated with Aln-TCO and tumor specific uptake (5.8 %ID/g) with TCO-CC49 in mice bearing LS174 xenografts. Given the results of this study, [68Ga]Ga-DOTA-PEG11-Tz can serve as an alternative to [111In]In-DOTA-PEG11-Tz.

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A 99mTc-Labelled Tetrazine for Bioorthogonal Chemistry. Synthesis and Biodistribution Studies with Small Molecule trans-Cyclooctene Derivatives

Cited by 22 publications

References 32 publications

An update on radiotracer development for molecular imaging of bacterial infections

An update on radiotracer development for molecular imaging of bacterial infections

New Imaging Tracers for the Infected Diabetic Foot (Nuclear and Optical Imaging)

Evaluation of a 68Ga-Labeled DOTA-Tetrazine as a PET Alternative to 111In-SPECT Pretargeted Imaging

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