Carbon‐11 labelling of an <i>N</i>‐sulfonylamino acid derivative: a potential tracer for MMP‐2 and MMP‐9 imaging

Kühnast, Bertrand; Bodenstein, Claudia; Wester, Hans; Weber, Walter M.

doi:10.1002/jlcr.695

Cited by 19 publications

(25 citation statements)

References 38 publications

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“…(17)). In vivo evaluation in mice demonstrated favorable pharmacokinetics for monitoring MMP-2 and MMP-9 activity and stability towards enzymatic degradation within the first 30 minutes after injection [101].…”

Section: The Matrix Metalloproteinase Enzymesmentioning

confidence: 99%

“…MMPs, particularly of MMP-2 and MMP-9, also called gelatinases, have been implicated as potential targets for therapeutic intervention in cancer and for imaging malignant tumors [101]. PET tracers that can provide noninvasive imaging of MMP activity in cancer may be useful in monitoring the therapeutic efficacy of MMP inhibitors, as well as identifying patients that will likely benefit the most from this type of chemotherapy.…”

Section: The Matrix Metalloproteinase Enzymesmentioning

confidence: 99%

“…(2R)-3-methyl-2-[[4-[(4-methoxybenzoyl]amino]-benzenesulfonyl]amino] butanoic acid was radiosynthesized by O-[ 11 C]methylation with [ 11 C]CH 3 I in a radiochemical yield of 50 -60% and specific activity ranging from 11 -26 GBq/μmol (EOB) [101] (Fig. (17)).…”

Section: The Matrix Metalloproteinase Enzymesmentioning

confidence: 99%

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C-11 Radiochemistry in Cancer Imaging Applications

Mach

2010

CTMC

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Carbon-11 (C-11) radiotracers are widely used for the early diagnosis of cancer, monitoring therapeutic response to cancer treatment, and pharmacokinetic investigations of anticancer drugs. PET imaging permits non-invasive monitoring of metabolic processes and molecular targets, while carbon-11 radiotracers allow a "hot-for cold" substitution of biologically active molecules. Advances in organic synthetic chemistry and radiochemistry as well as improved automated techniques for radiosynthesis have encouraged investigators in developing carbon-11 tracers for use in oncology imaging studies. The short half-life of carbon-11 (20.38 minutes) creates special challenges for the synthesis of C-11 labeled tracers; these include the challenges of synthesizing C-11 target compounds with high radiochemical yield, high radiochemical purity and high specific activity in a short time and on a very small scale. The optimization of conditions for making a carbon-11 tracer include the late introduction of the C-11 isotope, the rapid formation and purification of the target compound, and the use of automated systems to afford a high yield of the target compound in a short time. In this review paper, we first briefly introduce some basic principles of PET imaging of cancer; we then discuss principles of carbon-11 radiochemistry, focus on specific advances in radiochemistry, and describe the synthesis of C-11 radiopharmaceuticals developed for cancer imaging. The carbon-11 radiochemistry approaches described include the N,O, and S-alkylations of [(11)C]methyl iodide/[(11)C]methyl triflate and analogues of [(11)C]methyl iodide and their applications for making carbon-11 tracers; we then address recent advances in exploring a transmetallic complex mediated [(11)C]carbonyl reaction for oncologic targets.

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Section: The Matrix Metalloproteinase Enzymesmentioning

confidence: 99%

Section: The Matrix Metalloproteinase Enzymesmentioning

confidence: 99%

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C-11 Radiochemistry in Cancer Imaging Applications

Mach

2010

CTMC

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“…Derivative 17 was tested in in vitro gelatin degradation assays and showed IC 50 -values in the nanomolar range (MMP-2: 110 nM; MMP-9: 200 nM). Furthermore, no metabolites of inhibitor 17 were detected in serum stability studies in normal mice, but to date in vivo data of compound 17 in animal models with elevated MMP levels are lacking [129].…”

Section: Radiolabelled Mmpis: Synthesis In Vitro and In Vivo Evaluationmentioning

confidence: 99%

Molecular Imaging of Matrix Metalloproteinases In Vivo Using Small Molecule Inhibitors for SPECT and PET

Wagner

Breyholz²,

Faust³

et al. 2006

CMC

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Matrix metalloproteinases (MMPs) are a family of zinc- and calcium-dependent secreted or membrane anchored endopeptidases. MMPs are involved in many physiological processes but also take part in the pathophysiological mechanisms responsible for a wide range of diseases. Pathological expression and activation of MMPs are associated with cancer, atherosclerosis, stroke, arthritis, periodontal disease, multiple sclerosis and liver fibrosis. Thus, noninvasive visualisation and quantification of MMP activity in vivo are of great interest in basic research and clinical application. This can be achieved by scintigraphic molecular imaging techniques such as single photon emission computed tomography (SPECT) and positron emission tomography (PET) provided suitable radiolabelled tracers exist, e.g. radioactive inhibitors of matrix metalloproteinases (MMPIs). The approach to monitor MMP activity in vivo using radiolabelled small molecule inhibitors suitable for SPECT and PET is summarised in this review. Briefly, latest advances in scintigraphic imaging are introduced and followed by a report about the enzyme class of MMPs. The involvement of MMPs in cancer and atherosclerosis is exemplified and small molecule MMPIs are classified. Subsequently, the development of radiolabelled small molecule MMPIs, their synthesis and in vitro and in vivo evaluation is reviewed. Finally, an outlook on the clinical potential of labelled MMPIs in diagnostic algorithms is given.

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“…This overexpression of MMPs in tumors provides a target for medical imaging techniques such as single photon emission computed tomography (SPECT) imaging of tumors [8]. Gelatinase inhibitor analogues, labelled with the gamma-emitting radionuclide iodine-123, may enable non-invasive monitoring of cancer MMP levels, diagnosis of primary and secondary tumors, and tumor response to MMP inhibitor therapy using SPECT [24,25].…”

Section: Introductionmentioning

confidence: 99%

New radioiodinated carboxylic and hydroxamic matrix metalloproteinase inhibitor tracers as potential tumor imaging agents

Oltenfreiter

Staelens

Lejeune

et al. 2004

Nuclear Medicine and Biology

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Several studies have demonstrated a positive correlation between tumor progression and expression of extracellular proteinases such as matrix metalloproteinases (MMPs). MMP-2 and MMP-9 have become attractive targets for cancer research because of their increased expression in human malignant tumor tissues of various organs, providing a target for medical imaging techniques. Radioiodinated carboxylic and hydroxamic MMP inhibitors 2-(4'-[ (11) were synthesized by electrophilic aromatic substitution of the tributylstannyl derivatives and resulted in radiochemical yields of 60% ± 5% (n = 3) and 70% ± 5% (n = 6), respectively. In vitro zymography and enzyme assays showed high inhibition capacities of the inhibitors on gelatinases. In vivo biodistribution showed no long-term accumulation in organs and the possibility to accumulate in the tumor. These results warrant further studies of radioiodinated carboxylic and hydroxamic MMP inhibitor tracers as potential SPECT tumor imaging agents.

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Carbon‐11 labelling of an N‐sulfonylamino acid derivative: a potential tracer for MMP‐2 and MMP‐9 imaging

Cited by 19 publications

References 38 publications

C-11 Radiochemistry in Cancer Imaging Applications

C-11 Radiochemistry in Cancer Imaging Applications

Molecular Imaging of Matrix Metalloproteinases In Vivo Using Small Molecule Inhibitors for SPECT and PET

New radioiodinated carboxylic and hydroxamic matrix metalloproteinase inhibitor tracers as potential tumor imaging agents

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