Synthesis and evaluation of 68Ga-labeled imidazothiadiazole sulfonamide derivatives for PET imaging of carbonic anhydrase-IX

Nakashima, Kazuma; Iikuni, Shimpei; Okada, Yuya; Watanabe, Hiroyuki; Shimizu, Yoichi; Nakamoto, Yuji; Ono, Masahiro

doi:10.1016/j.nucmedbio.2020.11.008

Cited by 7 publications

(5 citation statements)

References 20 publications

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“…Recent studies have explored these compounds in PET by labeling them with Gallium 68 ([ 68 Ga]-US2) or fluorine 18 without directly correlating them to tumor hypoxia ( 157 , 158 ). Very recently, Nakashima et al also confirmed that [ 68 Ga]-labeled imidazothiadazole sulfonamide derivatives can assist in the visualization of hypoxic tumor tissue 2 h after intravenous injection ( 159 ).…”

Section: Medical Imagingmentioning

confidence: 96%

Advances in PET and MRI imaging of tumor hypoxia

et al. 2023

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Tumor hypoxia is a complex and evolving phenomenon both in time and space. Molecular imaging allows to approach these variations, but the tracers used have their own limitations. PET imaging has the disadvantage of low resolution and must take into account molecular biodistribution, but has the advantage of high targeting accuracy. The relationship between the signal in MRI imaging and oxygen is complex but hopefully it would lead to the detection of truly oxygen-depleted tissue. Different ways of imaging hypoxia are discussed in this review, with nuclear medicine tracers such as [18F]-FMISO, [18F]-FAZA, or [64Cu]-ATSM but also with MRI techniques such as perfusion imaging, diffusion MRI or oxygen-enhanced MRI. Hypoxia is a pejorative factor regarding aggressiveness, tumor dissemination and resistance to treatments. Therefore, having accurate tools is particularly important.

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Section: Medical Imagingmentioning

confidence: 96%

Advances in PET and MRI imaging of tumor hypoxia

et al. 2023

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“…An in vitro stability assay of [ 111 In]In-ADCS in murine plasma was performed according to our previously reported method [22]. To fresh murine plasma (200 μL) was added a solution of [ 111 In]In-ADCS (740 kBq, 50 μL in PBS).…”

Section: In Vitro Stability Assay In Murine Plasmamentioning

confidence: 99%

Synthesis and Evaluation of a Cathepsin B–Recognizing Trifunctional Chelating Agent to Improve Tumor Retention of Radioimmunoconjugates

Jinda,

Nakashima,

Watanabe

et al. 2024

Labelled Comp Radiopharmac

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Cathepsin B (CTSB) is a lysosomal protease that is overexpressed in tumor cells. Radioimmunoconjugates (RICs) composed of CTSB‐recognizing chelating agents are expected to increase the molecular weights of their radiometabolites by forming conjugates with CTSB in cells, resulting in their improved retention in tumor cells. We designed a novel CTSB‐recognizing trifunctional chelating agent, azide‐[111In]In‐DOTA‐CTSB‐substrate ([111In]In‐ADCS), to synthesize a RIC, trastuzumab‐[111In]In‐ADCS ([111In]In‐TADCS), and evaluated its utility to improve tumor retention of the RIC. [111In]In‐ADCS and [111In]In‐TADCS were synthesized with satisfactory yield and purity. [111In]In‐ADCS was markedly stable in murine plasma until 96 h postincubation. [111In]In‐ADCS showed binding to CTSB in vitro, and the conjugation was blocked by the addition of CTSB inhibitor. In the internalization assay, [111In]In‐TADCS exhibited high‐level retention in SK‐OV‐3 cells, indicating the in vitro utility of the CTSB‐recognizing unit. In the biodistribution assay, [111In]In‐TADCS showed high‐level tumor accumulation, but the retention was hardly improved. In the first attempt to combine a CTSB‐recognizing unit and RIC, these findings show the fundamental properties of the CTSB‐recognizing trifunctional chelating agent to improve tumor retention of RICs.

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“…Interestingly, radioactivity in the HT-29 tumor gradually increased with time and reached 8.71% injected dose/g at 24 h post injection and SPECT with 15 clearly and selectively visualized the HT-29 tumors in the living model mice [ 81 ]. The same authors, one year later, have replaced the radiometal 111 In with 67 Ga ( 43a ) and 68 Ga ( 43b ) which has a much longer decay half-life (3.26 d) and can be utilized more easily than 67 Ga (68 min) [ 84 ]. The obtained radiotracers 43a – b ( Scheme 11 ) showed similar radiochemical yield and purity than the previously one as well as the high radiolabelling in HT-29 cell line with respect to MDA-MB-231.…”

Section: Five-membered Heterocyclic Sulfonamidesmentioning

confidence: 99%

“…Indeed, changing the radiometal ( 111 In to 67 Ga) did not affect its affinity. However, in vivo biodistribution assay was observed a less tumor uptake of 67 Ga-derivative 16a compared to indium derivative ( 42 ) [ 84 ]. Finally, the Ono group’ reported an imidazothiadiazole sulfonamide derivative labelled with 99m Tc, the main isotope used in clinical practice, without DOTA instead the chelator agent hydroxamamide moiety ( 45 , Scheme 11 ) [ 85 ].…”

Section: Five-membered Heterocyclic Sulfonamidesmentioning

confidence: 99%

Five-Membered Heterocyclic Sulfonamides as Carbonic Anhydrase Inhibitors

2023

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The development of heterocyclic derivatives has progressed considerably over the past decades, and many new carbonic anhydrase inhibitors (CAIs) fall into this field. In particular, five-membered heterocyclic sulfonamides have been generally shown to be more effective inhibitors compared to six-membered rings ones. Despite the importance of oxygen and nitrogen five-membered heterocyclic aromatic rings in medicinal chemistry, the installation of sulfonamide moiety on such heterocycles has not received much attention. On the other hand, 1,3,4-thiadiazole/thiadiazoline ring-bearing sulfonamides are the scaffolds which have been widely used in a variety of pharmaceutically important CAIs such as acetazolamide, metazolamide and their many derivatives obtained by using the tail approach. Here, we reviewed the field focusing on the diverse biological activities of these CAIs, such as antiglaucoma, antiepileptic, antitumor and antiinfective properties. This review highlights developments involving five-membered heterocyclic sulfonamides over the last years, with a focus on their pharmacological/clinical applications.

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Synthesis and evaluation of 68Ga-labeled imidazothiadiazole sulfonamide derivatives for PET imaging of carbonic anhydrase-IX

Cited by 7 publications

References 20 publications

Advances in PET and MRI imaging of tumor hypoxia

Advances in PET and MRI imaging of tumor hypoxia

Synthesis and Evaluation of a Cathepsin B–Recognizing Trifunctional Chelating Agent to Improve Tumor Retention of Radioimmunoconjugates

Five-Membered Heterocyclic Sulfonamides as Carbonic Anhydrase Inhibitors

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