Published November 15, 2019 | Version v1
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Valorization of sultones and boratranes as versatile platforms for radiolabeling of fluorine-18: application for the development of radiotracers for hypoxia PET imaging

Creators

Description

This work focused on the development of versatile platforms for fluorine-18 labelling. The first platform contained a sultone moiety which was converted to [18F]fluorosulfonate by ring opening with [18F]fluoride. The sultone was coupled to 2-nitroimidazolyl ligands to obtain radiotracers for hypoxia PET imaging. A series of compounds were synthesized in order to compare their performance in PET imaging. Among them, [18F]FLUSONIM displayed high tumor/background ratios after a short delay post-injection on different animal models (rhabdomyosarcoma, glioblastoma and melanoma). The second platform was based on a boratrane structure, that was able to capture [18F]fluoride in aqueous medium to form zwitterionic [18F]mono-fluoroborate. (author)

Abstract (French)

Les travaux de these ont porte sur le developpement de deux plateformes de radiomarquage polyvalentes pour faciliter l'incorporation du fluor-18, un isotope de choix pour l'imagerie TEP (Tomographie par Emission de Positons). La premiere plateforme comporte une structure sultone conduisant a un [18F]fluorosulfonate par ouverture du cycle avec le [18F]fluorure. Celle-ci a ete valorisee par le couplage avec des ligands 2-nitroimidazoliques pour former un agent d'imagerie TEP specifique de l'hypoxie. Une serie de derives caracterises par des proprietes d'hydrophilie differentes a ete synthetisee afin de comparer leur efficacite en imagerie. Parmi ces derives, le [18F]FLUSONIM a revele dans differents modeles precliniques tumoraux (rhabdomyosarcome, tumeurs cerebrales et melanome) des ratios tumeur sur bruit de fond inegales jusqu'a present, et ce a des temps tres precoces post-injection. La deuxieme plateforme est de nature boratrane. Celle-ci est capable de reagir avec le [18F]fluorure en milieu physiologique pour former un [18F]monofluoroborate zwitterionique facile a separer du precurseur boratrane. (auteur)

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Additional details

Additional titles

Original title (French)
Valorisation des sultones et boratranes comme plateformes de radiomarquage au fluor-18. Application au developpement de radiotraceurs pour l'imagerie de l'hypoxie par Tomographie par Emission de Positons

Publishing Information

Imprint Pagination
253 p.
Report number
FRNC-TH--15758

INIS

Country of Publication
France
Country of Input or Organization
France
INIS RN
55054133
Subject category
S38: RADIATION CHEMISTRY, RADIOCHEMISTRY AND NUCLEAR CHEMISTRY; S62: RADIOLOGY AND NUCLEAR MEDICINE;
Resource subtype / Literary indicator
Thesis
Descriptors DEI
FLUORIDES; FLUOROBORATES; GLIOMAS; MELANOMAS; POSITRON COMPUTED TOMOGRAPHY; RADIOCHEMISTRY; RHABDOMYOSARCOMAS; TRACER TECHNIQUES; ZWITTERIONIC COMPOUNDS
Descriptors DEC
BORON COMPOUNDS; CARCINOMAS; CHEMISTRY; COMPUTERIZED TOMOGRAPHY; DIAGNOSTIC TECHNIQUES; DISEASES; EMISSION COMPUTED TOMOGRAPHY; EPITHELIOMAS; FLUORINE COMPOUNDS; HALIDES; HALOGEN COMPOUNDS; ISOTOPE APPLICATIONS; MYOSARCOMAS; NEOPLASMS; NERVOUS SYSTEM DISEASES; POLAR COMPOUNDS; SARCOMAS; TOMOGRAPHY

Optional Information

Notes
340 refs.; Available from the INIS Liaison Officer for France, see the INIS website for current contact and E-mail addresses