Imaging procedures such as 1-(2-[18F]FLUOROETHYL)-L-Tryptophan PET/CT in patients with cancers may help doctors assess a patient's response to treatment and help plan the best treatment in the future. The purpose is to see if there can be a better differentiation of tumor and non-tumor tissue where the tumor tissue has a higher uptake of Tryptophan.

Start Date29 Sep 2022

Sponsor / Collaborator

Barbara Ann Karmanos Cancer Institute

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100 Clinical Results associated with 1-(2-[18F]FLUOROETHYL)-L-Tryptophan

100 Translational Medicine associated with 1-(2-[18F]FLUOROETHYL)-L-Tryptophan

100 Patents (Medical) associated with 1-(2-[18F]FLUOROETHYL)-L-Tryptophan

Literatures (Medical) associated with 1-(2-[18F]FLUOROETHYL)-L-Tryptophan

12 Mar 2015·ACS Medicinal Chemistry LettersQ3 · MEDICINE

N¹-Fluoroalkyltryptophan Analogues: Synthesis and in vitro Study as Potential Substrates for Indoleamine 2,3-Dioxygenase

Q3 · MEDICINE

Article

Author: Laurent, Sophie ; Zervosen, Astrid ; Lemaire, Christian ; Henrottin, Jean ; Goldman, Serge ; Van den Eynde, Benoit ; Plenevaux, Alain ; Sapunaric, Frédéric ; Luxen, André

Indoleamine 2,3-dioxygenase (hIDO) is an enzyme that catalyzes the oxidative cleavage of the indole ring of l-tryptophan through the kynurenine pathway, thereby exerting immunosuppressive properties in inflammatory and tumoral tissues. The syntheses of 1-(2-fluoroethyl)-tryptophan (1-FETrp) and 1-((1-(2-fluoroethyl)-1H-1,2,3-triazol-4-yl)methyl)-tryptophan, two N (1)-fluoroalkylated tryptophan derivatives, are described here. In vitro enzymatic assays with these two new potential substrates of hIDO show that 1-FETrp is a good and specific substrate of hIDO. Therefore, its radioactive isotopomer, 1-[(18)F]FETrp, should be a molecule of choice to visualize tumoral and inflammatory tissues and/or to validate new potential inhibitors.

01 Feb 2010·Applied Radiation and Isotopes

Synthesis and evaluation of l-5-(2-[18F]fluoroethoxy)tryptophan as a new PET tracer

Article

Author: Wu, Shih-Chen ; Wang, Shih-Chen ; Huo, Li ; Li, Ruifen ; Dang, Yonghong ; Fu, Zhe

A convenient remote controlled synthesis of a new tryptophan analog, l-5-(2-[(18)F] fluoroethoxy)-tryptophan (5-(18)FEHTP) was described. The radiochemical yield within 65min was about 12-16% without decay correction, the radiochemical purity was over 98%, and 5-(18)FEHTP dissolved in saline was stable over 6h at room temperature. The biodistribution of 5-(18)FEHTP in mice and the high uptake of 5-(18)FEHTP in tumor demonstrated that it is very likely a new PET tracer for tumor imaging.

01 May 2008·Nuclear Medicine and BiologyQ4 · MEDICINE

Method for stabilizing non carrier added 2-[18F]fluoromethyl-l-phenylalanine, a new tumour tracer, during radiosynthesis and radiopharmaceutical formulation

Q4 · MEDICINE

Article

Author: Kersemans, Ken ; Bauwens, Matthias ; Mertens, John

INTRODUCTIONNon carrier added (NCA) 2-[(18)F]fluoromethyl-l-phenylalanine is currently used in a Phase I study. Improvement of the stability of the fluorobenzyl analogue, very sensitive to defluorination and hydrolysis, during the synthetic route and in the radiopharmaceutical formulation was devised.METHODSThe protected brominated precursor was synthesised in three steps. The labelling with [(18)F(-)] occurred in acetonitrile using K(2)CO(3)/K(2.2.2) (120 degrees C, 5 min). NCA 3-(2-[(18)F(-)]Fluoromethyl-phenyl)-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester recovered from HPLC was submitted to deprotection in TFA/CH(2)Cl(2) in the presence of CaCl(2). After evaporation and adsorption on a mini C18 column, the tracer was recovered in 4 ml of H(2)O. Appropriate amounts of CaCl(2) and NaCl solutions were added for isotonic formulation, and this solution was sterilised by a 0.2-microm Cathivex filter. Shelf-life stability in the presence of Ca(2+) and Mg(2+) ions was studied. Stereoisomeric purity was checked by chiral HPLC.RESULTSThe labelling showed a reproducible labelling yield of at least 90%. The followed strategy and the presence of Ca(2+) ions during deprotection, minimizing the loss of [(18)F(-)] from the labile fluorobenzyl group, allowed to obtain a decay-corrected yield of 75%. No racemisation was observed. The radiopharmaceutical formulation containing 0.04 M CaCl(2) allows a shelf-life of about 6 h without significant radiodefluorination.CONCLUSIONThe described synthetic route yields 40% of radiochemical pure NCA 2-[(18)F]fluoromethyl-l-phenylalanine within 105 min. A solution was found to reduce considerably the radiodefluorination. Addition of CaCl(2) prior to deprotection limits the loss of radiofluoride to less than 10%. The calcium ions present in the final radiopharmaceutical formulation (0.04 M) assure a shelf-life of at least 6 h.

100 Deals associated with 1-(2-[18F]FLUOROETHYL)-L-Tryptophan

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Indication	Highest Phase	Country/Location	Organization	Date
Brain metastases	Phase 1	US	Barbara Ann Karmanos Cancer Institute	29 Sep 2022
Breast Cancer	Phase 1	US	Barbara Ann Karmanos Cancer Institute	29 Sep 2022
Glioma	Phase 1	US	Barbara Ann Karmanos Cancer Institute	29 Sep 2022
Neuroendocrine Tumors	Phase 1	US	Barbara Ann Karmanos Cancer Institute	29 Sep 2022
Rectal Cancer	Phase 1	US	Barbara Ann Karmanos Cancer Institute	29 Sep 2022

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