- Biocatalyzed synthesis of both enantiopure fluoromisonidazole antipodes
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Fluoromisonidazole (FMISO or F-MISO) is a radiotracer for positron emission tomography when 18F-labeled and is administrated in its racemic form. Herein, a straightforward synthesis of both enantiopure antipodes is proposed through a one-pot two-step microwave protocol to obtain a fluorinated ketone precursor followed by bioreduction using alcohol dehydrogenases from Rhodococcus ruber (ADH-A) or Lactobacillus brevis (LBADH).
- Borz?cka, Wioleta,Lavandera, Iván,Gotor, Vicente
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Read Online
- Probes for Imaging of Hypoxia
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Exemplary probes for detecting hypoxic cells and tissue have the structure of
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Paragraph 0074
(2016/06/28)
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- Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof
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The invention features a class of 2-nitroimidazole compounds with a secondary basic nitrogen atom and a linker bearing one or more therapeutic agents, cytotoxic agents, detectable labels, or chelating groups. In particular, the invention provides 2-nitroimidazole compounds containing a cluster of boron atoms for use in boron neutron capture therapy (BNCT). The 2-nitroimidazole compounds can be used to treat hypoxic conditions, including, e.g., cancer, inflammation, and ischemia. The weakly basic 2-nitroimidazole compounds target to hypoxic tissue and provide increased tissue concentration overall.
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Page/Page column 17
(2008/06/13)
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- Weakly basic 2-nitroimidazoles for the non-invasive detection of tissue hypoxia
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The present invention incorporates weakly basic substituents (pKa about 8 or greater) such as pyrrolidine, piperidine, piperazine and azapane moieties in halogenated 2-nitromidazoles as a major improvement over prior art for the non-invasive detection of cellular hypoxia in normal and malignant tissues. The invention features the use of [18F] positron emission tomography, [19F] magnetic resonance spectroscopy, and [19F] magnetic resonance imaging. Improvements over prior art compounds are six-fold. 1) Salts of weakly basic reagents are highly water-soluble which facilitates administration. 2) Unreacted reagents are rapidly cleared from systemic circulation thereby decreasing background noise. 3) Reagents with weakly basic substituents are concentrated in tissue ?3 fold above plasma levels thereby increasing binding intensity and enhancing signal detection. 4) Conjugate bases of weakly basic reagents have intermediate octanol-water partition coefficients that facilitate their penetration into all tissues including brain. 5) Cellular adducts of reagents containing weakly basic substituents are more stable than reagents of prior art. 6) Reagents with weakly basic substituents are effective for the detection of transient hypoxia in solid tissue.
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Page/Page column 12
(2008/06/13)
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