Tumor uptake study of 18F-labeled N-acetylneuraminic acids

Ishiwata, Kiichi; Ido, Tatsuo; Nakajima, Tatsuo; Ohrui, Hiroshi; Kijima‐Suda, Isao; Itoh, Masayoshi

doi:10.1016/0883-2897(90)90102-7

Cited by 8 publications

(10 citation statements)

References 14 publications

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“…2‐Deoxy‐2‐[ 18 F]fluorosugar 22 was also obtained through anhydrous HF‐mediated electrophilic addition of [ 18 F]F 2 to the glucal 1 ; it was proposed that the epimerization at C‐3 proceeded through protonation of the oxygen bonded to C‐3, followed by 3‐ O ‐acetate cleavage assisted by attack from the acyloxy group at C‐4 and formation of a dioxolenium ion 41. Electrophilic radiofluorination was also the method of choice for the preparation of N ‐acetyl‐3‐[ 18 F]fluoroneuraminic acid ([ 18 F]Neu5Ac, 23 ), by stereoselective addition of [ 18 F]acetyl hypofluorite to the 2‐deoxy‐2,3‐dehydro‐Neu5Ac derivative 44. Uptake studies with [ 18 F]Neu5Ac demonstrated its unsuitability for tumor imaging, however 44…”

Section: Labeling Of Carbohydrate With 18f and 11cmentioning

confidence: 99%

“…Electrophilic radiofluorination was also the method of choice for the preparation of N ‐acetyl‐3‐[ 18 F]fluoroneuraminic acid ([ 18 F]Neu5Ac, 23 ), by stereoselective addition of [ 18 F]acetyl hypofluorite to the 2‐deoxy‐2,3‐dehydro‐Neu5Ac derivative 44. Uptake studies with [ 18 F]Neu5Ac demonstrated its unsuitability for tumor imaging, however 44…”

Section: Labeling Of Carbohydrate With 18f and 11cmentioning

confidence: 99%

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Carbohydrate‐Based Molecules for Molecular Imaging in Nuclear Medicine

Morais¹,

Falconer

Santos³

2013

Eur J Org Chem

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This review covers published literature describing the synthesis of labeled carbohydrates for use in molecular imaging, with a particular focus on the use of nuclear techniques (PET, SPECT). Recent advances in the radiosynthesis of [18F]FDG (electrophilic vs. nucleophilic radiofluorinations), a PET radiotracer based on glucose and the most widely PET tracer currently in use for cancer and inflammatory disease diagnosis, is considered. The powerful impact of [18F]FDG in the clinic has prompted intensive research efforts into glucose‐based radiotracers for PET and SPECT imaging. These achievements are also reviewed, along with the use of glycopeptides for nuclear molecular imaging. Finally, recent work on the radionuclide labeling of nucleosides and glycoconjugates is discussed.

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Section: Labeling Of Carbohydrate With 18f and 11cmentioning

confidence: 99%

Section: Labeling Of Carbohydrate With 18f and 11cmentioning

confidence: 99%

Carbohydrate‐Based Molecules for Molecular Imaging in Nuclear Medicine

Morais¹,

Falconer

Santos³

2013

Eur J Org Chem

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“…Introducing a fluorine at C-3 of sialic acid has been reported to antagonize sialic acid biosynthesis or modify sialylation (39)(40)(41)(42)(43)(44)(45)(46)(47). Because of the strong electron-withdrawing nature, the fluorine can destabilize the formation of positive charge within the carbohydrate ring to inhibit the catalytic activity of sialidases.…”

mentioning

confidence: 99%

“…Because of the strong electron-withdrawing nature, the fluorine can destabilize the formation of positive charge within the carbohydrate ring to inhibit the catalytic activity of sialidases. 3-Fluorosialyl fluoride was used as an effective inhibitor against sialidase (40) or Trypanosoma cruzi transsialidase (TcTs) (46,47), and these works have prompted us to design an ABPP probe for sialidases by using an alkyne-hinged 3-fluorosialyl fluoride (DFSA) that is expected to form a covalent adduct with sialidases ( Fig. 1).…”

mentioning

confidence: 99%

Cell-permeable probe for identification and imaging of sialidases

Tsai

Yen

Lin

et al. 2013

Proc. Natl. Acad. Sci. U.S.A.

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Alkyne-hinged 3-fluorosialyl fluoride (DFSA) containing an alkyne group was shown to be a mechanism-based target-specific irreversible inhibitor of sialidases. The ester-protected analog DFSA (PDFSA) is a membrane-permeable precursor of DFSA designed to be used in living cells, and it was shown to form covalent adducts with virus, bacteria, and human sialidases. The fluorosialyl–enzyme adduct can be ligated with an azide-annexed biotin via click reaction and detected by the streptavidin-specific reporting signals. Liquid chromatography-mass spectrometry/mass spectrometry analysis on the tryptic peptide fragments indicates that the 3-fluorosialyl moiety modifies tyrosine residues of the sialidases. DFSA was used to demonstrate influenza infection and the diagnosis of the viral susceptibility to the anti-influenza drug oseltamivir acid, whereas PDFSA was used for in situ imaging of the changes of sialidase activity in live cells.

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“…The use of labelled Sia or CMP-Sia is restricted because of the lack of plasma membrane transporters and the negative charge of unmodified Sia that limits its cellular permeability. Uptake studies with 18 F-labelled sialic acids N -acetyl-3-[ 18 F]fluorosialic acid (3-Sia) and N -acetyl-2-deoxy-2,3-difluorosialic acid (2,3-diSia) showed inefficient uptake and unsuitability for in vivo imaging [ 33 ]. An alternative to solve this problem is the use of modified permeable Sia analogs [ 34 , 35 ] or permeable Sia precursors that can be subsequently detected by imaging probes.…”

Section: Sialic Acid Imaging In Vivomentioning

confidence: 99%

Towards In Vivo Imaging of Cancer Sialylation

Martínez-Duncker

Salinas-Marín

Martínez‐Duncker

2011

International Journal of Molecular Imaging

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In vivo assessment of tumor glucose catabolism by positron emission tomography (PET) has become a highly valued study in the medical management of cancer. Emerging technologies offer the potential to evaluate in vivo another aspect of cancer carbohydrate metabolism related to the increased anabolic use of monosaccharides like sialic acid (Sia). Sia is used for the synthesis of sialylated oligosaccharides in the cell surface that in cancer cells are overexpressed and positively associated to malignancy and worse prognosis because of their role in invasion and metastasis. This paper addresses the key points of the different strategies that have been developed to image Sia expression in vivo and the perspectives to translate it from the bench to the bedside where it would offer the clinician highly valued complementary information on cancer carbohydrate metabolism that is currently unavailable in vivo.

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Tumor uptake study of 18F-labeled N-acetylneuraminic acids

Cited by 8 publications

References 14 publications

Carbohydrate‐Based Molecules for Molecular Imaging in Nuclear Medicine

Carbohydrate‐Based Molecules for Molecular Imaging in Nuclear Medicine

Cell-permeable probe for identification and imaging of sialidases

Towards In Vivo Imaging of Cancer Sialylation

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