title: Modified polysaccharides as potential (19)F magnetic resonance contrast agents.
abstract: The introduction of 3-aminobenzotrifluoride into partially oxidized alginic acid, dextran, and polygalacturonic acid (10-100 kDa) by means of the imine formation and a subsequent reduction resulted in water-soluble materials containing 1-14% of fluorine. They showed a single or split (19)F NMR signal in a narrow range of -63 to -63.5 ppm. The observed T1 and T2 were approximately 1 and 0.2 s at 400 or 500 MHz instruments, respectively. The samples showed low toxicity and uptake toward the HeLa cells similar to native polysaccharides and were preferentially localized in lysosomes. A tail intravenous injection of 5 mg of modified dextran containing 1% of fluorine revealed that the probe was not trapped in liver, spleen or kidneys, but was quickly cleared with urine. The proposed materials can be used for imaging of the gastrointestinal tract or the genitourinary system and act as a material for more complex (19)F MRI agent synthesis.
authors.affiliation: Department of Chemical Organic Technology and Petrochemistry, Faculty of Chemistry, Silesian University of Technology, Krzywoustego 4, Gliwice 44-100, Poland. Electronic address: tomasz.krawczyk@polsl.pl.
authors.forename: Tomasz
authors.initials: T
authors.lastname: Krawczyk
authors.affiliation: Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan.
authors.forename: Masafumi
authors.initials: M
authors.lastname: Minoshima
authors.affiliation: Immunology Frontier Research Center, Osaka University, Yamadaoka 3-1, Suita, Osaka 565-0871, Japan.
authors.forename: Fuminori
authors.initials: F
authors.lastname: Sugihara
authors.affiliation: Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan; Immunology Frontier Research Center, Osaka University, Yamadaoka 3-1, Suita, Osaka 565-0871, Japan.
authors.forename: Kazuya
authors.initials: K
authors.lastname: Kikuchi
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry; D000818:Animals; D002470:Cell Survival / Q000187:drug effects; D003287:Contrast Media / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D066235:Fluorine-19 Magnetic Resonance Imaging / Q000379:methods*; D006367:HeLa Cells; D006801:Humans; D008247:Lysosomes / Q000737:chemistry; D051379:Mice; D015394:Molecular Structure; D011134:Polysaccharides / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014556:Urine / Q000737:chemistry
chemical_list: D000814:Aniline Compounds; D003287:Contrast Media; D011134:Polysaccharides; C000197:3-aminobenzotrifluoride
keywords: (19)F MRI; Alginic acid; Dextran; HeLa; Polygalacturonic acid