Spin-labeled carbohydrates

Gnewuch, Thomas; Sosnovsky, George

doi:10.1021/cr00071a005

Cited by 36 publications

(12 citation statements)

References 83 publications

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“…The degree of coupling achievable by this method is about three-fold higher or more for the insoluble polysaccharides, starch and cellulose, than for the soluble polysaccharide dextran, similar to aminocarboxylate derivatization. Other workers have labeled dextrans with nitroxides using the alkoxide ion acylation method, but the degree of substitution has been reported to be similarly low (0.5%) (21,22).…”

Section: Biodistributionmentioning

confidence: 99%

Use of Paramagnetic Chelated Metal Derivatives of Polysaccharides and Spin‐Labeled Polysaccharides as Contrast Agents in Magnetic Resonance Imaging

Bligh

Harding

Sadler

et al. 1991

Magnetic Resonance in Med

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Soluble and insoluble polysaccharides were derivatized with diethylenetriaminepentaacetic acid (DTPA) and/or spin-labeled with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO). Polysaccharides derivatized with DTPA were prepared via cyanogen bromide activation, coupling to a diamine linker, and to DTPA anhydride. Spin-labeled polysaccharides were also prepared via cyanogen bromide activation. The extent of derivatization for dextran (18 kDa) was about 120 glucose units per DTPA, and for cellulose and starch about 15-30 units per DTPA. For spin-labeled polysaccharides, the average loading ranged from 1 nitroxide per 16 glucose units for starch to 181 for dextran (82 kDa). These derivatized paramagnetic polysaccharides were shown to be more effective relaxants than the small paramagnetic molecules alone. Both soluble and insoluble polysaccharide-linker-DTPA-Gd(III) complexes were effectively cleared from the body (rats) after oral administration. After intravenous administration, the biodistribution of dextran-linker-DTPA-Gd(III) complexes differed significantly from that of GdDTPA. Reduction of the nitroxide by ascorbic acid was retarded in the polysaccharide derivatives, particularly in starch derivatized with both nitroxide and linker-DTPA-Cu(II). These agents showed contrast enhancement in the gastrointestinal tract of rabbits.

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Section: Biodistributionmentioning

confidence: 99%

Use of Paramagnetic Chelated Metal Derivatives of Polysaccharides and Spin‐Labeled Polysaccharides as Contrast Agents in Magnetic Resonance Imaging

Bligh

Harding

Sadler

et al. 1991

Magnetic Resonance in Med

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“…A large number of publications have appeared in the literature involving nitroxyl radicals as living polymerization agents, magnetic materials, therapeutic agents, radical scavengers, contrast agents and drugs, just to mention a few. [1][2][3][4][5] Indeed, they have been used as spin labelling agents for electron spin resonance (ESR) spectroscopy and contrast agents for magnetic resonance imaging (MRI). [6][7][8][9] Very recently, nitroxyl radicals have been widely used as spin probes for low-frequency in vivo ESR imaging, as contrast agents for Overhauser imaging.…”

Section: Introductionmentioning

confidence: 99%

Poly(amidoamine)s carrying TEMPO residues for NMR imaging applications

Gussoni¹,

Greco

Ferruti

et al. 2008

New J. Chem.

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“…It is well known that the 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO) free nitroxyl radical has been attached to various organic compounds (such as aldehydes, ketons, azo compounds and carboxylic and amino acids) and biomolecules (such as lipids, proteins, steroids and metalloenzymes) (Gallez et al 1992;Berliner, 1976) to yield a wide variety of TEMPO-bearing molecules named as spinlabeled compounds (Rosen et al, 1999;Gnewuch & Sosnovsky, 1986). These types of nitroxide free radicals have different applications such as magnetic resonance imaging (Likhtenstein et al, 2008), protection from oxidative stress and irradiative damage (Hahn et al, 1994), controlled 'living' freeradical polymerization (Hawker, 1997), spin trapping and spin-labeling in various fields of chemistry, biology and material sciences (Tretyakov & Ovcharenko, 2009).…”

Section: Chemical Contextmentioning

confidence: 99%