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1.
Inorg Chem ; 59(17): 12025-12038, 2020 Sep 08.
Article in English | MEDLINE | ID: mdl-32820888

ABSTRACT

Four tris-bidentate catecholamide (CAM) ligands were synthesized, characterized, and evaluated as ligands for radiolabeling of gallium-68 for positron emission tomography (PET). Three of those ligands, 2,2-Glu-CAM, 3,3-Glu-CAM, and TREN-bisGlyGlu-CAM, incorporate ligand caps that contain a pendant carboxylic group for further conjugation to targeting moieties. The acyclic ligands all exhibited high (>80%) radiolabeling yields after short reaction times (<10 min) at room temperature, a distinct advantage over macrocyclic analogues that display slower kinetics. The stabilities of the four GaIII complexes are comparable to or higher than those of other acyclic ligands used for gallium-68 PET imaging, such as desferrioxamine, with pGa values ranging from 21 to >24, although the functionalizable ligands are less stable than the parent GaIII-TREN-CAM. In vivo imaging studies and ex vivo pharmacokinetic and biodistribution studies indicate that the parent [68Ga]Ga-TREN-CAM is stable in vivo but is rapidly cleared in <15 min, probably via a renal pathway. The rapid and mild radiolabeling conditions, high radiolabeling yields, and high stability in human serum (>95%) render TREN-bisGlyGlu-CAM a promising candidate for gallium-68 chelation.


Subject(s)
Catechols/chemistry , Gallium Radioisotopes/chemistry , Positron-Emission Tomography/methods , Animals , Drug Stability , Humans , Isotope Labeling , Kinetics , Ligands , Mice , Temperature
2.
Analyst ; 143(4): 999, 2018 02 12.
Article in English | MEDLINE | ID: mdl-29359211

ABSTRACT

Correction for 'Quantitative profiling of carbonyl metabolites directly in crude biological extracts using chemoselective tagging and nanoESI-FTMS' by Pan Deng, et al., Analyst, 2018, 143, 311-322.

3.
Biomacromolecules ; 17(4): 1253-60, 2016 Apr 11.
Article in English | MEDLINE | ID: mdl-26908114

ABSTRACT

Curcumin is known to have immense therapeutic potential but is hindered by poor solubility and rapid degradation in solution. To overcome these shortcomings, curcumin has been conjugated to chitosan through a pendant glutaric anhydride linker using amide bond coupling chemistry. The hybrid polymer has been characterized by UV-visible, fluorescence, and infrared spectroscopies as well as zeta potential measurements and SEM imaging. The conjugation reactivity was confirmed through gel permeation chromatography and quantification of unconjugated curcumin. An analogous reaction of curcumin with glucosamine, a small molecule analogue for chitosan, was performed and the purified product characterized by mass spectrometry, UV-visible, fluorescence, and infrared spectroscopies. Conjugation of curcumin to chitosan has greatly improved curcumin aqueous solubility and stability, with no significant curcumin degradation detected after one month in solution. The absorbance and fluorescence properties of curcumin are minimally perturbed (λmax shifts of 2 and 5 nm, respectively) by the conjugation reaction. This conjugation strategy required use of one out of two curcumin phenols (one of the main antioxidant functional groups) for covalent linkage to chitosan, thus temporarily attenuating its antioxidant capacity. Hydrolysis-based release of curcumin from the polymer, however, is accompanied by full restoration of curcumin's antioxidant potential. Antioxidant assays show that curcumin radical scavenging potential is reduced by 40% after conjugation, but that full antioxidant potential is restored upon hydrolytic release from chitosan. Release studies show that curcumin is released over 19 days from the polymer and maintains a concentration of 0.23 ± 0.12 µM curcumin/mg polymer/mL solution based on 1% curcumin loading on the polymer. Release studies in the presence of carbonic anhydrase, an enzyme with known phenolic esterase activity, show no significant difference from nonenzymatic release studies, implying that simple ester hydrolysis is the dominant release mechanism. Conjugation of curcumin to chitosan through a phenol ester modification provides improved stability and solubility to curcumin, with ester hydrolysis restoring the full antioxidant potential of curcumin.


Subject(s)
Antioxidants/pharmacology , Chitosan/chemistry , Curcumin/chemistry , Drug Carriers/pharmacology , Polymers/chemical synthesis , Carbonic Anhydrases/metabolism , Drug Carriers/chemical synthesis , Drug Carriers/chemistry , Glucosamine/chemistry , Mass Spectrometry , Polymers/chemistry , Spectrum Analysis
5.
Org Lett ; 16(21): 5564-7, 2014 Nov 07.
Article in English | MEDLINE | ID: mdl-25341492

ABSTRACT

A novel [2]catenane 2-C based on the tetraphenylethene (TPE) and orthogonal H-bonded cleft was successfully constructed. VT-NMR and TEM measurements demonstrate that 2-C could be self-assembled to induce an enabled aggregation-induced emission (AIE) in aqueous solution and solid state owing to its TPE unit as well as present unique acid-base controllable and reversible supramolecular self-assembled nanosuperstructures by interplay of a wide range of noncovalent interactions.


Subject(s)
Catenanes/chemistry , Macromolecular Substances/chemistry , Magnetic Resonance Spectroscopy , Molecular Structure , Spectrometry, Fluorescence
6.
Org Lett ; 15(6): 1274-7, 2013 Mar 15.
Article in English | MEDLINE | ID: mdl-23461354

ABSTRACT

A novel [2]rotaxane based on an orthogonal H-bonded motif and 3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP) with controlled topicity was successfully constructed, displaying excellent stimulated responses toward anion and solvent polarity. The preorganized host selectively recognized F(-) with high optical sensitivity and reversibility via enhanced positive cooperativity and noncovalent interaction by evidence of a shorter fluorescence lifetime.


Subject(s)
Fluorides/analysis , Pyrroles/chemical synthesis , Rotaxanes/chemistry , Fluorescence , Magnetic Resonance Spectroscopy , Molecular Structure , Pyrroles/chemistry , Rotaxanes/chemical synthesis
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