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Synthesis of a water-soluble 1,3-bis(diphenylene)-2-phenylallyl radical.

ABSTRACT: The design and synthesis of a water-soluble 1,3-bis(diphenylene)-2-phenylallyl (BDPA) radical via the conjugate addition of a derivatized fluorene nucelophile is described. The compound is designed for use in dynamic nuclear polarization NMR. Its 9 GHz EPR spectrum in glycerol/water is reported.

SUBMITTER: Dane EL

PROVIDER: S-EPMC2882179 | biostudies-literature | 2010 May

REPOSITORIES: biostudies-literature

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Synthesis of a water-soluble 1,3-bis(diphenylene)-2-phenylallyl radical.

Dane Eric L EL Swager Timothy M TM

The Journal of organic chemistry 20100501 10

The design and synthesis of a water-soluble 1,3-bis(diphenylene)-2-phenylallyl (BDPA) radical via the conjugate addition of a derivatized fluorene nucelophile is described. The compound is designed for use in dynamic nuclear polarization NMR. Its 9 GHz EPR spectrum in glycerol/water is reported. ...[more]

PMID: 20420445

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PEGylated, Water-Soluble, Stable Aminyl Radical.

Project description:We report the synthesis and kinetic study of PEGylated, water-soluble aminyl radical 2. The radical possesses four mPEG-3 groups replacing four methyl groups in the tert-butyl groups at the 3- and 6-positions of 1,3,6,8-tetra-tert-butyl carbazyl (TTBC). This structure is designed to mitigate the rapid decomposition of the radical via intramolecular 1,5-hydrogen atom transfer (1,5-HAT) that was observed in its constitutional isomer 1-H with four mPEG-3 groups in the vicinity of the nitrogen-centered radical (1- and 8-positions of TTBC). In dry, degassed acetone at 295 K, the radical 2 has a half-life, τ1/2 = 49 h (ΔH‡ = 17.9 ± 0.8 kcal mol-1), which is 3 orders of magnitude longer than that for 1-H, which decays via 1,5-HAT (τ1/2 = 48 s, ΔH‡ = 10.0 ± 0.3 kcal mol-1). Aminyl radical 2 aggregates at ambient conditions in water and has a half-life, τ1/2 = 2 h.

| S-EPMC5560026 | biostudies-literature

Synthesis and Anticancer Properties of Water-Soluble Zinc Ionophores 1

Project description:We have shown that water solubilized versions of a zinc ionophore increase intracellular concentrations of free zinc and have antiproliferative activity in exponential phase A549 lung cancer cultures. The gene expression profiles of A549 lung cancer cultures treated with the lead compound PCI-5002 reveal the activation of stress response pathways. Medium supplementation with zinc (25 μM) led to activation of additional oxidative stress response as well as apoptotic pathways. We propose that the pharmacologic delivery of zinc to tumors using water solubilized ionophores is a potential approach to cancer therapy. Keywords: Dose response

2007-02-07 | GSE6960 | GEO

Synthesis and Anticancer Properties of Water-Soluble Zinc Ionophores 2

Project description:We have demonstrated that water-soluble zinc ionophores can be administered to mice at relatively high doses and inhibit the growth of A549 lung cancer cells grown in xenograft models. Gene expression profiles of tumor specimens harvested from mice four hours after treatment confirmed that the activation of stress responsive genes occurs in vivo. These findings lead us to propose that the pharmacologic delivery of zinc to tumors using water solubilized ionophores is a potential approach to cancer therapy. Keywords: Dose response

2007-02-07 | GSE6962 | GEO

Synthesis and Anticancer Properties of Water-Soluble Zinc Ionophore: Cell Culture and Xenograft Model

Project description:This SuperSeries is composed of the SubSeries listed below.

2007-02-07 | GSE6972 | GEO

Direct free radical scavenging effects of water-soluble HMG-CoA reductase inhibitors.

Project description:3-Hydroxy-3-methylglutaryl coenzyme A reductase inhibitors, statins, are widely used for preventing cardiovascular and cerebrovascular diseases by controlling blood cholesterol level. Additionally, previous studies revealed the scavenging effects of statins on free radicals. We assessed direct scavenging activities of two water-soluble statins, fluvastatin and pravastatin, on multiple free radicals using electron spin resonance spectrometry with spin trapping method. We estimated reaction rate constants (k fv for fluvastatin, and k pv for pravastatin). Superoxide anion was scavenged by fluvastatin and pravastatin with k fv and k pv of 4.82 M-1s-1 and 49.0 M-1s-1, respectively. Scavenging effects of fluvastatin and pravastatin on hydroxyl radical were comparable; both k fv and k pv were >109 M-1s-1. Fluvastatin also eliminated tert-butyl peroxyl radical with relative k fv of 2.63 to that of CYPMPO, whereas pravastatin did not affect tert-butyl peroxyl radical. Nitric oxide was scavenged by fluvastatin and pravastatin with k fv and k pv of 68.6 M-1s-1 and 701 M-1s-1, respectively. Both fluvastatin and pravastatin had scavenging effects on superoxide anion, hydroxyl radical and nitric oxide radical. On the other hand, tert-butyl peroxyl radical was scavenged only by fluvastatin, suggesting that fluvastatin might have more potential effect than pravastatin to prevent atherosclerosis and ischemia/reperfusion injury via inhibiting oxidation of lipids.

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Ultrasound-assisted synthesis of water-soluble monosubstituted diruthenium compounds.

Project description:The elusive monosubstituted diruthenium complexes [Ru2Cl(DAniF)(O2CMe)3] (1), [Ru2Cl(DPhF)(O2CMe)3] (2), [Ru2Cl(D-p-CNPhF)(O2CMe)3] (3), [Ru2Cl(D-o-TolF)(O2CMe)3] (4), [Ru2Cl(D-m-TolF)(O2CMe)3] (5), [Ru2Cl(D-p-TolF)(O2CMe)3] (6) and [Ru2Cl(p-TolA)(O2CMe)3] (7) have been synthesized using for the first time ultrasound-assisted synthesis to carry out a substitution reaction in metal-metal bonded dinuclear compounds (DAniF- = N,N'-bis(4-anisyl)formamidinate; DPhF- = N,N'-diphenylformamidinate; D-p-CNPhF- = N,N'-bis(4-cyanophenyl)formamidinate; D-o/m/p-TolF- = N,N'-bis(2/3/4-tolyl)formamidinate; p-TolA- = N-4-tolylamidate). This is a simpler and greener method than the tedious procedures described in the literature, and it has permitted to obtain water-soluble complexes with good yields in a short period of time. A synthetic study has been implemented to find the best experimental conditions to prepare compounds 1-7. Two different types of ligands, formamidinate and amidate, have been used to check the generality of the method for the preparation of monosubstituted complexes. Five new compounds (2-6) have been obtained using a formamidinate ligand, the synthesis of the previously described compound 1 has been improved, and an unprecedented monoamidate complex has been achieved (7). The crystal structures of compounds 3 and 7 have been solved by single crystal X-ray diffraction. These compounds show the typical paddlewheel structure with three acetate ligands and one formamidinate (3) or amidate (7) bridging ligand at the equatorial positions. The axial positions are occupied by the chloride ligand giving rise to one-dimensional polymer structures that were previously unknown for monosubstituted compounds.

| S-EPMC8605285 | biostudies-literature

Facile Synthesis of Clickable, Water-soluble and Degradable Polyphosphoesters.

Project description:"Click" chemistry is a library of efficient and reliable reactions, which have been used to functionalize various classes of bio- and synthetic macromolecular systems for the incorporation of designed properties and functions. In this report, azide-alkyne Huisgen cycloaddition and thiol-yne reactions, two classical "click" chemistries, were employed to functionalize biodegradable, clickable polyphosphoester homopolymers and their water-soluble copolymers. A stable alkyne-functionalized phospholane monomer was synthesized, its organocatalyzed polymerization kinetics were evaluated, and the resulting (co)polymers were utilized to develop this facile method that provides the synthesis of clickable, water-soluble and degradable polyphosphoesters, which can be adapted for various applications.

| S-EPMC3410554 | biostudies-literature

Synthesis and anticancer properties of water-soluble zinc ionophores.

Project description:Several water-solubilized versions of the zinc ionophore 1-hydroxypyridine-2-thione (ZnHPT), synthesized as part of the present study, have been found both to increase the intracellular concentrations of free zinc and to produce an antiproliferative activity in exponential phase A549 human lung cancer cultures. Gene expression profiles of A549 cultures treated with one of these water-soluble zinc ionophores, PCI-5002, reveal the activation of stress response pathways under the control of metal-responsive transcription factor 1 (MTF-1), hypoxia-inducible transcription factor 1 (HIF-1), and heat shock transcription factors. Additional oxidative stress response and apoptotic pathways were activated in cultures grown in zinc-supplemented media. We also show that these water-soluble zinc ionophores can be given to mice at 100 micromol/kg (300 micromol/m(2)) with no observable toxicity and inhibit the growth of A549 lung and PC3 prostate cancer cells grown in xenograft models. Gene expression profiles of tumor specimens harvested from mice 4 h after treatment confirmed the in vivo activation of MTF-1-responsive genes. Overall, we propose that water-solubilized zinc ionophores represent a potential new class of anticancer agents.

| S-EPMC3033660 | biostudies-literature

Synthesis and characterization of water-soluble C60–peptide conjugates

Project description: Not available

| S-EPMC11022410 | biostudies-literature

Efficient synthesis of readily water-soluble sulfonic Acid carbamates.

Project description:A series of various readily water-soluble carbamates were synthesized with good yields. These compounds are useful chemical tracers for assessing the cooling progress in a georeservoir during geothermal power plant operation. Acylation of primary amines was carried out as well as using a solution of sodium bicarbonate and without the presence of salt. Products were characterized by 1H-NMR and 13C-NMR. Purity was confirmed through elemental analysis.

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