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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.

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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 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

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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.

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

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