Crown ether functionalized texaphyrin monomers and dimers

Preihs, Christian; Magda, Darren; Sessler, Jonathan L.

doi:10.1142/s108842461100315x

Cited by 5 publications

(1 citation statement)

References 23 publications

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“…The modification of the porphyrin core by enlargement (texaphyrins) and shrinkage (corroles) has been explored by Sessler's and Gross's groups, respectively (fig. 2) [46,47,48,49,50,51,52,53,54]. Mahammed and Gross [51] have shown that metal complexes of ‘shrinked’ porphyrins – metallocorroles – due to their enhanced stability in a higher +4 oxidation state than that of porphyrins possess a fair catalase-like in addition to SOD-like activity [46].…”

Section: Design Of Mn Porphyrin-based Redox Regulatorsmentioning

confidence: 99%

Design, Mechanism of Action, Bioavailability and Therapeutic Effects of Mn Porphyrin-Based Redox Modulators

Sheng²,

et al. 2012

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Based on aqueous redox chemistry and simple in vivo models of oxidative stress, Escherichia coli and Saccharomyces cerevisiae, the cationic Mn(III) N-substituted pyridylporphyrins (MnPs) have been identified as the most potent cellular redox modulators within the porphyrin class of drugs; their efficacy in animal models of diseases that have oxidative stress in common is based on their high ability to catalytically remove superoxide, peroxynitrite, carbonate anion radical, hypochlorite, nitric oxide, lipid peroxyl and alkoxyl radicals, thus suppressing the primary oxidative event. While doing so MnPs could couple with cellular reductants and redox-active proteins. Reactive species are widely accepted as regulators of cellular transcriptional activity: minute, nanomolar levels are essential for normal cell function, while submicromolar or micromolar levels impose oxidative stress, which is evidenced in increased inflammatory and immune responses. By removing reactive species, MnPs affect redox-based cellular transcriptional activity and consequently secondary oxidative stress, and in turn inflammatory processes. The equal ability to reduce and oxidize superoxide during the dismutation process and recently accumulated results suggest that pro-oxidative actions of MnPs may also contribute to their therapeutic effects. All our data identify the superoxide dismutase-like activity, estimated by log k_cat(O₂^–), as a good measure for the therapeutic efficacy of MnPs. Their accumulation in mitochondria and their ability to cross the blood-brain barrier contribute to their remarkable efficacy. We summarize herein the therapeutic effects of MnPs in cancer, central nervous system injuries, diabetes, their radioprotective action and potential for imaging. Few of the most potent modulators of cellular redox-based pathways, MnTE2-PyP⁵⁺, MnTDE-2-ImP⁵⁺, MnTnHex-2-PyP⁵⁺ and MnTnBuOE-2-PyP⁵⁺, are under preclinical and clinical development.

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Section: Design Of Mn Porphyrin-based Redox Regulatorsmentioning

confidence: 99%

Design, Mechanism of Action, Bioavailability and Therapeutic Effects of Mn Porphyrin-Based Redox Modulators

Sheng²,

et al. 2012

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A Highly Effective Strategy for Encapsulating Potassium Cations in Small Crown Ether Rings on a Dinuclear Palladium Complex

Lucio‐Martínez

Bermúdez

Ortigueira

et al. 2017

Chemistry A European J

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The potential of 15-crown-5 ethers to link large cations, such as potassium, is limited by the quasi-parallel arrangement of two oxygen donor moieties upon appropriate orientation of the corresponding ether-ring-containing molecules. Substrates bearing the two crown ethers that are capable of achieving such coordination are hitherto unknown. The synthesis and isolation of a tailor-made dinuclear palladacycle bearing 15-crown-5 ether rings on the metallated phenyls offers such a possibility, providing the adequate environment for the formation of the sandwiched [K(metallacycle-15-crown-5) ] moiety. This synthetic strategy also culminates in the isolation of the first palladacycle able to entrap a potassium cation through bonding to two 15-crown-5 ether rings in a single molecule.

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From Chemical Serendipity to Translational Chemistry: New Findings in the Reactivity of Palladacycles

et al. 2018

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In the world of science, in particular the section concerning the field of chemistry, when the results encountered during the experiment do not meet our expectations, our shrewdness may play an important role to open up new unexplored fields that could be much more interesting than what we were seeking. In those cases, our research undergoes an unforeseen shift, delivering novel and challenging results that may altogether alter our point of view and our future work. We have then struck serendipity. Specifically, in our investigation linked to palladacycles we have found that the new trends in their reactivity, as well as in their structure, have been, in many cases, related to this experience, broadening our research scope within this field. Herein, we describe our most relevant findings, which have shed new light upon the reactivity of palladacycles, thus opening new routes that lead to novel unexpected structures.

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Crown ether functionalized texaphyrin monomers and dimers

Cited by 5 publications

References 23 publications

Design, Mechanism of Action, Bioavailability and Therapeutic Effects of Mn Porphyrin-Based Redox Modulators

Design, Mechanism of Action, Bioavailability and Therapeutic Effects of Mn Porphyrin-Based Redox Modulators

A Highly Effective Strategy for Encapsulating Potassium Cations in Small Crown Ether Rings on a Dinuclear Palladium Complex

From Chemical Serendipity to Translational Chemistry: New Findings in the Reactivity of Palladacycles

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