Reductively Induced Catalytic DNA Cleavage of Water Soluble RhIII-Br8TMPyP

The cationic porphyrin 5,10,15,20-tetrakis (diisopropyl-guanidine)-21H,23H-porphine (DIGPor) selectively binds to DNA containing O -methylguanine (O -MeG) and inhibits the DNA repair enzyme O -methylguanine-DNA methyltransferase (MGMT). The O -MeG selectivity and MGMT inhibitory activity of DIGPor were improved by incorporating Zn into the porphyrin. The resulting metal complex (Zn-DIGPor) potentiated the activity of the DNA-alkylating drug temozolomide in an MGMT-expressing cell line. To the best of our knowledge, this is the first example of DNA-targeted MGMT inhibition.

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DNA‐Targeted Inhibition of MGMT

Marsoner

Schmidt

Triemer

et al. 2017

ChemBioChem

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Synthesis and applications of rhodium porphyrin complexes

et al. 2018

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Organotransition metal complexes capable of forming metalloradicals have been an intriguing subject of study for the past fifty years. Of these, rhodium porphyrin complexes have proven particularly interesting due to their straightforward synthesis and unique reactivity; indeed, these complexes are responsible for some highly influential transformations of organic compounds, including rare C-H and C-C bond activations. The complexity and selectivity of rhodium porphyrins has been attractive for catalytic transformations, with specific interest in their usage for selective carbon monoxide reduction for fuel cell applications. This review will highlight historical and modern syntheses of rhodium porphyrins, as well as their respective reactions with small molecules and applications therein. The discussion will be limited to rhodium porphyrins consisting of four pyrrolic rings bridged with four methine units.

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Selective octabromination of tetraarylporphyrins based on meso-substituent identity: Structural and electrochemical studies

Commins

Hill

Matsushita

et al. 2016

J. Porphyrins Phthalocyanines

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Synthesis and isolation of selectively brominated tetraarylporphyrin derivatives is reported. Treatment with bromine of meso-5,10,15,20-tetrakis(3,4,5-trimethoxyphenyl)porphyrin (1) or meso-5,10,15,20-tetrakis(3,5-di-[Formula: see text]-butyl-4-hydroxyphenyl)porphinatocopper(II) (2-Cu) yields products octabrominated at the 2,6-positions of meso-aryl substituents [5,10,15,20-tetrakis(2,6-dibromo-3,4,5-trimethoxyphenyl)porphyrin, [Formula: see text]Br81] or macrocyclic [Formula: see text]-positions. The latter of these ([Formula: see text]-brominated) was identified as the oxoporphyrinogen 2,3,7,8,12,13,17,18-octabromo-5,10,15,20- tetrakis(3,5-di-[Formula: see text]-butyl-4-oxo-cyclohexa-2,5-dienylidene)porphyrinogen 3 obtained due to the adventitious oxidation and demetalation of 2-Cu, which could be alkylated at its macrocyclic nitrogen atoms yielding N[Formula: see text],N[Formula: see text],N[Formula: see text],N[Formula: see text]-tetrakis(4-bromobenzyl)-2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetrakis(3,5-di-[Formula: see text]-butyl-4-oxo-cyclo hexa-2,5-dienylidene)porphyrinogen 4. The former compound [Formula: see text]Br81 was complexed with Zn(II) ([Formula: see text]Br81-Zn) or Cu(II) ([Formula: see text]Br81-Cu) and could also be subjected to further bromination yielding 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetrakis(2,6-dibromo-3,4,5-trimethoxyphenyl)porphyrin, Br[Formula: see text]1. The effect on the electrochemical properties of the 2,6-bromophenyl-substituted porphyrin compounds over the more highly brominated products was assessed.

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Reductively Induced Catalytic DNA Cleavage of Water Soluble RhIII-Br8TMPyP

Cited by 3 publications

References 27 publications

DNA‐Targeted Inhibition of MGMT

DNA‐Targeted Inhibition of MGMT

Synthesis and applications of rhodium porphyrin complexes

Selective octabromination of tetraarylporphyrins based on meso-substituent identity: Structural and electrochemical studies

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