Corrole: The Little Big Porphyrinoid

Paolesse, Roberto

doi:10.1055/s-2008-1078687

Cited by 130 publications

(66 citation statements)

References 34 publications

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“…4,6,15–17 The iron complexes were then prepared following two similar procedures, referred to as Method A and Method B, which differ from each other by the amount of iron chloride in the nitration reaction medium.…”

Section: Methodsmentioning

confidence: 99%

“…1 Although these macrocycles have been studied for many decades, it is only recently that several research groups have focused their attention on these compounds, 2,3 taking advantage of the significant advances achieved with respect to new synthetic protocols leading to triarylcorroles in high yield. 4,7 …”

Section: Introductionmentioning

confidence: 99%

“…4,9 In addition to this synthetic aspect, there is also the corrole’s intriguing coordination chemistry, characterized by the so-called “non-innocent” behavior of the macrocyclic ligand. 10,11 …”

Section: Introductionmentioning

confidence: 99%

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β-Nitro Derivatives of Iron Corrolates

et al. 2012

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Two different methods for the regioselective nitration of different meso-triarylcorroles leading to the corresponding β-substituted nitrocorrole iron complexes have been developed. A two-step procedure affords three Fe(III) nitrosyl products - the unsubstituted corrole, the 3-nitrocorrole and the 3,17-dinitrocorrole. In contrast, a one-pot synthetic approach drives the reaction almost exclusively to formation of the iron nitrosyl 3,17-dinitrocorrole. Electron-releasing substituents on the meso-aryl groups of the triarylcorroles induce higher yields and longer reaction times than what is observed for the synthesis of similar triarylcorroles with electron-withdrawing functionalities, and these results can be confidently attributed to the facile formation and stabilization of an intermediate iron corrole π-cation radical. Electron-withdrawing substituents on the meso-aryl groups of triarylcorrole also seem to labilize the axial nitrosyl group which, in the case of the pentafluorophenylcorrole derivative, results in the direct formation of a disubstituted iron μ-oxo dimer complex. The influence of meso-aryl substituents on the progress and products of the nitration reaction was investigated. In addition, to elucidate the most important factors which influence the redox reactivity of these different iron nitrosyl complexes, selected compounds were examined by cyclic voltammetry and thin-layer UV-visible or FTIR spectroelectrochemistry in CH2Cl2.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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β-Nitro Derivatives of Iron Corrolates

et al. 2012

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“…The synthetic routes for the preparation of corrole are now significantly improved [3, 4], allowing also studies of functionalization of the corrole [5], a fundamental step for exploitation of such a macrocycle in practical applications. The first examples of the potentialities of corrole derivatives in different fields have been reported in the literature [6].…”

Section: Introductionmentioning

confidence: 99%

Synthetic protocols for the nitration of corroles

Pomarico

Fronczek

Nardis

et al. 2011

J. Porphyrins Phthalocyanines

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The modification of peripheral positions of corroles by introduction of nitro groups is an important functionalization of this macrocycle. The nitro substituent strongly influences the corrole behavior leading to the preparation of macrocycles with different properties, which can be of interest for their exploitation as catalysts, sensing layers in chemical sensors or in the field of supramolecular chemistry. In the last few years we have developed different routes for the β-nitration of the corrole ring, and we report here novel synthetic protocols which can allow the formation of tri- and tetranitro derivatives, as demonstrated by X-ray analysis. In all of the methodologies used, the presence of isocorrole species as reaction intermediates was established, which regenerated the corresponding corrole by metal insertion.

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“…Corroles have received a great deal of attention in recent years (10)(11)(12)(13), owing to dramatic advances in methods for their preparation (14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31). Of interest here is a gallium(III) complex, 1 [Ga(tpfc)] (32)(33)(34)(35), where tpfc represents the trianion of 5,10,15-tris(pentafluorophenyl)corrole [H 3 (tpfc)].…”

mentioning

confidence: 99%

Cellular uptake and anticancer activity of carboxylated gallium corroles

Pribisko

Palmer²,

Grubbs

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

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We report derivatives of gallium(III) tris(pentafluorophenyl)corrole, 1 [Ga(tpfc)], with either sulfonic (2) or carboxylic acids (3, 4) as macrocyclic ring substituents: the aminocaproate derivative, 3 [Ga(ACtpfc)], demonstrated high cytotoxic activity against all NCI60 cell lines derived from nine tumor types and confirmed very high toxicity against melanoma cells, specifically the LOX IMVI and SK-MEL-28 cell lines. The toxicities of 1, 2, 3, and 4 [Ga(3-ctpfc)] toward prostate (DU-145), melanoma (SK-MEL-28), breast (MDA-MB-231), and ovarian (OVCAR-3) cancer cells revealed a dependence on the ring substituent: IC 50 values ranged from 4.8 to >200 μM; and they correlated with the rates of uptake, extent of intracellular accumulation, and lipophilicity. Carboxylated corroles 3 and 4, which exhibited about 10-fold lower IC 50 values (<20 μM) relative to previous analogs against all four cancer cell lines, displayed high efficacy (E max = 0). Confocal fluorescence imaging revealed facile uptake of functionalized gallium corroles by all human cancer cells that followed the order: 4 >> 3 > 2 >> 1 (intracellular accumulation of gallium corroles was fastest in melanoma cells). We conclude that carboxylated gallium corroles are promising chemotherapeutics with the advantage that they also can be used for tumor imaging.

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Corrole: The Little Big Porphyrinoid

Cited by 130 publications

References 34 publications

β-Nitro Derivatives of Iron Corrolates

β-Nitro Derivatives of Iron Corrolates

Synthetic protocols for the nitration of corroles

Cellular uptake and anticancer activity of carboxylated gallium corroles

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