Corrole‐Based Applications

Aviv, Iris; Gross, Zeev

doi:10.1002/chin.200735243

Cited by 16 publications

(24 citation statements)

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“…Corroles are tetrapyrrolic macrocycles with a porphyrin‐like inner core containing four nitrogen atoms serving as an equatorial coordination template for metal ions. Depending on the metal, these molecules can function as components in oxidation catalysis (Fe, Mn, Cr), reduction catalysis (Cr, Mn, Fe), group transfer catalysis (Rh, Fe), sensors of gaseous molecules (Co), and medicinal research (Aviv and Gross 2007; Aviv‐Harel and Gross 2009). The latter includes research performed on cellular and murine models of cancer (Agadjanian et al.…”

Section: Reactive Oxygen Species Scavenging By Metallocorrolesmentioning

confidence: 99%

Neuroprotection against superoxide anion radical by metallocorroles in cellular and murine models of optic neuropathy

Kanamori

Catrinescu

Mahammed

et al. 2010

Journal of Neurochemistry

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Corroles are tetrapyrrolic macrocycles that have come under increased attention because of their unique capabilities for oxidation catalysis, reduction catalysis, and biomedical applications. Corrole-metal complexes (metallocorroles) can decompose certain reactive oxygen species (ROS), similar to metalloporphyrins. We investigated whether Fe-, Mn-, and Ga-corroles have neuroprotective effects on neurons and correlated this with superoxide scavenging activity in vitro and in vivo. Apoptosis was induced in retinal ganglion cell-5 neuronal precursor cells by serum deprivation. Cell death was measured with sodium 3¢-[1-[(phenylamino)-carbonyl]-3,4-tetrazolium]-bis (4-methoxy-6-nitro) benzene-sulfonic acid hydrate and calcein-AM/propidium iodide assays. Fe-and Mn-corroles, but not the non-redox-active Ga-corrole used as control, reduced RGC-5 cell death after serum deprivation.Serum deprivation caused increased levels of intracellular superoxide, detected by an increase in the fluorescence intensity of 2-hydroxyethidium, and this was blocked by Feand Mn-corroles, but not Ga-corrole. In vivo real-time confocal imaging of retinas after optic nerve transection assessed the superoxide production within individual rat retinal ganglion cells. Fe-and Mn-corroles, but not Ga-corrole, scavenged neuronal superoxide in vivo. Given that the neuroprotective activity of metallocorroles correlated with superoxide scavenging activity, Fe-and Mn-corroles could be candidate drugs for delaying neuronal death after axonal injury in optic neuropathies, such as glaucoma. Keywords: metallocorroles, neuroprotection, neurons, superoxide, optic neuropathy. J. Neurochem. (2010) 114, 488-498. JOURNAL OF NEUROCHEMISTRY | 2010 | 114 | 488-498 doi: 10.1111/j.1471-4159.2010 et al. 2010). Over the past decade they have received increasing attention, following the major discoveries for their facile synthesis (Gross and Galili 1999;Gryko 2002). Porphyrins have been used in numerous applications, including the use of metalloporphyrins as neuroprotective agents that work via decomposition of ROS (Cuzzocrea et al. 2001). We predicted that metallocorroles, some of which can be highly specific ROS scavengers (reviewed in Table 1), might be useful small molecule drugs for inhibiting ROS-mediated signaling of cell death.To study this, we investigated the neuroprotective effect of iron (Fe), manganese (Mn), and gallium (Ga) corroles ( Fig. 1) in both in vitro and in vivo models of neuronal death. For the in vitro studies, we used serum-deprived neuronal precursor retinal ganglion cell (RGC)-5 cells, which when differentiated with low levels of staurosporine, have several features similar to that of mature neurons (Frassetto et al. 2006). For in vivo studies, we used confocal scanning laser ophthalmoscopy (CSLO) coupled with intravitreal fluorescent dyes to demonstrate that certain metallocorroles function as SOD mimetics. MethodsMaterials RGC-5 cells were a generous gift of Neeraj Agarwal, Ph.D.; Dulbecco's modified Eagle's medium and fetal bovine s...

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Section: Reactive Oxygen Species Scavenging By Metallocorrolesmentioning

confidence: 99%

Neuroprotection against superoxide anion radical by metallocorroles in cellular and murine models of optic neuropathy

Kanamori

Catrinescu

Mahammed

et al. 2010

Journal of Neurochemistry

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“…Corroles are a developing class of tetrapyrrole-based photosensitizers with relatively unexplored photophysical properties [ 1 , 2 , 3 , 4 ]. The simple and efficient procedure of corrole synthesis, combined with the pre-tuning of physical and chemical characteristics by varying the peripheral substituents [ 5 , 6 , 7 , 8 ], central metal [ 6 , 9 , 10 ], and axial ligands [ 11 , 12 ], has revived substantial interest in employing these contracted porphyrinoids in various fields.…”

Section: Introductionmentioning

confidence: 99%

Ultrafast Dynamics of Sb-Corroles: A Combined Vis-Pump Supercontinuum Probe and Broadband Fluorescence Up-Conversion Study

et al. 2017

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Corroles are a developing class of tetrapyrrole-based molecules with significant chemical potential and relatively unexplored photophysical properties. We combined femtosecond broadband fluorescence up-conversion and fs broadband Vis-pump Vis-probe spectroscopy to comprehensively characterize the photoreaction of 5,10,15-tris-pentafluorophenyl-corrolato-antimony(V)-trans-difluoride (Sb-tpfc-F2). Upon fs Soret band excitation at ~400 nm, the energy relaxed almost completely to Q band electronic excited states with a time constant of 500 ± 100 fs; this is evident from the decay of Soret band fluorescence at around 430 nm and the rise time of Q band fluorescence, as well as from Q band stimulated emission signals at 600 and 650 nm with the same time constant. Relaxation processes on a time scale of 10 and 20 ps were observed in the fluorescence and absorption signals. Triplet formation showed a time constant of 400 ps, with an intersystem crossing yield from the Q band to the triplet manifold of between 95% and 99%. This efficient triplet formation is due to the spin-orbit coupling of the antimony ion.

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“…Incidentally, these ortho-N-alkylpyridylporphyrins are also among the most (if not the most) potent scavengers of peroxynitrite so far [6,7]. These basic concepts on the ortho-N-alkylpyridinium-2ylporphyrin framework have been extensively explored to prepare a myriad of metalporphyrinoid complexes as redox modulators [2][3][4][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Impact of electrostatics in redox modulation of oxidative stress by Mn porphyrins: Protection of SOD-deficient Escherichia coli via alternative mechanism where Mn porphyrin acts as a Mn carrier

Rebouças

DeFreitas-Silva

Spasojević

et al. 2008

Free Radical Biology and Medicine

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Understanding the factors that determine the ability of Mn porphyrins to scavenge reactive species is essential for tuning their in vivo efficacy. We present herein the revised structure-activity relationships accounting for the critical importance of electrostatics in the Mn porphyrin-based redox modulation systems and show that the design of effective SOD mimics (per se) based on anionic porphyrins is greatly hindered by inappropriate electrostatics. A new strategy for the beta-octabromination of the prototypical anionic Mn porphyrins Mn(III) meso-tetrakis(p-carboxylatophenyl)porphyrin ([Mn(III)TCPP](3-) or MnTBAP(3-)) and Mn(III) meso-tetrakis(p-sulfonatophenyl)porphyrin ([Mn(III)TSPP](3-)), to yield the corresponding anionic analogues [Mn(III)Br(8)TCPP](3-) and [Mn(III)Br(8)TSPP](3-), respectively, is described along with characterization data, stability studies, and their ability to substitute for SOD in SOD-deficient Escherichia coli. Despite the Mn(III)/Mn(II) reduction potential of [Mn(III)Br(8)TCPP](3-) and [Mn(III)Br(8)TSPP](3-) being close to the SOD-enzyme optimum and nearly identical to that of the cationic Mn(III) meso-tetrakis(N-methylpyridinium-2-yl)porphyrin (Mn(III)TM-2-PyP(5+)), the SOD activity of both anionic brominated porphyrins ([Mn(III)Br(8)TCPP](3-), E(1/2)=+213 mV vs NHE, log k(cat)=5.07; [Mn(III)Br(8)TSPP](3-), E(1/2)=+209 mV, log k(cat)=5.56) is considerably lower than that of Mn(III)TM-2-PyP(5+) (E(1/2)=+220 mV, log k(cat)=7.79). This illustrates the impact of electrostatic guidance of O(2)(-) toward the metal center of the mimic. With low k(cat), the [Mn(III)TCPP](3-), [Mn(III)TSPP](3-), and [Mn(III)Br(8)TCPP](3-) did not rescue SOD-deficient E. coli. The striking ability of [Mn(III)Br(8)TSPP](3-) to substitute for the SOD enzymes in the E. coli model does not correlate with its log k(cat). In fact, the protectiveness of [Mn(III)Br(8)TSPP](3-) is comparable to or better than that of the potent SOD mimic Mn(III)TM-2-PyP(5+), even though the dismutation rate constant of the anionic complex is 170-fold smaller. Analyses of the medium and E. coli cell extract revealed that the major species in the [Mn(III)Br(8)TSPP](3-) system is not the Mn complex, but the free-base porphyrin [H(2)Br(8)TSPP](4-) instead. Control experiments with extracellular MnCl(2) showed the lack of E. coli protection, indicating that "free" Mn(2+) cannot enter the cell to a significant extent. We proposed herein the alternative mechanism where a labile Mn porphyrin [Mn(III)Br(8)TSPP](3-) is not an SOD mimic per se but carries Mn into the E. coli cell.

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Corrole‐Based Applications

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 16 publications

References 1 publication

Neuroprotection against superoxide anion radical by metallocorroles in cellular and murine models of optic neuropathy

Neuroprotection against superoxide anion radical by metallocorroles in cellular and murine models of optic neuropathy

Ultrafast Dynamics of Sb-Corroles: A Combined Vis-Pump Supercontinuum Probe and Broadband Fluorescence Up-Conversion Study

Impact of electrostatics in redox modulation of oxidative stress by Mn porphyrins: Protection of SOD-deficient Escherichia coli via alternative mechanism where Mn porphyrin acts as a Mn carrier

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