Aura of Corroles

Aviv‐Harel, Iris; Gross, Zeev

doi:10.1002/chem.200900920

Cited by 315 publications

(256 citation statements)

References 109 publications

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“…Characterization of 3 was performed using 1 H/ 19 F NMR spectroscopy and MALDI-TOF mass spectrometry, although these techniques did not distinguish between regioisomers with monosubstitution at the 5-, 10-, or 15-fluoro position. 1 The gallium corroles were solubilized in DMSO, and concentrations were determined by UV-Vis using calculated extinction coefficients: (1) e 420nm = 284,000 cm −1 ·M −1 , (2) e 424nm = 74,700 cm −1 ·M −1 , (3) e 420nm = 130,300 cm −1 ·M −1 , (4) e 426nm = 130,000 cm −1 ·M −1 (Fig. 1).…”

Section: Methodsmentioning

confidence: 99%

“…1 is highly fluorescent, with an emission quantum yield far exceeding that of its zinc porphyrin analog (36)(37)(38). The macrocyclic ring of this complex can be selectively modified to afford molecules that exhibit a wide range of physical and chemical properties (1). Previous work focused on a sulfonic acid derivative of Ga(tpfc), 2 [Ga(2,17-S 2 tpfc)]; notably, 2 possessed potent antitumor activity both in vitro (using human cancer cells) and in vivo (using murine model animals), making it a powerful reagent for both imaging and therapeutic targeting of cancer cells (39,40).…”

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confidence: 99%

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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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Section: Methodsmentioning

confidence: 99%

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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“…Driven by related studies on their well-known porphyrin congeners, corroles have recently been applied in various domains (e.g., catalysis, sensor design, molecular electronics, and medical imaging and therapy), in which corroles regularly display superiority compared to related oligopyrrolic macrocycles. [2] In spite of the tremendous synthetic progress that has been made in the corrole field over the last decade, [3,4] some synthetic challenges remain and further efforts are certainly still required to elucidate and exploit the full potential and promises that corroles hold for up-todate applications.…”

Section: Introductionmentioning

confidence: 99%

Synthetic, Structural, and Photophysical Exploration of meso‐Pyrimidinyl‐Substituted AB₂‐Corroles

Ngo

Puntoriero²,

Nastasi³

et al. 2010

Chemistry A European J

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meso-Pyrimidinyl-substituted AB(2)-corroles were efficiently synthesized starting from 5-mesityldipyrromethane and various 2-substituted 4,6-dichloropyrimidine-5-carbaldehydes. The corrole yield was significantly enhanced by optimization of the amount of Lewis acid catalyst (BF(3).OEt(2)). The main advantage of pyrimidinylcorroles over other meso-triarylcorroles is their wide range of functionalization possibilities, which has been explored by nucleophilic and electrophilic aromatic substitution, and Pd-catalyzed cross-coupling reactions. Stepwise substitution of the chlorine functions afforded asymmetrically substituted pyrimidinylcorroles. Due to the lability of the free-base corrole macrocycles, functionalization of the corrole periphery was preferentially performed on the Cu-metalated counterparts. Functionalized free-base AB(2)-pyrimidinylcorroles were, however, readily accessible by the reversible sequence Cu insertion and subsequent reductive demetalation. AB(2)-pyrimidinylcorroles can hence be regarded as highly versatile platforms towards more sophisticated corrole systems. X-ray analysis of a bis(4-tert-butylphenoxy)-substituted Cu-pyrimidinylcorrole showed the typical features of a Cu-corrole: short N-Cu distances and a saddled corrole plane. The absorption spectra and photophysical properties of some representative free-base AB(2)-pyrimidinylcorroles were examined in depth. The absorption spectra displayed typical corrole features: intense spin-allowed pi-pi* bands, which can be classified as Soret- and Q-type bands. The photophysical properties, investigated both in fluid solution at room temperature and in rigid matrix at 77 K, were governed by the lowest-lying pi-pi* singlet state; however, in most cases, a state with partial charge-transfer character (from the corrole ring to the pyrimidinyl group) was proposed to contribute to the dynamic properties of the emissive level.

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“…Recent developments on chemical functionalization approaches of corroles have given new impetus to the application of these compounds in several areas [1][2][3][4][5][6]. For example, they are used in the therapeutic field as inactivation agents for bacteria, viruses, and fungi; contrast agents for biomedical imaging; photosensitizers for photodynamic therapy to fight cancer [7][8][9][10][11][12][13][14][15][16]; and also as catalysts [5] and sensors [4].…”

Section: Introductionmentioning

confidence: 99%

Magnetite–Corrole Hybrid Nanoparticles

2018

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This study describes the first example of a hybrid material comprising corroleand silica-coated magnetite nanoparticles. Firstly, cuboid and spheroid magnetite nanoparticles were prepared using a simple hydrothermal route, followed by a silica coating. The hybrid nanoparticles were obtained by promoting a covalent link between a gallium (III)(pyridine) complex of 5,10,15-tris(pentafluorophenyl)corrole (GaPFC) and the surface of magnetite-silica core/shell nanoparticles (Fe 3 O 4 @SiO 2 ), shaped both as cuboids and spheroids. The hybrids were characterized using Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), ultraviolet-visible spectrophotometry (UV-Vis) and transmission electron microscopy (TEM). Preliminary studies on the capacity of singlet oxygen generation of the hybrid nanoparticles showed that these have lower efficiency values when compared to the pure corrole compound.

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Aura of Corroles

Cited by 315 publications

References 109 publications

Cellular uptake and anticancer activity of carboxylated gallium corroles

Cellular uptake and anticancer activity of carboxylated gallium corroles

Synthetic, Structural, and Photophysical Exploration of meso‐Pyrimidinyl‐Substituted AB₂‐Corroles

Magnetite–Corrole Hybrid Nanoparticles

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Aura of Corroles

Cited by 315 publications

References 109 publications

Cellular uptake and anticancer activity of carboxylated gallium corroles

Cellular uptake and anticancer activity of carboxylated gallium corroles

Synthetic, Structural, and Photophysical Exploration of meso‐Pyrimidinyl‐Substituted AB2‐Corroles

Magnetite–Corrole Hybrid Nanoparticles

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Synthetic, Structural, and Photophysical Exploration of meso‐Pyrimidinyl‐Substituted AB₂‐Corroles