Coordination chemistry of corroles with focus on main group elements

Aviv‐Harel, Iris; Gross, Zeev

doi:10.1016/j.ccr.2010.09.013

Cited by 213 publications

(180 citation statements)

References 77 publications

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“…Thus, they are "contracted" porphyrins, containing one C atoms less in the macrocycle [157][158][159][160][161]. The smaller macrocycle provides a tighter coordination environment and thus stabilizes high-valent transition metal ions with a smaller ionic radii, whereas low-valent metal complexes are highly reactive [162,163]. For the metal complexes, catalytic activity for a variety of reactions [164], including epoxidations [165] and catalytic CO 2 reduction [166] has been Fig.…”

Section: Corroles and Porphycenesmentioning

confidence: 98%

Surface chemistry of porphyrins and phthalocyanines

Gottfried

2015

Surface Science Reports

551

586

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Section: Corroles and Porphycenesmentioning

confidence: 98%

Surface chemistry of porphyrins and phthalocyanines

Gottfried

2015

Surface Science Reports

551

586

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“…Increased structural complexity of the individual molecules is believed to strongly affect the formation of intricate networks, as observed in previous studies of corrole derivatives [6][7][8]. Corroles [9,10] are emerging as highly potent agents in catalysis, photochemical sensing, molecular electronics and biomedicine [11][12][13]. Corrole molecules, exhibiting low symmetry (C 1 ) when adsorbed on metal substrates, facilitate non-trivial network structures, originating either from multiple conformational states [6,8] or dissociation of axial ligands [7].…”

Section: Introductionmentioning

confidence: 97%

Manipulation resolves non-trivial structure of corrole monolayer on Ag(111)

et al. 2015

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Non-trivial arrangement of molecules within a molecular network complicates structure determination due to interdigitation, partial overlap, or stacking. We demonstrate that combined imaging and lateral manipulation with a scanning tunneling microscope resolves the intricate structure of a molecular network in two-dimensions in a straightforward manner. The network, formed by a monolayer of 5,10,15-tris(pentafluorophenyl)-corrole molecules on Ag (111), is manipulated for the first time with single-molecule precision. Our results reveal a shingle-like packing of partially overlapping corrole molecules. Density functional theory calculations support our findings.

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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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Coordination chemistry of corroles with focus on main group elements

Cited by 213 publications

References 77 publications

Surface chemistry of porphyrins and phthalocyanines

Surface chemistry of porphyrins and phthalocyanines

Manipulation resolves non-trivial structure of corrole monolayer on Ag(111)

Cellular uptake and anticancer activity of carboxylated gallium corroles

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