A cytotoxic and cytostatic gold(<scp>iii</scp>) corrole

Teo, Ruijie D.; Gray, Harry B.; Lim, Punnajit; Termini, John; Domeshek, Elena; Gross, Zeev

doi:10.1039/c4cc06577h

Cited by 73 publications

(56 citation statements)

References 25 publications

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“…The uptake, intracellular accumulation, and potency (IC 50 ) varied by compound: carboxylated derivatives 3 and 4 augmented cell permeability, as revealed by enhanced uptake rates, and increased intracellular accumulation, resulting in higher potency compared with 1 and 2. The carboxylated corroles exhibited strong cytotoxic effects in prostate, melanoma, breast, and ovarian cancer cells; the effective cytotoxic dose (<20 μM) was lower than that of a widely used chemotherapeutic agent, cisplatin (45,46), as well as those of other gallium compounds under study as therapeutic agents (54)(55)(56). Compound 4 was exceptionally active as a cytotoxic agent against melanoma SK-MEL-28 cells (IC 50 = 4.8 μM); notably, >99% of cells exhibited intracellular corrole accumulation within 15 min.…”

Section: Discussionmentioning

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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Section: Discussionmentioning

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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“…[1,3,4,5,9,10] Gold(III) corroles by contrasta re innocent and relatively planar, regardless of the degree of peripheral steric hindrance. [11][12][13] The difference between copperand gold was strikingly illustrated in crystallographic studies of highly sterically hindered b-octakis(trifluoromethyl)-meso-triarylcorrole complexes, in which the copper complex was found to be extremely saddled, [4] with adjacent pyrrole rings essentially orthogonal to one another,w hile the gold complext urned out to be perfectly planar.…”

Section: Introductionmentioning

confidence: 97%

Ligand Noninnocence in Coinage Metal Corroles: A Silver Knife‐Edge

Thomas

Vázquez‐Lima

Fang

et al. 2015

Chemistry A European J

122

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A silver β-octabromo-meso-triarylcorrole has been found to exhibit a strongly saddled geometry, providing the first instance of a strongly saddled corrole complex involving a metal other than copper. The Soret maxima of the Ag octabromocorroles also redshift markedly in response to increasingly electron-donating para substituents on the meso-aryl groups. In both these respects, the Ag octabromocorroles differ from simple Ag triarylcorrole derivatives, which exhibit only mild saddling and substituent-insensitive Soret maxima. These results have been rationalized in terms of an innocent M(III)-corrole(3-) description for the simple Ag corroles and a noninnocent M(II)-corrole(·2-) description for the Ag octabromocorroles. In contrast, all copper corroles are thought to be noninnocent, while all gold corroles are innocent. Uniquely among metallocorroles, silver corroles thus seem poised on a knife-edge, so to speak, between innocent and noninnocent electronic structures and may tip either way, depending on the exact nature of the corrole ligand.

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“…For example, gold corrolesh ave found applicationsi no rganic solar cells and the photodynamic therapy of cancer. [8] Curiously,w ith the exception of an accidental synthesis involvinga nu nexpected ring contraction of ap orphyrin, there have been no reports of rheniumcorroles. [9] This is as ignificant gap in our knowledge because rhenium-oxoc orroles are not only potentially important as catalysts, [10] they may also find applicationsi nr adioimaging and -therapy.…”

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Metal–Ligand Misfits: Facile Access to Rhenium–Oxo Corroles by Oxidative Metalation

Einrem

Gagnon

Alemayehu

et al. 2015

Chemistry A European J

109

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With the exception of a single accidental synthesis, rhenium corroles are unknown, but of great interest as catalysts and potential radiopharmaceuticals. Oxidative metalation of meso-triarylcorroles with [Re2 (CO)10 ] in refluxing decalin has provided a facile and relatively high-yielding route to rhenium(V)-oxo corroles. The complexes synthesized could all be fully characterized by single-crystal X-ray structure analyses.

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A cytotoxic and cytostatic gold(iii) corrole

Abstract: The bis-sulfonated Au(iii) corrole (1-Au) was found to be much more cytotoxic and cytostatic than its Ga(iii) analog 1-Ga, which might be attributed to the lower affinity of 1-Au to serum albumin.

Cited by 73 publications

References 25 publications

Cellular uptake and anticancer activity of carboxylated gallium corroles

Cellular uptake and anticancer activity of carboxylated gallium corroles

Ligand Noninnocence in Coinage Metal Corroles: A Silver Knife‐Edge

Metal–Ligand Misfits: Facile Access to Rhenium–Oxo Corroles by Oxidative Metalation

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