Corrole-based applications

Aviv, Iris; Gross, Zeev

doi:10.1039/b618482k

Cited by 411 publications

(229 citation statements)

References 92 publications

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“…They are also tri-anionic compared with di-anionic porphyrin ligands (with respect to pyrrolic nitrogen deprotonation) (285). Thus, they tend to form high-oxidation-state air-stable Mn(IV) complexes (23). The synthesis of watersoluble derivatives led to their increased development for biomedicinal purposes (23).…”

Section: Corrolesmentioning

confidence: 99%

“…Thus, they tend to form high-oxidation-state air-stable Mn(IV) complexes (23). The synthesis of watersoluble derivatives led to their increased development for biomedicinal purposes (23). The first step in Mn(III) reduction is thermodynamically very unfavorable, as it occurs at very negative potentials (<À1 V vs. NHE in different solvents) (285).…”

Section: Corrolesmentioning

confidence: 99%

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Superoxide Dismutase Mimics: Chemistry, Pharmacology, and Therapeutic Potential

Batinić‐Haberle

Rebouças

Spasojević

2010

Antioxidants & Redox Signaling

467

689

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Oxidative stress has become widely viewed as an underlying condition in a number of diseases, such as ischemia-reperfusion disorders, central nervous system disorders, cardiovascular conditions, cancer, and diabetes. Thus, natural and synthetic antioxidants have been actively sought. Superoxide dismutase is a first line of defense against oxidative stress under physiological and pathological conditions. Therefore, the development of therapeutics aimed at mimicking superoxide dismutase was a natural maneuver. Metalloporphyrins, as well as Mn cyclic polyamines, Mn salen derivatives and nitroxides were all originally developed as SOD mimics. The same thermodynamic and electrostatic properties that make them potent SOD mimics may allow them to reduce other reactive species such as peroxynitrite, peroxynitrite-derived CO 3 _ À , peroxyl radical, and less efficiently H 2 O 2 . By doing so SOD mimics can decrease both primary and secondary oxidative events, the latter arising from the inhibition of cellular transcriptional activity. To better judge the therapeutic potential and the advantage of one over the other type of compound, comparative studies of different classes of drugs in the same cellular and=or animal models are needed. We here provide a comprehensive overview of the chemical properties and some in vivo effects observed with various classes of compounds with a special emphasis on porphyrin-based compounds. Antioxid. Redox Signal. 13, 877-918.

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Section: Corrolesmentioning

confidence: 99%

Section: Corrolesmentioning

confidence: 99%

Superoxide Dismutase Mimics: Chemistry, Pharmacology, and Therapeutic Potential

Batinić‐Haberle

Rebouças

Spasojević

2010

Antioxidants & Redox Signaling

467

689

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“…The catalytic power of MnTE-2-PyP 5+ is enhanced by the presence of electron-withdrawing positively charged ortho alkylpyridyl groups close to the metal center. These proximal positive charges contribute to both thermodynamic (favorable redox potential) [1,6] and kinetic (electrostatic attraction of the negatively charged substrate) [6,34] [39] have been developed that exploit the effects of cationic ortho quaternary nitrogens.…”

Section: Introductionmentioning

confidence: 99%

Pharmacokinetics of the potent redox-modulating manganese porphyrin, MnTE-2-PyP5+, in plasma and major organs of B6C3F1 mice

Spasojević

Chen

Noel

et al. 2008

Free Radical Biology and Medicine

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Mn(III)tetrakis(N-ethylpyridinium-2-yl)porphyrin, MnTE-2-PyP 5+ , a potent catalytic superoxide and peroxynitrite scavenger, has been beneficial in several oxidative stress-related disease thus far examined. Pharmacokinetic studies are essential for the better assessment of the therapeutic potential of MnTE-2-PyP 5+ and similar compounds, as well as for the modulation of their bioavailability and toxicity. Despite high hydrophilicity, this drug entered mitochondria after single 10 mg/kg intraperitoneal injection at levels high enough (5.1 µM; 2.95 ng/mg protein) to protect it against superoxide/peroxynitrite damage. Utilizing the same analytical approach, which involves the reduction of MnTE-2-PyP 5+ , followed by the exchange of Mn 2+ with Zn 2+ , and HPLC/fluorescence detection of ZnTE-2-PyP 4+ , we measured levels of MnTE-2-PyP 5+ in mouse plasma, liver, kidney, lung, heart, spleen, and brain over a period of 7 days after a single intraperitoneal injection of 10 mg/ kg. Two B6C3F1 female mice per time point were used. The pharmacokinetic profile in plasma and organs was complex; thus a non-compartmental approach was utilized to calculate the area under the curve (AUC), c max , t max , and drug elimination half-time (t 1/2 ). In terms of levels of MnTE-2-PyP 5+ found, the organs can be classified into 3 distinct groups: (1) high levels: kidney, liver, and spleen; (2) moderate levels: lung and heart; and (3) low levels: brain. The maximal levels in plasma, kidney, spleen, lung, and heart are reached within first 45 minutes whereas in case of liver a prolonged absorption phase was observed with the maximal concentration reached at 8 hours. Moreover, accumulation of the drug in brain continues beyond time of the experiment (7 days) and is likely driven by the presence of negatively charged phospholipids. For tissues other than brain, a slow elimination phase (single exponential decay, t 1/2 = 60 to 135 hours) is observed. The calculated pharmacokinetic parameters will be used to design optimal dosing regimens in future preclinical studies utilizing this and similar compounds.

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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-based applications

Cited by 411 publications

References 92 publications

Superoxide Dismutase Mimics: Chemistry, Pharmacology, and Therapeutic Potential

Superoxide Dismutase Mimics: Chemistry, Pharmacology, and Therapeutic Potential

Pharmacokinetics of the potent redox-modulating manganese porphyrin, MnTE-2-PyP5+, in plasma and major organs of B6C3F1 mice

Cellular uptake and anticancer activity of carboxylated gallium corroles

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