Variables That Influence Cellular Uptake and Cytotoxic/Cytoprotective Effects of Macrocyclic Iron Complexes

Haber, Adi; Aviram, Michael; Gross, Zeev

doi:10.1021/ic202204u

Cited by 23 publications

(25 citation statements)

References 39 publications

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“…(78,194) and the similarity of E 1/2 of Mn corroles in acetonitrile and in an aqueous system, the values of E 1/2 in aqueous medium for several corroles plotted in SAR (Fig. 4) were estimated (80,104,196) (Fig. 1).…”

Section: Mn(iii) Corrolesmentioning

confidence: 99%

“…5). When translated into experimental data, it appears that E 1/2 for these compounds is identical in either solvent: water or acetonitrile (80,104,196 (28). However, with Mn corroles, the electron-donating groups are required for modifying their E 1/2 from * + 1000 to * + 700 mV versus NHE (196).…”

Section: Mn(iii) Corrolesmentioning

confidence: 99%

“…The SAR (showed with thick blue line) is valid for many redox-active compounds regardless of their structure: metalloporphyrins, Mn(IV) biliverdins, Mn(III) salens, Mn(II) polyamines, Mn(III) corroles, and Mn(II) aqua complex (271). The E 1/2 values for Mn IV C/Mn III C redox couple (given in Table 1) were determined in phosphate buffer for anionic Mn corrole with two sulfonatopyrrolic groups and three meso pentaphenyl groups, but in acetonitrile for cationic Mn corrole, which bears two meso para-methylpyridyl groups and one meso substituent with derivatized tetrapfluorophenyl group (80,104,196) (Fig. 1).…”

Section: Mn(iii) Corrolesmentioning

confidence: 99%

“…For injuries of central nervous systems, see review from Warner and Sheng groups (236); while for inflammation and immunity disorders, see contribution from Piganelli group (208). For the corrole-based SOD mimics, see references from Gross's group (103,104).…”

Section: Introductionmentioning

confidence: 99%

“…The design of metallocorrole (MC)-based class of SOD mimics is briefly discussed next (104). The design of Mn(II) cyclic polyamines, which resulted in an optimized molecule, M40403 has been extensively covered by Riley's group (14,167,(226)(227)(228)232).…”

mentioning

confidence: 99%

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SOD Therapeutics: Latest Insights into Their Structure-Activity Relationships and Impact on the Cellular Redox-Based Signaling Pathways

Batinić‐Haberle

Tovmasyan

Roberts

et al. 2014

Antioxidants & Redox Signaling

206

458

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Significance: Superoxide dismutase (SOD) enzymes are indispensable and ubiquitous antioxidant defenses maintaining the steady-state levels of O 2 $ -; no wonder, thus, that their mimics are remarkably efficacious in essentially any animal model of oxidative stress injuries thus far explored. Recent Advances: Structure-activity relationship (half-wave reduction potential [E 1/2 ] versus log k cat ), originally reported for Mn porphyrins (MnPs), is valid for any other class of SOD mimics, as it is dominated by the superoxide reduction and oxidation potential. The biocompatible E 1/2 of *+300 mV versus normal hydrogen electrode (NHE) allows powerful SOD mimics as mild oxidants and antioxidants (alike O 2 $ -) to readily traffic electrons among reactive species and signaling proteins, serving as fine mediators of redox-based signaling pathways. Based on similar thermodynamics, both SOD enzymes and their mimics undergo similar reactions, however, due to vastly different sterics, with different rate constants. Critical Issues: Although log k cat (O 2 $ -) is a good measure of therapeutic potential of SOD mimics, discussions of their in vivo mechanisms of actions remain mostly of speculative character. Most recently, the therapeutic and mechanistic relevance of oxidation of ascorbate and glutathionylation and oxidation of protein thiols by MnP-based SOD mimics and subsequent inactivation of nuclear factor jB has been substantiated in rescuing normal and killing cancer cells. Interaction of MnPs with thiols seems to be, at least in part, involved in up-regulation of endogenous antioxidative defenses, leading to the healing of diseased cells. Future Directions: Mechanistic explorations of single and combined therapeutic strategies, along with studies of bioavailability and translational aspects, will comprise future work in optimizing redox-active drugs. Antioxid. Redox Signal. 20, 2372Signal. 20, -2415

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Section: Mn(iii) Corrolesmentioning

confidence: 99%

Section: Mn(iii) Corrolesmentioning

confidence: 99%

Section: Mn(iii) Corrolesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

See 3 more Smart Citations

SOD Therapeutics: Latest Insights into Their Structure-Activity Relationships and Impact on the Cellular Redox-Based Signaling Pathways

Batinić‐Haberle

Tovmasyan

Roberts

et al. 2014

Antioxidants & Redox Signaling

206

458

View full text Add to dashboard Cite

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Photocytotoxicity and G‐quadruplex DNA interaction of water‐soluble gallium(III) tris(N‐methyl‐4‐pyridyl)corrole complex

Zhang

Wen

et al. 2015

Applied Organom Chemis

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A water-soluble cationic gallium corrole, 5,10,15-tris(N-methyl-4-pyridyl)corrolatogallium(III) (3), was prepared and characterized. The photocytotoxicity of 3 was investigated using Hep G2 cancer cell line. Upon treatment with corrole 3 and irradiation, fragmentation of tumor cell nuclei was observed, which led to apoptosis. Flow cytometric analysis clearly showed the efficient induction of apoptotic cell death, and corrole 3 exhibited high photocytotoxicity towards Hep G2 cancer cells (IC 50 = 60 nM). Furthermore, the binding behavior of corrole 3 with c-MYC G-quadruplex DNA, a potent target for antitumor drugs, was investigated using spectroscopic methods and molecular docking simulation.

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Methyl Benzoate Gallium(III) corrole complexes: DNA‐binding, Photocleavage Activity, Cytotoxicity on Tumor Cells

Wang

Yuan

et al. 2016

Applied Organom Chemis

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Two new gallium corrole complexes, 10‐(4‐Methoxycarbonylphenyl) ‐5, 15‐bis(pentafluorophenyl)corrolatogallium(III)(1‐Ga) and 5,15‐bis(4‐Methoxycarbonylphenyl)‐10‐(pentafluorophenyl)corrolatogallium(III)(2‐Ga), were synthesized and characterized. The interaction of these gallium corrole complexes with CT‐DNA was studied by fluorescence methods, UV–visible, viscosity measurements, molecular docking as well as agarose gel electrophoresis. The results revealed that both 1‐Ga and 2‐Ga interact with DNA via major groove binding and could cleavage the supercoiled plasmid DNA efficiently under irradiation. The inhibitor and singlet oxygen test indicated that singlet oxygen was the reactive oxygen species involved in the photocleavage DNA initiated by 1‐Ga or 2‐Ga. Cell viability experiments indicated that 1‐Ga and 2‐Ga show high photocytotoxicity and low dark toxicity towards tested QGY‐7701 and MHCC‐H/L tumor cell lines. Fluorescence probe tests showed the absorbed 1‐Ga and 2‐Ga in tumor cells are mainly localized in mitochondria, and the mitochondria membrane potential disruption was observed after irradiation.

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Variables That Influence Cellular Uptake and Cytotoxic/Cytoprotective Effects of Macrocyclic Iron Complexes

Cited by 23 publications

References 39 publications

SOD Therapeutics: Latest Insights into Their Structure-Activity Relationships and Impact on the Cellular Redox-Based Signaling Pathways

SOD Therapeutics: Latest Insights into Their Structure-Activity Relationships and Impact on the Cellular Redox-Based Signaling Pathways

Photocytotoxicity and G‐quadruplex DNA interaction of water‐soluble gallium(III) tris(N‐methyl‐4‐pyridyl)corrole complex

Methyl Benzoate Gallium(III) corrole complexes: DNA‐binding, Photocleavage Activity, Cytotoxicity on Tumor Cells

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