DNA Binding and Catalytic Properties of Positively Charged Corroles

Gershman, Zoya; Goldberg, Israel; Gross, Zeev

doi:10.1002/ange.200700757

Cited by 24 publications

(16 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The potency of metal corroles (Mn, Fe, and Ga), as well as the ability to attenuate atherosclerosis (144), has thus far been ascribed to peroxynitrite or H 2 O 2 scavenging; catalytic action was provided by the reduction of Mn(IV) corrole to Mn(III) corrole with either nitrite or ascorbate. The k cat ranged from *4Â10 4 (negatively charged corrole with three pentafluorophenyl meso groups and two sulfonated pyrrolic positions) to 4Â10 5 M À1 s À1 (positively charged corrole with pentafluorophenyl group on one meso bridge and two para methylpyridyl groups on two opposing meso bridges) (127). The values for Fe corroles are much higher: 2Â10 6 M À1 s À1 for a positively charged corrole (200).…”

Section: Corrolesmentioning

confidence: 99%

Superoxide Dismutase Mimics: Chemistry, Pharmacology, and Therapeutic Potential

Batinić‐Haberle

Rebouças

Spasojević

2010

Antioxidants & Redox Signaling

467

689

View full text Add to dashboard Cite

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.

show abstract

Section: Corrolesmentioning

confidence: 99%

Superoxide Dismutase Mimics: Chemistry, Pharmacology, and Therapeutic Potential

Batinić‐Haberle

Rebouças

Spasojević

2010

Antioxidants & Redox Signaling

467

689

View full text Add to dashboard Cite

show abstract

“…[6e, f] Gross and co-workers were the first to synthesize cationic corroles and find that they can interact with DNA, [7] and we reported that some cationic corroles are capable of stabilizing G-quadruplex structures and inhibiting the activity of telomerase. [8] To study the structure-activity relationships of corroles, we attached pyridinium, piperidine, dimethylamino, and amide moieties to the corrole skeleton because these functional groups have shown a good affinity for DNA.…”

Section: Introductionmentioning

confidence: 99%

“…X-ray crystallographic studies of corrolatocopper and -manganese complexes show that they are typically saddle-type, which are very similar to a plane. [7,18] These structures make cationic corroles prone to matching the G-quartet, which could strengthen the interaction of the molecular ligand and Gquadruplex. In view of these points, some metal ions with high-oxidation states, such as copper(II) and manganese(II), were inserted into corroles to form trivalent complexes.…”

Section: Introductionmentioning

confidence: 99%

“…Considering the specific structures of metalated corroles, [7,18] we anticipated these compounds would show some interesting properties through interaction with G-quadruplex DNA. Thus, a metal-corrole complex may possibly play an important role in replacing one of the metal ions that is normally coordinated in and at the ends of the central ion channel of the quadruplex.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Cationic Metal–Corrole Complexes: Design, Synthesis, and Properties of Guanine‐Quadruplex Stabilizers

Zhang

Weng

et al. 2008

Chemistry A European J

View full text Add to dashboard Cite

A series of pyridinium and quaternary ammonium copper corroles has been designed and synthesized. All new compounds have been fully characterized by NMR spectroscopy, high-resolution mass spectrometry, UV/Vis spectrscopy, and elemental analysis. Biochemical studies have indicated that all of these corrole derivatives can stabilize G-quadruplex structures, with corrole 4 being the most effective according to the results of circular dichroism (CD) melting experiments, polymerase chain reaction (PCR) stop assays, and surface plasmon resonance (SPR) experiments. Moreover, both corroles 3 and 4 tend to induce the human telomeric sequence to form hybrid G-quadruplex structures, whereas corroles 8 and 9 are more inclined to induce the human telomeric sequence to form antiparallel G-quadruplex structures.

show abstract

“…Transcription inhibition is observed with certain organometallic complexes [17][18][19][20][21][22][23][24][25][26][27] and we sought to examine this process as a possible mechanism for the cytotoxic behavior of the corrole family. This transcription assay provides a straightforward, inexpensive, and facile method for assessing transcription inhibition, which will lead to more detailed information about the effects of these molecules in live cells.…”

mentioning

confidence: 99%

An <em>In Vitro</em> Enzymatic Assay to Measure Transcription Inhibition by Gallium(III) and H<sub>3</sub> 5,10,15-tris(pentafluorophenyl)corroles

Tang

Pribisko

Henning

et al. 2015

JoVE

View full text Add to dashboard Cite

Chemotherapy often involves broad-spectrum cytotoxic agents with many side effects and limited targeting. Corroles are a class of tetrapyrrolic macrocycles that exhibit differential cytostatic and cytotoxic properties in specific cell lines, depending on the identities of the chelated metal and functional groups. The unique behavior of functionalized corroles towards specific cell lines introduces the possibility of targeted chemotherapy.Many anticancer drugs are evaluated by their ability to inhibit RNA transcription. Here we present a step-by-step protocol for RNA transcription in the presence of known and potential inhibitors. The evaluation of the RNA products of the transcription reaction by gel electrophoresis and UVVis spectroscopy provides information on inhibitive properties of potential anticancer drug candidates and, with modifications to the assay, more about their mechanism of action.Little is known about the molecular mechanism of action of corrole cytotoxicity. In this experiment, we consider two corrole compounds: gallium(III) 5,10,15-(tris)pentafluorophenylcorrole (Ga(tpfc)) and freebase analogue 5,10,15-(tris)pentafluorophenylcorrole (tpfc). An RNA transcription assay was used to examine the inhibitive properties of the corroles. Five transcription reactions were prepared: DNA treated with Actinomycin D, triptolide, Ga(tpfc), tpfc at a [complex]:[template DNA base] ratio of 0.01, respectively, and an untreated control.The transcription reactions were analyzed after 4 hr using agarose gel electrophoresis and UV-Vis spectroscopy. There is clear inhibition by Ga(tpfc), Actinomycin D, and triptolide.This RNA transcription assay can be modified to provide more mechanistic detail by varying the concentrations of the anticancer complex, DNA, or polymerase enzyme, or by incubating the DNA or polymerase with the complexes prior to RNA transcription; these modifications would differentiate between an inhibition mechanism involving the DNA or the enzyme. Adding the complex after RNA transcription can be used to test whether the complexes degrade or hydrolyze the RNA. This assay can also be used to study additional anticancer candidates.

show abstract

DNA Binding and Catalytic Properties of Positively Charged Corroles

Cited by 24 publications

References 39 publications

Superoxide Dismutase Mimics: Chemistry, Pharmacology, and Therapeutic Potential

Superoxide Dismutase Mimics: Chemistry, Pharmacology, and Therapeutic Potential

Cationic Metal–Corrole Complexes: Design, Synthesis, and Properties of Guanine‐Quadruplex Stabilizers

An <em>In Vitro</em> Enzymatic Assay to Measure Transcription Inhibition by Gallium(III) and H<sub>3</sub> 5,10,15-tris(pentafluorophenyl)corroles

Contact Info

Product

Resources

About