Effect of perezone on arrhythmias and markers of cell injury during reperfusion in the anesthetized rat

Tellez, J.; Carvajal, Karla; Cruz, David; Cárabez, A.; Chávez, Edmundo

doi:10.1016/s0024-3205(99)00411-7

Cited by 20 publications

(6 citation statements)

References 20 publications

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“…Perezone is a sesquiterpenoic benzoquinone isolated from the roots of Perezia adnata [21], and its anti-cancer mechanism is unknown. cMAP analysis has shown that three high scored matches for perezone expression profile are the alkylation agents: lomustine, semustine and 15-delta prostaglandin J2, suggesting that perezone might act as an alkylating agent.…”

Section: Discussionmentioning

confidence: 99%

Expression profiling identifies epoxy anthraquinone derivative as a DNA topoisomerase inhibitor

et al. 2010

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To discover novel drugs for neuroblastoma treatment, we have previously screened a panel of drugs and identified 30 active agents against neuroblastoma cells. Here we performed microarray gene expression analysis to monitor the impact of these agents on a neuroblastoma cell line and used the connectivity map (cMAP) to explore putative mechanism of action of unknown drugs. We first compared the expression profiles of ten compounds shared in both our dataset and cMAP database and observed the high connectivity scores for 7 of 10 matched drugs regardless of the differences of cell lines utilized. The screen of cMAP for uncharacterized drugs indicated the signature of Epoxy anthraquinone derivative (EAD) matched the profiles of multiple known DNA targeted agents (topoisomerase I/II inhibitors, DNA intercalators, and DNA alkylation agents) as predicted by its structure. Similar result was obtained by querying against our internal NB-cMAP (http://pob.abcc.ncifcrf.gov/cgi-bin/cMAP), a database containing the profiles of 30 active drugs. These results suggest that Epoxy anthraquinone derivative may inhibit neuroblastoma cells by targeting DNA replication inhibition. Experimental data also demonstrate that Epoxy anthraquinone derivative indeed induces DNA double-strand breaks through DNA alkylation and inhibition of topoisomerase activity. Our study indicates that Epoxy anthraquinone derivative may be a novel DNA topoisomerase inhibitor that can be potentially used for treatment of neuroblastoma or other cancer patients.

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Section: Discussionmentioning

confidence: 99%

Expression profiling identifies epoxy anthraquinone derivative as a DNA topoisomerase inhibitor

et al. 2010

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“…Perezone or pipitzaoic acid, a sesquiterpene quinone, is recognized as the first secondary metabolite isolated in the New World (American Continent), from roots of Perezia plants, currently Acourtia . This molecule has been the target of many chemical studies, it has also been used as a pigment showing in addition several pharmacological effects, vg the release of mitochondrial Ca 2+ . In addition, perezone and some of its derivatives are able to produce cytotoxic activity …”

Section: Introductionmentioning

confidence: 99%

“…This molecule has been the target of many chemical studies, [3][4][5][6][7][8] it has also been used as a pigment [9] showing in addition several pharmacological effects, [10][11][12][13] vg the release of mitochondrial Ca 2 + . [14] In addition, perezone and some of its derivatives are able to produce cytotoxic activity. [15][16][17][18][19] It is also appropriated to note that a theoretical study in order to explain certain stereoelectronic effects, has been published; [20] this in addition to several electronic properties reported for various aniline perezone derivates, particularly to figure out the electronic behavior related to the quinone ring.…”

Section: Introductionmentioning

confidence: 99%

Computational Characterization of Perezone, Isoperezone and their Sulfur‐Derivatives: Anti‐inflammatory Activity.

et al. 2019

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Using DFT and in silico methods a theoretical study, to verify the spectroscopically characterization, this in addition to determine the anti‐inflammatory activity of a set of eight sulfur derivatives of perezone and isoperezone was performed. In this sense, conformational studies for the target sulfurs were carried out, in order to obtain the corresponding minimum energy structures. Also, the vibrational frequencies analysis, the magnitude of 1H NMR and 13C NMR spectra for perezone, isoperezone, and its sulfur‐derivatives, obtained by the DFT/B3LYP/6‐311++G(d,p) method correlated satisfactorily with the experimental data. Moreover, the calculation of physicochemical properties, and the prediction of the anti‐inflammatory activity, employing both PASS predictor and docking studies towards COX‐2 for the target compounds, showed that Benzy perezone is a good candidate as a therapeutic agent; finally, the anti‐inflammatory activity of Benzy perezone was evaluated in vivo, showing a similar naproxen activity.

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“…This important molecule has been the target of many chemical, structural, and biological studies, e.g., its reactivity into pipitzols [3,4,5], its transformation into isoperezone [6], several green contributions [7,8], structural elucidation (NMR studies) [9,10,11]. It is important to note that it has been used as a pigment [9] highlighting several pharmacological effects [12,13,14,15], such as the release [16] of mitochondrial Ca 2+ , and finally, the ability of some of its derivatives to produce cytotoxic activity [17,18,19].…”

Section: Introductionmentioning

confidence: 99%

Green Approach Extraction of Perezone from the Roots of Acourtia platyphilla (A. Grey): A Comparison of Four Activating Modes and Supercritical Carbon Dioxide

et al. 2019

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Perezone, a sesquiterpene quinone, is a very important molecule due to its pharmacological activities in addition to the fact that it is considered to be the first secondary metabolite isolated in the new world (America–Mexico, 1852). This study aims to offer a green comparative study about the extraction of the target molecule from the roots of the vegetable specimen Acourtia platyphilla (A. Grey). The study was performed comparing five different modes of extraction: supercritical CO2, electromagnetic infrared and microwave irradiations, mechanical-wave ultrasound versus typical mantle heating procedure. An exhaustive comparative-discussion of the obtained results is provided. It is worth noting that the corresponding quantifications were established using 1H NMR, correlating appropriately the integrals of the vinylic proton H-6 of perezone with the aromatic singlet of p-dinitrobenzene employed as an internal reference. It is also important to highlight that the four presented procedures are novel modes to extract perezone. Finally, a complementary study about the solubility of the target sesquiterpene quinone related to the use of supercritical CO2 is also reported.

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Effect of perezone on arrhythmias and markers of cell injury during reperfusion in the anesthetized rat

Cited by 20 publications

References 20 publications

Expression profiling identifies epoxy anthraquinone derivative as a DNA topoisomerase inhibitor

Expression profiling identifies epoxy anthraquinone derivative as a DNA topoisomerase inhibitor

Computational Characterization of Perezone, Isoperezone and their Sulfur‐Derivatives: Anti‐inflammatory Activity.

Green Approach Extraction of Perezone from the Roots of Acourtia platyphilla (A. Grey): A Comparison of Four Activating Modes and Supercritical Carbon Dioxide

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