N-tert-Butyl and N-methyl nitrones derived from aromatic aldehydes inhibit macromolecular permeability increase induced by ischemia/reperfusion in hamsters

Dias, Ayres G.; Santos, Carlos E.V.; Cyrino, Fátima Z. G. A.; Bouskela, Eliete; Costa, Paulo R.R.

doi:10.1016/j.bmc.2009.04.004

Cited by 17 publications

(12 citation statements)

References 16 publications

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“…LQB 123 was synthesized as described in Kim et al [17] and Dias et al [18]. Stock solutions of LQB-123 were prepared in dimethyl sulfoxide (DMSO, MERCK-USA), with the final concentration of the solvent used in the experiments never exceeding 1%.…”

Section: Methodsmentioning

confidence: 99%

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Mutagenic and Cytotoxicity LQB 123 Profile: Safety and Tripanocidal Effect of a Phenyl-t-Butylnitrone Derivative

Cupello

Saraiva

Ippolito

et al. 2017

BioMed Research International

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The therapeutic options for Chagas disease are limited and its treatment presents a number of drawbacks including toxicity, drug resistance, and insufficient effectiveness against the chronic stage of the disease. Therefore, new therapeutical options are mandatory. In the present work, we evaluated the effect of a phenyl-tert-butylnitrone (PBN) derivate, LQB 123, against Trypanosoma cruzi forms. LQB 123 presented a trypanocidal effect against bloodstream trypomastigotes (IC50 = 259.4 ± 6.1 μM) and intracellular amastigotes infecting peritoneal macrophages (IC50 = 188.2 ± 47.5 μM), with no harmful effects upon the mammalian cells (CC50 values greater than 4 mM), resulting in a high selectivity index (CC50/IC50 > 20). Additionally, metacyclic trypomastigotes submitted to LQB 123 presented an IC50 of about 191.8 ± 10.5 μM and epimastigotes forms incubated with different concentrations of LQB 123 presented an inhibition of parasite growth with an IC50 of 255.1 ± 3.6 μM. Finally, we investigated the mutagenic potential of the nitrone by the Salmonella/microsome assay and observed no induction of mutagenicity even in concentrations as high as 33000 μM. Taken together, these results present a nonmutagenic compound, with trypanocidal activity against all relevant forms of T. cruzi, offering new insights into CD treatment suggesting additional in vivo tests.

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Section: Methodsmentioning

confidence: 99%

“…LQB-123 was as active as or more active than α -tocopherol, shark cartilage, and fish oil, used as references [17, 18] Thereafter, O -isoprenylated- N -methylarylnitrones analogues have been synthetized and the antineoplastic effects on human cancer cell lines (Jurkat and leukemia) were demonstrated [19]. …”

Section: Introductionmentioning

confidence: 99%

Mutagenic and Cytotoxicity LQB 123 Profile: Safety and Tripanocidal Effect of a Phenyl-t-Butylnitrone Derivative

Cupello

Saraiva

Ippolito

et al. 2017

BioMed Research International

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“…[45,266], nitrone spin traps have been widely used as protective agents in several biological models, such as I/R injury to the heart [53,267,268], brain [269,270] and lung [271], stroke [47,55,272,273] neurodegenerative diseases [274-276], cancer [54,56,277,278], ageing [248,279], visual impairment [49,280] and loss of hearing function [281-283]. In two review articles published by Floyd et al .…”

Section: Therapeutic Applications Of Nitronesmentioning

confidence: 99%

Potential Implication of The Chemical Properties and Bioactivity of Nitrone Spin Traps for Therapeutics

2012

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Nitrone therapeutics has been employed in the treatment of oxidative stress-related diseases such as neurodegeneration, cardiovascular disease and cancer. The nitrone-based compound NXY-059, which is the first drug to reach clinical trials for the treatment of acute ischemic stroke, has provided promise for the development of more robust pharmacological agents. However, the specific mechanism of nitrone bioactivity remains unclear. In this review, we present a variety of nitrone chemistry and biological activity that could be implicated for the nitrone’s pharmacological activity. The chemistries of spin trapping and spin adduct reveal insights on the possible roles of nitrones for altering cellular redox status through radical scavenging or nitric oxide donation, and their biological effects are presented. An interdisciplinary approach towards the development of novel synthetic antioxidants with improved pharmacological properties encompassing theoretical, synthetic, biochemical and in vitro/in vivo studies is covered.

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“…The formation of 11 is somewhat surprising, because both previously reported theoretical studies [20] and experimental data [21] suggest that only the substituent anti to the nitrogen lone pair migrates during this process. Because nitrone 6 exists exclusively as its Z-stereoisomer, [22] we expect both oxaziridines 7 a and 7 b to be trans-substituted. In both cases, therefore, an H atom should be at the anti position and migrate selectively.…”

mentioning

confidence: 99%

Peptide Fragment Coupling Using a Continuous‐Flow Photochemical Rearrangement of Nitrones

et al. 2013

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Go with the flow: A general approach for amide bond formation by way of a continuous‐flow photochemical rearrangement of nitrones was described (see scheme). Simple aryl‐alkyl amide bonds as well as complex peptide bonds were constructed efficiently with a residence time less than 20 minutes. A tetrapeptide was synthesized in this way and the method could be applied to peptide fragment coupling.

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N-tert-Butyl and N-methyl nitrones derived from aromatic aldehydes inhibit macromolecular permeability increase induced by ischemia/reperfusion in hamsters

Cited by 17 publications

References 16 publications

Mutagenic and Cytotoxicity LQB 123 Profile: Safety and Tripanocidal Effect of a Phenyl-t-Butylnitrone Derivative

Mutagenic and Cytotoxicity LQB 123 Profile: Safety and Tripanocidal Effect of a Phenyl-t-Butylnitrone Derivative

Potential Implication of The Chemical Properties and Bioactivity of Nitrone Spin Traps for Therapeutics

Peptide Fragment Coupling Using a Continuous‐Flow Photochemical Rearrangement of Nitrones

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