Molecular Rearrangement of an Aza-Scorpiand Macrocycle Induced by pH: A Computational Study

Julián-Ortiz, Jesús Vicente de; Verdejo, Begoña; Polo, Víctor; Besalú, Emili; Garcı́a-España, Enrique

doi:10.3390/ijms17071131

Cited by 9 publications

(22 citation statements)

References 22 publications

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“…Whole cell protein extraction, cytosolic protein extraction, and nuclear protein extraction were carried out according to established protocols [44,45]. Equal protein amounts were separated by polyacrylamide gel electrophoresis and transferred to a polyvinylidene difluoride membrane.…”

Section: Methodsmentioning

confidence: 99%

“…In brief, brain sections were stained with H&E or Cresyl violet solution according to standard procedures [33,44,48–50], and then mounted onto microscope slides with Permount (Thermo Fisher Scientific). Staining was visualized under a light microscope.…”

Section: Methodsmentioning

confidence: 99%

“…Immunofluorescence staining was performed according to our previously published protocols [44,50]. Briefly, brain sections (6 μm) or cultured cells were incubated with primary antibodies against 8-hydroxyguanosine (8-OHdG, Abcam), Nrf2 (1:100, Abcam), SIRT1 (1:50, Santa Cruz), caspase-3 (1:100, Cell Signaling), and NeuN (1:200, cat# MAB377, EMD Millipore, USA) overnight at 4 °C.…”

Section: Methodsmentioning

confidence: 99%

“…Two investigators blinded to sample group counted cells in six randomly selected high-power fields (400 ×) in each coronal section. The mean percentage of positive cells per section was calculated [44,49], and the final average number of positive cells was determined in four sections per animal.…”

Section: Methodsmentioning

confidence: 99%

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Cerebroprotection by salvianolic acid B after experimental subarachnoid hemorrhage occurs via Nrf2- and SIRT1-dependent pathways

Zhang

et al. 2018

Free Radical Biology and Medicine

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Salvianolic acid B (SalB), a natural polyphenolic compound extracted from the herb of Salvia miltiorrhiza, possesses antioxidant and neuroprotective properties and has been shown to be beneficial for diseases that affect vasculature and cognitive function. Here we investigated the protective effects of SalB against subarachnoid hemorrhage (SAH)-induced oxidative damage, and the involvement of underlying molecular mechanisms. In a rat model of SAH, SalB inhibited SAH-induced oxidative damage. The reduction in oxidative damage was associated with suppressed reactive oxygen species generation; decreased lipid peroxidation; and increased glutathione peroxidase, glutathione, and superoxide dismutase activities. Concomitant with the suppressed oxidative stress, SalB significantly reduced neurologic impairment, brain edema, and neural cell apoptosis after SAH. Moreover, SalB dramatically induced nuclear factor-erythroid 2-related factor 2 (Nrf2) nuclear translocation and increased expression of heme oxygenase-1 and NADPH: quinine oxidoreductase-1. In a mouse model of SAH, Nrf2 knockout significantly reversed the antioxidant effects of SalB against SAH. Additionally, SalB activated sirtuin 1 (SIRT1) expression, whereas SIRT1-specific inhibitor sirtinol pretreatment significantly suppressed SalB-induced SIRT1 activation and Nrf2 expression. Sirtinol pretreatment also reversed the antioxidant and neuroprotective effects of SalB. In primary cultured cortical neurons, SalB suppressed oxidative damage, alleviated neuronal degeneration, and improved cell viability. These beneficial effects were associated with activation of the SIRT1 and Nrf2 signaling pathway and were reversed by sirtinol treatment. Taken together, these in vivo and in vitro findings suggest that SalB provides protection against SAH-triggered oxidative damage by upregulating the Nrf2 antioxidant signaling pathway, which may be modulated by SIRT1 activation.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Cerebroprotection by salvianolic acid B after experimental subarachnoid hemorrhage occurs via Nrf2- and SIRT1-dependent pathways

Zhang

et al. 2018

Free Radical Biology and Medicine

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“…A preliminary version of the present paper can be found in Internet [9]. The simplified structures presented in Figure 1 were taken from X-ray geometries.…”

Section: Introductionmentioning

confidence: 99%

Molecular Rearrangement of an Aza-Scorpiand Macrocycle Induced by pH. A Computational Study

Julián-Ortiz

Verdejo

Besalú

et al. 2015

Proceedings of MOL2NET, International Conference on Multidisciplinary Sciences

Self Cite

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Rearrangements and their control are a hot topic in supramolecular chemistry due to the possibilities that these phenomena open in the design of synthetic receptors and molecular machines. Macrocycle aza-scorpiands constitute an interesting system that can reorganize their spatial structure depending on pH variations or the presence of metal cations. In this study, the relative stabilities of these conformations were predicted computationally by semi-empirical and density functional theory approximations, and the reorganization from closed to open conformations was simulated by using the Monte Carlo multiple minimum method.

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Molecular Switches for any pH: A Systematic Study of the Versatile Coordination Behaviour of Cyclam Scorpionands

Lau

Clegg

Price

et al. 2017

Chemistry A European J

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Molecular switches have many potential applications in nanoscience and biomedicine. Transition metal complexes that can be switched from an inert, unreactive state to a catalytically active one by a simple change in conditions (e.g. pH shift) or by binding to a specific biomolecular target-so-called target-activated metal complexes (TAMCs)-hold particular allure as a means of harnessing the potent but at times indiscriminate reactivity of metal-based drugs. Towards this goal, we have prepared a series of ten structurally related ligands, each of which bears a different pendant side-arm functional group appended to a common macrocyclic core, along with copper(II) and nickel(II) complexes of these cyclam-based "molecular scorpionands". X-ray crystal structures reveal a variety of binding modes between pendant side-arm and metal centre that depend on the constituent donor atoms. To investigate the switchability of side-arm coordination in solution, spectrophotometric pH titrations were carried out for all 20 metal complexes. The majority of the complexes undergo spectroscopic changes that are consistent with a switch in pendant coordination state at a specific pH. This ligand series represents a comprehensive model platform from which to build pH-switchable metal complexes for applications in nanoscience and biomedicine.

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Molecular Rearrangement of an Aza-Scorpiand Macrocycle Induced by pH: A Computational Study

Cited by 9 publications

References 22 publications

Cerebroprotection by salvianolic acid B after experimental subarachnoid hemorrhage occurs via Nrf2- and SIRT1-dependent pathways

Cerebroprotection by salvianolic acid B after experimental subarachnoid hemorrhage occurs via Nrf2- and SIRT1-dependent pathways

Molecular Rearrangement of an Aza-Scorpiand Macrocycle Induced by pH. A Computational Study

Molecular Switches for any pH: A Systematic Study of the Versatile Coordination Behaviour of Cyclam Scorpionands

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