22-06-2020: Updating Operation Mode in the SeRMN – UAB

From 22-6-2020, all authorized SeRMN users can make use of the self-service mode in the 250auto, 360MHz and 400MHz spectrometers, exclusively from 9AM to 5PM, using the booking program (http://sermn.uab.cat/reserves/). The experiment request service is also active for all those samples that are not recorded in self-service mode:

    Solution NMR form: http://sct.uab.cat/sermn/peticio_servei/RMN_solucio
    Solid State NMR: http://sct.uab.cat/sermn/peticio_servei/RMN_estat_soli
MRI/MRS studies (Biospec) : http://sct.uab.cat/sermn/peticio_servei/mri_mrs
    Another Request : http://sct.uab.cat/sermn/peticio_servei/altres_solicituds

At the moment, the 250robot spectrometer is reserved exclusively for this type of work.

It is very important that the following mandatory rules are respectedt
1. Self-service exclusively from 9AM to 5PM. SeRMN access is not allowed outside of this time slot as there will be no SeRMN staff.
2. Only 1 person per machine is allowed. Always respect two meters of distance separation between people.
3. It is necessary to follow the established protocols of hygiene and safety at a personal level (mask, hand disinfection …)
4. Before and, above all, after using the keyboard and other tools to carry out the experiments (spinner, calibrator …) it is necessary to disinfect them with the hygiene material that you will find available.

Any questions or clarifications, you can contact the staff of the SeRMN who will be present from 9AM to 5PM or through the address .

Evidence of Enantiomers of Spiroglycol. Distinction by Using α,α′-Bis(trifluoromethyl)-9,10-anthracenedimethanol as a Chiral Solvating Agent and by Derivatization with Chiral Acids

Albert Virgili, Albert Granados, Carlos Jaime, Rosa Suárez-López, Teodor Parella and Eva Monteagudo

Cite this: J. Org. Chem. 2020, 85, 11, 7247–7257 https://doi.org/10.1021/acs.joc.0c00578

Herein, we perform for the first time a preliminary NMR and computational study of the spiroglycol structure. Spiroglycol is a highly symmetrical molecule, but it should be chiral due to the presence of a chiral axis. The presence of two enantiomers was demonstrated performing NMR enantiodifferentiation experiments using α,α′-bis(trifluoromethyl)-9,10-anthracenedimethanol (ABTE) as a chiral solvating agent (CSA). The addition of 0.6 equiv of ABTE allows the differentiation of several spiroglycol proton signals. The lack of resolution observed in the proton spectrum can be tackled through the corresponding 13C NMR spectrum where a significant enantiodifferentiation at the spirocarbon atom was observed. In order to physically separate both enantiomers, a SPG derivatization with camphorsulfonic acid and Mosher’s acid was performed affording the corresponding diastereoisomeric ester mixtures. Computations performed with the Gaussian16 package showed that the enantiodifferentiation is mainly due to the different compound thermodynamics stability.

COVID-19: Reobrim el SeRMN-UAB el dilluns 25 de Maig /Reopening the NMR Service from Monday 25th May

Després de més de dos mesos d’obligat tancament, el SeRMN reobrirà les seves instal.lacions a partir del proper dilluns dia 25 de Maig. Ja que s’han de mantenir certes precaucions de seguretat i higiene, començarem amb un funcionament limitat, provisional i progressiu a mida que es vagi normalitzant la situació del COVID19. Les normes bàsiques de funcionament són:

1. No hi ha autoservei. No cal fer reserva en el nostre sistema de reserves com es fa habitualment. Les mostres seran analitzades exclusivament pel personal del SeRMN.

2. Prèviament, cal fer una sol.licitud de prestació de servei per a cada mostra a través dels formularis de la nostra plana web:

    Sol.licitud RMN en solució : http://sct.uab.cat/sermn/peticio_servei/RMN_solucio
    RMN en estat sòlid : http://sct.uab.cat/sermn/peticio_servei/RMN_estat_solid
    Estudis MRI/MRS (Biospec) : http://sct.uab.cat/sermn/peticio_servei/mri_mrs
Altra Sol.licitud : http://sct.uab.cat/sermn/peticio_servei/altres_solicituds

3. Pels usuaris que treballin a l’edifici de les Facultats de Ciències i Biociències, cal portar la mostra presencialment al SeRMN en horari de matí (9AM-1PM). És important que la mostra estigui ben etiquetada i prèviament desinfectada. L’accés al SeRMN està restringit. Just a l’entrada del SeRMN hi haurà una taula de recepció per desinfectar/deixar/recuperar les mostres (veure http://sct.uab.cat/sermn/sample_delivery_provisional).

4. Degut a l’accés restringit que hi ha a l’edifici de les Facultats de Ciències i Biociències, recomanen als usuaris externs sense autorització d’accés a l’edifici (altres facultats de la UAB, instituts i empreses del PRUAB, i instituts i empreses externes al PRUAB) que es posin en contacte amb el personal del SeRMN per email o per telèfon (93 581 3785 o al 93 581 2291) per concretar el lliurament/recollida de mostres.

Per qualsevol dubte o qüestió, podeu contactar-nos a través del nostre mail institucional () o en els nostres correus personals.

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After more than two months of forced closure, the SeRMN will reopen its facilities from next Monday, May 25. Since certain safety and hygiene precautions must be maintained, we will start with a limited, provisional and progressive operation as the COVID-19 situation normalizes. The basic rules of operation are:

1-. There is no self-service. There is no need to make a reservation in our booking system as usual. Samples will be analyzed exclusively by the SeRMN staff.

2-. Previously, a request for service for each sample through the forms on our website is required:

    Solution NMR form: http://sct.uab.cat/sermn/peticio_servei/RMN_solucio
    Solid State NMR: http://sct.uab.cat/sermn/peticio_servei/RMN_estat_soli
MRI/MRS studies (Biospec) : http://sct.uab.cat/sermn/peticio_servei/mri_mrs
    Another Request : http://sct.uab.cat/sermn/peticio_servei/altres_solicituds

3.- For users working in the building of the Faculties of Sciences and Biosciences, the sample must be brought in person at the SeRMN in the morning (9 AM-1PM). It is important that the sample is well labeled and previously disinfected. The access to the SeRMN lab is restricted. Right at the entrance of the SeRMN there will be a reception table where you must disinfect / leave / recover your samples (see http://sct.uab.cat/sermn/sample_delivery_provisional).

4. Due to the restricted access to the building of the Faculties of Sciences and Biosciences, we strongly recommend to external users without authorization access to the building (other faculties of the UAB, institutes and companies of the PRUAB, and institutes and companies external to the PRUAB) that contact with the staff of the SeRMN by email or telephone (93 581 3785 or 93 581 2291) to specify the delivery of samples.

For any questions or concerns, you can contact us via our institutional email () or in our personal emails.

In vivo MRI/MRS longitudinal study of immunotherapy in Alzheimer’s

Progression of Alzheimer’s disease and effect of scFv-h3D6 immunotherapy in the 3xTg-AD mouse model: An in vivo longitudinal study using Magnetic Resonance Imaging and Spectroscopy by Güell-Bosch J, Lope-Piedrafita S, Esquerda-Canals G, Montoliu-Gaya L, and Villegas S. NMR in Biomedicine 33(5):e4263; DOI: 10.1002/nbm.4263.

Alzheimer’s disease (AD) is an incurable disease that affects most of the 47 million people estimated as living with dementia worldwide. The main histopathological hallmarks of AD are extracellular β-amyloid (Aβ) plaques and intracellular neurofibrillary tangles (NFTs) composed of hyperphosphorylated tau protein.  In recent years, Aβ-immunotherapy has been revealed as a potential tool in AD treatment. One strategy consists of using single-chain variable fragments (scFvs), which avoids the fragment crystallizable (Fc) effects that are supposed to trigger a microglial response, leading to microhemorrhages and vasogenic edemas, as evidenced in clinical trials with bapineuzumab. The scFv-h3D6 generated by our research group derives from this monoclonal antibody, which targets the N-terminal of the Aβ peptide and recognizes monomers, oligomers and fibrils.

In this study, 3xTg-AD mice were intraperitoneally and monthly treated with 100 μg of scFv-h3D6 (a dose of ~3.3 mg/kg) or PBS, from 5 to 12 months of age (-mo), the age at which the mice were sacrificed and samples collected for histological and biochemical analyses. During treatments, four monitoring sessions using magnetic resonance imaging and spectroscopy (MRI/MRS) were performed at 5, 7, 9, and 12 months of age. MRI/MRS techniques allow, in a non-invasive manner, to draw an in vivo picture of concrete aspects of the pathology and to monitor its development across time. Compared with the genetic background, 3xTg-AD mice presented a smaller volume in almost all cerebral regions and ages examined, an increase in both the intra and extracellular Aβ1-42 at 12-mo, and an inflammation process at this age, in both the hippocampus (IL-6 and mIns) and cortex (IL-6). In addition, treatment with scFv-h3D6 partially recovered the values in brain volume, and Aβ, IL-6, and mIns concentrations, among others, encouraging further studies with this antibody fragment.

Alarm Status #covid-19

Due to the alarm status by the Covid-19 the UAB’s Nuclear Magnetic Resonance Service will be temporally closed. For any questions you can contact us by email at the institutional address

Reopening the NMR Service from Monday 25th May
http://sermn.uab.cat/2020/05/reobrim-el-sermn-uab/

Measuring Long-Range Heteronuclear NMR Correlations in Natural Products

LR-HSQMBC versus LR-selHSQMBC: Enhancing the Observation ofTiny Long-Range Heteronuclear NMR Correlations

Kumar Motiram-Corral, Pau Nolis, Josep Saurí, and Teodor Parella

https://doi.org/10.1021/acs.jnatprod.0c00058

selHSQMBC

ABSTRACT:The detection of ultra-long-range (4JCHand higher) heteronuclear connectivities can complement the conventionaluse of HMBC/HSQMBC data in structure elucidation NMR studies of proton-deficient natural products, where two-bond andthree-bond correlations are usually observed. The performance of the selHSQMBC experiment with respect to its broadbandHSQMBC counterpart is evaluated. Despite its frequency-selectivity nature, selHSQMBC efficiently prevents any unwanted signalphase and intensity modulations due to passive proton−proton coupling constants typically involved in HSQMBC. As a result,selHSQMBC offers a significant sensitivity enhancement and provides pure in-phase multiplets, improving the detection levels forshort- and long-range cross-peaks corresponding to small heteronuclear coupling values. This is particularly relevant for experimentsoptimized to smallnJCHvalues (2−3 Hz), referred to as LR-selHSQMBC, where key cross-peaks that are not visible in the equivalentbroadband LR-HSQMBC spectrum can become observable in optimum conditions.

Microwave-Assisted Synthesis of SPION-Reduced Graphene Oxide Hybrids for Magnetic Resonance Imaging (MRI)

by Llenas M, Sandoval S, Costa PM, Oró-Solé J, Lope-Piedrafita S, Ballesteros B, Al-Jamal KT, Tobias G. Nanomaterials 24;9(10), 1364; DOI: 10.3390/nano9101364.

Magnetic resonance imaging (MRI) is a useful tool for disease diagnosis and treatment monitoring. Superparamagnetic iron oxide nanoparticles (SPION) show good performance as transverse relaxation (T2) contrast agents, thus facilitating the interpretation of the acquired images. Attachment of SPION onto nanocarriers prevents their agglomeration, improving the circulation time and efficiency. Graphene derivatives, such as graphene oxide (GO) and reduced graphene oxide (RGO), are appealing nanocarriers since they have both high surface area and functional moieties that make them ideal substrates for the attachment of nanoparticles. A fast, simple, and environmentally friendly microwave-assisted approach for the synthesis of SPION-RGO hybrids has been demonstrated in this study. Different iron precursor/GO ratios were used leading to SPION, with a median diameter of 7.1 nm, homogeneously distributed along the RGO surface. Good relaxivity (r2*) values were obtained in MRI studies and no significant toxicity was detected within in vitro tests following GL261 glioma and J774 macrophage-like cells for 24 h with SPION-RGO, demonstrating the applicability of the hybrids as T2-weighted MRI contrast agents.

A new strategy for the regioselective functionalization of C60 fullerenes

Supramolecular Fullerene Sponges as Catalytic Masks for Regioselective Functionalization of C60“, by Carles Fuertes-Espinosa, Cristina García-Simón, Míriam Pujals, Marc Garcia-Borràs, Laura Gómez, Teodor Parella, Judit Juanhuix, Inhar Imaz, Daniel Maspoch, Miquel Costas and Xavi Ribas.

Chem, in press (2020). DOI: 10.1016/j.chempr.2019.10.010

The supramolecular mask protocol is a significant step forward for the regioselective functionalization of fullerenes. The exquisite ability to form pure-isomer poly-functionalized C60 adducts, overcoming tedious and non-practical chromatographic separations, allows for their direct testing in solar cell prototypes. Furthermore, the supramolecular mask strategy can be applied to C70 or higher fullerenes, opening a plethora of poly-functionalized fullerene derivatives to be synthesized and tested. Moreover, apart from the nucleophilic cyclopropanations reported herein, the protocol is currently being expanded to Diels-Alder (DA), 1,3-dipolar cycloadditions and PC60BM-type cyclopropanations, thus enabling a variety of regioselective functionalization reactions. This supramolecular mask strategy can help the discovery of the next generation of improved solar cells (organic or perovskite based) or new drug candidates.

This research has been carried out in close collaboration with Dr. Xavi Ribas (from the QBIS-CAT research group of the University of Girona (UdG)), the Catalan Institute of Nanotechnology (ICN2), the ALBA-BCN synchrotron and the NMR Service of the Autonomous University of Barcelona ( UAB). The results have just been published in the online version of the prestigious CHEM scientific journal .

Removal of the synthetic hormone methyltestosterone from aqueous solution using a β-cyclodextrin/silica composite

Lucas Bragança Carvalho, Pricila Maria BatistaChagas, Tamara Rezende Marques, Angelina Razafitianamaharavo, Manuel Pelletier, Pau Nolis, Carlos Jaime, Sérgio Scherrer Thomasi, Lucianade Matos Alves Pinto.

Journal of Environmental Chemical Engineering – Available online 20 October 2019

ABSTRACT Contamination of water with steroid residues can cause a number of environmental damages, affecting exposed organisms including man. The development of technologies for treatment or removal of this type of micropollutant from water is of paramount importance. In this study, citric acid was used to functionalize β-cyclodextrin (bCD) on the silica surface generating an organic-inorganic hybrid composite for application in molecular sequestration. The functionalization percentage was high, with about 62.6% of the composite mass corresponding to the organic part of the material. 13C NMR and infrared spectroscopic analysis indicate that the functionalization mechanism occurs by an esterification reaction between the citric acid with the silanol groups from silica and the primary hydroxyls of the bCDs. Fast adsorption of the methyltestosterone steroid was observed at acid pH, with a high adsorption capacity of 11 mg g-1. The best kinetic and isotherm models fit indicated that the adsorption occurred by a physical mechanism at independent sites with the steroid molecule possibly captured by two bCDs. The removal process was spontaneous and exothermic, with the existence of weak interactions between the hormone and the composite, and its regeneration is quite fast efficient with the displacement of the complexation equilibrium. The results obtained in this study demonstrate the considerable potential of the composite for use in the treatment of wastewater containing the steroid studied, and its efficacy should be evaluated for other steroid molecules.