Tomás Torroba

• University of Burgos

Plastic waste management is a pressing ecological, social, and economic challenge. The saliva of the lepidopteran Galleria mellonella larvae is capable of oxidizing and depolymerizing polyethylene in hours at room temperature. Here, we analyze by cryo–electron microscopy (cryo-EM) G. mellonella ’s saliva directly from the native source. The three-d...

Aim: To investigate the use of synthetic preimplantation factor (sPIF) as a potential therapeutic tool for improving glucose-stimulated insulin secretion (GSIS), glucose tolerance and insulin sensitivity in the setting of diabetes. Materials and methods: We used a preclinical murine model of type 2 diabetes (T2D) induced by high-fat diet (HFD) f...

We describe the proof of concept of a portable testing setup for the detection of triacetone triperoxide (TATP), a common component in improvised explosive devices. The system allows for field testing and generation of real-time results to test for TATP vapor traces in air by simply using circulation of the air samples through the sensing mechanism...

A new series of perylene and hemicoronene diimides, obtained by visible light photocyclization, are presented, between them some remarkable examples that are soluble in only water, and give nanoparticles by self-association. Those compounds work as new fluorescent materials in water by complexation with cucurbit[7]uril, as well as selective G-quadr...

Water-soluble coronenes, that form nanoparticles by self-association, work as new fluorescent materials by complexation with cucurbit[7]uril, as well as selective turn-on fluorogenic sensors for nitroaromatic explosives with remarkable selectivity, by using only water as solvent.

Functional organic dyes play a key role in many fields, namely in biotechnology and medical diagnosis. Herein, we report two novel 2,3- and 3,4-dihydroxyphenyl substituted rosamines (3 and 4, respectively) that were successfully synthesized through a microwave-assisted protocol. The best reaction yields were obtained for rosamine 4, which also show...

New 1,2-azolylamidino complexes cis-[Ru(bipy)2(NH═C(R)az*-κ2N,N)](OTf)2 (R = Me, Ph; az* = pz, indz, dmpz) are synthesized via chloride abstraction after a subsequent base-catalyzed coupling of a nitrile with the previously coordinated 1,2-azole. The synthetic procedure allows the easy obtainment of complexes having different electronic and steric...

We describe the synthesis of fluorogenic arylureas and amides and their interaction with primary or secondary amines under air and light in organic-aqueous mixtures to give rise to a new class of persistent organic radicals, described on the basis of their electron paramagnetic resonance (EPR), as well as UV–vis, fluorescence, NMR, and quantum mech...

A structure-activity relationship (SAR) study in terms of G-quadruplex binding ability and antiproliferative activity of six fluorescent perylenemonoimide (PMIs) derivatives is reported. A positive charge seems to be the key to target G4. This study also reveals the importance of the element substitution in the potential biological activity of PMIs...

The chemistry of the heterocyclic compounds containing one nitrogen as part of the six- membered ring, as well as two oxygen atoms (dioxazines), one oxygen and one sulfur atoms (oxathiazines), or two sulfur atoms (dithiazines) has been compiled in previous editions of Comprehensive Heterocyclic Chemistry.1, 2, 3 For the present edition, this chapte...

We describe the proof of concept of a portable testing setup for the detection of triacetone triperoxide (TATP), a common component in improvised explosive devices, which will allow for field-testing...

New cis-(1,2-azole)-aquo bis(2,2'-bipyridyl)ruthenium(II) (1,2-azole (az*H) = pzH (pyrazole), dmpzH (3,5-dimethylpyrazole), and indzH (indazole)) complexes are synthesized via chlorido abstraction from cis-[Ru(bipy)2Cl(az*H)]OTf. The latter are obtained from cis-[Ru(bipy)2Cl2] after the subsequent coordination of the 1,2-azole. All the compounds ar...

The water adducts of triacetone triperoxide (TATP) have been observed by using broadband rotational spectroscopy. This work opens a new way for the gas‐phase detection of this improvised explosive. The observed clusters exhibit unusual water dynamics and rarely observed multicenter interactions. TATP‐H2O is formed from the D3 symmetry conformer of...

Triacetone triperoxide (TATP) is an explosive which, due to its ease of synthesis and difficulty of detection, is a common choice for the improvised explosive devices used by terrorists. TATP has no dipole moment so it is undetectable using conventional rotational spectroscopy. However, using supersonic jets it is possible to observe the TATP–H2O p...

Cationic fac-[Re(CO)3(pz*H)(pypzH)]OTf (pz*H = pyrazole, pzH; 3,5-dimethylpyrazole, dmpzH; indazole, indzH; 3-(2-pyridyl)pyrazole, pypzH) were obtained from fac-[ReBr(CO)3(pypzH)] by halide abstraction with AgOTf and subsequent addition of the corresponding pyrazole. Successive deprotonation with Na2CO3 and NaOH gave neutral fac-[Re(CO)3(pz*H)(pypz...

The straightforward reaction of [Ir2(ppy)4(µ-Cl)2] with an excess of aliphatic amines yields luminescent iridium complexes of general formula [IrCl(ppy)2(amine)] [amine = n-octylamine (1), t-butylamine (2), piperidine (3)]. The higher sterical hindrance of the amine in complex 2 was the responsible of its equilibrium with the starting materials. Th...

A series of new ruthenium(II) vinyl complexes has been prepared incorporating perylenemonoimide (PMI) units. This fluorogenic moiety was functionalised with terminal alkyne or pyridyl groups, allowing attachment to the metal either as a vinyl ligand or through the pyridyl nitrogen. The inherent low solubility of the perylene compounds was improved...

We report the use of a tetraborylated perylenediimide as starting material for the preparation of a tetracorannulene-perylenediimide that is able to bind up to two fullerene-C60 molecules by host-guest molecular recognition with preference over C70. Titration with fullerene-C60 is followed by a dramatic shift of the aromatic signals in 1H NMR and a...

The cyclic depsipeptide cereulide toxin it is a very well‐known potassium electrogenic ionophore particularly sensitive to pancreatic beta cells. The mechanistic details of its specific activity are unknown. Here, we describe a series of synthetic substituted cereulide potassium ionophores that cause impressive selective activation of glucose‐induc...

Quantum chemical calculations can afford valuable information to understand the chemical processes and the structural features of chemical species. This tool has become very informative, and several aspects can be discussed on the thioamides under a theoretical point of view such as the effects of structure in their planarity and some cases with de...

The synthesis of 3-(2pyridyl)pyrazole (pypzH) by conventional methods requires refluxing at high temperatures during more than 16 h, but this is reduced to two consecutive steps of 2 h at 100 °C, and of 10 min at 50 °C in a microwave (MW) assisted synthesis. Its coordination as chelating ligand to the “fac-ReIBr(CO)3” and “RuII(bipy)2” fragments al...

The preparation of new monodisperse polycrystalline palladium nanoparticles uniformly distributed on the surface of polymers, by simply adding a palladium(II) solution in water to the polymers, is described. The polymer...

5th-6th July 2018, Porto, Portugal

A new fluorescent, non‐cytotoxic perylene diimide derivative with two biotins at the peri position, PDI2B, has been synthesized. This molecule is able to interact selectively with G‐quadruplexes with scarce or no affinity towards single‐ or double‐stranded DNA. These features have enabled us to design a simple, effective, safe, cheap, and selective...

We report the development of new fluorogenic silica nanomaterials that were able to generate fluorescence in the presence of vapours of triacetone triperoxide, TATP, an improvised explosive used in terrorist...

We have developed a fluorogenic perylenediimide functionalized polyacrylate capable to generate color and fluorescence changes in the presence of triacetone triperoxide, TATP, an improvised explosive used in terrorist attacks, under solvent-free, solid state conditions. The material works by accumulating the volatile TATP until it reaches a thresho...

We report the development of new chemical probes for cereulide, a toxic metabolite produced by specific strains of Bacillus cereus, through displacement of potassium cations from a preformed specific complex and a subsequent change in the fluorescence emission. For this purpose, we designed fluorescent probes for potassium cations that were suitabl...

Supplementary

11th-15th June 2017, Dijon, France

Purpose Consumer confidence in the European food industry has been shaken by a number of recent scandals due to food fraud and accidental contamination, reminding the authors that deliberate incidents can occur. Food defence methods aim to prevent or mitigate deliberate attacks on the food supply chain but are not a legal requirement. The purpose o...

7th-8th October 2016, Sintra, Portugal

We have developed a new fluorogenic polymer capable of detecting the presence of mercury contamination in fish samples. The modified polymer emits blue light when irradiated with UV light proportional to the quantity of mercury, as MeHg⁺ or Hg²⁺, present in fish. The quantitative relation between the concentration of mercury in fish and the increas...

We have developed new functionalized polymers capable to be easily coated by gold nanoparticles, uniformly distributed on the surface of the polymers, by simply adding a gold(III) solution in water to the polymers. The polymer supported gold nanoparticles material was used as an efficient portable and reusable catalyst for Suzuki reactions in mixed...

(1)H NMR spectroscopy at 400 MHz in toluene-d8 of evaporated mixtures of lithium ethoxide and titanium(iv) isopropoxide in ethanol, used to prepare the spinel Li4Ti5O12 by the sol-gel method, may help clarify why the atomic ratio 5Li : 5Ti and not 4Li : 5Ti is the right choice to obtain the pure phase when performing hydrolysis at room temperature....

This personal account describes our contribution to the design of selective fluorogenic probes for contaminants of high environmental impact. For this purpose, we have developed a new family of highly versatile fluorogenic reagents that were able to show large differences in their fluorescence in the presence of selected analytes. They were used in...

2nd-4th September 2015, Évora, Portugal

Selected new fluorogenic probes that interact in different ways with Hg2+ and MeHg+ have been prepared and used for the chemical speciation of both cations in aqueous solution as well as in HEK293 cells. The best selective speciation of Hg2+ and MeHg+ has been achieved by in vitro approaches based on fluorogenic probes supported in cultured cells,...

Enantiopure 3-carboxamide-1,4-benzodiazepin-5-ones were synthesized via the Ugi reaction followed by the Staudinger/aza-Wittig or reduction reactions in only two steps. A complete reversal of diastereoselectivity was achieved depending on the cyclization methodology employed. The different orientation of the C3 substituent in our 3-substituted 1,4-...

26th-28th November 2014, Porto, Portugal

The reaction of N-(2-phthalimidoethyl)-N-alkylisopropylamines and S2Cl2 gave 4-N-(2-phthalimidoethyl)-N-alkylamino-5-chloro-1,2-dithiol-3-thiones that quantitatively cycloadded to dimethyl or diethyl acetylenedicarboxylate to give stable thioacid chlorides, which in turn reacted with one equivalent of aniline or a thiole to give thioanilides or a d...

8th-10th September 2014, Caparica, Portugal

Two families of regioisomeric 1,4-benzodiazepines, 4-benzyl-3H-benzo[e][1,4]diazepin-5-ones and 4-benzoyl-4,5-dihydro-3H-benzo[e][1,4]diazepines, have been synthesized through a similar Ugi/reduction cyclization sequence. Their conformation and stability depend on the position of the tautomeric imine/enamine equilibrium present in the diazepine nuc...

An array of fluorogenic probes is able to discriminate between nerve agents, sarin, soman, tabun, VX and their mimics, in water or organic solvent, by qualitative fluo-rescence patterns and quantitative multivariate analysis, thus making the system suitable for the in-the-field detection of traces of chemical warfare agents as well as to differenti...

The scandium triflate catalyzed cycloaddition reaction of polycyclic 1,2-dithiolethiones to maleimides is described. The reaction constitutes an easy approach to linear as well as branched oligomeric cis-fused dihydro[1,3]dithiolo[4,5-c]pyrrole-4,6-dione rings interconnected by 3,5-diylidenethiomorpholine-2,6-dithione or ylidene-6-thioxo[1,2]dithio...

This work describes the preparation of luminescent, high-performance aromatic polyamides. The fluorescent behaviour was achieved by preparing a diacid monomer containing a fluorescent dipicolinic acid derivative and polymerising it with commercially available aromatic diacid and diamine monomers to give polyisophthalamides. These materials can be s...

We report new indene derivatives that are good fluorogenic probes for the cyanide anion, one of which is a highly selective and sensitive fluorogenic probe for the fluorescent detection-as well as reliable quantification-of the cyanide anion in water or buffer, with a 10(3) -fold increase of fluorescence and low detection limit. It is therefore use...

Complementary regioselective synthesis of iminohydantoins from isocyanoacetamides controlled by the substituent on the amide group has been described. 4-Iminohydantoins were the major products when the starting materials were N-alkyl isocyanoamides, whereas 2-iminohydantoins were the major products with N-aryl isocyanoamides.

The transmembrane anion transport activity of a series of synthetic molecules inspired by the structure of tambjamine alkaloids can be tuned by varying the lipophilicity of the receptor, with carriers within a certain log P range performing best.

A diastereoselective synthesis of helix-forming pseudopeptidic hydantoins by an Ugi 4CC/cyclization/reduction/Ugi 4CC sequence of reactions, giving mainly the l-adduct when benzoic acids were used, is described.

We report a fluorogenic probe that is able to discriminate a range of primary or secondary biogenic amines and their natural or synthetic mimics, in water or buffer, by means of the turn-on transient generation of green fluorescence, with high quantum yields and low detection limits, thus making the system suitable for the detection of abuse drugs,...

Synthetic prodiginine obatoclax shows promise as a potential anticancer drug. This compound promotes apoptosis of cancer cells, although the mechanism of action is unclear. To date, only the inhibition of BCL-2 proteins has been proposed as a mechanism of action. To gain insight into other possible modes of action, we have studied the anion-binding...

The tambjamine alkaloids and related synthetic analogs are potent transmembrane anion tranporters promoting bicarbonate/chloride exchange in model phospholipid liposomes and discharging pH gradients in living cells.

A fluorescent probe for ω-aminoacids behaves as a molecular ruler, changing the yellow fluorescent emission into blue as a function of the distance between the terminal ammonium and the carboxylate groups, permitting the quantitative detection of ω-aminoacids, their metabolites and related drugs, such as pregabalin or gabapentin, from pharmaceutica...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The reaction of diisopropyl sulfide and S2Cl2 in chlorobenzene, in the presence of DABCO, gives 4-isopropylthio-5-isoplopyldithio-1,2-dithiole-3-thion (1) and the dimeric 5,5'-dithiobis(4-isopropylthio-1,2-dithiol-3-thione) (2). If the reaction is performed in the presence of diisopropyl disulfide at the last st-age of the reaction, disulfide 1 is...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Sequential Ugi reaction between p-substituted arylglyoxals, alkylamines, cyclohexyl isocyanide and 3-azido-(S)-2-(tert-butoxycarbonylamino)propanoic acid, followed by a Staudinger/aza-Wittig cyclization in the presence of triphenylphosphine, gave rise to enantiomerically pure N-cyclohexyl 4-alkyl-2-aryl-5-oxo-(S)-6-(tert-butoxycarbonylamino)-4,5,6,...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The synthesis of some new polysulfur-nitrogen heterocycles by cycloaddition of an ynamine to bisdithiolothiazine ketothiones or dithiones is described and the interconversion between regioisomers is studied by DFT calculations, showing that the double bond isomerizes at room temperature. This series is a new selective and sensitive chromogenic prob...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The cyclobutanone oxime 6 reacts with disulfur dichloride, N-chlorosuccinimide, and Hunig's base to give three unexpected 10 pi pseudo azulenes in low yield: the dark blue cyclopenta-1,2-dithiole 7, its red isomer 10, and the orange cyclopenta-1,2-thiazine 8. The benzo derivative 14 of oxime 6 gives an analogous benzo product 15 together with the m...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Push-pull chromophores based on 1-dicyanomethylene-2-chloro-3-aminoindene are readily synthesized. These compounds undergo dramatic colour changes in the presence of metal cations as a result of the interaction of the amino substituent with the analytes. One of these compounds is a selective copper(ii) colorimetric probe in acetonitrile solution, d...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Bicarbonate is involved in a wide range of biological processes, which include respiration, regulation of intracellular pH and fertilization. In this study we use a combination of NMR spectroscopy and ion-selective electrode techniques to show that the natural product prodigiosin, a tripyrrolic molecule produced by microorganisms such as Streptomyc...

5-Oxobenzo[e][1,4]diazepine-3-carboxamides were synthesized by sequential Ugi reaction-Staudinger/aza-Wittig cyclization. The pseudopeptidic backbone of the new benzodiazepine derivatives superimposed well with type I, I', II, and II' beta-turn motifs. The intermediate Ugi adducts were characterized as two conformers of the enol form by the correla...

A quinoline-indene derivative is described as a new highly selective and sensitive chromogenic and turn-on fluorogenic probe for the naked-eye detection of copper(II) cation in water-acetonitrile 1:1 mixture.