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Dr. Francesca Ghirga
Center For Life Nano [email protected], Istituto Italiano di Tecnologia, Rome 00161, Italy

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0 secondary metabolites
0 Natural products chemistry
0 targeted therapy
0 Natural products as anticancer agents
0 Antibiotic resistance modulation by natural products

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Natural products as anticancer agents
secondary metabolites

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Review
Published: 04 June 2021 in Cancers
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Glioblastoma (GBM) is the most aggressive form of glioma tumor in adult brain. Among the numerous factors responsible for GBM cell proliferation and invasion, neurotransmitters such as dopamine, serotonin and glutamate can play key roles. Studies performed in mice housed in germ-free (GF) conditions demonstrated the relevance of the gut-brain axis in a number of physiological and pathological conditions. The gut–brain communication is made possible by vagal/nervous and blood/lymphatic routes and pave the way for reciprocal modulation of functions. The gut microbiota produces and consumes a wide range of molecules, including neurotransmitters (dopamine, norepinephrine, serotonin, gamma-aminobutyric acid [GABA], and glutamate) that reach their cellular targets through the bloodstream. Growing evidence in animals suggests that modulation of these neurotransmitters by the microbiota impacts host neurophysiology and behavior, and affects neural cell progenitors and glial cells, along with having effects on tumor cell growth. In this review we propose a new perspective connecting neurotransmitter modulation by gut microbiota to glioma progression.

ACS Style

Giuseppina D’Alessandro; Clotilde Lauro; Deborah Quaglio; Francesca Ghirga; Bruno Botta; Flavia Trettel; Cristina Limatola. Neuro-Signals from Gut Microbiota: Perspectives for Brain Glioma. Cancers 2021, 13, 2810 .

AMA Style

Giuseppina D’Alessandro, Clotilde Lauro, Deborah Quaglio, Francesca Ghirga, Bruno Botta, Flavia Trettel, Cristina Limatola. Neuro-Signals from Gut Microbiota: Perspectives for Brain Glioma. Cancers. 2021; 13 (11):2810.

Chicago/Turabian Style

Giuseppina D’Alessandro; Clotilde Lauro; Deborah Quaglio; Francesca Ghirga; Bruno Botta; Flavia Trettel; Cristina Limatola. 2021. "Neuro-Signals from Gut Microbiota: Perspectives for Brain Glioma." Cancers 13, no. 11: 2810.

Journal article
Published: 14 May 2021 in Molecules
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The chemical profile of the female inflorescence extracts from seven Cannabis sativa L. dioecious cultivars (Carmagnola, Fibranova, Eletta Campana, Antal, Tiborszallasi, Kompolti, and Tisza) was monitored at three harvesting stages (4, 14, and 30 September), reaching from the beginning of flowering to end of flowering/beginning of seed formation, using untargeted nuclear magnetic resonance (NMR) and targeted (ultra-high-performance liquid chromatography (UHPLC) and spectrophotometry) analyses. The tetrahydrocannabinol content was always below the legal limits (<0.6%) in all the analyzed samples. The NMR metabolite profile (sugars, organic acids, amino acids, and minor compounds) subjected to principal components analysis (PCA) showed a strong variability according to the harvesting stages: samples harvested in stage I were characterized by a high content of sucrose and myo-inositol, whereas the ones harvested in stage II showed high levels of succinic acid, alanine, valine, isoleucine, phenylalanine, and threonine. Samples harvested in stage III were characterized by high levels of glucose, fructose, choline, trigonelline, malic acid, formic acid, and some amino acids. The ratio between chlorophylls and carotenoids content indicated that all plants grew up exposed to the sun, the Eletta Campana cultivar having the highest pigment amount. Tiborszallasi cultivar showed the highest polyphenol content. The highest antioxidant activity was generally observed in stage II. All these results suggested that the Cannabis sativa L. inflorescences of each analyzed dioecious hemp cultivar presented a peculiar chemical profile affected by the harvesting stage. This information could be useful for producers and industries to harvest inflorescences in the appropriate stage to obtain samples with a peculiar chemical profile suitable for proper applications.

ACS Style

Mattia Spano; Giacomo Di Matteo; Cinzia Ingallina; Bruno Botta; Deborah Quaglio; Francesca Ghirga; Silvia Balducci; Silvia Cammarone; Enio Campiglia; Anna Giusti; Giuliana Vinci; Mattia Rapa; Salvatore Ciano; Luisa Mannina; Anatoly Sobolev. A Multimethodological Characterization of Cannabis sativa L. Inflorescences from Seven Dioecious Cultivars Grown in Italy: The Effect of Different Harvesting Stages. Molecules 2021, 26, 2912 .

AMA Style

Mattia Spano, Giacomo Di Matteo, Cinzia Ingallina, Bruno Botta, Deborah Quaglio, Francesca Ghirga, Silvia Balducci, Silvia Cammarone, Enio Campiglia, Anna Giusti, Giuliana Vinci, Mattia Rapa, Salvatore Ciano, Luisa Mannina, Anatoly Sobolev. A Multimethodological Characterization of Cannabis sativa L. Inflorescences from Seven Dioecious Cultivars Grown in Italy: The Effect of Different Harvesting Stages. Molecules. 2021; 26 (10):2912.

Chicago/Turabian Style

Mattia Spano; Giacomo Di Matteo; Cinzia Ingallina; Bruno Botta; Deborah Quaglio; Francesca Ghirga; Silvia Balducci; Silvia Cammarone; Enio Campiglia; Anna Giusti; Giuliana Vinci; Mattia Rapa; Salvatore Ciano; Luisa Mannina; Anatoly Sobolev. 2021. "A Multimethodological Characterization of Cannabis sativa L. Inflorescences from Seven Dioecious Cultivars Grown in Italy: The Effect of Different Harvesting Stages." Molecules 26, no. 10: 2912.

Review article
Published: 11 December 2020 in Organic Chemistry Frontiers
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We review the successful application of computer-aided methods to screen a unique and high-diversity in house collection library composed of around 1000 individual natural products.

ACS Style

Francesca Ghirga; Deborah Quaglio; Mattia Mori; Silvia Cammarone; Antonia Iazzetti; Antonella Goggiamani; Cinzia Ingallina; Bruno Botta; Andrea Calcaterra. A unique high-diversity natural product collection as a reservoir of new therapeutic leads. Organic Chemistry Frontiers 2020, 8, 996 -1025.

AMA Style

Francesca Ghirga, Deborah Quaglio, Mattia Mori, Silvia Cammarone, Antonia Iazzetti, Antonella Goggiamani, Cinzia Ingallina, Bruno Botta, Andrea Calcaterra. A unique high-diversity natural product collection as a reservoir of new therapeutic leads. Organic Chemistry Frontiers. 2020; 8 (5):996-1025.

Chicago/Turabian Style

Francesca Ghirga; Deborah Quaglio; Mattia Mori; Silvia Cammarone; Antonia Iazzetti; Antonella Goggiamani; Cinzia Ingallina; Bruno Botta; Andrea Calcaterra. 2020. "A unique high-diversity natural product collection as a reservoir of new therapeutic leads." Organic Chemistry Frontiers 8, no. 5: 996-1025.

Journal article
Published: 26 November 2020 in Cancer Letters
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Aberrant activation of the Hedgehog (Hh) pathway leads to the development of several tumors, including medulloblastoma (MB), the most common pediatric brain malignancy. Hh inhibitors acting on GLI1, the final effector of Hh signaling, offer a valuable opportunity to overcome the pitfalls of the existing therapies to treat Hh-driven cancers. In this study, the toxicity, delivery, biodistribution, and anticancer efficacy of Glabrescione B (GlaB), a selective GLI1 inhibitor, were investigated in preclinical models of Hh-dependent MB. To overcome its poor water solubility, GlaB was formulated with a self-assembling amphiphilic polymer forming micelles, called mPEG5kDa-cholane. mPEG5kDa-cholane/GlaB showed high drug loading and stability, low cytotoxicity, and long permanence in the bloodstream. We found that mPEG5kDa-cholane efficiently enhanced the solubility of GlaB, thus avoiding the use of organic solvents. mPEG5kDa-cholane/GlaB possesses favorable pharmacokinetics and negligible toxicity. Remarkably, GlaB encapsulated in mPEG5kDa-cholane micelles was delivered through the blood-brain barrier and drastically inhibited tumor growth in both allograft and orthotopic models of Hh-dependent MB. Our findings reveal that mPEG5kDa-cholane/GlaB is a good candidate for the treatment of Hh-dependent tumors and provide relevant implications for the translation of GlaB into clinical practice.

ACS Style

Paola Infante; Alessio Malfanti; Deborah Quaglio; Silvia Balducci; Sara De Martin; Francesca Bufalieri; Francesca Mastrotto; Irene Basili; Mariangela Garofalo; Ludovica Lospinoso Severini; Mattia Mori; Isabella Manni; Marta Moretti; Carmine Nicoletti; Giulia Piaggio; Paolo Caliceti; Bruno Botta; Francesca Ghirga; Stefano Salmaso; Lucia Di Marcotullio. Glabrescione B delivery by self-assembling micelles efficiently inhibits tumor growth in preclinical models of Hedgehog-dependent medulloblastoma. Cancer Letters 2020, 499, 220 -231.

AMA Style

Paola Infante, Alessio Malfanti, Deborah Quaglio, Silvia Balducci, Sara De Martin, Francesca Bufalieri, Francesca Mastrotto, Irene Basili, Mariangela Garofalo, Ludovica Lospinoso Severini, Mattia Mori, Isabella Manni, Marta Moretti, Carmine Nicoletti, Giulia Piaggio, Paolo Caliceti, Bruno Botta, Francesca Ghirga, Stefano Salmaso, Lucia Di Marcotullio. Glabrescione B delivery by self-assembling micelles efficiently inhibits tumor growth in preclinical models of Hedgehog-dependent medulloblastoma. Cancer Letters. 2020; 499 ():220-231.

Chicago/Turabian Style

Paola Infante; Alessio Malfanti; Deborah Quaglio; Silvia Balducci; Sara De Martin; Francesca Bufalieri; Francesca Mastrotto; Irene Basili; Mariangela Garofalo; Ludovica Lospinoso Severini; Mattia Mori; Isabella Manni; Marta Moretti; Carmine Nicoletti; Giulia Piaggio; Paolo Caliceti; Bruno Botta; Francesca Ghirga; Stefano Salmaso; Lucia Di Marcotullio. 2020. "Glabrescione B delivery by self-assembling micelles efficiently inhibits tumor growth in preclinical models of Hedgehog-dependent medulloblastoma." Cancer Letters 499, no. : 220-231.

Review
Published: 09 August 2020 in Molecules
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Antibiotic resistance is now considered a worldwide problem that puts public health at risk. The onset of bacterial strains resistant to conventional antibiotics and the scarcity of new drugs have prompted scientific research to re-evaluate natural products as molecules with high biological and chemical potential. A class of natural compounds of significant importance is represented by alkaloids derived from higher plants. In this review, we have collected data obtained from various research groups on the antimicrobial activities of these alkaloids against conventional antibiotic-resistant strains. In addition, the structure–function relationship was described and commented on, highlighting the high potential of alkaloids as antimicrobials.

ACS Style

Bruno Casciaro; Laura Mangiardi; Floriana Cappiello; Isabella Romeo; Maria Rosa Loffredo; Antonia Iazzetti; Andrea Calcaterra; Antonella Goggiamani; Francesca Ghirga; Maria Luisa Mangoni; Bruno Botta; Deborah Quaglio. Naturally-Occurring Alkaloids of Plant Origin as Potential Antimicrobials against Antibiotic-Resistant Infections. Molecules 2020, 25, 3619 .

AMA Style

Bruno Casciaro, Laura Mangiardi, Floriana Cappiello, Isabella Romeo, Maria Rosa Loffredo, Antonia Iazzetti, Andrea Calcaterra, Antonella Goggiamani, Francesca Ghirga, Maria Luisa Mangoni, Bruno Botta, Deborah Quaglio. Naturally-Occurring Alkaloids of Plant Origin as Potential Antimicrobials against Antibiotic-Resistant Infections. Molecules. 2020; 25 (16):3619.

Chicago/Turabian Style

Bruno Casciaro; Laura Mangiardi; Floriana Cappiello; Isabella Romeo; Maria Rosa Loffredo; Antonia Iazzetti; Andrea Calcaterra; Antonella Goggiamani; Francesca Ghirga; Maria Luisa Mangoni; Bruno Botta; Deborah Quaglio. 2020. "Naturally-Occurring Alkaloids of Plant Origin as Potential Antimicrobials against Antibiotic-Resistant Infections." Molecules 25, no. 16: 3619.

Research article
Published: 27 July 2020 in The Journal of Organic Chemistry
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Colistin is a last-resort antibiotic for treatment of multidrug resistant Gram-negative bacterial infections. Recently, a natural ent-beyerene diterpene was identified as a promising inhibitor of the enzyme responsible for colistin re-sistance mediated by lipid A aminoarabinosylation, in Gram-negative bacteria, namely ArnT (undecaprenyl phospha-te-alpha-4-amino-4-deoxy-L-arabinose arabinosyl transferase). Here, semi-synthetic analogs of hit were designed, synthetized and tested against colistin-resistant Pseudomonas aeruginosa strains including clinical isolates, to exploit the versatility of the diterpene scaffold. Microbiological assays coupled with molecular modeling indicated that for a more efficient colistin adjuvant activity, likely resulting from inhibition of the ArnT activity by the selected com-pounds and therefore from their interaction with the catalytic site of ArnT, an ent-beyerane scaffold is required along with an oxalate like group at C-18/C-19, or a sugar residue at C-19 to resemble L-Ara4N. The ent-beyerane skeleton is identified for the first time as a privileged scaffold for further cost-effective development of valuable colistin re-sistance inhibitors.

ACS Style

Deborah Quaglio; Maria Luisa Mangoni; Roberta Stefanelli; Silvia Corradi; Bruno Casciaro; Valeria Vergine; Federica Lucantoni; Luca Cavinato; Silvia Cammarone; Maria Rosa Loffredo; Floriana Cappiello; Andrea Calcaterra; Silvia Erazo; Francesca Ghirga; Mattia Mori; Francesco Imperi; Fiorentina Ascenzioni; Bruno Botta. ent-Beyerane Diterpenes as a Key Platform for the Development of ArnT-Mediated Colistin Resistance Inhibitors. The Journal of Organic Chemistry 2020, 85, 10891 -10901.

AMA Style

Deborah Quaglio, Maria Luisa Mangoni, Roberta Stefanelli, Silvia Corradi, Bruno Casciaro, Valeria Vergine, Federica Lucantoni, Luca Cavinato, Silvia Cammarone, Maria Rosa Loffredo, Floriana Cappiello, Andrea Calcaterra, Silvia Erazo, Francesca Ghirga, Mattia Mori, Francesco Imperi, Fiorentina Ascenzioni, Bruno Botta. ent-Beyerane Diterpenes as a Key Platform for the Development of ArnT-Mediated Colistin Resistance Inhibitors. The Journal of Organic Chemistry. 2020; 85 (16):10891-10901.

Chicago/Turabian Style

Deborah Quaglio; Maria Luisa Mangoni; Roberta Stefanelli; Silvia Corradi; Bruno Casciaro; Valeria Vergine; Federica Lucantoni; Luca Cavinato; Silvia Cammarone; Maria Rosa Loffredo; Floriana Cappiello; Andrea Calcaterra; Silvia Erazo; Francesca Ghirga; Mattia Mori; Francesco Imperi; Fiorentina Ascenzioni; Bruno Botta. 2020. "ent-Beyerane Diterpenes as a Key Platform for the Development of ArnT-Mediated Colistin Resistance Inhibitors." The Journal of Organic Chemistry 85, no. 16: 10891-10901.

Review
Published: 13 June 2020 in Antibiotics
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The discovery of antibiotics has revolutionized the medicine and treatment of microbial infections. However, the current scenario has highlighted the difficulties in marketing new antibiotics and an exponential increase in the appearance of resistant strains. On the other hand, research in the field of drug-discovery has revaluated the potential of natural products as a unique source for new biologically active molecules and scaffolds for the medicinal chemistry. In this review, we first contextualized the worldwide problem of antibiotic resistance and the importance that natural products of plant origin acquire as a source of new lead compounds. We then focused on terpenes and their potential development as antimicrobials, highlighting those studies that showed an activity against conventional antibiotic-resistant strains.

ACS Style

Floriana Cappiello; Maria Rosa Loffredo; Cristina Del Plato; Silvia Cammarone; Bruno Casciaro; Deborah Quaglio; Maria Luisa Mangoni; Bruno Botta; Francesca Ghirga. The Revaluation of Plant-Derived Terpenes to Fight Antibiotic-Resistant Infections. Antibiotics 2020, 9, 1 .

AMA Style

Floriana Cappiello, Maria Rosa Loffredo, Cristina Del Plato, Silvia Cammarone, Bruno Casciaro, Deborah Quaglio, Maria Luisa Mangoni, Bruno Botta, Francesca Ghirga. The Revaluation of Plant-Derived Terpenes to Fight Antibiotic-Resistant Infections. Antibiotics. 2020; 9 (6):1.

Chicago/Turabian Style

Floriana Cappiello; Maria Rosa Loffredo; Cristina Del Plato; Silvia Cammarone; Bruno Casciaro; Deborah Quaglio; Maria Luisa Mangoni; Bruno Botta; Francesca Ghirga. 2020. "The Revaluation of Plant-Derived Terpenes to Fight Antibiotic-Resistant Infections." Antibiotics 9, no. 6: 1.

Journal article
Published: 29 April 2020 in Current Protein & Peptide Science
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Cationic antimicrobial peptides (AMPs) are an interesting class of gene-encoded molecules endowed with a broad-spectrum of anti-infective activity and immunomodulatory properties. They represent promising candidates for the development of new antibiotics, mainly due to their membraneperturbing mechanism of action that very rarely induces microbial resistance. However, bringing AMPs into the clinical field is hampered by some intrinsic limitations, encompassing low peptide bioavailability at the target site and high peptide susceptibility to proteolytic degradation. In this regard, nanotechnologies represent an innovative strategy to circumvent these issues. According to the literature, a large variety of nanoparticulate systems have been employed for drug-delivery, bioimaging, biosensors or nanoantibiotics. The possibility of conjugating different types of molecules, including AMPs, to these systems, allows the production of nanoformulations able to enhance the biological profile of the compound while reducing its cytotoxicity and prolonging its residence time. In this minireview, inorganic gold nanoparticles (NPs) and biodegradable polymeric NPs made of poly(lactide-coglycolide) are described with particular emphasis on examples of the conjugation of AMPs to them, to highlight the great potential of such nanoformulations as alternative antimicrobials.

ACS Style

Bruno Casciaro; Francesca Ghirga; Deborah Quaglio; Maria Luisa Mangoni. Inorganic Gold and Polymeric Poly(Lactide-co-glycolide) Nanoparticles as Novel Strategies to Ameliorate the Biological Properties of Antimicrobial Peptides. Current Protein & Peptide Science 2020, 21, 429 -438.

AMA Style

Bruno Casciaro, Francesca Ghirga, Deborah Quaglio, Maria Luisa Mangoni. Inorganic Gold and Polymeric Poly(Lactide-co-glycolide) Nanoparticles as Novel Strategies to Ameliorate the Biological Properties of Antimicrobial Peptides. Current Protein & Peptide Science. 2020; 21 (4):429-438.

Chicago/Turabian Style

Bruno Casciaro; Francesca Ghirga; Deborah Quaglio; Maria Luisa Mangoni. 2020. "Inorganic Gold and Polymeric Poly(Lactide-co-glycolide) Nanoparticles as Novel Strategies to Ameliorate the Biological Properties of Antimicrobial Peptides." Current Protein & Peptide Science 21, no. 4: 429-438.

Journal article
Published: 20 April 2020 in Molecules
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The chemical composition of the inflorescences from four Cannabis sativa L. monoecious cultivars (Ferimon, Uso-31, Felina 32 and Fedora 17), recently introduced in the Lazio Region, was monitored over the season from June to September giving indications on their sensorial, pharmaceutical/nutraceutical proprieties. Both untargeted (NMR) and targeted (GC/MS, UHPLC, HPLC-PDA/FD and spectrophotometry) analyses were carried out to identify and quantify compounds of different classes (sugars, organic acids, amino acids, cannabinoids, terpenoids, phenols, tannins, flavonoids and biogenic amines). All cultivars in each harvesting period showed a THC content below the Italian legal limit, although in general THC content increased over the season. Citric acid, malic acid and glucose showed the highest content in the late flowering period, whereas the content of proline drastically decreased after June in all cultivars. Neophytadiene, nerolidol and chlorogenic acid were quantified only in Felina 32 cultivar, characterized also by a very high content of flavonoids, whereas alloaromadendrene and trans-cinnamic acid were detected only in Uso-31 cultivar. Naringenin and naringin were present only in Fedora 17 and Ferimon cultivars, respectively. Moreover, Ferimon had the highest concentration of biogenic amines, especially in July and August. Cadaverine was present in all cultivars but only in September. These results suggest that the chemical composition of Cannabis sativa L. inflorescences depends on the cultivar and on the harvesting period. Producers can use this information as a guide to obtain inflorescences with peculiar chemical characteristics according to the specific use.

ACS Style

Cinzia Ingallina; Anatoly P. Sobolev; Simone Circi; Mattia Spano; Caterina Fraschetti; Antonello Filippi; Antonella Di Sotto; Silvia Di Giacomo; Giulia Mazzoccanti; Francesco Gasparrini; Deborah Quaglio; Enio Campiglia; Simone Carradori; Marcello Locatelli; Giuliana Vinci; Mattia Rapa; Salvatore Ciano; Anna Maria Giusti; Bruno Botta; Francesca Ghirga; Donatella Capitani; Luisa Mannina. Cannabis sativa L. Inflorescences from Monoecious Cultivars Grown in Central Italy: An Untargeted Chemical Characterization from Early Flowering to Ripening. Molecules 2020, 25, 1908 .

AMA Style

Cinzia Ingallina, Anatoly P. Sobolev, Simone Circi, Mattia Spano, Caterina Fraschetti, Antonello Filippi, Antonella Di Sotto, Silvia Di Giacomo, Giulia Mazzoccanti, Francesco Gasparrini, Deborah Quaglio, Enio Campiglia, Simone Carradori, Marcello Locatelli, Giuliana Vinci, Mattia Rapa, Salvatore Ciano, Anna Maria Giusti, Bruno Botta, Francesca Ghirga, Donatella Capitani, Luisa Mannina. Cannabis sativa L. Inflorescences from Monoecious Cultivars Grown in Central Italy: An Untargeted Chemical Characterization from Early Flowering to Ripening. Molecules. 2020; 25 (8):1908.

Chicago/Turabian Style

Cinzia Ingallina; Anatoly P. Sobolev; Simone Circi; Mattia Spano; Caterina Fraschetti; Antonello Filippi; Antonella Di Sotto; Silvia Di Giacomo; Giulia Mazzoccanti; Francesco Gasparrini; Deborah Quaglio; Enio Campiglia; Simone Carradori; Marcello Locatelli; Giuliana Vinci; Mattia Rapa; Salvatore Ciano; Anna Maria Giusti; Bruno Botta; Francesca Ghirga; Donatella Capitani; Luisa Mannina. 2020. "Cannabis sativa L. Inflorescences from Monoecious Cultivars Grown in Central Italy: An Untargeted Chemical Characterization from Early Flowering to Ripening." Molecules 25, no. 8: 1908.

Rapid communication
Published: 30 January 2020 in ACS Medicinal Chemistry Letters
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Novel diterpenoids were isolated from the extracts of Fabiana densa var. ramulosa and found to display a selective activity against Gram-positive bacterial strains with negligible cytotoxicity toward human keratinocytes. This study highlighted the role played by the acidic group at C18 of the tetracyclic ent-beyerene scaffold for antibacterial effects and how the length and flexibility of the alkyl chain between the two carbonyl groups are crucial factors to increase the antimicrobial activity of the molecules, supporting the development of natural products from F. densa and their derivatives for treatment of microbial infections.

ACS Style

Deborah Quaglio; Silvia Corradi; Silvia Erazo; Valeria Vergine; Simone Berardozzi; Fabio Sciubba; Floriana Cappiello; Maria Elisa Crestoni; Fiorentina Ascenzioni; Francesco Imperi; Franco Delle Monache; Mattia Mori; Maria Rosa Loffredo; Francesca Ghirga; Bruno Casciaro; Bruno Botta; Maria Luisa Mangoni. Structural Elucidation and Antimicrobial Characterization of Novel Diterpenoids from Fabiana densa var. ramulosa. ACS Medicinal Chemistry Letters 2020, 11, 760 -765.

AMA Style

Deborah Quaglio, Silvia Corradi, Silvia Erazo, Valeria Vergine, Simone Berardozzi, Fabio Sciubba, Floriana Cappiello, Maria Elisa Crestoni, Fiorentina Ascenzioni, Francesco Imperi, Franco Delle Monache, Mattia Mori, Maria Rosa Loffredo, Francesca Ghirga, Bruno Casciaro, Bruno Botta, Maria Luisa Mangoni. Structural Elucidation and Antimicrobial Characterization of Novel Diterpenoids from Fabiana densa var. ramulosa. ACS Medicinal Chemistry Letters. 2020; 11 (5):760-765.

Chicago/Turabian Style

Deborah Quaglio; Silvia Corradi; Silvia Erazo; Valeria Vergine; Simone Berardozzi; Fabio Sciubba; Floriana Cappiello; Maria Elisa Crestoni; Fiorentina Ascenzioni; Francesco Imperi; Franco Delle Monache; Mattia Mori; Maria Rosa Loffredo; Francesca Ghirga; Bruno Casciaro; Bruno Botta; Maria Luisa Mangoni. 2020. "Structural Elucidation and Antimicrobial Characterization of Novel Diterpenoids from Fabiana densa var. ramulosa." ACS Medicinal Chemistry Letters 11, no. 5: 760-765.

Review
Published: 19 January 2020 in Molecules
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The Pictet-Spengler reaction (P-S) is one of the most direct, efficient, and variable synthetic method for the construction of privileged pharmacophores such as tetrahydro-isoquinolines (THIQs), tetrahydro-β-carbolines (THBCs), and polyheterocyclic frameworks. In the lustro (five-year period) following its centenary birthday, the P-S reaction did not exit the stage but it came up again on limelight with new features. This review focuses on the interesting results achieved in this period (2011–2015), analyzing the versatility of this reaction. Classic P-S was reported in the total synthesis of complex alkaloids, in combination with chiral catalysts as well as for the generation of libraries of compounds in medicinal chemistry. The P-S has been used also in tandem reactions, with the sequences including ring closing metathesis, isomerization, Michael addition, and Gold- or Brønsted acid-catalyzed N-acyliminium cyclization. Moreover, the combination of P-S reaction with Ugi multicomponent reaction has been exploited for the construction of highly complex polycyclic architectures in few steps and high yields. The P-S reaction has also been successfully employed in solid-phase synthesis, affording products with different structures, including peptidomimetics, synthetic heterocycles, and natural compounds. Finally, the enzymatic version of P-S has been reported for biosynthesis, biotransformations, and bioconjugations.

ACS Style

Andrea Calcaterra; Laura Mangiardi; Giuliano Delle Monache; Deborah Quaglio; Silvia Balducci; Simone Berardozzi; Antonia Iazzetti; Roberta Franzini; Bruno Botta; Francesca Ghirga. The Pictet-Spengler Reaction Updates Its Habits. Molecules 2020, 25, 414 .

AMA Style

Andrea Calcaterra, Laura Mangiardi, Giuliano Delle Monache, Deborah Quaglio, Silvia Balducci, Simone Berardozzi, Antonia Iazzetti, Roberta Franzini, Bruno Botta, Francesca Ghirga. The Pictet-Spengler Reaction Updates Its Habits. Molecules. 2020; 25 (2):414.

Chicago/Turabian Style

Andrea Calcaterra; Laura Mangiardi; Giuliano Delle Monache; Deborah Quaglio; Silvia Balducci; Simone Berardozzi; Antonia Iazzetti; Roberta Franzini; Bruno Botta; Francesca Ghirga. 2020. "The Pictet-Spengler Reaction Updates Its Habits." Molecules 25, no. 2: 414.

Journals
Published: 09 November 2019 in Organic & Biomolecular Chemistry
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A regioselective intramolecular hydroarylation of 7-(prop-2-yn-1-yloxy)-2H-chromen-2-one derivatives to afford 10-substituted-2H,8H-pyrano[2,3-f]chromen-2-ones by means of Au(i) catalysis.

ACS Style

Antonio Arcadi; Alessia Ciogli; Giancarlo Fabrizi; Andrea Fochetti; Roberta Franzini; Francesca Ghirga; Antonella Goggiamani; Antonia Iazzetti. Synthesis of pyrano[2,3-f]chromen-2-ones vs. pyrano[3,2-g]chromen-2-ones through site controlled gold-catalyzed annulations. Organic & Biomolecular Chemistry 2019, 17, 10065 -10072.

AMA Style

Antonio Arcadi, Alessia Ciogli, Giancarlo Fabrizi, Andrea Fochetti, Roberta Franzini, Francesca Ghirga, Antonella Goggiamani, Antonia Iazzetti. Synthesis of pyrano[2,3-f]chromen-2-ones vs. pyrano[3,2-g]chromen-2-ones through site controlled gold-catalyzed annulations. Organic & Biomolecular Chemistry. 2019; 17 (47):10065-10072.

Chicago/Turabian Style

Antonio Arcadi; Alessia Ciogli; Giancarlo Fabrizi; Andrea Fochetti; Roberta Franzini; Francesca Ghirga; Antonella Goggiamani; Antonia Iazzetti. 2019. "Synthesis of pyrano[2,3-f]chromen-2-ones vs. pyrano[3,2-g]chromen-2-ones through site controlled gold-catalyzed annulations." Organic & Biomolecular Chemistry 17, no. 47: 10065-10072.

Journal article
Published: 09 October 2019 in Cancers
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: Pharmacological Hedgehog (Hh) pathway inhibition has emerged as a valuable anticancer strategy. A number of small molecules able to block the pathway at the upstream receptor Smoothened (Smo) or the downstream effector glioma-associated oncogene 1 (Gli1) has been designed and developed. In a recent study, we exploited the high versatility of the natural isoflavone scaffold for targeting the Hh signaling pathway at multiple levels showing that the simultaneous targeting of Smo and Gli1 provided synergistic Hh pathway inhibition stronger than single administration. This approach seems to effectively overcome the drug resistance, particularly at the level of Smo. Here, we combined the pharmacophores targeting Smo and Gli1 into a single and individual isoflavone, compound 22, which inhibits the Hh pathway at both upstream and downstream level. We demonstrate that this multitarget agent suppresses medulloblastoma growth in vitro and in vivo through antagonism of Smo and Gli1, which is a novel mechanism of action in Hh inhibition.

ACS Style

Ludovica Lospinoso Severini; Deborah Quaglio; Irene Basili; Francesca Ghirga; Francesca Bufalieri; Miriam Caimano; Silvia Balducci; Marta Moretti; Isabella Romeo; Elena Loricchio; Marella Maroder; Bruno Botta; Mattia Mori; Paola Infante; Lucia Di Marcotullio. A Smo/Gli Multitarget Hedgehog Pathway Inhibitor Impairs Tumor Growth. Cancers 2019, 11, 1518 .

AMA Style

Ludovica Lospinoso Severini, Deborah Quaglio, Irene Basili, Francesca Ghirga, Francesca Bufalieri, Miriam Caimano, Silvia Balducci, Marta Moretti, Isabella Romeo, Elena Loricchio, Marella Maroder, Bruno Botta, Mattia Mori, Paola Infante, Lucia Di Marcotullio. A Smo/Gli Multitarget Hedgehog Pathway Inhibitor Impairs Tumor Growth. Cancers. 2019; 11 (10):1518.

Chicago/Turabian Style

Ludovica Lospinoso Severini; Deborah Quaglio; Irene Basili; Francesca Ghirga; Francesca Bufalieri; Miriam Caimano; Silvia Balducci; Marta Moretti; Isabella Romeo; Elena Loricchio; Marella Maroder; Bruno Botta; Mattia Mori; Paola Infante; Lucia Di Marcotullio. 2019. "A Smo/Gli Multitarget Hedgehog Pathway Inhibitor Impairs Tumor Growth." Cancers 11, no. 10: 1518.

Journal article
Published: 01 September 2019 in Toxins
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Staphylococcus aureus is a major human pathogen causing a wide range of nosocomial infections including pulmonary, urinary, and skin infections. Notably, the emergence of bacterial strains resistant to conventional antibiotics has prompted researchers to find new compounds capable of killing these pathogens. Nature is undoubtedly an invaluable source of bioactive molecules characterized by an ample chemical diversity. They can act as unique platform providing new scaffolds for further chemical modifications in order to obtain compounds with optimized biological activity. A class of natural compounds with a variety of biological activities is represented by alkaloids, important secondary metabolites produced by a large number of organisms including bacteria, fungi, plants, and animals. In this work, starting from the screening of 39 alkaloids retrieved from a unique in-house library, we identified a heterodimer β-carboline alkaloid, nigritanine, with a potent anti-Staphylococcus action. Nigritanine, isolated from Strychnos nigritana, was characterized for its antimicrobial activity against a reference and three clinical isolates of S. aureus. Its potential cytotoxicity was also evaluated at short and long term against mammalian red blood cells and human keratinocytes, respectively. Nigritanine showed a remarkable antimicrobial activity (minimum inhibitory concentration of 128 µM) without being toxic in vitro to both tested cells. The analysis of the antibacterial activity related to the nigritanine scaffold furnished new insights in the structure–activity relationships (SARs) of β-carboline, confirming that dimerization improves its antibacterial activity. Taking into account these interesting results, nigritanine can be considered as a promising candidate for the development of new antimicrobial molecules for the treatment of S. aureus-induced infections.

ACS Style

Bruno Casciaro; Andrea Calcaterra; Floriana Cappiello; Mattia Mori; Maria Loffredo; Francesca Ghirga; Maria Mangoni; Bruno Botta; Deborah Quaglio. Nigritanine as a New Potential Antimicrobial Alkaloid for the Treatment of Staphylococcus aureus-Induced Infections. Toxins 2019, 11, 511 .

AMA Style

Bruno Casciaro, Andrea Calcaterra, Floriana Cappiello, Mattia Mori, Maria Loffredo, Francesca Ghirga, Maria Mangoni, Bruno Botta, Deborah Quaglio. Nigritanine as a New Potential Antimicrobial Alkaloid for the Treatment of Staphylococcus aureus-Induced Infections. Toxins. 2019; 11 (9):511.

Chicago/Turabian Style

Bruno Casciaro; Andrea Calcaterra; Floriana Cappiello; Mattia Mori; Maria Loffredo; Francesca Ghirga; Maria Mangoni; Bruno Botta; Deborah Quaglio. 2019. "Nigritanine as a New Potential Antimicrobial Alkaloid for the Treatment of Staphylococcus aureus-Induced Infections." Toxins 11, no. 9: 511.

Journal article
Published: 28 August 2019 in Cell Communication and Signaling
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Glioma is the most common and primary brain tumors in adults. Despite the available multimodal therapies, glioma patients appear to have a poor prognosis. The Hedgehog (Hh) signaling is involved in tumorigenesis and emerged as a promising target for brain tumors. Glabrescione B (GlaB) has been recently identified as the first direct inhibitor of Gli1, the downstream effector of the pathway. We established the overexpression of Gli1 in murine glioma cells (GL261) and GlaB effect on cell viability. We used 1H-nuclear magnetic resonance (NMR) metabolomic approach to obtain informative metabolic snapshots of GL261 cells acquired at different time points during GlaB treatment. The activation of AMP activated protein Kinase (AMPK) induced by GlaB was established by western blot. After the orthotopic GL261 cells injection in the right striatum of C57BL6 mice and the intranasal (IN) GlaB/mPEG5kDa-Cholane treatment, the tumor growth was evaluated. The High Performance Liquid Chromatography (HPLC) combined with Mass Spectrometry (MS) was used to quantify GlaB in brain extracts of treated mice. We found that GlaB affected the growth of murine glioma cells both in vitro and in vivo animal model. Using an untargeted 1H-NMR metabolomic approach, we found that GlaB stimulated the glycolytic metabolism in glioma, increasing lactate production. The high glycolytic rate could in part support the cytotoxic effects of GlaB, since the simultaneous blockade of lactate efflux with α-cyano-4-hydroxycinnamic acid (ACCA) affected glioma cell growth. According to the metabolomic data, we found that GlaB increased the phosphorylation of AMPK, a cellular energy sensor involved in the anabolic-to-catabolic transition. Our results indicate that GlaB inhibits glioma cell growth and exacerbates Warburg effect, increasing lactate production. In addition, the simultaneous blockade of Gli1 and lactate efflux amplifies the anti-tumor effect in vivo, providing new potential therapeutic strategy for this brain tumor.

ACS Style

Giuseppina D’Alessandro; Deborah Quaglio; Lucia Monaco; Clotilde Lauro; Francesca Ghirga; Cinzia Ingallina; Michela De Martino; Sergio Fucile; Alessandra Porzia; Maria Amalia Di Castro; Federica Bellato; Francesca Mastrotto; Mattia Mori; Paola Infante; Paola Turano; Stefano Salmaso; Paolo Caliceti; Lucia Di Marcotullio; Bruno Botta; Veronica Ghini; Cristina Limatola. 1H-NMR metabolomics reveals the Glabrescione B exacerbation of glycolytic metabolism beside the cell growth inhibitory effect in glioma. Cell Communication and Signaling 2019, 17, 1 -12.

AMA Style

Giuseppina D’Alessandro, Deborah Quaglio, Lucia Monaco, Clotilde Lauro, Francesca Ghirga, Cinzia Ingallina, Michela De Martino, Sergio Fucile, Alessandra Porzia, Maria Amalia Di Castro, Federica Bellato, Francesca Mastrotto, Mattia Mori, Paola Infante, Paola Turano, Stefano Salmaso, Paolo Caliceti, Lucia Di Marcotullio, Bruno Botta, Veronica Ghini, Cristina Limatola. 1H-NMR metabolomics reveals the Glabrescione B exacerbation of glycolytic metabolism beside the cell growth inhibitory effect in glioma. Cell Communication and Signaling. 2019; 17 (1):1-12.

Chicago/Turabian Style

Giuseppina D’Alessandro; Deborah Quaglio; Lucia Monaco; Clotilde Lauro; Francesca Ghirga; Cinzia Ingallina; Michela De Martino; Sergio Fucile; Alessandra Porzia; Maria Amalia Di Castro; Federica Bellato; Francesca Mastrotto; Mattia Mori; Paola Infante; Paola Turano; Stefano Salmaso; Paolo Caliceti; Lucia Di Marcotullio; Bruno Botta; Veronica Ghini; Cristina Limatola. 2019. "1H-NMR metabolomics reveals the Glabrescione B exacerbation of glycolytic metabolism beside the cell growth inhibitory effect in glioma." Cell Communication and Signaling 17, no. 1: 1-12.

Rapid communication
Published: 26 February 2019 in ACS Medicinal Chemistry Letters
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Based on hit-likeness and chemical diversity, a number of chalcones and chalcone-mimetic compounds were selected as putative Notch inhibitors. The evaluation of the antiproliferative effect combined with the inhibition of Notch1 expression in KOPTK1 cell line identified compound 18, featuring a tetrahydronaphthalene-based scaffold, as a new promising Notch-blocking agent.

ACS Style

Deborah Quaglio; Nadezda Zhdanovskaya; Gloria Tobajas; Viviana Cuartas; Silvia Balducci; Michael S. Christodoulou; Giancarlo Fabrizi; Marta Gargantilla; Eva-María Priego; Álvaro Carmona Pestaña; Daniele Passarella; Isabella Screpanti; Bruno Botta; Rocco Palermo; Mattia Mori; Francesca Ghirga; María-Jesús Pérez-Pérez. Chalcones and Chalcone-mimetic Derivatives as Notch Inhibitors in a Model of T-cell Acute Lymphoblastic Leukemia. ACS Medicinal Chemistry Letters 2019, 10, 639 -643.

AMA Style

Deborah Quaglio, Nadezda Zhdanovskaya, Gloria Tobajas, Viviana Cuartas, Silvia Balducci, Michael S. Christodoulou, Giancarlo Fabrizi, Marta Gargantilla, Eva-María Priego, Álvaro Carmona Pestaña, Daniele Passarella, Isabella Screpanti, Bruno Botta, Rocco Palermo, Mattia Mori, Francesca Ghirga, María-Jesús Pérez-Pérez. Chalcones and Chalcone-mimetic Derivatives as Notch Inhibitors in a Model of T-cell Acute Lymphoblastic Leukemia. ACS Medicinal Chemistry Letters. 2019; 10 (4):639-643.

Chicago/Turabian Style

Deborah Quaglio; Nadezda Zhdanovskaya; Gloria Tobajas; Viviana Cuartas; Silvia Balducci; Michael S. Christodoulou; Giancarlo Fabrizi; Marta Gargantilla; Eva-María Priego; Álvaro Carmona Pestaña; Daniele Passarella; Isabella Screpanti; Bruno Botta; Rocco Palermo; Mattia Mori; Francesca Ghirga; María-Jesús Pérez-Pérez. 2019. "Chalcones and Chalcone-mimetic Derivatives as Notch Inhibitors in a Model of T-cell Acute Lymphoblastic Leukemia." ACS Medicinal Chemistry Letters 10, no. 4: 639-643.

Journal article
Published: 14 September 2018 in Beilstein Journal of Organic Chemistry
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An efficient strategy for the synthesis of 6-unsubstituted indolo[1,2-c]quinazolines is described. The Pd-catalyzed reaction ofo-(o-aminophenylethynyl) trifluoroacetanilides with Ar–B(OH)2afforded 2-(o-aminophenyl)-3-arylindoles, that were converted to 12-arylindolo[1,2-c]quinazolines by adding dimethylformamide dimethyl acetal (DMFDMA) to the reaction mixture after extractive work-up. This reaction outcome is different from the previously reported Pd-catalyzed sequential reaction of the same substrates with Ar–I, Ar–Br and ArN2+BF4−, that afforded 12-arylindolo[1,2-c]quinazolin-6(5H)-ones. Moreover, 12-unsubstituted indolo[1,2-c]quinazolines can be obtained both by reacting 2-(o-aminophenyl)indoles with DMFDMA or by sequential Pd-catalyzed reaction ofo-(o-aminophenylethynyl)aniline with DMFDMA.

ACS Style

Antonio Arcadi; Sandro Cacchi; Giancarlo Fabrizi; Francesca Ghirga; Antonella Goggiamani; Antonia Iazzetti; Fabio Marinelli. Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization withN,N-dimethylformamide dimethyl acetal. Beilstein Journal of Organic Chemistry 2018, 14, 2411 -2417.

AMA Style

Antonio Arcadi, Sandro Cacchi, Giancarlo Fabrizi, Francesca Ghirga, Antonella Goggiamani, Antonia Iazzetti, Fabio Marinelli. Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization withN,N-dimethylformamide dimethyl acetal. Beilstein Journal of Organic Chemistry. 2018; 14 (1):2411-2417.

Chicago/Turabian Style

Antonio Arcadi; Sandro Cacchi; Giancarlo Fabrizi; Francesca Ghirga; Antonella Goggiamani; Antonia Iazzetti; Fabio Marinelli. 2018. "Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization withN,N-dimethylformamide dimethyl acetal." Beilstein Journal of Organic Chemistry 14, no. 1: 2411-2417.

Journals
Published: 27 August 2018 in Organic Chemistry Frontiers
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The present review deals with an updated visit to the olefin metathesis reaction as a powerful tool for the construction of sophisticated macromolecular architectures.

ACS Style

Deborah Quaglio; Giovanni Zappia; Elisa De Paolis; Silvia Balducci; Bruno Botta; Francesca Ghirga. Olefin metathesis reaction as a locking tool for macrocycle and mechanomolecule construction. Organic Chemistry Frontiers 2018, 5, 3022 -3055.

AMA Style

Deborah Quaglio, Giovanni Zappia, Elisa De Paolis, Silvia Balducci, Bruno Botta, Francesca Ghirga. Olefin metathesis reaction as a locking tool for macrocycle and mechanomolecule construction. Organic Chemistry Frontiers. 2018; 5 (20):3022-3055.

Chicago/Turabian Style

Deborah Quaglio; Giovanni Zappia; Elisa De Paolis; Silvia Balducci; Bruno Botta; Francesca Ghirga. 2018. "Olefin metathesis reaction as a locking tool for macrocycle and mechanomolecule construction." Organic Chemistry Frontiers 5, no. 20: 3022-3055.

Article
Published: 26 April 2017 in European Journal of Organic Chemistry
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The cover picture shows the mechanistic pathway involved in the ring-opening cross-metathesis (ROM-CM) reaction of resorc[4]arene macrocycles. The red ruthenium atoms lead the way in the formation of a dimeric product, starting from a bicyclic olefin and passing through ruthenium–resorc[4]arene complexes. NMR techniques in combination with organic reaction skills enabled the development of a quantitative analytical protocol for the characterization of the reaction outcome: beside highly strained and unstrained olefins, the macrocycles themselves could be appropriate substrates for “macrocyclization” reactions according to a ROM-CM mechanism. Details are discussed in the Full Paper by B. Botta, G. Uccello-Barretta et al. on page 2407 ff (DOI: 10.1002/ejoc.201601502).

ACS Style

Federica Aiello; Federica Balzano; Francesca Ghirga; Ilaria D'acquarica; Bruno Botta; Gloria Uccello-Barretta; Deborah Quaglio. Front Cover: First Detection of a Ruthenium-Carbene-Resorc[4]arene Complex During the Progress of a Metathesis Reaction (Eur. J. Org. Chem. 17/2017). European Journal of Organic Chemistry 2017, 2017, 2385 -2385.

AMA Style

Federica Aiello, Federica Balzano, Francesca Ghirga, Ilaria D'acquarica, Bruno Botta, Gloria Uccello-Barretta, Deborah Quaglio. Front Cover: First Detection of a Ruthenium-Carbene-Resorc[4]arene Complex During the Progress of a Metathesis Reaction (Eur. J. Org. Chem. 17/2017). European Journal of Organic Chemistry. 2017; 2017 (17):2385-2385.

Chicago/Turabian Style

Federica Aiello; Federica Balzano; Francesca Ghirga; Ilaria D'acquarica; Bruno Botta; Gloria Uccello-Barretta; Deborah Quaglio. 2017. "Front Cover: First Detection of a Ruthenium-Carbene-Resorc[4]arene Complex During the Progress of a Metathesis Reaction (Eur. J. Org. Chem. 17/2017)." European Journal of Organic Chemistry 2017, no. 17: 2385-2385.

Article
Published: 27 February 2017 in European Journal of Organic Chemistry
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For the first time we describe the detection of a ruthenium-carbene-resorc[4]arene complex produced, as a key intermediate, during an olefin metathesis reaction carried out on a resorc[4]arene bicyclic olefin with [Ru(=CHPh)Cl2(PCy3)2] Grubbs first-generation (G1ST) catalyst. The complex was identified by using high-resolution (600 MHz) 1H, 31P NMR and DOSY spectroscopy, in a non-invasive fashion. The singlet at δ = 19.98 ppm (1H NMR), attributed to the alkylidene proton in the G1ST catalyst and that at δ = 53.37 ppm (31P NMR), attributed to the phosphorus atom coordinated with the metal, were selected as probes for a kinetic analysis. The intensity of these signals decreased at the expense of the singlets at 19.26 (1H NMR) and 52.68 ppm (31P NMR), diagnostic for the formation of the ruthenium-carbene-resorc[4]arene complex 3a[Ru]. The resorc[4]arene activated olefin proved to behave as a key propagating species leading to oligomers according to a ROMP pathway.

ACS Style

Federica Aiello; Federica Balzano; Francesca Ghirga; Ilaria D'acquarica; Bruno Botta; Gloria Uccello-Barretta; Deborah Quaglio. First Detection of a Ruthenium-Carbene-Resorc[4]arene Complex During the Progress of a Metathesis Reaction. European Journal of Organic Chemistry 2017, 2017, 2407 -2415.

AMA Style

Federica Aiello, Federica Balzano, Francesca Ghirga, Ilaria D'acquarica, Bruno Botta, Gloria Uccello-Barretta, Deborah Quaglio. First Detection of a Ruthenium-Carbene-Resorc[4]arene Complex During the Progress of a Metathesis Reaction. European Journal of Organic Chemistry. 2017; 2017 (17):2407-2415.

Chicago/Turabian Style

Federica Aiello; Federica Balzano; Francesca Ghirga; Ilaria D'acquarica; Bruno Botta; Gloria Uccello-Barretta; Deborah Quaglio. 2017. "First Detection of a Ruthenium-Carbene-Resorc[4]arene Complex During the Progress of a Metathesis Reaction." European Journal of Organic Chemistry 2017, no. 17: 2407-2415.