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Dr. Andrea Calcaterra
Department of Chemistry and Technology of Drugs, Sapienza - University of Rome, Rome, Italy

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Research Keywords & Expertise

0 Natural products chemistry
0 Isolation and total synthesis of natural products
0 Natural products as anticancer agents
0 Antibiotic resistance modulation by natural products
0 Synthesis of macrocycles for drug delivery and molecular recognition

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Natural products as anticancer agents

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Journal article
Published: 04 August 2021 in International Journal of Molecular Sciences
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The Smoothened (SMO) receptor is the most druggable target in the Hedgehog (HH) pathway for anticancer compounds. However, SMO antagonists such as vismodegib rapidly develop drug resistance. In this study, new SMO antagonists having the versatile purine ring as a scaffold were designed, synthesised, and biologically tested to provide an insight to their mechanism of action. Compound 4s was the most active and the best inhibitor of cell growth and selectively cytotoxic to cancer cells. 4s induced cell cycle arrest, apoptosis, a reduction in colony formation and downregulation of PTCH and GLI1 expression. BODIPY-cyclopamine displacement assays confirmed 4s is a SMO antagonist. In vivo, 4s strongly inhibited tumour relapse and metastasis of melanoma cells in mice. In vitro, 4s was more efficient than vismodegib to induce apoptosis in human cancer cells and that might be attributed to its dual ability to function as a SMO antagonist and apoptosis inducer.

ACS Style

Ana Zárate; Christian Espinosa-Bustos; Simón Guerrero; Angélica Fierro; Felipe Oyarzún-Ampuero; Andrew Quest; Lucia Di Marcotullio; Elena Loricchio; Miriam Caimano; Andrea Calcaterra; Matías González-Quiroz; Adam Aguirre; Jaime Meléndez; Cristian Salas. A New Smoothened Antagonist Bearing the Purine Scaffold Shows Antitumour Activity In Vitro and In Vivo. International Journal of Molecular Sciences 2021, 22, 8372 .

AMA Style

Ana Zárate, Christian Espinosa-Bustos, Simón Guerrero, Angélica Fierro, Felipe Oyarzún-Ampuero, Andrew Quest, Lucia Di Marcotullio, Elena Loricchio, Miriam Caimano, Andrea Calcaterra, Matías González-Quiroz, Adam Aguirre, Jaime Meléndez, Cristian Salas. A New Smoothened Antagonist Bearing the Purine Scaffold Shows Antitumour Activity In Vitro and In Vivo. International Journal of Molecular Sciences. 2021; 22 (16):8372.

Chicago/Turabian Style

Ana Zárate; Christian Espinosa-Bustos; Simón Guerrero; Angélica Fierro; Felipe Oyarzún-Ampuero; Andrew Quest; Lucia Di Marcotullio; Elena Loricchio; Miriam Caimano; Andrea Calcaterra; Matías González-Quiroz; Adam Aguirre; Jaime Meléndez; Cristian Salas. 2021. "A New Smoothened Antagonist Bearing the Purine Scaffold Shows Antitumour Activity In Vitro and In Vivo." International Journal of Molecular Sciences 22, no. 16: 8372.

Journal article
Published: 02 June 2021 in Molecules
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An alternative Au(I)-catalyzed synthetic route to functionalized 1,2-dihydroquinolines is reported. This novel approach is based on the use of N-ethoxycarbonyl protected-N-propargylanilines as building blocks that rapidly undergo the IMHA reaction affording the 6-endo cyclization product in good to high yields. In the presence of N-ethoxycarbonyl-N-propargyl-meta-substituted anilines, the regiodivergent cyclization at the ortho-/para-position is achieved by the means of catalyst fine tuning.

ACS Style

Antonio Arcadi; Andrea Calcaterra; Giancarlo Fabrizi; Andrea Fochetti; Antonella Goggiamani; Antonia Iazzetti; Federico Marrone; Vincenzo Marsicano; Giulia Mazzoccanti; Andrea Serraiocco. Synthesis of 4-Substituted-1,2-Dihydroquinolines by Means of Gold-Catalyzed Intramolecular Hydroarylation Reaction of N-Ethoxycarbonyl-N-Propargylanilines. Molecules 2021, 26, 3366 .

AMA Style

Antonio Arcadi, Andrea Calcaterra, Giancarlo Fabrizi, Andrea Fochetti, Antonella Goggiamani, Antonia Iazzetti, Federico Marrone, Vincenzo Marsicano, Giulia Mazzoccanti, Andrea Serraiocco. Synthesis of 4-Substituted-1,2-Dihydroquinolines by Means of Gold-Catalyzed Intramolecular Hydroarylation Reaction of N-Ethoxycarbonyl-N-Propargylanilines. Molecules. 2021; 26 (11):3366.

Chicago/Turabian Style

Antonio Arcadi; Andrea Calcaterra; Giancarlo Fabrizi; Andrea Fochetti; Antonella Goggiamani; Antonia Iazzetti; Federico Marrone; Vincenzo Marsicano; Giulia Mazzoccanti; Andrea Serraiocco. 2021. "Synthesis of 4-Substituted-1,2-Dihydroquinolines by Means of Gold-Catalyzed Intramolecular Hydroarylation Reaction of N-Ethoxycarbonyl-N-Propargylanilines." Molecules 26, no. 11: 3366.

Preprint content
Published: 12 May 2021
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ACS Style

Andrea Calcaterra; Giancarlo Fabrizi; Bruno Botta; Juan Jose Guevara. Convergent total synthesis of (±)-kuwanol E. 2021, 1 .

AMA Style

Andrea Calcaterra, Giancarlo Fabrizi, Bruno Botta, Juan Jose Guevara. Convergent total synthesis of (±)-kuwanol E. . 2021; ():1.

Chicago/Turabian Style

Andrea Calcaterra; Giancarlo Fabrizi; Bruno Botta; Juan Jose Guevara. 2021. "Convergent total synthesis of (±)-kuwanol E." , no. : 1.

Review
Published: 02 May 2021 in Separations
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Many efforts have been made to separate basic compounds, which are challenging to resolve in reversed phase liquid chromatography. In this process, they are strongly retained and the peak shape undergoes significant distortion. The principal origin of this has been identified with the non-negligible interaction with residual deprotonated silanols. Consequently, all solutions that efficiently shield silanols are being sought. This review is an upgrade on the use of the electrostatic repulsion reversed phase (ERRP) approach: retention of bases, in protonated form, can be achieved by modulating the charge repulsion caused by the presence of positive charges in the chromatographic system. This study successfully (i) introduced fixed positive charges in the structure of stationary phases, (ii) used cationic and hydrophobic additives in the mobile phase, and (iii) used the ERRP-like approach employed at the preparative level for peptide purification.

ACS Style

Giulia Mazzoccanti; Francesco Gasparrini; Andrea Calcaterra; Claudio Villani; Alessia Ciogli. Static vs. Dynamic Electrostatic Repulsion Reversed Phase Liquid Chromatography: Solutions for Pharmaceutical and Biopharmaceutical Basic Compounds. Separations 2021, 8, 59 .

AMA Style

Giulia Mazzoccanti, Francesco Gasparrini, Andrea Calcaterra, Claudio Villani, Alessia Ciogli. Static vs. Dynamic Electrostatic Repulsion Reversed Phase Liquid Chromatography: Solutions for Pharmaceutical and Biopharmaceutical Basic Compounds. Separations. 2021; 8 (5):59.

Chicago/Turabian Style

Giulia Mazzoccanti; Francesco Gasparrini; Andrea Calcaterra; Claudio Villani; Alessia Ciogli. 2021. "Static vs. Dynamic Electrostatic Repulsion Reversed Phase Liquid Chromatography: Solutions for Pharmaceutical and Biopharmaceutical Basic Compounds." Separations 8, no. 5: 59.

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.

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.

Journal article
Published: 23 June 2020 in Molecules
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With the aim to identify novel inhibitors of parasitic nematode thymidylate synthase (TS), we screened in silico an in-house library of natural compounds, taking advantage of a model of nematode TS three-dimensional (3D) structure and choosing candidate compounds potentially capable of enzyme binding/inhibition. Selected compounds were tested as (i) inhibitors of the reaction catalyzed by TSs of different species, (ii) agents toxic to a nematode parasite model (C. elegans grown in vitro), (iii) inhibitors of normal human cell growth, and (iv) antitumor agents affecting human tumor cells grown in vitro. The results pointed to alvaxanthone as a relatively strong TS inhibitor that causes C. elegans population growth reduction with nematocidal potency similar to the anthelmintic drug mebendazole. Alvaxanthone also demonstrated an antiproliferative effect in tumor cells, associated with a selective toxicity against mitochondria observed in cancer cells compared to normal cells.

ACS Style

Piotr Maj; Mattia Mori; Justyna Sobich; Joanna Markowicz; Łukasz Uram; Zbigniew Zieliński; Deborah Quaglio; Andrea Calcaterra; Ylenia Cau; Bruno Botta; Wojciech Rode. Alvaxanthone, a Thymidylate Synthase Inhibitor with Nematocidal and Tumoricidal Activities. Molecules 2020, 25, 2894 .

AMA Style

Piotr Maj, Mattia Mori, Justyna Sobich, Joanna Markowicz, Łukasz Uram, Zbigniew Zieliński, Deborah Quaglio, Andrea Calcaterra, Ylenia Cau, Bruno Botta, Wojciech Rode. Alvaxanthone, a Thymidylate Synthase Inhibitor with Nematocidal and Tumoricidal Activities. Molecules. 2020; 25 (12):2894.

Chicago/Turabian Style

Piotr Maj; Mattia Mori; Justyna Sobich; Joanna Markowicz; Łukasz Uram; Zbigniew Zieliński; Deborah Quaglio; Andrea Calcaterra; Ylenia Cau; Bruno Botta; Wojciech Rode. 2020. "Alvaxanthone, a Thymidylate Synthase Inhibitor with Nematocidal and Tumoricidal Activities." Molecules 25, no. 12: 2894.

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.

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: 04 August 2018 in Biomedicine & Pharmacotherapy
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Psoriasis is one of the most common chronic autoinflammatory skin disease, associated with hyperproliferation and abnormal differentiation of keratinocytes, inflammation, and angiogenesis. The available treatments for psoriasis are not curative and may have numerous side effects, and topical administration is preferred over systemic therapy due to the reduced systemic burden of the drug. Thus, novel and more efficacious formulations of anti-inflammatory and/or differentiating compounds for topical application could be very useful for the disease management and for improving the quality of life of the patients. Here we evaluated the potential as anti-psoriatic of an equimolar mixture of two compounds, 2,4-Monofurfurylidene-tetra-O-methylsorbitol (Compound A) and 4,6-dimethyl-2-(3,4,5-trimethoxyphenylamino)pyrimidine (Compound B), that, used individually, are known to possess immunomodulating properties (Compound A) and keratolitic and anti-inflammatory activity (Compound B). Human immortalized keratinocyte cell line (HaCaT cells) and primary human keratinocyte cells from adult donor (HEKa) were used as in vitro experimental models. We show that the mix A + B exhibits antiproliferative activity and induces terminal differentiation more efficiently than compounds A and B used individually. We confirm that the compound B is the active ingredient of the mixture and the mainly responsible for anti-psoriatic activity, but the mix A + B is more effective and possesses lower cytotoxicity than the compound B alone. This could be ascribable to the association with compound A, that is known to possess, in addition to the immunomodulating ability, antioxidant and antiradical action. Our results indicate that mix A + B could be a suitable candidate for a new cosmeceutical formulation for topical treatment of psoriasis.

ACS Style

Annalucia Serafino; Giuseppe Nicotera; Federica Andreola; Daniela Giovannini; Manuela Zonfrillo; Gianluca Sferrazza; Andrea Calcaterra; Carlo De Angelis; Claudio Camponeschi; Pasquale Pierimarchi. Synergistic antiproliferative and differentiating effect of 2,4-monofurfurylidene-tetra-O-methylsorbitol and 4,6-dimethyl-2-(3,4,5-trimethoxyphenylamino)pyrimidine on primary and immortalized keratinocytes. Biomedicine & Pharmacotherapy 2018, 107, 155 -167.

AMA Style

Annalucia Serafino, Giuseppe Nicotera, Federica Andreola, Daniela Giovannini, Manuela Zonfrillo, Gianluca Sferrazza, Andrea Calcaterra, Carlo De Angelis, Claudio Camponeschi, Pasquale Pierimarchi. Synergistic antiproliferative and differentiating effect of 2,4-monofurfurylidene-tetra-O-methylsorbitol and 4,6-dimethyl-2-(3,4,5-trimethoxyphenylamino)pyrimidine on primary and immortalized keratinocytes. Biomedicine & Pharmacotherapy. 2018; 107 ():155-167.

Chicago/Turabian Style

Annalucia Serafino; Giuseppe Nicotera; Federica Andreola; Daniela Giovannini; Manuela Zonfrillo; Gianluca Sferrazza; Andrea Calcaterra; Carlo De Angelis; Claudio Camponeschi; Pasquale Pierimarchi. 2018. "Synergistic antiproliferative and differentiating effect of 2,4-monofurfurylidene-tetra-O-methylsorbitol and 4,6-dimethyl-2-(3,4,5-trimethoxyphenylamino)pyrimidine on primary and immortalized keratinocytes." Biomedicine & Pharmacotherapy 107, no. : 155-167.

Review
Published: 26 July 2018 in Sensors
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This article reviews recent portable sensor technologies to apply in the Cultural Heritage (CH) fields. The review has been prepared in the form of a retrospective description of the sensor’s history and technological evolution, having: new nanomaterials for transducers, miniaturized, portable and integrated sensors, the wireless transmission of the analytical signals, ICT_Information Communication Technology and IoT_Internet of Things to apply to the cultural heritage field. In addition, a new trend of movable tattoo sensors devices is discussed, referred to in situ analysis, which is especially important when scientists are in the presence of un-movable and un-tangible Cultural Heritage and Art Work objects. The new proposed portable contact sensors (directly applied to art work objects and surfaces) are non-invasive and non-destructive to the different materials and surfaces of which cultural heritage is composed.

ACS Style

Federica Valentini; Andrea Calcaterra; Simonetta Antonaroli; Maurizio Talamo. Smart Portable Devices Suitable for Cultural Heritage: A Review. Sensors 2018, 18, 2434 .

AMA Style

Federica Valentini, Andrea Calcaterra, Simonetta Antonaroli, Maurizio Talamo. Smart Portable Devices Suitable for Cultural Heritage: A Review. Sensors. 2018; 18 (8):2434.

Chicago/Turabian Style

Federica Valentini; Andrea Calcaterra; Simonetta Antonaroli; Maurizio Talamo. 2018. "Smart Portable Devices Suitable for Cultural Heritage: A Review." Sensors 18, no. 8: 2434.

Journal article
Published: 28 April 2018 in International Journal of Molecular Sciences
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The in vitro biocompatibility of Graphene Oxide (GO) nanosheets, which were obtained by the electrochemical exfoliation of graphite electrodes in an electrolytic bath containing salts, was compared with the pristine Single Wall Carbon Nanotubes (p-SWCNTs) under the same experimental conditions in different human cell lines. The cells were treated with different concentrations of GO and SWCNTs for up to 48 h. GO did not induce any significant morphological or functional modifications (demonstrating a high biocompatibility), while SWNCTs were toxic at any concentration used after a few hours of treatment. The cell viability or cytotoxicity were detected by the trypan blue assay and the lactate dehydrogenase LDH quantitative enzymatic test. The Confocal Laser Scanning Microscopy (CLSM) and transmission electron microscopy (TEM) analysis demonstrated the uptake and internalization of GO sheets into cells, which was localized mainly in the cytoplasm. Different results were observed in the same cell lines treated with p-SWCNTs. TEM and CLSM (Confocal Laser Scanning Microscopy) showed that the p-SWCNTs induced vacuolization in the cytoplasm, disruption of cellular architecture and damage to the nuclei. The most important result of this study is our finding of a higher GO biocompatibility compared to the p-SWCNTs in the same cell lines. This means that GO nanosheets, which are obtained by the electrochemical exfoliation of a graphite-based electrode (carried out in saline solutions or other physiological working media) could represent an eligible nanocarrier for drug delivery, gene transfection and molecular cell imaging tests.

ACS Style

Federica Valentini; Emanuela Mari; Alessandra Zicari; Andrea Calcaterra; Maurizio Talamo; Maria Giovanna Scioli; Augusto Orlandi; Stefania Mardente. Metal Free Graphene Oxide (GO) Nanosheets and Pristine-Single Wall Carbon Nanotubes (p-SWCNTs) Biocompatibility Investigation: A Comparative Study in Different Human Cell Lines. International Journal of Molecular Sciences 2018, 19, 1316 .

AMA Style

Federica Valentini, Emanuela Mari, Alessandra Zicari, Andrea Calcaterra, Maurizio Talamo, Maria Giovanna Scioli, Augusto Orlandi, Stefania Mardente. Metal Free Graphene Oxide (GO) Nanosheets and Pristine-Single Wall Carbon Nanotubes (p-SWCNTs) Biocompatibility Investigation: A Comparative Study in Different Human Cell Lines. International Journal of Molecular Sciences. 2018; 19 (5):1316.

Chicago/Turabian Style

Federica Valentini; Emanuela Mari; Alessandra Zicari; Andrea Calcaterra; Maurizio Talamo; Maria Giovanna Scioli; Augusto Orlandi; Stefania Mardente. 2018. "Metal Free Graphene Oxide (GO) Nanosheets and Pristine-Single Wall Carbon Nanotubes (p-SWCNTs) Biocompatibility Investigation: A Comparative Study in Different Human Cell Lines." International Journal of Molecular Sciences 19, no. 5: 1316.

Journal article
Published: 01 January 2018 in European Journal of Medicinal Chemistry
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Mycobacterium tuberculosis (Mtb) protein tyrosine phosphatases A and B (PtpA and PtpB) have been recognized as potential molecular targets for the development of new therapeutic strategies against tuberculosis (TB). In this context, we have recently reported that the naturally occurring Diels-Alder-type adduct Kuwanol E is an inhibitor of PtpB (K = 1.6 ± 0.1 μM). Here, we describe additional Diels-Alder-type adducts isolated from Morus nigra roots bark that inhibit PtpB at sub-micromolar concentrations. The two most potent compounds, namely Kuwanon G and Kuwanon H, showed K values of 0.39 ± 0.27 and 0.20 ± 0.01 μM, respectively, and interacted with the active site of the enzyme as suggested by kinetics and mass spectrometry studies. Molecular docking coupled with intrinsic fluorescence analysis and isothermal titration calorimetry (ITC) further characterized the interaction of these promising PtpB inhibitors. Notably, in an Mtb survival assay inside macrophages, Kuwanon G showed inhibition of Mtb growth by 61.3%. All these results point to the common Diels-Alder-type adduct scaffold, and highlight its relevance for the development of PtpB inhibitors as candidate therapeutics for TB.

ACS Style

Alessandra Mascarello; Angela Camila Orbem Menegatti; Andrea Calcaterra; Priscila Graziela Alves Martins; Louise Domeneghini Chiaradia-Delatorre; Ilaria D'Acquarica; Franco Ferrari; Valentina Pau; Adriana Sanna; Alessandro De Logu; Maurizio Botta; Bruno Botta; Hernán Terenzi; Mattia Mori. Naturally occurring Diels-Alder-type adducts from Morus nigra as potent inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B. European Journal of Medicinal Chemistry 2018, 144, 277 -288.

AMA Style

Alessandra Mascarello, Angela Camila Orbem Menegatti, Andrea Calcaterra, Priscila Graziela Alves Martins, Louise Domeneghini Chiaradia-Delatorre, Ilaria D'Acquarica, Franco Ferrari, Valentina Pau, Adriana Sanna, Alessandro De Logu, Maurizio Botta, Bruno Botta, Hernán Terenzi, Mattia Mori. Naturally occurring Diels-Alder-type adducts from Morus nigra as potent inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B. European Journal of Medicinal Chemistry. 2018; 144 ():277-288.

Chicago/Turabian Style

Alessandra Mascarello; Angela Camila Orbem Menegatti; Andrea Calcaterra; Priscila Graziela Alves Martins; Louise Domeneghini Chiaradia-Delatorre; Ilaria D'Acquarica; Franco Ferrari; Valentina Pau; Adriana Sanna; Alessandro De Logu; Maurizio Botta; Bruno Botta; Hernán Terenzi; Mattia Mori. 2018. "Naturally occurring Diels-Alder-type adducts from Morus nigra as potent inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B." European Journal of Medicinal Chemistry 144, no. : 277-288.

Review
Published: 01 January 2018 in Journal of Pharmaceutical and Biomedical Analysis
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This review article is aimed at providing an overview of the current market of chiral drugs by exploring which is the nowadays tendency, for the pharmaceutical industry, either to exploit the chiral switching practice from already marketed racemates or to develop de novo enantiomerically pure compounds. A concise illustration of the main techniques developed to assess the absolute configuration (AC) and enantiomeric purity of chiral drugs has been given, where greater emphasis was placed on the contribution of enantioselective chromatography (HPLC, SFC and UHPC). Afterwards, we focused our study on the cohort of 45 new drugs that have been approved by the US Food and Drug Administration (FDA) in 2015. We extracted the chemical structure of the new drugs from the FDA approval chemistry reviews available on the database of the agency's Center for Drug Evaluation and Research (CDER), and we selected a subgroup (i.e., 44% of the cohort) of small-molecule active pharmaceutical ingredients (APIs) containing one or more chirality centers. On the basis of the FDA dossiers examined, it emerged that all the chiral drugs approved by the FDA in 2015 are enantiomerically pure compounds with a well-defined AC, with the exception of one, namely lesinurad, which has been licensed as the racemate of two enantiomeric atropoisomers, arising because of the hindered rotation around the single C-N bond in the naphthalene ring. Finally, none of the previously developed racemates has been switched to the single-enantiomer version in 2015.

ACS Style

Andrea Calcaterra; Ilaria D’Acquarica. The market of chiral drugs: Chiral switches versus de novo enantiomerically pure compounds. Journal of Pharmaceutical and Biomedical Analysis 2018, 147, 323 -340.

AMA Style

Andrea Calcaterra, Ilaria D’Acquarica. The market of chiral drugs: Chiral switches versus de novo enantiomerically pure compounds. Journal of Pharmaceutical and Biomedical Analysis. 2018; 147 ():323-340.

Chicago/Turabian Style

Andrea Calcaterra; Ilaria D’Acquarica. 2018. "The market of chiral drugs: Chiral switches versus de novo enantiomerically pure compounds." Journal of Pharmaceutical and Biomedical Analysis 147, no. : 323-340.

Research paper
Published: 01 January 2018 in Journal of Enzyme Inhibition and Medicinal Chemistry
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This work aims at elucidating the mechanism and kinetics of hydrolysis of GANT61, the first and most-widely used inhibitor of the Hedgehog (Hh) signalling pathway that targets Glioma-associated oncogene homologue (Gli) proteins, and at confirming the chemical nature of its bioactive form. GANT61 is poorly stable under physiological conditions and rapidly hydrolyses into an aldehyde species (GANT61-A), which is devoid of the biological activity against Hh signalling, and a diamine derivative (GANT61-D), which has shown inhibition of Gli-mediated transcription. Here, we combined chemical synthesis, NMR spectroscopy, analytical studies, molecular modelling and functional cell assays to characterise the GANT61 hydrolysis pathway. Our results show that GANT61-D is the bioactive form of GANT61 in NIH3T3 Shh-Light II cells and SuFu−/− mouse embryonic fibroblasts, and clarify the structural requirements for GANT61-D binding to Gli1. This study paves the way to the design of GANT61 derivatives with improved potency and chemical stability. Graphical Abstract

ACS Style

Andrea Calcaterra; Valentina Iovine; Bruno Botta; Deborah Quaglio; Ilaria D’Acquarica; Alessia Ciogli; Antonia Iazzetti; Romina Alfonsi; Ludovica Lospinoso Severini; Paola Infante; Lucia Di Marcotullio; Mattia Mori; Francesca Ghirga. Chemical, computational and functional insights into the chemical stability of the Hedgehog pathway inhibitor GANT61. Journal of Enzyme Inhibition and Medicinal Chemistry 2018, 33, 349 -358.

AMA Style

Andrea Calcaterra, Valentina Iovine, Bruno Botta, Deborah Quaglio, Ilaria D’Acquarica, Alessia Ciogli, Antonia Iazzetti, Romina Alfonsi, Ludovica Lospinoso Severini, Paola Infante, Lucia Di Marcotullio, Mattia Mori, Francesca Ghirga. Chemical, computational and functional insights into the chemical stability of the Hedgehog pathway inhibitor GANT61. Journal of Enzyme Inhibition and Medicinal Chemistry. 2018; 33 (1):349-358.

Chicago/Turabian Style

Andrea Calcaterra; Valentina Iovine; Bruno Botta; Deborah Quaglio; Ilaria D’Acquarica; Alessia Ciogli; Antonia Iazzetti; Romina Alfonsi; Ludovica Lospinoso Severini; Paola Infante; Lucia Di Marcotullio; Mattia Mori; Francesca Ghirga. 2018. "Chemical, computational and functional insights into the chemical stability of the Hedgehog pathway inhibitor GANT61." Journal of Enzyme Inhibition and Medicinal Chemistry 33, no. 1: 349-358.

Research article
Published: 26 December 2017 in Journal of Analytical Methods in Chemistry
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Paper-based cultural heritage objects are subject to natural deterioration due to internal and external factors, that is, the presence of heavy metals, incorrect conservation, humidity, exposure of the artifacts to pollutants, light, and high temperatures. To contrast the decay of the original objects, it is necessary to study and apply innovative specific techniques, set up novel preservation methodologies, and implement or synthesize new products. As the nanomaterial science field developed over the last decades, the usage of nanomaterials in cultural heritage gained a prominent role. Such an excitement for the novel materials opened the path for an uncontrolled transfer of nanoparticles developed for different applications to paper restoration, neglecting all their possible interactions with the support or the graphic media. The aim of this work was to synthesize new nanomaterialsexpressly conceivedfor the treatment of library materials. To evaluate their possible insertion in the official conservation treatments that are subjected to validation by Istituto Centrale Restauro e Conservazione Patrimonio Archivistico e Librario, the new nanomaterials were tested both on laboratory paper samples and on original documents. This work presents the results of these studies (some of which still preliminary) stressing the positive and extremely promising outcomes of this research.

ACS Style

Marina Bicchieri; Federica Valentini; Andrea Calcaterra; Maurizio Talamo. Newly Developed Nano-Calcium Carbonate and Nano-Calcium Propanoate for the Deacidification of Library and Archival Materials. Journal of Analytical Methods in Chemistry 2017, 2017, 1 -8.

AMA Style

Marina Bicchieri, Federica Valentini, Andrea Calcaterra, Maurizio Talamo. Newly Developed Nano-Calcium Carbonate and Nano-Calcium Propanoate for the Deacidification of Library and Archival Materials. Journal of Analytical Methods in Chemistry. 2017; 2017 ():1-8.

Chicago/Turabian Style

Marina Bicchieri; Federica Valentini; Andrea Calcaterra; Maurizio Talamo. 2017. "Newly Developed Nano-Calcium Carbonate and Nano-Calcium Propanoate for the Deacidification of Library and Archival Materials." Journal of Analytical Methods in Chemistry 2017, no. : 1-8.

Article
Published: 23 October 2017 in Electroanalysis
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Micro-Raman and X-Ray Fluorescence combined with electrochemical techniques proved to be suitable for the unambiguous identification of the green pigment in a very deteriorated historical leather. The colouring matter resulted in a mixture of blue and yellow. Raman identified the blue indigo, whereas iron and arsenic were identified by XRF. The redox status of these two elements was investigated by Square Wave Cathodic Stripping Voltammetry (SWCSV). Results demonstrated the presence of As(III), probably As2S3 (orpiment), and Fe(III), characterising the red earths. The quantitative results obtained by SWCSV were also confirmed for Fe and As by ICP-MS (Inductively Coupled Plasma Mass spectrometry). Voltammetric techniques, applied here for the identification of the redox status of the elements, contained in pigments, are useful to understand two important aspects: the chemical-physical composition of the colors and the best strategy to be applied for the preservation of the pigments in ancient/deteriorated artwork objects.

ACS Style

Federica Valentini; Marina Bicchieri; Andrea Calcaterra; Maurizio Talamo. Raman, X-Ray Fluorescence Spectroscopies and Graphene Oxide Modified Screen Printed Electrodes to Identify the Pigments and Earth Present in Ancient Leather Samples. Electroanalysis 2017, 29, 2873 -2881.

AMA Style

Federica Valentini, Marina Bicchieri, Andrea Calcaterra, Maurizio Talamo. Raman, X-Ray Fluorescence Spectroscopies and Graphene Oxide Modified Screen Printed Electrodes to Identify the Pigments and Earth Present in Ancient Leather Samples. Electroanalysis. 2017; 29 (12):2873-2881.

Chicago/Turabian Style

Federica Valentini; Marina Bicchieri; Andrea Calcaterra; Maurizio Talamo. 2017. "Raman, X-Ray Fluorescence Spectroscopies and Graphene Oxide Modified Screen Printed Electrodes to Identify the Pigments and Earth Present in Ancient Leather Samples." Electroanalysis 29, no. 12: 2873-2881.

Article
Published: 19 October 2017 in Electroanalysis
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Fullerene Black (FB) and Extracted Fullerene Black (EFB) were used in modified screen-printed electrodes producing electrochemical transducers (FB-SPEs and EFB-SPEs). A complete electrochemical study was performed and the best results are obtained working with FB-SPEs, especially in terms of: 1. improved electron-transfer kinetic mechanisms and 2. sensitivity and selectivity toward Acetaminophen (Ac) and Guanine (G). These latter represent two important electro-active targets to quantify in medicine field application, because: Ac is a preferred alternative (as analgesic-antipyretic agent) to aspirin, particularly for patients who cannot tolerate aspirin; the oxidation signal of G is useful for the fabrication of emerging analytical tools, such as DNA chipsand user-friendly diagnostic devices. Ac and G are quantify by using FB-SPEs electrochemical devices, with an extended linearity (1–300 μM for Ac; 0.1–300 μM for G), an excellent sensitivity (2.82 μA μM−1 cm−2 in the case of Ac; and 0.183 μA μM−1 cm−2 in the case of G), a low detection limit (0.01 μM for Ac; 0.005 μM for G), a very good reproducibility (both: intra-; inter-electrodes reproducibility RSD % ranging from 0.3–0.5 for Ac; and 0.50–0.85 for G) and a very fast response time (6 s for Ac; 5 s in the case of G). In addition, high selectivity is obtained at FB-SPEs, meaning that the FB-SPEs electrochemical transducers are suitable to simultaneously quantify Ac and G in real samples, having several different (highly concentrated) interference.

ACS Style

Federica Valentini; Elena Ciambella; Franco Cataldo; Andrea Calcaterra; Luca Menegatti; Maurizio Talamo. Fullerene Black Modified Screen Printed Electrodes for the Quantification of Acetaminophen and Guanine. Electroanalysis 2017, 29, 2863 -2872.

AMA Style

Federica Valentini, Elena Ciambella, Franco Cataldo, Andrea Calcaterra, Luca Menegatti, Maurizio Talamo. Fullerene Black Modified Screen Printed Electrodes for the Quantification of Acetaminophen and Guanine. Electroanalysis. 2017; 29 (12):2863-2872.

Chicago/Turabian Style

Federica Valentini; Elena Ciambella; Franco Cataldo; Andrea Calcaterra; Luca Menegatti; Maurizio Talamo. 2017. "Fullerene Black Modified Screen Printed Electrodes for the Quantification of Acetaminophen and Guanine." Electroanalysis 29, no. 12: 2863-2872.

Article
Published: 18 January 2017 in ChemBioChem
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In recent years many advances have been made in the fight against HIV-1 infection. However, the lack of a vaccine, together with the increasing resistance to the highly active anti-retroviral therapy (HAART), make HIV-1 infection still a serious global emergency. Thus, new compounds with original modes of action are continuously required, and natural products have ever been a very interesting class of pharmacologically active molecules. Some of them have been used since ancient times against viral infections. Here we present a work in which we suggest that kuwanon-L, a natural product active as an HIV-1 integrase (IN) inhibitor, might exert its overall antiviral activity through binding to multiple viral targets. Specific enzymatic tests, together with a time-of-addition (TOA) experiment, support our hypothesis of binding both to IN and to reverse transcriptase (RT). Overall, this compound can be considered an attractive lead for the development of new classes of antiviral agents able to overcome the problem of resistance, due to its ability to exert its action by binding simultaneously to multiple viral targets.

ACS Style

Riccardo Martini; Francesca Esposito; Angela Corona; Roberto Ferrarese; Elisa Rita Ceresola; Laura Visconti; Cristina Tintori; Alessandro Barbieri; Andrea Calcaterra; Valentina Iovine; Filippo Canducci; Enzo Tramontano; Maurizio Botta. Natural Product Kuwanon-L Inhibits HIV-1 Replication through Multiple Target Binding. ChemBioChem 2017, 18, 374 -377.

AMA Style

Riccardo Martini, Francesca Esposito, Angela Corona, Roberto Ferrarese, Elisa Rita Ceresola, Laura Visconti, Cristina Tintori, Alessandro Barbieri, Andrea Calcaterra, Valentina Iovine, Filippo Canducci, Enzo Tramontano, Maurizio Botta. Natural Product Kuwanon-L Inhibits HIV-1 Replication through Multiple Target Binding. ChemBioChem. 2017; 18 (4):374-377.

Chicago/Turabian Style

Riccardo Martini; Francesca Esposito; Angela Corona; Roberto Ferrarese; Elisa Rita Ceresola; Laura Visconti; Cristina Tintori; Alessandro Barbieri; Andrea Calcaterra; Valentina Iovine; Filippo Canducci; Enzo Tramontano; Maurizio Botta. 2017. "Natural Product Kuwanon-L Inhibits HIV-1 Replication through Multiple Target Binding." ChemBioChem 18, no. 4: 374-377.

Journals
Published: 23 December 2016 in Organic & Biomolecular Chemistry
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Protonated basket resorcin[4]arenes are suitable for enantiodiscrimination of alanine di- and tripeptides in the gas phase.

ACS Style

C. Fraschetti; M. Montagna; M. E. Crestoni; A. Calcaterra; F. Aiello; L. Santi; A. Filippi. Kinetic enantioselectivity of a protonated bis(diamido)-bridged basket resorcin[4]arene towards alanine peptides. Organic & Biomolecular Chemistry 2016, 15, 1183 -1189.

AMA Style

C. Fraschetti, M. Montagna, M. E. Crestoni, A. Calcaterra, F. Aiello, L. Santi, A. Filippi. Kinetic enantioselectivity of a protonated bis(diamido)-bridged basket resorcin[4]arene towards alanine peptides. Organic & Biomolecular Chemistry. 2016; 15 (5):1183-1189.

Chicago/Turabian Style

C. Fraschetti; M. Montagna; M. E. Crestoni; A. Calcaterra; F. Aiello; L. Santi; A. Filippi. 2016. "Kinetic enantioselectivity of a protonated bis(diamido)-bridged basket resorcin[4]arene towards alanine peptides." Organic & Biomolecular Chemistry 15, no. 5: 1183-1189.