Research Groups‎ > ‎

Separation Science, Stereochemistry of Organic/Bioactive Compounds (CHIM/06)


Head of Laboratory: Claudio Villani
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Main Topics

Organic stereochemistry, studies on stereolabile compounds by dynamic HPLC and dynamic NMR methods. Studies of solvent and medium effects on stereochemical stability, linear solvation energy relationships
Absolute configuration determinations, physical separation of enantiomers by chromatography, preparation of chiral stationary phases for HPLC applications, modification of solid porous materials.
Studies on recognition mechanisms in bimolecular systems, with emphasis on chirality, NMR, UV-Vis, ECD, ESI-MS solution and gas-phase studies of diastereomeric complexes, computational studies by molecular docking procedures.
Development of new computational tools oriented to perform: a) molecular docking procedures; b) mono- and multi-equilibrium dynamic-chromatography analyses.

National and International Collaborations

National: University of Milano, Brescia, Padova, Firenze, Bologna, Ferrara, Chieti, Potenza; CNR: Roma Montelibretti; Istituto Superiore di Sanità, Roma
International: University of Geneva (J. Lacour); University of Reno, Nevada (W. Chalifoux);

Facilities

HPLC and UHPLC workstations, SFC equipment with MS and PDA detectors; preparative HPLC systems; ion-trap and Orbitrap ESI-MS systems; FT-IR and ECD spectrometers; polarimeter

ERC Panels

PE Physical Science and Engineering.
PE5_6 New materials: oxides, alloys, composite, organic-inorganic hybrid, nanoparticles.
PE5_16 Supramolecular chemistry
PE5_17 Organic chemistry


Grants (2015-2018)

Fresenius Kabi Anti-Infective Srl; Chiesi Farmaceutici SpA; Supelco Inc (USA); Merck Serono group; 

Laboratory Members

Claudio Villani, 
Marco Pierini, 
Ilaria D’Acquarica, 
Alessia Ciogli, 
Francesco Gasparrini (Emeritus), 
Omar H. Ismail; 
Giulia Mazzoccanti; 
Roberta Franzini; 
Michela De Martino

Pubblicazioni 2015-2018

C. Di Meo, E. Montanari, L. Manzi, C. Villani, T. Coviello, P. Matricardi Carbohydrate Polymers115, 2015, 502-509  

C. Di Meo, F. Cilurzo, M. Licciardi, C. Scialabba, R. Sabia, D. Paolino, C. Villani, D. Capitani, M. Fresta, G. Giammona, P. Matricardi Pharm. Res.2015, 32,1557-1569  

L. Sciascera, O. Ismail, A. Ciogli, D. Kotoni, A. Cavazzini, L. Botta, T. Szczerba, J. Kocergin, C. Villani, F. Gasparrini J. Chromatogr A1383, 2015, 160-168  

A. Renzetti, A. Di Crescenzo, F. Nie, A.D. Bond, S. Gérard, J. Sapi, A. Fontana, C. Villani  Chirality27, 2015,779-783 

G. Mazzeo, S. Abbate, G. Longhi, E. Castiglioni, C. Villani Chirality27, 2015, 907-913 

R. Sabia, M. De Martino, A. Cavazzini, C. Villani  Chirality28, 2015, 17-21

S. Menta, S. Carradori, D. Secci, C. Faggi, L. Mannina, R. Cirilli, M. Pierini,  Journal of Organic Chemistry, 80 (24), 2015, 11932-11940. 

S. Rizzo, S. Menta, T. Benincori, R. Ferretti, M. Pierini, R. Cirilli, F. Sannicolò,  Chirality, 27 (12), 2015, 888-899. 

S. Arnaboldi, R. Cirilli, A. Forni, A. Gennaro, A.A. Isse, V. Mihali, P.R. Mussini, M. Pierini, S. Rizzo, F. Sannicolò,  Electrochimica Acta, 179, 2015, 250-262. 

S. Menta, M. Pierini, R. Cirilli, F. Grisi, A. Perfetto, A. Ciogli,  Chirality, 27 (10), 2015, 685-692.

O. H. Ismail, A. Ciogli, C. Villani, M. De Martino, M. Pierini, A. Cavazzini, D. S. Bell, F. Gasparrini J. Chromatogr A1427, 2016, 55-68  

G. Longhi, E. Castiglioni, C. Villani, R. Sabia, S. Menichetti, C. Viglianisi, F. Devlin, S. Abbate Journal of Photochemistry and Photobiology – A; Chemistry331, 2016, 138-145 

G. M. Labrador, J. Bosson, Z. S. Breitbach, Y. Lim, E. R. Francotte, R. Sabia, C. Villani, D. W. Armstrong, J. Lacour Chirality 282016, 282-289 

M. Catani, O. Ismail, A. Cavazzini, A. Ciogli, C. Villani, L. Pasti, C. Bergantin, D. Cabooter, G. Desmet,  F. Gasparrini J. Chromatogr A1454, 2016, 78-85

O. Ismail, M. Catani, L. Pasti, A. Cavazzini, A. Ciogli, C. Villani, D. Kotoni, F. Gasparrini, D. S. Bell J. Chromatogr A  1466, 2016, 96-104

A. Ciogli, S. Vivek Kumar, M. Mancinelli, A. Mazzanti, S. Perumal, C. Severi, and C. Villani Org. Biomol. Chem.2016

V. Paradiso, S. Menta, M. Pierini, G. Della Sala, A. Ciogli, F. Grisi, Catalysts, 6 (11), 2016, 177. 

S. Carradori, M. Pierini, S. Menta, D. Secci, R. Fioravanti, R. Cirilli, Journal of Chromatography A, 1467, 2016, 221-227. 

A. Ammazzalorso, B. De Filippis, C. Maccallini, M. Pierini, Current Bioactive Compounds, 12 (3), 2016, 136-145. 

S. Menta, S. Carradori, G. Siani, D. Secci, L. Mannina, A.P. Sobolev, R. Cirilli, M. Pierini, RSC Advances, 6 (75), 2016, 71262-71272.

Ghirga, I.; Quaglio, D.; Ghirga, P.; Berardozzi, S.; Zappia, G.; Botta, B.; Mori, M.; D’Acquarica, I.* “Occurrence of enantioselectivity in nature: the case of (S)-norcoclaurine”. Chirality, 28 (2016) 169−180.

Bonamore, A.; Calisti, L.; Calcaterra, A.; Ismail, O.H.; Gargano, M.; D’Acquarica, I.; Botta, B.; Boffi, A.; Macone, A. “A novel enzymatic strategy for the synthesis of substituted tetrahydroisoquinolines”. ChemistrySelect, 1 (2016) 1525–1528.

D’Acquarica, I.*; Ghirga, F.; Quaglio, D.; Cerreto, A.; Ingallina, C.; Tafi, A.; Botta, B. “Molecular recognition of natural products by resorc[4]arene receptors”. Curr. Pharm. Des., 22 (2016) 1715−1729. 

Ingallina, C.; D’Acquarica, I.; Delle Monache, G.; Ghirga, F.; Quaglio, D.; Ghirga, P.; Berardozzi, S.; Markovic, V.; Botta, B. “The Pictet-Spengler reaction still on stage”. Curr. Pharm. Des., 22 (2016) 1808−1850.

Iovine, V.; Benni, I.; Sabia, R.; D’Acquarica, I.*; Fabrizi, G.; Botta, B.; Calcaterra, A. “Total synthesis of kuwanol E”. J. Nat. Prod., 79 (2016) 2495−2503.

Di Marcotullio, L.; Infante, P.; Alfonsi, R.; Ingallina, C.; Quaglio, D.; D’Acquarica, I.; Ghirga, F.; Di Magno, L.; Canettieri, G.; Screpanti, I.; Gulino, A.; Botta, B.; Mori, M.; Bernardi, F. “Inhibition of Hedgehog-dependent tumors and cancer stem cells by a newly-identified naturally occurring chemotype”. Cell Death Dis., 7 (2016) e2376.

P. Simone, G. Pierri, D. Capitani, A. Ciogli, G. Angelini, O. Ursini, G. Gentile, A. Cavazzini, C. J. Chromatogr A1498, 2017, 46-55 

S. Frattari, R. Sabia, F. Gironi, C. Villani Can. J. Chem. Eng. 95, 2017, 863–870. 

G. Manzi, N. Zoratto, S. Matano, R. Sabia, C. Villani, T. Coviello, P. Matricardi, C. Di Meo  Carbohydrate Polymers 174,2017, 706-715 

W. Yang, G. Longhi, S. Abbate, A. Lucotti, M. Tommasini, C. Villani, V.J. Catalano, A.O. Lykhin, S.A. Varganov, and W.A. Chalifoux J. Am. Chem. Soc.,139 (37) 2017, 13102–13109 

O. H Ismail, M. Antonelli, A. Ciogli, C. Villani, A. Cavazzini, M. Catani, S. Felletti, D.S. Bell, F. Gasparrini, J. Chromatogr. A, 1520,2017, 91-102 

G. Mazzoccanti, O. H. Ismail, C. Villani, I. D’Acquarica, F. Gasparrini, C. Manzo, M. Wilcox, A. Cavazzini Chem. Commun. 53, 2017, 12262—12265 

R. Ferretti, S. Carradori, P. Guglielmi, M. Pierini, A. Casulli, R. Cirilli, Journal of Pharmaceutical and Biomedical Analysis, 140, 2017, 38-44. 

M. Pierini, S. Carradori, S. Menta, D. Secci, R. Cirilli, Journal of Chromatography A, 1499, 2017, 140-148. 

S. Gabrieli, R. Cirilli, T. Benincori, M. Pierini, S. Rizzo, S. Rossi, European Journal of Organic Chemistry, 2017 (4), 2017, 861-870. 

S. Rizzo, S. Arnaboldi, V. Mihali, R. Cirilli, A. Forni, A. Gennaro, A.A. Isse, M. Pierini, P.R. Mussini, F. Sannicolo',  Angewandte Chemie - International Edition, 56 (8), 2017, 2079-2082.

Aiello, F.; Balzano, F.; Ghirga, F.; D’Acquarica, I.; Botta, B.; Uccello-Barretta, G.; Quaglio, D. First detection of a ruthenium-carbene-resorc[4]arene complex during the progress of a metathesis reaction. Eur. J. Org. Chem. (2017) 2407–2415.

Ghirga, F.; Bonamore, A.; Calisti, L.; D’Acquarica, I.*; Mori, M.; Botta, B.; Boffi, A.; Macone, A. “Green routes for the production of enantiopure benzylisoquinoline alkaloids”. Int. J. Mol. Sci., 18 (2017) 2464–2482.

A. Ciogli, O.H. Ismail, G. Mazzoccanti, C. Villani, F. Gasparrini J Sep Sci2018

S. Menta, A. Ciogli, C. Villani, F. Gasparrini and M. Pierini Analitica Chimica Acta2018 

S. Belviso, A. Capasso, E. Santoro, L. Najafi, F. Lelj, S. Superchi, D. Casarini, C. Villani, S. Bellani, A.E. Del Rio Castillo, D. Spirito, F. Bonaccorso Adv. Funct. Mater. 2018 

S. Belviso, E. Santoro, F. Lelj, D. Casarini, C. Villani, R. Franzini, S. Superchi Eur JOC2018

R. Zappacosta, A. Di Crescenzo, V. Ettorre, A. Fontana, M. Pierini, G. Siani, Chem Plus Chem83, 2018, 35 – 41

Mascarello, A.; Orbem Menegatti, A.C.; Calcaterra, A.; Martins, P.G.A.; Chiaradia-Delatorre L.D.; D’Acquarica, I.; Ferrari, F.; Pau, V.; Sanna, A.; De Logu, A.; Botta, M.; Botta, B.; Terenzi, H.; Mori, M. “Naturally occurring Diels-Alder-type adducts from Morus nigra as potent inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B”. Eur. J. Med. Chem., 144 (2018) 277–288. 

Calcaterra, A; D’Acquarica, I.* “The market of chiral drugs: chiral switches versus de novo enantiomerically pure compounds”. J. Pharm. Biomed. Anal., 147 (2018) 323–340.

Calcaterra, A.; Iovine, V.; Botta, B.; Quaglio, D.; D’Acquarica, I.; Ciogli, A.; Iazzetti, A.; Infante, P.; Alfonsi, R.; Lospinoso Severini, L.; Di Marcotullio, L.; Mori, M.; Ghirga, F. “Chemical, computational and functional insights into the chemical stability of the Hedgehog pathway inhibitor GANT61”.J. Enzym. Inhib. Med. Ch., 33 (2018) 349–358. 

Cevatemre, B.; Erkısa, M.; Aztopal, N.; Karakas, D.; Alper, P.; Tsimplouli, C.; Sereti, E.; Dimas, K.; Armutak, E.I.I.; Gurevin, E.G.; Uvez, A.; Mori, M.; Berardozzi, S.; Ingallina, C.; D’Acquarica, I.; Botta, B.; Ozpolat, B.; Ulukaya, E. “A promising natural product, pristimerin, results in cytotoxicity against breast cancer stem cells in vitro and xenografts in vivo through apoptosis and an incomplete autopaghy in breast cancer”. Pharmacol. Res., 129 (2018) 500–514.