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Papers by Marco Berettoni

Research paper thumbnail of CCDC 1044933: Experimental Crystal Structure Determination

An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Research paper thumbnail of L-arabino-disaccharides of anthracyclines, processes for their preparation, and pharmaceutical compositions containing them

Research paper thumbnail of Pharmacological Profile of New Deamino Analogues of Sabarubicin (MEN 10755)

Letters in Drug Design & Discovery, 2005

Sabarubicin (MEN 10755) is the progenitor of a third generation of synthetic anthracycline oligos... more Sabarubicin (MEN 10755) is the progenitor of a third generation of synthetic anthracycline oligosaccharides. Sabarubicin deamino analogues MEN 10959 and MEN 12297 were evaluated for topoisomerase II poisoning, cytotoxic potency and antitumor activity in human xenografts. The new analogues were able to induce DNA cleavage mediated by both DNA topoisomerase IIα and β and a good correlation was found regarding their cytotoxic activity. The two analogues possess also a different spectrum of antitumor activity, compared to sabarubicin.

Research paper thumbnail of New anthracycline disaccharides. Synthesis of L-daunosaminyl-?(1 ?4)-2-deoxy-L-rhamnosyl and of L-daunosaminyl-?(1 ?4)-2-deoxy-L-fucosyl daunorubicin analogues

Journal of the Chemical Society, Perkin Transactions 1, 1996

New anthracycline disaccharides. Synthesis of L-daunosaminyl-[small alpha](1 [rightward arrow] 4)... more New anthracycline disaccharides. Synthesis of L-daunosaminyl-[small alpha](1 [rightward arrow] 4)-2-deoxy-L-rhamnosyl and of L-daunosaminyl-[small alph...-Journal of the Chemical Society, Perkin Transactions 1 (RSC Publishing) DOI: 10.1039/P19960001327

Research paper thumbnail of Unprecedented outcome of the allene photoaddition to a fused α,β-unsaturated ketone

Tetrahedron Letters, 1993

... Bettolo*, Lorenzo Montaanini di Mirabello and Sergio Romeo Dipartimento di Chimica a Centro d... more ... Bettolo*, Lorenzo Montaanini di Mirabello and Sergio Romeo Dipartimento di Chimica a Centro di Studio dei CNR per la Chimica delle Sostanze Organiche Natural! ... Ital., 122, 55 (1992). 2. Guthrie RW, Philipp A., Valenta Z., Wiesner K., Tetrahedron Lett., No. 34, 2945 (1965). ...

Research paper thumbnail of NMR-Spectroscopic, computational and mass-spectrometric investigations on the cis/trans analogues of 2,3,4-trihydronaphthalene-1-one

Tetrahedron, 2003

NMR-Spectroscopic, computational and mass-spectrometric studies of the cis/trans isomers of N-[8-... more NMR-Spectroscopic, computational and mass-spectrometric studies of the cis/trans isomers of N-[8-(acetylamino)-4-(2,2-dimethyl-1,1-diphenyl-silapropoxy)-6-fluoro-5-methyl-1-one-2,3,4-trihydronaphthyl]acetamide (1a and 1b), obtained as intermediates in the synthesis of an important class of alkaloid molecules, are reported. 1H and 13C NMR analyses show an unusual axial preference of the TBDPSi– (tert-butyldiphenylsilyl) group in position 4 in both the isomers. Mass spectrometric evidence demonstrates that trans isomer has a

Research paper thumbnail of Doxorubicin Disaccharide Analogue: Apoptosis-Related Improvement of Efficacy In Vivo

JNCI Journal of the National Cancer Institute, 1997

Notes Supported by a grant from the ''Medizinisch-Wissenschaftlicher Fonds des Burgermeisters der... more Notes Supported by a grant from the ''Medizinisch-Wissenschaftlicher Fonds des Burgermeisters der Bundeshauptstadt Wien.'' We thank Helga Dammerer and Gerhard Breitenecker for technical advice in performing immunohistochemistry. Manuscript

Research paper thumbnail of Studies for a Diastereoselective Synthesis of the Tetracyclic Diterpenic Diol Stemarin: A Model Study for a New Preparation of the Key Intermediate and the Synthesis of (+)-18-Deoxystemarin

Helvetica Chimica Acta, 1991

... by Marco Berettoni, Rinaldo Marini Bettolo*, Vittorio Montanari, Teresa Prencipe, and Sergio ... more ... by Marco Berettoni, Rinaldo Marini Bettolo*, Vittorio Montanari, Teresa Prencipe, and Sergio Romeo Dipartimento di Chimica and Centro di Studio del CNR per la Chimica delle Sostanze Organiche ... [8] RL Cargill, D. F. Bushey, JR Dalton, R. S. Prasad, RD Dyer, J. Bordner, J ...

Research paper thumbnail of Benzofused hydroxamic acids: Useful fragments for the preparation of histone deacetylase inhibitors. Part 1: Hit identification

Bioorganic & Medicinal Chemistry Letters, 2013

Research paper thumbnail of Synthesis and biological evaluation of rebeccamycin analogues modified at the imide moiety

Bioorganic & Medicinal Chemistry Letters, 2012

Glycosylated indolocarbazoles related to the antibiotic rebeccamycin represent an important class... more Glycosylated indolocarbazoles related to the antibiotic rebeccamycin represent an important class of antitumour drugs. In the course of our structure-activity relationship studies, new rebeccamycin analogues modified at the imide moiety were synthesised. The antiproliferative activity of the compounds was evaluated on three human cancer cell lines, A2780 (ovarian cancer), H460 (lung cancer), and GLC4 (small-cell lung cancer). The in vitro cytotoxicity of compounds 2 and 4, characterised respectively by a 1,3-dioxolan and (1,3-dioxolan-4-yl)methylene groups linked to the imide moiety, was higher than the reference compound, edotecarin. The effect of compound 2 in inducing tumour regression in the A2780 xenograft model was also investigated.

Research paper thumbnail of Novel anthracycline oligosaccharides: influence of chemical modifications of the carbohydrate moiety on biological activity

Bioorganic & Medicinal Chemistry, 2002

Several observations highlight the importance of the carbohydrate moiety for the biological activ... more Several observations highlight the importance of the carbohydrate moiety for the biological activity of antitumoural anthracyclines. Here is reported the synthesis, cytotoxicity and topoisomerase II-mediated DNA cleavage intensity of the new oligosaccharide anthracyclines 1--4 modified in the sugar residue. Evaluation of cytotoxic potency on different cell lines, resulted in quite similar values among the different analogues. On the other hand, topoisomerase II-mediated DNA breaks level was different for the various compounds, and was not related to cytotoxicity, thus supporting previous observations reported for some monosaccharide anthracyclines modified in the carbohydrate portion.

Research paper thumbnail of Design and synthesis of novel sulfonamide-containing bradykinin hB2 receptor antagonists. Synthesis and structure-relationships of α,α-tetrahydropyranylglycine

Bioorganic & Medicinal Chemistry, 2012

A series of a,a-cycloalkylglycine sulfonamide compounds of general formula 1 has previously been ... more A series of a,a-cycloalkylglycine sulfonamide compounds of general formula 1 has previously been identified by our group as selective human B 2 (hB 2) receptor antagonists. Here we report the in vitro and in vivo BK antagonist activity of a further evolution of the series, consisting in compounds of the general formula 2, containing either an alkyl piperazine or a 4-alkyl piperidine ring bearing various positively charged groups (R 0). These studies unexpectedly revealed quite a flat nanomolar/subnanomolar SAR for the binding affinity, while differences were seen in the in vitro functional activities. We propose that variations in the residence time may explain these results.

Research paper thumbnail of Synthesis of 14-fluorodoxorubicin

Tetrahedron Letters, 2002

Research paper thumbnail of CCDC 1044933: Experimental Crystal Structure Determination

An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Research paper thumbnail of L-arabino-disaccharides of anthracyclines, processes for their preparation, and pharmaceutical compositions containing them

Research paper thumbnail of Pharmacological Profile of New Deamino Analogues of Sabarubicin (MEN 10755)

Letters in Drug Design & Discovery, 2005

Sabarubicin (MEN 10755) is the progenitor of a third generation of synthetic anthracycline oligos... more Sabarubicin (MEN 10755) is the progenitor of a third generation of synthetic anthracycline oligosaccharides. Sabarubicin deamino analogues MEN 10959 and MEN 12297 were evaluated for topoisomerase II poisoning, cytotoxic potency and antitumor activity in human xenografts. The new analogues were able to induce DNA cleavage mediated by both DNA topoisomerase IIα and β and a good correlation was found regarding their cytotoxic activity. The two analogues possess also a different spectrum of antitumor activity, compared to sabarubicin.

Research paper thumbnail of New anthracycline disaccharides. Synthesis of L-daunosaminyl-?(1 ?4)-2-deoxy-L-rhamnosyl and of L-daunosaminyl-?(1 ?4)-2-deoxy-L-fucosyl daunorubicin analogues

Journal of the Chemical Society, Perkin Transactions 1, 1996

New anthracycline disaccharides. Synthesis of L-daunosaminyl-[small alpha](1 [rightward arrow] 4)... more New anthracycline disaccharides. Synthesis of L-daunosaminyl-[small alpha](1 [rightward arrow] 4)-2-deoxy-L-rhamnosyl and of L-daunosaminyl-[small alph...-Journal of the Chemical Society, Perkin Transactions 1 (RSC Publishing) DOI: 10.1039/P19960001327

Research paper thumbnail of Unprecedented outcome of the allene photoaddition to a fused α,β-unsaturated ketone

Tetrahedron Letters, 1993

... Bettolo*, Lorenzo Montaanini di Mirabello and Sergio Romeo Dipartimento di Chimica a Centro d... more ... Bettolo*, Lorenzo Montaanini di Mirabello and Sergio Romeo Dipartimento di Chimica a Centro di Studio dei CNR per la Chimica delle Sostanze Organiche Natural! ... Ital., 122, 55 (1992). 2. Guthrie RW, Philipp A., Valenta Z., Wiesner K., Tetrahedron Lett., No. 34, 2945 (1965). ...

Research paper thumbnail of NMR-Spectroscopic, computational and mass-spectrometric investigations on the cis/trans analogues of 2,3,4-trihydronaphthalene-1-one

Tetrahedron, 2003

NMR-Spectroscopic, computational and mass-spectrometric studies of the cis/trans isomers of N-[8-... more NMR-Spectroscopic, computational and mass-spectrometric studies of the cis/trans isomers of N-[8-(acetylamino)-4-(2,2-dimethyl-1,1-diphenyl-silapropoxy)-6-fluoro-5-methyl-1-one-2,3,4-trihydronaphthyl]acetamide (1a and 1b), obtained as intermediates in the synthesis of an important class of alkaloid molecules, are reported. 1H and 13C NMR analyses show an unusual axial preference of the TBDPSi– (tert-butyldiphenylsilyl) group in position 4 in both the isomers. Mass spectrometric evidence demonstrates that trans isomer has a

Research paper thumbnail of Doxorubicin Disaccharide Analogue: Apoptosis-Related Improvement of Efficacy In Vivo

JNCI Journal of the National Cancer Institute, 1997

Notes Supported by a grant from the ''Medizinisch-Wissenschaftlicher Fonds des Burgermeisters der... more Notes Supported by a grant from the ''Medizinisch-Wissenschaftlicher Fonds des Burgermeisters der Bundeshauptstadt Wien.'' We thank Helga Dammerer and Gerhard Breitenecker for technical advice in performing immunohistochemistry. Manuscript

Research paper thumbnail of Studies for a Diastereoselective Synthesis of the Tetracyclic Diterpenic Diol Stemarin: A Model Study for a New Preparation of the Key Intermediate and the Synthesis of (+)-18-Deoxystemarin

Helvetica Chimica Acta, 1991

... by Marco Berettoni, Rinaldo Marini Bettolo*, Vittorio Montanari, Teresa Prencipe, and Sergio ... more ... by Marco Berettoni, Rinaldo Marini Bettolo*, Vittorio Montanari, Teresa Prencipe, and Sergio Romeo Dipartimento di Chimica and Centro di Studio del CNR per la Chimica delle Sostanze Organiche ... [8] RL Cargill, D. F. Bushey, JR Dalton, R. S. Prasad, RD Dyer, J. Bordner, J ...

Research paper thumbnail of Benzofused hydroxamic acids: Useful fragments for the preparation of histone deacetylase inhibitors. Part 1: Hit identification

Bioorganic & Medicinal Chemistry Letters, 2013

Research paper thumbnail of Synthesis and biological evaluation of rebeccamycin analogues modified at the imide moiety

Bioorganic & Medicinal Chemistry Letters, 2012

Glycosylated indolocarbazoles related to the antibiotic rebeccamycin represent an important class... more Glycosylated indolocarbazoles related to the antibiotic rebeccamycin represent an important class of antitumour drugs. In the course of our structure-activity relationship studies, new rebeccamycin analogues modified at the imide moiety were synthesised. The antiproliferative activity of the compounds was evaluated on three human cancer cell lines, A2780 (ovarian cancer), H460 (lung cancer), and GLC4 (small-cell lung cancer). The in vitro cytotoxicity of compounds 2 and 4, characterised respectively by a 1,3-dioxolan and (1,3-dioxolan-4-yl)methylene groups linked to the imide moiety, was higher than the reference compound, edotecarin. The effect of compound 2 in inducing tumour regression in the A2780 xenograft model was also investigated.

Research paper thumbnail of Novel anthracycline oligosaccharides: influence of chemical modifications of the carbohydrate moiety on biological activity

Bioorganic & Medicinal Chemistry, 2002

Several observations highlight the importance of the carbohydrate moiety for the biological activ... more Several observations highlight the importance of the carbohydrate moiety for the biological activity of antitumoural anthracyclines. Here is reported the synthesis, cytotoxicity and topoisomerase II-mediated DNA cleavage intensity of the new oligosaccharide anthracyclines 1--4 modified in the sugar residue. Evaluation of cytotoxic potency on different cell lines, resulted in quite similar values among the different analogues. On the other hand, topoisomerase II-mediated DNA breaks level was different for the various compounds, and was not related to cytotoxicity, thus supporting previous observations reported for some monosaccharide anthracyclines modified in the carbohydrate portion.

Research paper thumbnail of Design and synthesis of novel sulfonamide-containing bradykinin hB2 receptor antagonists. Synthesis and structure-relationships of α,α-tetrahydropyranylglycine

Bioorganic & Medicinal Chemistry, 2012

A series of a,a-cycloalkylglycine sulfonamide compounds of general formula 1 has previously been ... more A series of a,a-cycloalkylglycine sulfonamide compounds of general formula 1 has previously been identified by our group as selective human B 2 (hB 2) receptor antagonists. Here we report the in vitro and in vivo BK antagonist activity of a further evolution of the series, consisting in compounds of the general formula 2, containing either an alkyl piperazine or a 4-alkyl piperidine ring bearing various positively charged groups (R 0). These studies unexpectedly revealed quite a flat nanomolar/subnanomolar SAR for the binding affinity, while differences were seen in the in vitro functional activities. We propose that variations in the residence time may explain these results.

Research paper thumbnail of Synthesis of 14-fluorodoxorubicin

Tetrahedron Letters, 2002