Sebastiano Sciuto - Academia.edu (original) (raw)
Papers by Sebastiano Sciuto
European Journal of Medicinal Chemistry, 2015
Resveratrol, a polyphenol present in grapes and other edible plants, possesses several important ... more Resveratrol, a polyphenol present in grapes and other edible plants, possesses several important pharmacological activities, including anticancer activity. Nevertheless, its therapeutic use is still limited because of some unfavourable physicochemical and pharmacokinetic properties, mainly, poor cellular uptake and too rapid metabolism resulting in elimination from the body. To meet these drawbacks, some resveratrol conjugates would be useful, which would possess improved stability, uptake and bioavailability than the lead compound, and the ability to release it once it is internalized into the cell. In this paper we report a synthetic strategy which allowed us to obtain new amphiphilic resveratrol derivatives starting from different selectively protected resveratrol phosphoramidites or even from the resveratrol triphosphoramidite. Specifically, resveratrol was conjugated through phosphate bridge(s) to different lipophilic groups related to membrane lipids, such as cholesteryl or diacylglycero moieties. All the new lipoconjugates were tested towards human neuroblastoma SH-SY5Y cells and proved to be significantly more active than resveratrol, with a concentration-dependent activity.
![Research paper thumbnail of Glycoclusters presenting lactose on calix[4]arene cores display trypanocidal activity](https://attachments.academia-assets.com/45836847/thumbnails/1.jpg)
](Tetrahedron, 2011
A new series of water-soluble tetravalent glycoclusters incorporating b-lactosyl residues attache... more A new series of water-soluble tetravalent glycoclusters incorporating b-lactosyl residues attached to a central calix[4]arene core was synthesised using azideealkyne Cu(I)-catalysed cycloaddition ('click chemistry'). Carbohydrate moieties were attached either to the upper or lower rim of rigid cone-shaped or partial cone macrocycles via 14e21 atom spacer arms. The glycoclusters with a C 4 -symmetrical arrangement of b-lactosyl residues showed trypanocidal activity, with one of them showing comparable activity to established anti-trypanosomal drug benznidazole in in vitro anti-parasite assays.
Bioconjugate Chemistry, 2013
Antisense oligonucleotides are promising therapeutic agents against a variety of diseases. Effect... more Antisense oligonucleotides are promising therapeutic agents against a variety of diseases. Effective delivery of these molecules is critical in view of their clinical application. Despite the richness of synthetic strategies addressed to the lipophilic modification of oligodeoxynucleotides (ODNs) for enhancing their pharmacokinetic behavior and trans-membrane delivery, the phosphatidyl group (1,2-di-O-acyl-sn-glycero-3-phosphoryl) has been never used as the lipophilic moiety of lipid-ODN conjugates. The present paper reports a general procedure for synthesizing 5'-phosphatidyl-ODNs. By this procedure, phosphatidyl conjugates of a VEGF antisense-ODN have been prepared, which differ in the fatty acid composition of their phosphatidyl moiety. These new lipid-ODN conjugates, which have been characterized on the basis of their physicochemical properties, showed an improved resistance to exonucleases and were able to lower the VEGF-mRNA expression in human SH-SY5Y neuroblastoma cells more effectively than the relevant free antisense-ODN did.
J Nat Prod, 1985
A new metabolite, 6-arnino-6-carboxy-2-trirnethylammoniohexanoate has been isolated from the red ... more A new metabolite, 6-arnino-6-carboxy-2-trirnethylammoniohexanoate has been isolated from the red alga Srhttera nicaeensis, and its structure was determined by spectral and chemical methods. Its distribution in about fifty species of Rhodophyceae has been investigated.
Zeitschrift Fur Naturforschung C Journal of Biosciences, 2007
The stilbenoids E-resveratrol (E-3,5,4Ј-trihydroxystilbene, 1), E-3,5,4Ј-trimethoxystilbene (2), ... more The stilbenoids E-resveratrol (E-3,5,4Ј-trihydroxystilbene, 1), E-3,5,4Ј-trimethoxystilbene (2), E-3,4,4Ј-trimethoxystilbene (3) and E-3,4Ј-dimethoxy-5-hydroxystilbene (4) were converted by photoisomerization to their corresponding Z-isomers 5Ð8. Compounds 1Ð8 were subjected to antiproliferative activity bioassays towards a set of four different human cancer cell lines, namely DU-145 (androgen not responsive human prostate tumor), LNCaP (androgen responsive human prostate tumor), M-14 (human melanoma) and KB (human mouth epidermoid carcinoma). The methylated analogues of 1 are more active than the natural lead in the majority of bioassays. The most active compound was Z-3,5,4Ј-trimethoxystilbene , which showed against DU-145 and LNCaP cells GI 50 values close to those of the anticancer drug vinorelbine; 6 resulted more active than its E-isomer 2 towards DU-145, LNCaP and especially KB cell lines. A number of methylated Z-isomers displayed a higher activity than their E-isomers, but E-resveratrol (1) was more active than Z-resveratrol (5) towards all the tested cell lines.
Comparative biochemistry and physiology. B, Comparative biochemistry, 1988
1. Melanosomes from skin and liver of Rana esculenta L. have been isolated and some chemical prop... more 1. Melanosomes from skin and liver of Rana esculenta L. have been isolated and some chemical properties of the relevant melanin and protein components were compared. 2. In both cases the pigments show spectroscopic (ESR) and chemical characteristics similar to those of eumelanins. The melanin content in skin melanosomes is higher than in the liver counterparts. 3. Amino acid patterns of the two protein components are different in their quantitative composition and both are characterized by high levels of glycine and proline. 4. The results as a whole indicate that skin and liver melanosomes from the same animal markedly differ in their chemical composition.
Zeitschrift für Naturforschung C, 2007
The stilbenoids E-resveratrol (E-3,5,4Ј-trihydroxystilbene, 1), E-3,5,4Ј-trimethoxystilbene (2), ... more The stilbenoids E-resveratrol (E-3,5,4Ј-trihydroxystilbene, 1), E-3,5,4Ј-trimethoxystilbene (2), E-3,4,4Ј-trimethoxystilbene (3) and E-3,4Ј-dimethoxy-5-hydroxystilbene (4) were converted by photoisomerization to their corresponding Z-isomers 5Ð8. Compounds 1Ð8 were subjected to antiproliferative activity bioassays towards a set of four different human cancer cell lines, namely DU-145 (androgen not responsive human prostate tumor), LNCaP (androgen responsive human prostate tumor), M-14 (human melanoma) and KB (human mouth epidermoid carcinoma). The methylated analogues of 1 are more active than the natural lead in the majority of bioassays. The most active compound was Z-3,5,4Ј-trimethoxystilbene , which showed against DU-145 and LNCaP cells GI 50 values close to those of the anticancer drug vinorelbine; 6 resulted more active than its E-isomer 2 towards DU-145, LNCaP and especially KB cell lines. A number of methylated Z-isomers displayed a higher activity than their E-isomers, but E-resveratrol (1) was more active than Z-resveratrol (5) towards all the tested cell lines.
Phytochemistry, 1974
Seedlings of a yellow betaxanthin-producing variety of Celosia plumosa when fed with appropriate ... more Seedlings of a yellow betaxanthin-producing variety of Celosia plumosa when fed with appropriate precursors are capable of synthesizing the red-violet pigment normally present in red varieties of the same species, namely amaranthin.
Olives and Olive Oil in Health and Disease Prevention, 2010
Phytochemistry, 1982
was identified in aqueous-ethanolic extracts of the red alga Rytiphloea tinctoria.
Phytochemistry, 1975
The sterol composition of 17 red algae has been determined. Only C-27 sterols have been found in ... more The sterol composition of 17 red algae has been determined. Only C-27 sterols have been found in substantial amounts; details of the structural elucidation of liagosterol (cholesta-5,23diene-3#$25-diol) are given. The possible taxonomic significance of the sterol distribution is briefly discussed.
Phycologia, 1979
... H. rubens is a 'species' included by Kylin (1956) in the Cruoriaceae (Gigar... more ... H. rubens is a 'species' included by Kylin (1956) in the Cruoriaceae (Gigartinales), transferred to the Peyssonneliaceae (Cryptonemiales) by Parke & ... 1902; Norton, 1970), France (van den Hoek & Donze, 1966), Portugal (Ardre, 1970), the Atlantic coast of Spain (Donze, 1968 ...
Marine Pollution Bulletin, 1979
Journal of Natural Products, 1993
... ANGELA PATTI, RAFFAELE MORRONE, Istituto del CNR per Io Studio M e Sostrrnze Naturali di lntm... more ... ANGELA PATTI, RAFFAELE MORRONE, Istituto del CNR per Io Studio M e Sostrrnze Naturali di lntmse Alimentare e Chimico-Farmareutico, Via &I Santuario 110, 95028 VaIwa2, ltaIy ROSA CHILLEMI, MARIO PIA-~-I-ELLI, and ... J. Miura-Fraboni and S. Englard, FEMS Mimbiol. ...
Journal of Natural Products, 1988
European Journal of Medicinal Chemistry, 2015
Resveratrol, a polyphenol present in grapes and other edible plants, possesses several important ... more Resveratrol, a polyphenol present in grapes and other edible plants, possesses several important pharmacological activities, including anticancer activity. Nevertheless, its therapeutic use is still limited because of some unfavourable physicochemical and pharmacokinetic properties, mainly, poor cellular uptake and too rapid metabolism resulting in elimination from the body. To meet these drawbacks, some resveratrol conjugates would be useful, which would possess improved stability, uptake and bioavailability than the lead compound, and the ability to release it once it is internalized into the cell. In this paper we report a synthetic strategy which allowed us to obtain new amphiphilic resveratrol derivatives starting from different selectively protected resveratrol phosphoramidites or even from the resveratrol triphosphoramidite. Specifically, resveratrol was conjugated through phosphate bridge(s) to different lipophilic groups related to membrane lipids, such as cholesteryl or diacylglycero moieties. All the new lipoconjugates were tested towards human neuroblastoma SH-SY5Y cells and proved to be significantly more active than resveratrol, with a concentration-dependent activity.
Tetrahedron, 2011
A new series of water-soluble tetravalent glycoclusters incorporating b-lactosyl residues attache... more A new series of water-soluble tetravalent glycoclusters incorporating b-lactosyl residues attached to a central calix[4]arene core was synthesised using azideealkyne Cu(I)-catalysed cycloaddition ('click chemistry'). Carbohydrate moieties were attached either to the upper or lower rim of rigid cone-shaped or partial cone macrocycles via 14e21 atom spacer arms. The glycoclusters with a C 4 -symmetrical arrangement of b-lactosyl residues showed trypanocidal activity, with one of them showing comparable activity to established anti-trypanosomal drug benznidazole in in vitro anti-parasite assays.
Bioconjugate Chemistry, 2013
Antisense oligonucleotides are promising therapeutic agents against a variety of diseases. Effect... more Antisense oligonucleotides are promising therapeutic agents against a variety of diseases. Effective delivery of these molecules is critical in view of their clinical application. Despite the richness of synthetic strategies addressed to the lipophilic modification of oligodeoxynucleotides (ODNs) for enhancing their pharmacokinetic behavior and trans-membrane delivery, the phosphatidyl group (1,2-di-O-acyl-sn-glycero-3-phosphoryl) has been never used as the lipophilic moiety of lipid-ODN conjugates. The present paper reports a general procedure for synthesizing 5'-phosphatidyl-ODNs. By this procedure, phosphatidyl conjugates of a VEGF antisense-ODN have been prepared, which differ in the fatty acid composition of their phosphatidyl moiety. These new lipid-ODN conjugates, which have been characterized on the basis of their physicochemical properties, showed an improved resistance to exonucleases and were able to lower the VEGF-mRNA expression in human SH-SY5Y neuroblastoma cells more effectively than the relevant free antisense-ODN did.
J Nat Prod, 1985
A new metabolite, 6-arnino-6-carboxy-2-trirnethylammoniohexanoate has been isolated from the red ... more A new metabolite, 6-arnino-6-carboxy-2-trirnethylammoniohexanoate has been isolated from the red alga Srhttera nicaeensis, and its structure was determined by spectral and chemical methods. Its distribution in about fifty species of Rhodophyceae has been investigated.
Zeitschrift Fur Naturforschung C Journal of Biosciences, 2007
The stilbenoids E-resveratrol (E-3,5,4Ј-trihydroxystilbene, 1), E-3,5,4Ј-trimethoxystilbene (2), ... more The stilbenoids E-resveratrol (E-3,5,4Ј-trihydroxystilbene, 1), E-3,5,4Ј-trimethoxystilbene (2), E-3,4,4Ј-trimethoxystilbene (3) and E-3,4Ј-dimethoxy-5-hydroxystilbene (4) were converted by photoisomerization to their corresponding Z-isomers 5Ð8. Compounds 1Ð8 were subjected to antiproliferative activity bioassays towards a set of four different human cancer cell lines, namely DU-145 (androgen not responsive human prostate tumor), LNCaP (androgen responsive human prostate tumor), M-14 (human melanoma) and KB (human mouth epidermoid carcinoma). The methylated analogues of 1 are more active than the natural lead in the majority of bioassays. The most active compound was Z-3,5,4Ј-trimethoxystilbene , which showed against DU-145 and LNCaP cells GI 50 values close to those of the anticancer drug vinorelbine; 6 resulted more active than its E-isomer 2 towards DU-145, LNCaP and especially KB cell lines. A number of methylated Z-isomers displayed a higher activity than their E-isomers, but E-resveratrol (1) was more active than Z-resveratrol (5) towards all the tested cell lines.
Comparative biochemistry and physiology. B, Comparative biochemistry, 1988
1. Melanosomes from skin and liver of Rana esculenta L. have been isolated and some chemical prop... more 1. Melanosomes from skin and liver of Rana esculenta L. have been isolated and some chemical properties of the relevant melanin and protein components were compared. 2. In both cases the pigments show spectroscopic (ESR) and chemical characteristics similar to those of eumelanins. The melanin content in skin melanosomes is higher than in the liver counterparts. 3. Amino acid patterns of the two protein components are different in their quantitative composition and both are characterized by high levels of glycine and proline. 4. The results as a whole indicate that skin and liver melanosomes from the same animal markedly differ in their chemical composition.
Zeitschrift für Naturforschung C, 2007
The stilbenoids E-resveratrol (E-3,5,4Ј-trihydroxystilbene, 1), E-3,5,4Ј-trimethoxystilbene (2), ... more The stilbenoids E-resveratrol (E-3,5,4Ј-trihydroxystilbene, 1), E-3,5,4Ј-trimethoxystilbene (2), E-3,4,4Ј-trimethoxystilbene (3) and E-3,4Ј-dimethoxy-5-hydroxystilbene (4) were converted by photoisomerization to their corresponding Z-isomers 5Ð8. Compounds 1Ð8 were subjected to antiproliferative activity bioassays towards a set of four different human cancer cell lines, namely DU-145 (androgen not responsive human prostate tumor), LNCaP (androgen responsive human prostate tumor), M-14 (human melanoma) and KB (human mouth epidermoid carcinoma). The methylated analogues of 1 are more active than the natural lead in the majority of bioassays. The most active compound was Z-3,5,4Ј-trimethoxystilbene , which showed against DU-145 and LNCaP cells GI 50 values close to those of the anticancer drug vinorelbine; 6 resulted more active than its E-isomer 2 towards DU-145, LNCaP and especially KB cell lines. A number of methylated Z-isomers displayed a higher activity than their E-isomers, but E-resveratrol (1) was more active than Z-resveratrol (5) towards all the tested cell lines.
Phytochemistry, 1974
Seedlings of a yellow betaxanthin-producing variety of Celosia plumosa when fed with appropriate ... more Seedlings of a yellow betaxanthin-producing variety of Celosia plumosa when fed with appropriate precursors are capable of synthesizing the red-violet pigment normally present in red varieties of the same species, namely amaranthin.
Olives and Olive Oil in Health and Disease Prevention, 2010
Phytochemistry, 1982
was identified in aqueous-ethanolic extracts of the red alga Rytiphloea tinctoria.
Phytochemistry, 1975
The sterol composition of 17 red algae has been determined. Only C-27 sterols have been found in ... more The sterol composition of 17 red algae has been determined. Only C-27 sterols have been found in substantial amounts; details of the structural elucidation of liagosterol (cholesta-5,23diene-3#$25-diol) are given. The possible taxonomic significance of the sterol distribution is briefly discussed.
Phycologia, 1979
... H. rubens is a 'species' included by Kylin (1956) in the Cruoriaceae (Gigar... more ... H. rubens is a 'species' included by Kylin (1956) in the Cruoriaceae (Gigartinales), transferred to the Peyssonneliaceae (Cryptonemiales) by Parke & ... 1902; Norton, 1970), France (van den Hoek & Donze, 1966), Portugal (Ardre, 1970), the Atlantic coast of Spain (Donze, 1968 ...
Marine Pollution Bulletin, 1979
Journal of Natural Products, 1993
... ANGELA PATTI, RAFFAELE MORRONE, Istituto del CNR per Io Studio M e Sostrrnze Naturali di lntm... more ... ANGELA PATTI, RAFFAELE MORRONE, Istituto del CNR per Io Studio M e Sostrrnze Naturali di lntmse Alimentare e Chimico-Farmareutico, Via &I Santuario 110, 95028 VaIwa2, ltaIy ROSA CHILLEMI, MARIO PIA-~-I-ELLI, and ... J. Miura-Fraboni and S. Englard, FEMS Mimbiol. ...
Journal of Natural Products, 1988