A straightforward synthetic access to symmetrical glycosyl disulfides and biological evaluation thereof (327 views visite)
Org Biomol Chem (ISSN: 1477-0520, 1477-0539, 1477-0539electronic), 2011 Sep 21; 9(18): 6278-6283.
Export to Esporta in BibTeX Export to Esporta in EndNote
Paper type Tipo di articolo: Journal Article,
Impact factor: 3.696, 5-year impact factor Impact factor a 5 anni: 3.652
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-80052216122&partnerID=40&md5=ad3176e16240b23c9685272708d99a51
Keywords Parole chiave: Biological Evaluation, Cytotoxic Activities, Glycosyl Disulfides, Human Tumor Cells, Sequential Approach, Synthetic Compounds, Cell Culture, Cytotoxicity, Selenium Compounds, Reaction Intermediates, Antineoplastic Agent, Article, Cell Survival, Chemistry, Drug Effect, Oxidation Reduction Reaction, Synthesis, Tumor Cell Line, Oxidation-Reduction,
Affiliations Affiliazioni:
*** IBB - CNR ***
Dipartimento di Chimica Organica e Biochimica, Università Federico II di Napoli, via Cinthia 4, I-80126 Naples, Italy
Facoltà di Scienze Biotecnologiche, Università di Napoli Federico II, via Mezzocannone 16, 80134 Naples, Italy
Istituto di Biostrutture e Bioimmagini, CNR, via Mezzocannone 16, 80134 Naples, Italy
Facolt di Scienze Biotecnologiche, Universit di Napoli Federico II, via Mezzocannone 16, 80134 Naples, Italy
References Riferimenti:
Pei, Z., Aastrup, T., Anderson, H., Ramström, O., (2005) Bioorg. Med. Chem. Lett., 15, p. 270
André, S., Pei, Z., Siebert, H.-C., Ramström, O., Gabius, H.-J., (2006) Bioorg. Med. Chem., 14, p. 6314
Pei, Z., Larsson, R., Aastrup, T., Anderson, H., Lehn, J.-M., Ramström, O., (2006) Biosens. Bioelectron., 22, p. 42
Caraballo, R., Sakulsombat, M., Ramström, O., (2010) Chem. Commun., 46, p. 8469
Richtmyer, N.K., Carr, C.J., Hudson, C.S., (1943) J. Am. Chem. Soc., 65, p. 1477
Cerny, M., Vrkoc, J., Stanek, J., (1959) Collect. Czech. Chem. Commun., 24, p. 64
Horton, D., (1963) Methods Carbohydr. Chem., 2, p. 433
Kiefel, M.J., Thomson, R.J., Radovanovic, M., Von Itzstein, M., (1999) J. Carbohydr. Chem., 18, p. 937
Knapp, S., Darout, E., Amorelli, B., (2006) J. Org. Chem., 71, p. 1380
Floyd, N., Vijayakrishnan, B., Koeppe, A.R., Davis, B.G., (2009) Angew. Chem., Int. Ed., 48, p. 7798
Bhar, D., Chandrasekaran, S., (1997) Carbohydr. Res., 301, p. 221
Szilagy, L., Illyes, T.-Z., Herczegh, P., (2001) Tetrahedron Lett., 42, p. 3901
Davis, B.G., Ward, S.J., Rendle, P.M., (2001) Chem. Commun., p. 189
Ribeiro Morais, G., Falconer, R.A., (2007) Tetrahedron Lett., 48, p. 7637
Aversa, M.C., Barattucci, A., Bonaccorsi, P., (2009) Eur. J. Org. Chem., p. 6455
Stellenboom, N., Hunter, R., Caira, M.R., Szilagy, L., (2010) Tetrahedron Lett., 51, p. 5309
Valerio, S., Iadonisi, A., Adinolfi, M., Ravidà, A., (2007) J. Org. Chem., 72, p. 6097
Adinolfi, M., Iadonisi, A., Ravidà, A., Schiattarella, M., (2003) Tetrahedron Lett., 44, p. 7863
Ibatullin, F.M., Selivanov, S.I., Shavva, A.G., (2001) Synthesis, p. 419
Pezzella, A., Iadonisi, A., Valerio, S., Panzella, L., Napolitano, A., Adinolfi, M., D'Ischia, M., (2009) J. Am. Chem. Soc., 131, p. 15270. , For a stepwise approach to (phenylselenyl)thioglycosides and their application to protein glycoconjugation via disulfide linkage
Gamblin, D.P., Garnier, P., Van Kasteren, S., Oldham, N.J., Fairbanks, A.J., Davis, B.G., (2004) Angew. Chem., Int. Ed., 43, p. 828. , For a recent kinetic study on the formation of disulfide and SSe linkages
Steinmann, D., Nauser, T., Koppenol, W.H., (2010) J. Org. Chem., 75, p. 6696
Sharpless, K.B., Young, M.W., (1975) J. Org. Chem., 40, p. 947
Smith Iii, A.B., Richmond, R.E., (1983) J. Am. Chem. Soc., 105, p. 575
Huang, X., Liu, X., Luo, Q., Liu, J., Shen, J., (2011) Chem. Soc. Rev., 40, p. 1171
Rajanbabu, T.V., Ayers, T.A., Halliday, G.A., You, K.K., Calabrese, J.C., (1997) J. Org. Chem., 62, p. 6012
Miquel, N., Vignando, S., Russo, G., Lay, L., (2004) Synlett, 341
Hummel, G., Hindsgaul, O., (1999) Angew. Chem., Int. Ed., 38, p. 1782
Martins Alho, M.A., D'Accorso, N.B., Thiel, I.M.E., (1996) J. Heterocycl. Chem., 33, p. 1339
Renaudie, L., Daniellou, R., Augè, C., Le Narvor, C., (2004) Carbohydr. Res., 339, p. 693
Gillies, R.G., Didier, N., Denton, M., (1986) Anal. Biochem., 159, p. 109
Andr, S., Pei, Z., Siebert, H. -C., Ramstr m, O., Gabius, H. -J., (2006) Bioorg. Med. Chem., 14, p. 6314
Richtmyer, N. K., Carr, C. J., Hudson, C. S., (1943) J. Am. Chem. Soc., 65, p. 1477
Kiefel, M. J., Thomson, R. J., Radovanovic, M., Von Itzstein, M., (1999) J. Carbohydr. Chem., 18, p. 937
Davis, B. G., Ward, S. J., Rendle, P. M., (2001) Chem. Commun., p. 189
Aversa, M. C., Barattucci, A., Bonaccorsi, P., (2009) Eur. J. Org. Chem., p. 6455
Ibatullin, F. M., Selivanov, S. I., Shavva, A. G., (2001) Synthesis, p. 419
Gamblin, D. P., Garnier, P., Van Kasteren, S., Oldham, N. J., Fairbanks, A. J., Davis, B. G., (2004) Angew. Chem., Int. Ed., 43, p. 828. , For a recent kinetic study on the formation of disulfide and SSe linkages
Sharpless, K. B., Young, M. W., (1975) J. Org. Chem., 40, p. 947
Smith Iii, A. B., Richmond, R. E., (1983) J. Am. Chem. Soc., 105, p. 575
Rajanbabu, T. V., Ayers, T. A., Halliday, G. A., You, K. K., Calabrese, J. C., (1997) J. Org. Chem., 62, p. 6012
Martins Alho, M. A., D'Accorso, N. B., Thiel, I. M. E., (1996) J. Heterocycl. Chem., 33, p. 1339
Gillies, R. G., Didier, N., Denton, M., (1986) Anal. Biochem., 159, p. 109
Org Biomol Chem (ISSN: 1477-0520, 1477-0539, 1477-0539electronic), 2011 Sep 21; 9(18): 6278-6283.
Export to Esporta in BibTeX Export to Esporta in EndNote
Paper type Tipo di articolo: Journal Article,
Impact factor: 3.696, 5-year impact factor Impact factor a 5 anni: 3.652
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-80052216122&partnerID=40&md5=ad3176e16240b23c9685272708d99a51
Keywords Parole chiave: Biological Evaluation, Cytotoxic Activities, Glycosyl Disulfides, Human Tumor Cells, Sequential Approach, Synthetic Compounds, Cell Culture, Cytotoxicity, Selenium Compounds, Reaction Intermediates, Antineoplastic Agent, Article, Cell Survival, Chemistry, Drug Effect, Oxidation Reduction Reaction, Synthesis, Tumor Cell Line, Oxidation-Reduction,
Affiliations Affiliazioni:
*** IBB - CNR ***
Dipartimento di Chimica Organica e Biochimica, Università Federico II di Napoli, via Cinthia 4, I-80126 Naples, Italy
Facoltà di Scienze Biotecnologiche, Università di Napoli Federico II, via Mezzocannone 16, 80134 Naples, Italy
Istituto di Biostrutture e Bioimmagini, CNR, via Mezzocannone 16, 80134 Naples, Italy
Facolt di Scienze Biotecnologiche, Universit di Napoli Federico II, via Mezzocannone 16, 80134 Naples, Italy
References Riferimenti:
Pei, Z., Aastrup, T., Anderson, H., Ramström, O., (2005) Bioorg. Med. Chem. Lett., 15, p. 270
André, S., Pei, Z., Siebert, H.-C., Ramström, O., Gabius, H.-J., (2006) Bioorg. Med. Chem., 14, p. 6314
Pei, Z., Larsson, R., Aastrup, T., Anderson, H., Lehn, J.-M., Ramström, O., (2006) Biosens. Bioelectron., 22, p. 42
Caraballo, R., Sakulsombat, M., Ramström, O., (2010) Chem. Commun., 46, p. 8469
Richtmyer, N.K., Carr, C.J., Hudson, C.S., (1943) J. Am. Chem. Soc., 65, p. 1477
Cerny, M., Vrkoc, J., Stanek, J., (1959) Collect. Czech. Chem. Commun., 24, p. 64
Horton, D., (1963) Methods Carbohydr. Chem., 2, p. 433
Kiefel, M.J., Thomson, R.J., Radovanovic, M., Von Itzstein, M., (1999) J. Carbohydr. Chem., 18, p. 937
Knapp, S., Darout, E., Amorelli, B., (2006) J. Org. Chem., 71, p. 1380
Floyd, N., Vijayakrishnan, B., Koeppe, A.R., Davis, B.G., (2009) Angew. Chem., Int. Ed., 48, p. 7798
Bhar, D., Chandrasekaran, S., (1997) Carbohydr. Res., 301, p. 221
Szilagy, L., Illyes, T.-Z., Herczegh, P., (2001) Tetrahedron Lett., 42, p. 3901
Davis, B.G., Ward, S.J., Rendle, P.M., (2001) Chem. Commun., p. 189
Ribeiro Morais, G., Falconer, R.A., (2007) Tetrahedron Lett., 48, p. 7637
Aversa, M.C., Barattucci, A., Bonaccorsi, P., (2009) Eur. J. Org. Chem., p. 6455
Stellenboom, N., Hunter, R., Caira, M.R., Szilagy, L., (2010) Tetrahedron Lett., 51, p. 5309
Valerio, S., Iadonisi, A., Adinolfi, M., Ravidà, A., (2007) J. Org. Chem., 72, p. 6097
Adinolfi, M., Iadonisi, A., Ravidà, A., Schiattarella, M., (2003) Tetrahedron Lett., 44, p. 7863
Ibatullin, F.M., Selivanov, S.I., Shavva, A.G., (2001) Synthesis, p. 419
Pezzella, A., Iadonisi, A., Valerio, S., Panzella, L., Napolitano, A., Adinolfi, M., D'Ischia, M., (2009) J. Am. Chem. Soc., 131, p. 15270. , For a stepwise approach to (phenylselenyl)thioglycosides and their application to protein glycoconjugation via disulfide linkage
Gamblin, D.P., Garnier, P., Van Kasteren, S., Oldham, N.J., Fairbanks, A.J., Davis, B.G., (2004) Angew. Chem., Int. Ed., 43, p. 828. , For a recent kinetic study on the formation of disulfide and SSe linkages
Steinmann, D., Nauser, T., Koppenol, W.H., (2010) J. Org. Chem., 75, p. 6696
Sharpless, K.B., Young, M.W., (1975) J. Org. Chem., 40, p. 947
Smith Iii, A.B., Richmond, R.E., (1983) J. Am. Chem. Soc., 105, p. 575
Huang, X., Liu, X., Luo, Q., Liu, J., Shen, J., (2011) Chem. Soc. Rev., 40, p. 1171
Rajanbabu, T.V., Ayers, T.A., Halliday, G.A., You, K.K., Calabrese, J.C., (1997) J. Org. Chem., 62, p. 6012
Miquel, N., Vignando, S., Russo, G., Lay, L., (2004) Synlett, 341
Hummel, G., Hindsgaul, O., (1999) Angew. Chem., Int. Ed., 38, p. 1782
Martins Alho, M.A., D'Accorso, N.B., Thiel, I.M.E., (1996) J. Heterocycl. Chem., 33, p. 1339
Renaudie, L., Daniellou, R., Augè, C., Le Narvor, C., (2004) Carbohydr. Res., 339, p. 693
Gillies, R.G., Didier, N., Denton, M., (1986) Anal. Biochem., 159, p. 109
Andr, S., Pei, Z., Siebert, H. -C., Ramstr m, O., Gabius, H. -J., (2006) Bioorg. Med. Chem., 14, p. 6314
Richtmyer, N. K., Carr, C. J., Hudson, C. S., (1943) J. Am. Chem. Soc., 65, p. 1477
Kiefel, M. J., Thomson, R. J., Radovanovic, M., Von Itzstein, M., (1999) J. Carbohydr. Chem., 18, p. 937
Davis, B. G., Ward, S. J., Rendle, P. M., (2001) Chem. Commun., p. 189
Aversa, M. C., Barattucci, A., Bonaccorsi, P., (2009) Eur. J. Org. Chem., p. 6455
Ibatullin, F. M., Selivanov, S. I., Shavva, A. G., (2001) Synthesis, p. 419
Gamblin, D. P., Garnier, P., Van Kasteren, S., Oldham, N. J., Fairbanks, A. J., Davis, B. G., (2004) Angew. Chem., Int. Ed., 43, p. 828. , For a recent kinetic study on the formation of disulfide and SSe linkages
Sharpless, K. B., Young, M. W., (1975) J. Org. Chem., 40, p. 947
Smith Iii, A. B., Richmond, R. E., (1983) J. Am. Chem. Soc., 105, p. 575
Rajanbabu, T. V., Ayers, T. A., Halliday, G. A., You, K. K., Calabrese, J. C., (1997) J. Org. Chem., 62, p. 6012
Martins Alho, M. A., D'Accorso, N. B., Thiel, I. M. E., (1996) J. Heterocycl. Chem., 33, p. 1339
Gillies, R. G., Didier, N., Denton, M., (1986) Anal. Biochem., 159, p. 109
A straightforward synthetic access to symmetrical glycosyl disulfides and biological evaluation thereof
Symmetrical glycosyl disulfides can be prepared within a few hours from per-O-acetylated precursors via a sequential approach entailing short reactions and no purification of any intermediate. The final thiolate-to-disulfide oxidation step is noticeably accelerated by low amounts of phenyl diselenide under air. Applicability of the strategy to non-saccharidic symmetrical alkyl disulfides has also been examined. A preliminary assay of the cytotoxic activity of symmetrical 1,1'-disulfides was performed on two human tumor cell lines, and a noteworthy activity was recorded for a range of these synthetic compounds.
Symmetrical glycosyl disulfides can be prepared within a few hours from per-O-acetylated precursors via a sequential approach entailing short reactions and no purification of any intermediate. The final thiolate-to-disulfide oxidation step is noticeably accelerated by low amounts of phenyl diselenide under air. Applicability of the strategy to non-saccharidic symmetrical alkyl disulfides has also been examined. A preliminary assay of the cytotoxic activity of symmetrical 1,1'-disulfides was performed on two human tumor cell lines, and a noteworthy activity was recorded for a range of these synthetic compounds.
A straightforward synthetic access to symmetrical glycosyl disulfides and biological evaluation thereof
A straightforward synthetic access to symmetrical glycosyl disulfides and biological evaluation thereof
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Ferrara LA, Soro S, Marotta T, Mancini M
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Impact Factor: 0
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7 Records (6 escludendo Abstract e Conferenze).
Impact factor totale: 19.903 (19.903 escludendo Abstract e Conferenze).
Impact factor a 5 anni totale: 20.177 (20.177 escludendo Abstract e Conferenze).
Vai a fine pagina Versione per copia e incolla facile Esporta tutto in BibTeX Esporta tutto in EndNote
Roviello GN, Iannitti R, Roviello V, Palumbo R, Simonyan H, Vicidomini C
* Synthesis and biological evaluation of a novel Amadori compound (315 visite)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2017 Feb; 49(2): 327-335.
Impact Factor: 2.906
Dettagli Esporta in BibTeX Esporta in EndNote
Mishra CB, Kumari S, Angeli A, Monti SM, Buonanno M, Prakash A, Tiwari M, Supuran CT
* Design, synthesis and biological evaluation of N-(5-methyl-isoxazol-3-yl/1, 3, 4-thiadiazol-2-yl)-4-(3-substitutedphenylureido) benzenesulfonamides as human carbonic anhydrase isoenzymes I, II, VII and XII inhibitors (268 visite)
J Enzyme Inhib Med Chem, 2016; 17: 1-6.
Impact Factor: 3.428
Dettagli Esporta in BibTeX Esporta in EndNote
Roviello GN, Ricci A, Bucci EM, Pedone C
* Synthesis, biological evaluation and supramolecular assembly of novel analogues of peptidyl nucleosides (884 visite)
Mol Biosyst (ISSN: 1742-206x, 1742-2051, 1742-2051electronic), 2011 May; 7(5): 1773-1778.
Impact Factor: 3.534
Dettagli Esporta in BibTeX Esporta in EndNote
De Luca S, De Capua A, Saviano M, Della Moglie R, Aloj L, Tarallo L, Pedone C, Morelli G
* Synthesis and biological evaluation of cyclic and branched peptide analogues as ligands for cholecystokinin type 1 receptor (365 visite)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 1464-3391electronic), 2007 Sep 1; 15(17): 5845-5853.
Impact Factor: 2.662
Dettagli Esporta in BibTeX Esporta in EndNote
Ragno R, Simeoni S, Castellano S, Vicidomini C, Mai A, Caroli A, Tramontano A, Bonaccini C, Trojer P, Bauer I, Brosch G, Sbardella G
* Small molecule inhibitors of histone arginine methyltransferases: Homology modeling, molecular docking, binding mode analysis, and biological evaluations (483 visite)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2007 Mar 22; 50(6): 1241-1253.
Impact Factor: 4.895
Dettagli Esporta in BibTeX Esporta in EndNote
Paesano N, Marzocco S, Vicidomini C, Saturnino C, Autore G, De Martino G, Sbardella G
* Synthesis and biological evaluation of 3-benzyl-1-methyl- and 1-methyl-3-phenyl-isothioureas as potential inhibitors of iNOS (395 visite)
Bioorganic & Medicinal Chemistry Letters (ISSN: 0960-894x), 2005 Feb 1; 15(3): 539-543.
Impact Factor: 2.478
Dettagli Esporta in BibTeX Esporta in EndNote
Ferrara LA, Soro S, Marotta T, Mancini M
Chronobiological Evaluation Of Cardiovascular Reactivity (238 visite)
Atherosclerosis And Cardiovascular Disease Descovich G C Gaddi A Magri Gl Lenzi S, 1989; 4(a): 10-10.
Impact Factor: 0
Dettagli Esporta in BibTeX Esporta in EndNote
7 Records (6 escludendo Abstract e Conferenze).
Impact factor totale: 19.903 (19.903 escludendo Abstract e Conferenze).
Impact factor a 5 anni totale: 20.177 (20.177 escludendo Abstract e Conferenze).
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