A straightforward synthetic access to symmetrical glycosyl disulfides and biological evaluation thereof (352 views)
Org Biomol Chem (ISSN: 1477-0520, 1477-0539, 1477-0539electronic), 2011 Sep 21; 9(18): 6278-6283.
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Paper type: Journal Article,
Impact factor: 3.696, 5-year impact factor: 3.652
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-80052216122&partnerID=40&md5=ad3176e16240b23c9685272708d99a51
Keywords: 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:
*** 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:
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 BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 3.696, 5-year impact factor: 3.652
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-80052216122&partnerID=40&md5=ad3176e16240b23c9685272708d99a51
Keywords: 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:
*** 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:
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
| ▼ Chemical modification of natural molecules, such as peptides and polysaccharides, to be employed as therapeutic agents as well as sensor diagnostic tools |
A straightforward synthetic access to symmetrical glycosyl disulfides and biological evaluation thereof
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7 Records (6 excluding Abstracts).
Total impact factor: 19.903 (19.903 excluding Abstracts).
Total 5 year impact factor: 20.177 (20.177 excluding Abstracts).
Total impact factor: 19.903 (19.903 excluding Abstracts).
Total 5 year impact factor: 20.177 (20.177 excluding Abstracts).
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