Synthesis And Structural Characterization Of 6i, 6ii-Diamino-6i, 6ii-Dideoxy-Cyclomaltoheptaose, A Difunctionalized Beta-Cyclodextrin(356 views visite) Di Blasio B, Galdiero S, Saviano M, Pedone C, Benedetti E, Rizzarelli E, Pedotti S, Vecchio G, Gibbons WA
Keywords Parole chiave: Crystal Structure, Cyclodextrins, Cyclomaltoheptaose, Difunctionalized β-Cyclodextrin, Beta Cyclodextrin Derivative, Article, Crystallography, Drug Structure, Drug Synthesis, Priority Journal, Reaction Analysis, Stereochemistry, Beta-Cyclodextrins, Carbohydrate Sequence, Magnetic Resonance Spectroscopy, Models, Molecular, Molecular Sequence Data, Optical Rotation, Spectrometry, Fast Atom Bombardment, X-Ray Diffraction, Difunctionalized -Cyclodextrin,
Affiliations Affiliazioni: Dipartimento di Chimica, Università della Basilicata, Via N.Sauro 85, I-85100 Potenza, Italy Biocrystallography Research Centre, Dipartimento di Chimica, Unirersita Federico II di Napoli, via Mezzocannone 4, I-80134 Naples, Italy Dipartimento di Scienze Chimiche, Università di Catania, V. le A. Doria 8, I-95125 Catania, Italy Inst. Stud. Sostanze Naturali I., CNR, V. le A. Doria 8, I-95125 Catania, Italy Pharmaceutical Chemistry Department, University of London, 29 / 39, Brunswick Sq., London WCIN IAX, United Kingdom
References Riferimenti: Bender, M., Komiyama, M., (1978) Cyclodextrin Chemistry, , Springer, Berli
Fuchs, R., Habermann, N., Klufers, P., (1993) Angew. Chem., Int. Ed. Engl., 32, pp. 852-858
Szejtli, J., (1990) Staerke, 42, pp. 444-447. , and references therein
Tabushi, I., (1988) Coord. Chem. Rev., 86, pp. 1-42
Breslow, R., Overman, L., (1970) J. Am. Chem. Soc., 92, pp. 1075-1077
Tabushi, I., Shimizu, N., Sugimoto, T., Shiozuka, M., Yamamura, K., (1977) J. Am. Chem. Soc., 99, pp. 7100-7102
Maccarrone, G., Rizzarelli, E., Vecchio, G., (1994) Transition Metals in Supramolecular Chemistry, pp. 351-370. , L. Fabbrizi and A. Poggi (Eds.) Kluwer Academic, Dordrecht
Corradini, R., Dossena, A., Impellizzeri, G., Maccarrone, G., Marchelli, R., Rizzarelli, E., Sartor, G., Vecchio, G., (1994) J. Am. Chem. Soc., 116, pp. 10267-10274
Cucinotta, V., D'Alessandro, F., Impellizzeri, G., Vecchio, G., (1992) J. Chem. Soc., Chem. Commun., pp. 1743-1745
Bonomo, R.P., Cucinotta, V., D'Alessandro, F., Impellizzeri, G., Maccarrone, G., Rizzarelli, E., Vecchio, G., (1993) J. Incl. Phenom., 15, pp. 167-180
Tabushi, I., Shimokawa, K., Fujita, K., (1977) Tetrahedron Lett., 18, pp. 1527-1530
Tabushi, I., Nabeshima, T., Fujita, K., Matsunaga, A., Imoto, T., (1985) J. Org. Chem., 50, pp. 2638-2643
Parrot-Lopez, H., Galons, H., Dupas, S., Miocque, M., Tsoucaris, G., (1990) Bull. Soc. Chim. Fr., 127, pp. 568-571
Sheldrick, G.M., (1975) SHELX 76: Programs for Crystal Structure Determination, , University of Cambridge, UK
Egert, E., Sheldrick, G.M., (1985) Acta Crystallogr., Sect. A, 41, pp. 262-268
Germain, G., Main, P., Woolfson, M.M., (1971) Acta Crystallogr., Sect. A, 27, pp. 368-376
Altomare, A., Burla, M.C., Camalli, M., Cascarano, G., Giacovazzo, C., Gugliardi, C., Polidori, G., (1994) J. Appl. Cryst., p. 435
Bonono, R.P., Blasio, B.D., Maccarone, G., Pavone, V., Pedone, C., Rizzarelli, E., Saviano, M., Vecchio, G., J. Inorg. Biochem., , submitted for publication
Egert, E., (1983) Acta Crystallogr., Sect. A, 39, p. 936
Frenk, B.A., (1986) Structure Determination Package, A System of Computer Programs, , College Station, TX, and Enraf-Nonius, Delft, Holland
Cromer, D.T., Waber, J.T., (1974) International Tables for X-ray Crystallography, 4, p. 99. , Kynoch, Birmingham Table 2.2B
Cremer, D., Pople, J.A., (1975) J. Am. Chem. Soc., 97, pp. 1354-1358
Blasio, B.D., Pavone, V., Nastri, F., Isernia, C., Saviano, M., Pedone, C., Cucinotta, V., Vecchio, G., (1992) Proc. Natl. Acad. Sci. USA, 89, pp. 7218-7221
Jones, P.C., Kirby, A.J., (1979) J. Chem. Soc., Chem. Commun., pp. 288-289
Jones, P.O., Kirby, A.J., (1984) J. Am. Chem. Soc., 106, pp. 6207-6212
Condorelli, G., Costanzo, L.L., De Guidi, G., Giuffrida, S., Rizzarelli, E., Vecchio, G., (1994) J. Inorg. Biochem., 54, pp. 257-265
Cucinotta, V., Mangano, A., Nobile, G., Santoro, A.M., Vecchio, G., (1993) J. Inorg. Biochem., 52, pp. 183-190
Clarke, R. J., Coates, J. H., Lincoln, S. F., (1988) Adv. Carbohydr. Chem. Biochem., 46, pp. 205-249
D'Souza, V. T., Bender, M. L., (1987) Acc. Chem. Res., 20, pp. 146-152
Brown, S. E., Coates, J. H., Durkworth, P. A., Lincoln, S. F., Easton, C. J., May, B. L., (1993) J. Chem. Soc., Faraday Trans., 89, pp. 1035-1040
Eliseev, A. V., Schneider, H. -J., (1994) J. Am. Chem. Soc., 116, pp. 6081-6088
Yatsimirskii, A. K., Eliseev, A. V., (1991) J. Chem. Soc., Perkin Trans. 2, pp. 1769-1865
Bonomo, R. P., Cucinotta, V., D'Alessandro, F., Impellizzeri, G., Maccarrone, G., Rizzarelli, E., Vecchio, G., (1993) J. Incl. Phenom., 15, pp. 167-180
Sheldrick, G. M., (1975) SHELX 76: Programs for Crystal Structure Determination, , University of Cambridge, UK
Bonono, R. P., Blasio, B. D., Maccarone, G., Pavone, V., Pedone, C., Rizzarelli, E., Saviano, M., Vecchio, G., J. Inorg. Biochem., , submitted for publication
Frenk, B. A., (1986) Structure Determination Package, A System of Computer Programs, , College Station, TX, and Enraf-Nonius, Delft, Holland
Cromer, D. T., Waber, J. T., (1974) International Tables for X-ray Crystallography, 4, p. 99. , Kynoch, Birmingham Table 2. 2B
Blasio, B. D., Pavone, V., Nastri, F., Isernia, C., Saviano, M., Pedone, C., Cucinotta, V., Vecchio, G., (1992) Proc. Natl. Acad. Sci. USA, 89, pp. 7218-7221
Jones, P. C., Kirby, A. J., (1979) J. Chem. Soc., Chem. Commun., pp. 288-289
Jones, P. O., Kirby, A. J., (1984) J. Am. Chem. Soc., 106, pp. 6207-6212
Synthesis And Structural Characterization Of 6i, 6ii-Diamino-6i, 6ii-Dideoxy-Cyclomaltoheptaose, A Difunctionalized Beta-Cyclodextrin
6 (I), 6 (II) -Diamino-6 (I), 6 (II) -dideoxy-cyclomaltoheptaose was prepared using the regioselective procedure described by Tabushi. The difunctionalized beta-cyclodextrin crystallizes as hextadecahydrate in the orthorhombic space group P2 (1) 2 (1) 2 (1), with a = 11. 395 (3), b = 32. 989 (9), c = 17. 560 (5) Angstrom, V = 6601 Angstrom (3), Z = 4, The structure was solved by molecular replacement techniques using the program PATSEE and was refined to a conventional final R = 0. 058 for the 5031 observed reflections with 1 greater than or equal to 3 sigma (I). The beta-CD macrocycle presents only slight differences with respect to uncomplexed hydrated or methylated beta-CD. The macrocycle structure maintains an approximate seven-fold symmetry. The round shape of the cyclodextrin ring is stabilized by intramolecular O-H. O H-bonds between the secondary hydroxyl groups of neighbouring glucose residues. Along the a axis, the beta-CD molecules are arranged in columns; the macrocycles form a herring-bone pattern, so that the cavity of each beta-CD molecule is closed at each end by neighbouring molecules. The macrocycles are directly linked to each other by H-bonds involving either primary and secondary hydroxyl or amino groups of symmetry-related molecules. The resulting layers are connected to each other by a dense intermolecular hydrogen-bond network, in which solvent molecules participate
Synthesis And Structural Characterization Of 6i, 6ii-Diamino-6i, 6ii-Dideoxy-Cyclomaltoheptaose, A Difunctionalized Beta-Cyclodextrin
Petraglia F, Singh AA, Carafa V, Nebbioso A, Conte M, Scisciola L, Valente S, Baldi A, Mandoli A, Petrizzi VB, Ingenito C, De Falco S, Cicatiello V, Apicella I, Janssen-megens EM, Kim B, Yi G, Logie C, Heath S, Ruvo M, Wierenga ATJ, Flicek P, Yaspo ML, Della Valle V, Bernard O, Tomassi S, Novellino E, Feoli A, Sbardella G, Gut I, Vellenga E, Stunnenberg HG, Mai A, Martens JHA, Altucci L * Combined HAT/EZH2 modulation leads to cancer-selective cell death(198 visite) Oncotarget (ISSN: 1949-2553electronic, 1949-2553linking), 2018 May 22; 9(39): 25630-25646. Impact Factor:5.008 DettagliEsporta in BibTeXEsporta in EndNote
Santulli G, Cipolletta E, Sorriento D, Del Giudice C, Anastasio A, Monaco S, Maione AS, Condorelli G, Puca A, Trimarco B, Illario M, Iaccarino G * CaMK4 gene deletion induces hypertension(277 visite) J Am Heart Assoc Journal Of The American Heart Association (ISSN: 2047-9980), 2012; 1(4): N/D-N/D. Impact Factor:2.882 DettagliEsporta in BibTeXEsporta in EndNote
Antonini A, Vitale C, Barone P, Cilia R, Righini A, Bonuccelli U, Abbruzzese G, Ramat S, Petrone A, Quatrale R, Marconi R, Ceravolo R, Stefani A, Lopiano L, Zappia M, Capus L, Morgante L, Tamma F, Tinazzi M, Colosimo C, Guerra UP, Valzania F, Fagioli G, Distefano A, Bagnato A, Feggi L, Anna S, Maria Teresa Rosaria De Cr, Nobili F, Mazzuca N, Baldari S, Eleopra R, Bestetti A, Benti R, Varrone A, Volterrani D, Massa R, Stocchi F, Schillaci O, Dore F, Zibetti M, Castellano G, Battista SG, Giorgetti G * The relationship between cerebral vascular disease and parkinsonism: The VADO study(406 visite) Parkinsonism Relat D (ISSN: 1353-8020, 1873-5126, 1873-5126electronic), 2012; 18(6): 775-780. Impact Factor:3.274 DettagliEsporta in BibTeXEsporta in EndNote
Malvindi MA, Greco A, Conversano F, Figuerola A, Corti M, Bonora M, Lascialfari A, Doumari HA, Moscardini M, Cingolani R, Gigli G, Casciaro S, Pellegrino T, Ragusa A * MR Contrast Agents(224 visite) Small Animal Imaging, 2011 Jul 8; 21(13): 2548-2555. Impact Factor:1.784 DettagliEsporta in BibTeXEsporta in EndNote
Bruni AC, Bernardi L, Colao R, Rubino E, Smirne N, Frangipane F, Terni B, Curcio SA, Mirabelli M, Clodomiro A, Di Lorenzo R, Maletta R, Anfossi M, Gallo M, Geracitano S, Tomaino C, Muraca MG, Leotta A, Lio SG, Pinessi L, Rainero I, Sorbi S, Nee L, Milan G, Pappata S, Postiglione A, Abbamondi N, Forloni G, St George Hyslop P, Rogaeva E, Bugiani O, Giaccone G, Foncin JF, Spillantini MG, Puccio G * Worldwide distribution of PSEN1 Met146Leu mutation: A large variability for a founder mutation(399 visite) Neurology (ISSN: 0028-3878, 1526-632x, 1526-632xelectronic), 2010 Mar 9; 74(10): 798-806. Impact Factor:8.017 DettagliEsporta in BibTeXEsporta in EndNote
Canettieri G, Di Marcotullio L, Greco A, Coni S, Antonucci L, Infante P, Pietrosanti L, De Smaele E, Ferretti E, Miele E, Pelloni M, De Simone G, Pedone E, Gallinari P, Giorgi A, Steinkuhler C, Vitagliano L, Pedone C, Schinin ME, Screpanti I, Gulino A *