Design and synthesis of a γ1β8- cyclodextrin oligomer: A new platform with potential application as a dendrimeric multicarrier

Chemistry - A European Journal

Volumn 19, Issue 36, 2013, Pages 12086-12092

  Barge, Alessandro ^a   Caporaso, Marina ^a   Cravotto, Giancarlo ^a   Martina, Katia ^a   Tosco, Paolo ^a   Aime, Silvio ^a   Carrera, Carla ^a   Gianolio, Eliana ^a   Pariani, Giorgio ^a   Corpillo, Davide ^b  

^a UNIVERSITY OF TURIN   (Italy)

^b Bioindustry Park Silvano Fumero SpA   (Italy)

Author keywords

click chemistry; cyclodextrin oligomers; Gd based contrast agents; imaging agents; microwave chemistry

Indexed keywords

1 ,3-DIPOLARCYCLOADDITION; CLICK CHEMISTRY; CONTRAST AGENT; IMAGING AGENT; MICROWAVE CHEMISTRY; MOLECULAR DYNAMICS SIMULATIONS; NUCLEAR MAGNETIC RELAXATION DISPERSION; SYNTHESIS AND CHARACTERIZATIONS;

CYCLOADDITION; DRUG DELIVERY; GADOLINIUM; MOLECULAR DYNAMICS; MOLECULAR IMAGING; OLIGOMERS;

CYCLODEXTRINS;

EID: 84883232243     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301215     Document Type: Article

References (57)

1. a) M. A. Mintzer, M. W. Grinstaff, Chem. Soc. Rev. 2011, 40, 173-190
2. b) K. Riehemann, S.W. Schneider, T. A. Luger, B. Godin, M. Ferrari, H. Fuchs, Angew. Chem. 2009, 121, 886-913
3. Angew. Chem. Int. Ed. 2009, 48, 872-897
4. c) W. J. Stark, Angew. Chem. 2011, 123, 1276-1293
5. Angew. Chem. Int. Ed. 2011, 50, 1242-1258
6. d) C. C. Lee, J. A. MacKay, J. M. J. Frechet, F C. Szoka, Nat. Biotechnol. 2005, 23, 1517-1526.
7. L. Rçglin, E. H. M. Lempens, E. W. Meijer, Angew. Chem. 2011, 123, 106-117
8. Angew. Chem. Int. Ed. 2011, 50, 102-112.
9. a) A. Samad, Y. Sultana, M. Aqil, Curr. Drug Delivery 2007, 4, 297-305
10. b) W. T. Al-Jamal, K. Kostarelos, Acc. Chem. Res. 2011, 44, 1094-1104.
11. a) D. Peer, J. M. Karp, S. Hong, O. C. Farokhzad, R. Margalit, R. Langer, Nat. Nanotechnol. 2007, 2, 751-760
12. b)J. Shi, Z. Xiao, N. Kamaly, O. C. Farokhzad, Acc. Chem. Res. 2011, 44, 1123-1134.
13. Y.-W. Jun, J.-H. Lee, J. Cheon, Angew. Chem. 2008, 120, 5200-5213
14. Angew. Chem. Int. Ed. 2008, 47, 5122-5135.
15. a) J. L. Perry, K. P. Herlihy, M. E. Napier, J. M. Desimone, Acc. Chem. Res. 2011, 44, 990-998
16. b) S. E. A. Gratton, S.S. Williams, M. E. Napier, P. D. Pohlhaus, Z. Zhou, K. B. Wiles, B. W. Maynor, C. Shen, T. Olafsen, E. T. Samulski, J. M. Desimone, Acc. Chem. Res. 2008, 41, 1685-1695.
17. S. D. Perrault, C. Walkey, T. Jennings, H. C. Fischer, W. C. W. Chan, Nano Lett. 2009, 9, 1909-1915.
18. a) Y. Teow, P. V. Asharani, M. P. Handec, S. Valiyaveettil, Chem. Commun. 2011, 47, 7025-7038
19. b) K. L. Aillon, Y. Xie, N. El-Gendy, C. J. Berkland, M. L. Forrest, Adv. Drug Delivery Rev. 2009, 61, 457-466
20. c) K. R. Vega-Villa, J. K. Takemoto, J. A. Yâcez, C. M. Remsberg, M. L. Forrest, N M. Davies, Adv. Drug Delivery Rev. 2008, 60, 929-938.
21. a) M. E. Davis, J. E. Zuckerman, C. H. J. Choi, D. Seligson, A. Tol-cher, C A. Alabi, Y Yen, J. D. Heidel, A. Ribas, Nature 2010, 464, 1067-1070
22. b) Y Zhu, L Che, H. He, Y Jia, J. Zhang, X. Li, J. Controlled Release 2011, 152, 317-324
23. c) M. Adeli, F Hakimpoor, M. Parsamanesh, M. Kalantari, Z. Sobhani, F. Attyabi, Polymer 2011, 52, 2401-2413.
24. a) H. S. Christensen, B. W Sigurskjold, T. G Frihed, L. G. Marine-scu, C M. Pedersen, M. Bols, Eur. J. Org. Chem. 2011, 5279-5290
25. b) S. Aime, E. Gianolio, F. Arena, A. Barge, K. Martina, G Hero-poulos, G Cravotto, Org. Biomol. Chem. 2009, 7, 370-379.
26. a) T. Lecourt, Y Blériot, R. Auzély-Velty, M. Sollogoub, Chem. Commun. 2010, 46, 2238-2240
27. b) T. Jiang, M. Li, D. S. Lawrence, J. Org. Chem. 1995, 60, 7293-7297
28. c) R. Breslow, X. Zhang, R. Xu, M. Maletic, R. Merger, J. Am. Chem. Soc. 1996, 118, 11678-11679.
29. a) M. Fathalla, A. Neuberger, S.-C Li, R. Schmehl, U. Diebold, J. Jayawickramarajah, J. Am. Chem. Soc. 2010, 132, 9966-9967
30. b) G. K. Rawal, P. Zhang, C.-C. Ling, Org. Lett. 2010, 12, 3096-3099
31. c) Z. Kotkovâ, J. Kotek, D. Jirâk, P. Jendelovâ, V Herynek, Z. Berkovâ, P. Hermann, I. Lukes, Chem. Eur. J. 2010, 16, 10094-10102.
32. a) G. Cravotto, V V Fokin, D. Garella, A. Binello, L. Boffa, A. Barge, J. Comb. Chem. 2010, 12, 13-15
33. b) A. Barge, S. Tagliapietra, A. Binello, G. Cravotto, Curr. Org. Chem. 2011, 15, 189-203.
34. G. Cravotto, F. Mendicuti, K. Martina, S. Tagliapietra, B. Robaldo, A. Barge, Synlett 2008, 2642-2646.
35. K. Martina, F. Trotta, B. Robaldo, N. Belliardi, L. Jicsinszky, G. Cravotto, Tetrahedron Lett. 2007, 48, 9185-9189.
36. S. Srinivasachari, K. M. Fichter, T. M. Reineke, J. Am. Chem. Soc. 2008, 130, 4618-4627.
37. P. Tosco, OpenCDSurf, http://opencdsurf.sourceforge.net, 2012.
38. D. Xu, Y. Zhang, PLoS One 2009, 4, e8140.
39. J.-L M. Abboud, C. Foces-Foces, R. Notario, R. E. Trifonov, A. P. Volovodenko, V A. Ostrovskii, I. Alkorta, J. Elguero, Eur. J. Org. Chem. 2001, 3013-3024.
40. S. Aime, E. Gianolio, F. Uggeri, S. Tagliapietra, A. Barge, G. Cravotto, J. Inorg. Biochem. 2006, 100, 931-938.
41. V Janout, B. Jing, S. L. Regen, J. Am. Chem. Soc. 2005, 127, 15862-15870.
42. Y. Shakalisava, F. Regan, Electrophoresis 2006, 27, 3048-3056.
43. M. Narita, F. Hamada, J. Chem. Soc. Perkin Trans. 2 2000, 4, 823-832.
44. J. Carrazana, A. Jover, F. Meijide, V H. Soto, J. Vasquez Tato, J. Phys. Chem. B 2005, 109, 9719.
45. S. Aime, M. Botta, M. Fasano, E. Terreno in Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging (Eds.: A. E. Mer-bach, É. Tóth), Wiley, Chichester, 2001, pp. 193-241.
46. D. H. Powell, O. M. N Dhubhghaill, D. Pubanz, L. Helm, Y S. Lebe-dev, W Schlaepfer, A. E. Merbach, J. Am. Chem. Soc. 1996, 118, 9333-9346.
47. a)N Bloembergen, J. Chem. Phys. 1957, 27, 572-573
48. b) I. Solomon, Phys. Rev. 1955, 99, 559-565.
49. a) L. Tei, A. Barge, S. Geninatti Crich, R. Pagliarin, V Negri, D. Ra-mella, G. Cravotto, S. Aime, Chem. Eur. J. 2010, 16, 8080-8087
50. b) E. Battistini, E. Gianolio, R. Gref, P. Couvreur, S. Fuzerova, M. Othman, S. Aime, B. Badet, P. Durand, Chem. Eur. J. 2008, 14, 4551-4561
51. c) P. Caravan, J. J. Ellison, T. J. McMurry, R. B. Lauffer, Chem. Rev. 1999, 99, 2293-2352.
52. M. Botta, Eur. J. Inorg. Chem. 2000, 399-407.
53. S. Aime, M. Botta, F. Fedeli, E. Gianolio, E. Terreno, P. Anelli, Chem. Eur. J. 2001, 7, 5261-5269.
54. S. Geninatti Crich, C. Cabella, A. Barge, S. Belfiore, C. Ghirelli, L. Lattuada, S. Lanzardo, A. Mortillaro, L. Tei, M. Visigalli, G. Forni, S. Aime, J. Med. Chem. 2006, 49, 4926-4936.
55. A. Barge, G. Cravotto, E. Gianolio, F. Fedeli, Contrast Media Mol. Imaging 2006, 1, 184-188.
56. MOE version2010.11, Chemical Computing Group Inc., Montreal, Quebec, 2011.
57. D. A. Case, T. E. Cheatham III, T. Darden, H. Gohlke, R. Luo, K. M. Merz, Jr., A. Onufriev, C. Simmerling, B. Wang, R. Woods, J. Comput. Chem. 2005, 26, 1668-1688.