Design and synthesis of lipids for the fabrication of functional lipidic cubic-phase biomaterials

Journal of Organic Chemistry

Volumn 77, Issue 23, 2012, Pages 10583-10595

  Osornio, Yazmin M ^a   Uebelhart, Peter ^a   Bosshard, Silvan ^a   Konrad, Fabian ^a   Siegel, Jay S ^a   Landau, Ehud M ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BICONTINUOUS; CUBIC PHASIS; MATERIAL PROPERTY; MONOOLEIN; OPTICAL TRANSPARENCY; THIOESTERS;

AMIDES; AMINO ACIDS; ESTERIFICATION; ESTERS; FUNCTIONAL MATERIALS; GLYCEROL; PHASE STABILITY;

LIPIDS;

AMIDE; AMINO ACID; AZOBENZENE; BIOMATERIAL; CARBAMIC ACID; ESTER; GLYCEROL OLEATE; LIPID; LIPIDIC CUBIC PHASE; NITROBENZENE; THIOESTER; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONJUGATION; HYDROLYSIS; LIPID BILAYER; LIPOGENESIS; LIPOPHILICITY; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE;

BIOCOMPATIBLE MATERIALS; DRUG DESIGN; GLYCERIDES; GLYCEROL; LIPIDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, BIOLOGICAL;

EID: 84870924184     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301659c     Document Type: Article

References (44)

1. Gruner, S. M. J. Phys. Chem. 1989, 93, 7562-7570
2. Tardieu, A.; Luzzati, V. Biochim. Biophys. Acta 1970, 219, 11-17
3. Larsson, K.; Fontell, K.; Krog, N. Chem. Phys. Lipids 1980, 27, 321-328
4. Larsson, K. J. Phys. Chem. 1989, 93, 7304-7314
5. Lynch, M. L.; Spicer, P. T. Bicontinuous Liquid Crystals; CRC Press Taylor & Francis Group: Boca Raton, 2005; Vol. 127.
6. Landau, E. M.; Rosenbusch, J. P. Proc. Natl. Acad. Sci. U. S. A. 1996, 93, 14532-14535
7. Cherezov, V.; Rosenbaum, D. M.; Hanson, M. A.; Rasmussen, S. G. F.; Thian, F. S.; Kobilka, T. S.; Choi, H.-J.; Kuhn, P.; Weis, W. I.; Kobilka, B. K.; Stevens, R. C. Science 2007, 318, 1258-1265
8. Shimamura, T.; Shiroishi, M.; Weyand, S.; Tsujimoto, H.; Winter, G.; Katritch, V.; Abagyan, R.; Cherezov, V.; Liu, W.; Han, G. W.; Kobayashi, T.; Stevens, R. C.; Iwata, S. Nature 2011, 475, 65-70
9. Haga, K.; Kruse, A. C.; Asada, H.; Yurugi-Kobayashi, T.; Shiroishi, M.; Zhang, C.; Weis, W. I.; Okada, T.; Kobilka, B. K.; Haga, T.; Kobayashi, T. Nature 2012, 482, 547-551
10. Helmut, K. CRC Handbook of Organic Photochemistry and Photobiology, 2 nd ed.; CRC Press: Boca Raton, FL, 2004.
11. Muraoka, T.; Kinbara, K.; Aida, T. Nature 2006, 440, 512-515
12. Aujard, I.; Benbrahim, C.; Gouget, M.; Ruel, O.; Baudin, J.-B.; Neveu, P.; Jullien, L. Chem.î-̧Eur. J. 2006, 12, 6865-6879
13. Lim, L. Y. G.; Su, Y.; Braet, F.; Thordarson, P. Aust. J. Chem. 2009, 62, 653-656
14. Dang, H. T.; Kang, G. J.; Yoo, E. S.; Hong, J.; Choi, J. S.; Kim, H. S.; Chung, H. Y.; Jung, J. H. Bioorg. Med. Chem. 2011, 19, 1520-1527
15. Aneetha, H.; ODell, D. K.; Tan, B.; Walker, J. M.; Hurley, T. D. Bioorg. Med. Chem. Lett. 2009, 19, 237-241
16. Si, S.; Dinda, E.; Mandal, T. K. Chem.î-̧Eur. J. 2007, 13, 9850-9861
17. Duarte, R. d. C.; Ongaratto, R.; Piovesan, L. A.; de Lima, V. R.; Soldi, V.; Merlo, A. A.; Montes DOca, M. G. Tetrahedron Lett. 2012, 53, 2454-2460
18. Bieberich, E.; Hu, B.; Silva, J.; MacKinnon, S.; Yu, R. K.; Fillmore, H.; Broaddus, W. C.; Ottenbrite, R. M. Cancer Lett. 2002, 181, 55-64
19. Chen, F. M. F.; Benoiton, N. L. Can. J. Chem. 1987, 65, 1224-1227
20. Hunston, R. N.; Gerothanassis, I. P.; Lauterwein, J. J. Am. Chem. Soc. 1985, 107, 2654-2661
21. Deber, C. M.; Bovey, F. A.; Carver, J. P.; Blout, E. R. J. Am. Chem. Soc. 1970, 92, 6191-6198
22. Troganis, A.; Gerothanassis, I. P.; Athanassiou, Z.; Mavromoustakos, T.; Hawkes, G. E.; Sakarellos, C. Biopolymers 2000, 53, 72-83
23. Gronowitz, S.; Herslof, B.; Michelsen, P.; Akesson, B. Chem. Phys. Lipids 1978, 22, 307-321
24. Sonnet, P. E.; Moore, G. G. Lipids 1989, 24, 743-745
25. Li, A. H.; Moro, S.; Forsyth, N.; Melman, N.; Ji, X. D.; Jacobson, K. A. J. Med. Chem. 1999, 42, 706-721
26. Driolia, S.; Bonora, G. M.; Ballico, M. Open Org. Chem. J. 2008, 2, 17-25
27. Rogers, S. A.; Bero, J. D.; Melander, C. ChemBioChem 2010, 11, 396-410
28. Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804-3805
29. Feichtinger, K.; Sings, H. L.; Baker, T. J.; Matthews, K.; Goodman, M. J. Org. Chem. 1998, 63, 8432-8439
30. Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009-3016
31. Schwartz, C.; Raible, J.; Mott, K.; Dussault, P. H. Org. Lett. 2006, 8, 3199-3201
32. Rodefeld, L.; Tochtermann, W. Tetrahedron 1998, 54, 5893-5898
33. Wagner, A.; Heitz, M. P.; Mioskowski, C. Tetrahedron Lett. 1989, 30, 557-558
34. Wang, G. J.; Li, H.; Yu, M. M.; Guo, C. W.; Chen, X. F.; Li, G.; Zhou, E. L. Liq. Cryst. 2000, 27, 867-873
35. Yoon, N. M.; Pak, C. S.; Brown, H. C.; Krishnam., S; Stocky, T. P. J. Org. Chem. 1973, 38, 2786-2792
36. Nicolas, E.; Clemente, J.; Ferrer, T.; Albericio, F.; Giralt, E. Tetrahedron 1997, 53, 3179-3194
37. Loewik, D. W. P. M.; Meijer, J. T.; Minten, I. J.; Van Kalkeren, H.; Heckenmuller, L.; Schulten, I.; Sliepen, K.; Smittenaar, P.; Van Hest, J. C. M. J. Pept. Sci. 2008, 14, 127-133
38. Marshall, J. L.; Erickson, K. C.; Folsom, T. K. Tetrahedron Lett. 1970, 4011-4012
39. DAddona, D.; Bochet, C. G. Tetrahedron Lett. 2001, 42, 5227-5229
40. Pfister, J. R.; Wymann, W. E. Synthesis 1983, 38-40
41. Asseline, U.; Chassignol, M.; Draus, J.; Durand, M.; Maurizot, J. C. Bioorg. Med. Chem. 2003, 11, 3499-3511
42. Zorko, M.; Majerle, A.; Sarlah, D.; Keber, M. M.; Mohar, B.; Jerala, R. Antimicrob. Agents Ch. 2005, 49, 2307-2313
43. El Garah, M.; Palmino, F.; Cherioux, F. Langmuir 2010, 26, 943-949
44. Jungermann, E.; Gerecht, J. F.; Krems, I. J. J. Am. Chem. Soc. 1956, 78, 172-174