Synthesis and self-assembly of an amino-functionalized hybrid hydrocarbon/fluorocarbon double-chain phospholipid

Langmuir

Volumn 27, Issue 17, 2011, Pages 10859-10866

  Li, Jiehua ^a   Chen, Yezhong ^a   Wang, Zhigao ^a   Ding, Mingming ^a   Tan, Hong ^a   Fu, Qiang ^a   Jiang, Xia ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC MEDIA; BIOMEMBRANES; CRITICAL MICELLE CONCENTRATION (CMC); DISSIPATIVE PARTICLE DYNAMICS; DOUBLE CHAIN; ETHER LINKAGES; FTIR; HYDROCARBON CHAINS; MATERIAL SURFACE; ONE CHAIN; PHYSIOLOGICAL CONDITION; POTENTIAL ABILITY; PROTEIN ADSORPTION; SELF ASSEMBLED STRUCTURES; SELF-ASSEMBLE; SELF-ASSEMBLY BEHAVIORS;

ADSORPTION; AMIDES; CRITICAL MICELLE CONCENTRATION; DYNAMIC LIGHT SCATTERING; ETHERS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MICELLES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS; RESONANCE; SELF ASSEMBLY; TRANSMISSION ELECTRON MICROSCOPY;

PHOSPHOLIPIDS;

AMINE; HYDROCARBON; PHOSPHOLIPID;

ADSORPTION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PARTICLE SIZE; SURFACE PROPERTY; SYNTHESIS;

ADSORPTION; AMINES; HYDROCARBONS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PARTICLE SIZE; PHOSPHOLIPIDS; SURFACE PROPERTIES;

EID: 80052255050     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la201610w     Document Type: Article

References (53)

1. Singer, S. J.; Nicolson, G. L. Science 1972, 175, 720-731
2. Chandrakumar, N. S.; Hajdu, J. J. Org. Chem. 1983, 48, 1197-1202
3. D'Arrigo, P.; Fasoli, E.; Pedrocchi-Fantoni, G.; Rossi, C.; Saraceno, C.; Tessaro, D.; Servi, S. Chem. Phys. Lipids 2007, 147, 113-118
4. van der Luit, A. H.; Vink, S. R.; Klarenbeek, J. B.; Perrissoud, D.; Solary, E.; Verheij, M.; van Blitterswijk, W. J. Mol. Cancer Ther. 2007, 6, 2337-2345
5. Coghia, P.; Vaiana, N.; Pezzano, M. G.; Rizzi, L.; Kaiser, M.; Brun, R.; Romeo, S. Bioorg. Med. Chem. Lett. 2008, 18, 4658-4660
6. Shenoy, D. K.; Barger, W. R.; Singh, A.; Panchal, R. G.; Misakian, M.; Stanford, V. M.; Kasianowicz, J. Nano Lett. 2005, 5, 1181-1185
7. Rosseto, R.; Hajdu, J. Chem. Phys. Lipids 2010, 163, 110-116
8. Gupta, U.; Jain, N. K. Adv. Drug. Delivery Rev. 2010, 62, 478-490
9. Dal-Maso, A. D.; Dellacasagrande, J.; Legendre, F.; Tiraby, G.; Blonski, C.; Hoffmann, P. Eur. J. Med. Chem. 2008, 43, 1758-1766
10. Klein, E.; Ciobanu, M.; Klein, J.; Machi, V.; Leborgne, C.; Vandamme, T.; Frisch, B.; Pons, F.; Kichler, A.; Zuber, G.; Lebeau, L. Bioconjugate Chem. 2010, 21, 360-371
11. Tan, H.; Liu, J.; Li, J.; Luo, J.; Xie, X.; Zhong, Y.; Fu, Q. Biomacromolecules 2006, 7, 2591-2599
12. Chung, Y. C.; Chiu, Y. H.; Wu, Y. W.; Tao, Y. T. Biomaterials 2005, 26, 2313-2324
13. Futamura, K.; Matsuno, R.; Konno, T.; Takai, M.; Ishihara, K. Langmuir 2008, 24, 10340-10344
14. Chin-Quee, S. L.; Hsu, S. H.; Nguyen-Ehrenreich, K. L.; Tai, J. T.; Abraham, G. M.; Pacetti, S. D.; Chan, Y. F.; Nakazawa, G.; Kolodgie, F. D.; Virmani, R.; Ding, N. N.; Coleman, L. A. Biomaterials 2010, 31, 648-657
15. Sun, X. L.; Liu, H.; Orban, J. M.; Sun, L.; Chaikof, E. L. Bioconjugate Chem. 2001, 12, 673-677
16. Daly, S. M.; Heffernan, L. A.; Barger, W. R.; Shenoy, D. K. Langmuir 2006, 22, 1215-1222
17. Kratz, K.; Breitenkamp, K.; Hule, R.; Pochan, D.; Emrick, T. Macromolecules 2009, 42, 3227-3229
18. Seuring, J.; Reiss, P.; Koert, U.; Agarwal, S. Chem. Phys. Lipids 2010, 163, 367-372
19. Kai, T.; Sun, X.-L.; Faucher, K. M.; Apkarian, R. P.; Chaikof, E. L. J. Org. Chem. 2005, 70, 2606-2615
20. Kenworthy, A. K.; Simon, S. A.; McIntosh, T. J. Biophys. J. 1995, 68, 1903-1920
21. Drescher, S.; Meister, A.; Graf, G.; Hause, G.; Blume, A.; Dobner, B. Chem.-Eur. J. 2008, 14, 6796-6804
22. Chaikof, E. L.; Tseng, P.; Rele, S. M.; Jordan, S. W.; Sun, X. L. Langmuir 2006, 22, 1201-1208
23. Svenson, S.; Thompson, D. H. J. Org. Chem. 1998, 63, 7180-7182
24. Clary, L.; Santaella, C.; Vierling, P. Tetrahedron 1995, 51, 13073-13088
25. Santaella, C.; Vierling, P.; Riess, J. G. New J. Chem. 1991, 15, 685-692
26. McIntosh, T. J.; Simon, S. A.; Vierling, P.; Santaella, C.; Ravily, V. Biophys. J. 1996, 71, 1853-1868
27. Schmutz, M.; Michels, B.; Marie, P.; Krafft, M. P. Langmuir 2003, 19, 4889-4894
28. Takagi, T.; Takai, K.; Baba, T.; Kanamori, T. J. Fluorine Chem. 2007, 128, 133-138
29. Riess, J. G.; Krafft, M. P. Biomaterials 1998, 19, 1529-1539
30. Clary, L.; Verderone, G.; Santaella, C.; Vierling, P. Biochim. Biophys. Acta 1997, 1328, 55-64
31. Ravily, V.; Santaella, C.; Vierling, P. Biochim. Biophys. Acta 1996, 1285, 79-90
32. Ravily, V.; Clary, L.; Santaella, C.; Vierling, P.; Duportail, G. Chem. Phys. Lipids 1997, 90, 75-86
33. Clary, L.; Ravily, V.; Santaella, C.; Vierling, P. J. Controlled Release 1998, 51, 259-267
34. Sunamoto, J.; Goto, M.; Iwamoto, K.; Kondo, H.; Sato, T. Biochim. Biophys. Acta 1990, 1024, 209-219
35. Fabio, K.; Di Giorgio, C.; Vierling, P. Biochim. Biophys. Acta 2005, 1724, 203-214
36. Hoogerbrugge, P. J.; Koelman, J. Europhys. Lett. 1992, 19, 155-160
37. Groot, R. D.; Warren, P. B. J. Chem. Phys. 1997, 107, 4423-4435
38. Groot, R. D.; Madden, T. J. J. Chem. Phys. 1998, 108, 8713-8724
39. Wang, Z. G.; Li, J. H.; Tan, H.; Zhang, X. Q.; Fu, Q. Mol. Simulat. 2009, 35, 638-647
40. Wong, J. E.; Duchscherer, T. M.; Pietraru, G.; Cramb, D. T. Langmuir 1999, 15, 6181-6186
41. Fayed, T. A. Colloids Surf., A 2004, 236, 171-177
42. Oda, R.; Huc, I.; Danino, D.; Talmon, Y. Langmuir 2000, 16, 9759-9769
43. Yamanaka, T.; Ogihara, N.; Ohhori, T.; Hayashi, H.; Muramatsu, T. Chem. Phys. Lipids 1997, 90, 97-107
44. Johnsson, M.; Wagenaar, A.; Stuart, M. C. A.; Engberts, J. B. F. N. Langmuir 2003, 19, 4609-4618
45. Kuwahara, H.; Hamada, M.; Ishikawa, Y.; Kunitake, T. J. Am. Chem. Soc. 1993, 115, 3002-3003
46. Schmidt, M. E.; Shin, S.; Rice, S. A. J. Chem. Phys. 1996, 104, 2101-2113
47. Guittard, F.; Geribaldi, S. J. Fluorine Chem. 2001, 107, 363-374
48. Yamanaka, T.; Ogihara, N.; Ohhori, T.; Hayashi, H.; Muramatsu, T. Chem. Phys. Lipids 1997, 90, 97-107
49. Berkowitz, M. L.; Bostick, D. L.; Pandit, S. Chem. Rev. 2006, 106, 1527-1539
50. Clarke, R. J. Adv. Colloid Interface Sci. 2001, 89, 263-281
51. Petrov, J. G.; Andreeva, T. D.; Kurth, D. G.; Möhwald, H. J. Phys. Chem. B 2005, 109, 14102-14111
52. Gonzalez-Pérez, A.; Schmutz, M.; Waton, G.; Romero, M. J.; Krafft, M. P. J. Am. Chem. Soc. 2007, 129, 756-757
53. Ojogun, V. A.; Lehmler, H. J.; Knutson, B. L. J. Colloid Interface Sci. 2009, 338, 82-91