Synthesis and characterization of silica-supported L-Lysine-based dendritic branches

Langmuir

Volumn 18, Issue 22, 2002, Pages 8660-8665

  Driffield, Malcolm ^a   Goodall, David M ^a   Klute, Anita S ^b   Smith, David K ^a   Wilson, Karen ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOPROPYLSILICA; DENDRITIC MATERIALS; ELEMENTAL ANALYSIS; LYSINE; OPTIMUM SURFACE COVERAGE;

CHEMICAL MODIFICATION; CHROMATOGRAPHIC ANALYSIS; CRYSTAL GROWTH; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL); X RAY PHOTOELECTRON SPECTROSCOPY;

SILICA;

EID: 0037195297     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la0203842     Document Type: Article

References (69)

1. For selected reviews of dendrimer chemistry, see: (a) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendrimers and Dendrons: Concepts, Syntheses, Applications; VCH: Weinheim, Germany, 2001.
2. (b) Chow, H.-F.; Mong, T. K.-K.; Nongrum, M. F.; Wan, C.-W. Tetrahedron 1998, 54, 8543-8660.
3. (c) Matthews, O. A.; Shipway, A. N.; Stoddart, J. F. Prog. Polym. Sci. 1998, 23, 1-56.
4. (d) Smith, D. K.; Diederich, F. Chem. Eur. J. 1998, 4, 1353-1361.
5. (e) Fischer, M.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1999, 38, 884-905.
6. (f) Grayson, S. M.: Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819-3867.
7. (g) Dykes, G. M. J. Chem. Technol. Biotechnol. 2001, 76, 903-918.
8. SEC is widely used in dendrimer chemistry, for selected examples featuring this technique, see: (a) Morikawa, A.; Kakimoto, M.; Imai, Y. Macromolecules 1991, 24, 3469-3474.
9. (b) Mourey, T. H.; Turner, S. R.; Rubinstein, M.; Fréchet, J. M. J.; Hawker, C. J.; Wooley, K. L. Macromolecules 1992, 25, 2401-2406.
10. (c) Shah, G.; Dubin, P. L.; Kaplan, J. I.; Newkome, G. R.; Moorefield, C. N.; Baker, G. R. J. Colloid Interface Sci. 1996, 183, 397-407.
11. (d) Striegel, A. M.; Plattner, R. D.; Willett, J. L. Anal. Chem. 1999, 71, 978-986.
12. (e) Bu, L. J.; Nonidez, W. K.; Mays, J. W.; Tan, N. B. Macromolecules 2000, 33 4445-4452.
13. (f) Ahmed, S. M.; Budd, P. M.; McKeown, N. B.; Evans, K. P.; Beaumont, G. L.; Donaldson, C.; Brennan, C. M. Polymer, 2001, 42, 889-896.
14. (a) Jendrusch-Borkowski, B.; Awad, J.; Wasgestian, F. J. Inc. Phenom. Macromol. Chem. 1999, 35, 355-359.
15. (b) Pan, Y. J.; Ford, W. T. Macromolecules 2000, 33, 3731-3738.
16. (a) van der Wal, S.; Mengerink, Y.; Brackman, J. C.; de Brabander, E. M. M.; Jeronimus-Stratingh, C. M.; Bruins, A. P. J. Chromatogr. A 1998, 825. 135-147.
17. (b) Pan, Y. J.; Ford, W. T. J. Org. Chem. 1999, 64, 8588-8593.
18. (c) Tajarobi, F.; El-Sayed, M.; Rege, B. D.; Polli, J. E.; Ghandehari, H. Int. J. Pharm. 2001, 215, 263-267.
19. For capillary electrophoresis see: (a) Stöckigt, D.; Lohmer, G.; Belder, D. Rapid Commun. Mass Spec. 1996, 10, 521-526.
20. (b) Pesak, D. J.; Moore, J. S.; Wheat, T. E. Macromolecules 1997, 30, 6467-6482.
21. (c) Balogh, L. de Leuze-Jallouli, A.; Dvornic, P.; Kunugi, Y. T.; Blumstein, A.; Tomalia, D. A. Macromolecules 1999, 32, 1036-1042.
22. Gel electrophoresis is widely used to monitor interactions between dendrimers and biologically important molecules such as DNA. For recent example see: (a) Choi, J. S.; Lee, E. J.; Choi, Y. H.; Jeung, Y. J. Park, J. S. Bioconjugate Chem. 1999, 10, 62-65.
23. (b) Shah, D. S.; Sakthivel, T.; Toth, I.; Florence, A. T.; Wilderspin, A. F. Int. J. Pharm. 2000, 208, 41-48.
24. (c) Arima, H.; Kihara, F. Hirayama, F. Uekama, K. Bioconjugate Chem. 2001, 12, 476-484.
25. Jayaraman, G.; Li, Y. F.; Moore, J. A.; Cramer, S. M. J. Chromatogr. A 1995, 702, 143-155.
26. Polese, A.; Mio, C.; Bertucco, A. J. Chem. Eng. Data 1999, 44, 839-845.
27. (a) Kuzdzal, S. A.; Monnig, C. A.; Newkome, G. R.; Moorefield, C. N. J. Chem. Soc., Chem. Commun. 1994, 2139-2140.
28. (b) Tanaka, N.; Fukutome, T.; Hosoya, K.; Kimata, K.; Araki, T. J. Chromatogr. A 1995, 716, 57-67.
29. (c) Tanaka, N.; Fukutome, T.; Tanigawa, T.; Hosoya, K.; Kimata, K.; Araki, T.; Unger, K. K. J. Chromatogr. A 1995, 699, 331-341.
30. (d) Castagnola, M.; Cassiano, L.; Lupi, A.; Messana, I.; Patamia, M.; Rabino, R.; Rossetti, D. V.; Giardina, B. J. Chromatogr. A 1995, 694, 463-469.
31. (e) Tanaka, N.; Iwasaki, H.; Fukutome, T.; Hosoya, K.; Araki, T. J. High Res. Chromatogr. 1997, 20, 529-538.
32. (f) Kuzdzal. S. A.; Monnig, C. A.; Newkome, G. R; Moorefield, C. N. J. Am. Chem. Soc. 1997, 119, 2255-2261.
33. (g) Gray, A. L.; Hsu, J. T. J. Chromatogr. A 1998, 824, 119-124.
34. (h) Stathakis, C.; Arriaga, E. A.; Dovichi, E. A.; Dovichi, N. J. J. Chromatogr. A 1998, 817, 233-238.
35. (i) Haynes, J. L.; Shamsi, S. A.; Dey, J.; Warner, I. M. J. Liq. Chromatogr. Relat. Technol. 1998, 21, 611-624.
36. Dendritically modified silicas are also of considerable interest for their applications in catalysis, but such examples are beyond the scope of this article.
37. Newkome, G. R.; Yoo, K. S.; Kabir, A.; Malik, A. Tetrahedron Lett. 2001, 42, 7537-7541.
38. Sakai, K.; Teng, T. C.; Katada, A.; Harada, T.; Uemura, S.; Asami, Y.; Sakata, M.; Kunitake, M.; Hirayama, C. Chem. Lett. 2001, 510-511.
39. Guo, Z. X.; Yu, J. J. Mater. Chem. 2002, 12, 468-472.
40. Mathews, B. T.; Beezer, A. E.; Snowden, M. J.; Hardy, M. J.; Mitchell, J. C. New. J. Chem. 2001, 25, 807-818.
41. Mathews, B. T.; Beezer, A. E.; Snowden, M. J.; Hardy, M. J.; Mitchell, J. C. Chromatographia 2001, 53, 147-155.
42. Denkewalter, R. G.; Kolc, J.; Lukasavage, W. J. U.S. Patent No. 4,289,872, 1981.
43. (b) Tam, J. P. Proc. Natl. Acad. Sci. 1988, 85, 5409-5413.
44. (c) Roy, R.; Zanini, D.; Meunier, S. J.; Romanowska, A. J. Chem. Soc., Chem. Commun. 1993, 1869-1873.
45. (d) Grandjean, C.; Rommens, C.; Gras-Masse, H.; Melnyk, O. Angew. Chem., Int. Ed. 2000, 39, 1068-1072.
46. (a) Smith, D. K. Chem. Commun. 1999, 1685-1686.
47. (b) Dykes, G. M.; Brierley, L. J.; Smith, D. K.; McGrail, P. T.; Seeley, G. J. Chem. Eur. J. 2001, 7, 4730-4739.
48. Driffield, M.; Goodall, D. M.; Klute, A. S.; Smith, D. K. unpublished results.
49. DCC coupling, mediated with HOBt to avoid racemisation, is a classic method for peptide synthesis. (a) Sheehan, J. C.; Cruickshan, P. A.; Boshart, G. L. J. Org. Chem. 1961, 26, 2525-2528.
50. (b) Sheehan, J. C.; Preston, J.; Cruickshank, P. A. J. Am. Chem. Soc. 1965, 87, 2492-2493.
51. TBTU is a peptide coupling reagent that is specifically suited to solid-phase peptide synthesis. Knorr, R.; Trzeciak, X. A.; Bannwarth, W.; Gillessen, D. Tetrahedron Lett. 1989, 30, 1927-1930.
52. HATU is a modern, very active peptide coupling reagent. (a) Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397-4398.
53. (b) Bofill, J. M.; Albericio, F. J. Chem. Res. (S) 1996, 302-303.
54. (a) Miller, M. L.; Linton, R. W. Anal. Chem. 1985, 57, 2314-2319.
55. (b) Linton, R. W.; Miller, M. L.; Maciel, G. E.; Hawkins, B. L. Surf. Interface Anal. 1985, 7, 196-203.
56. (c) Barrett, D. A.; Brown, V. A.; Davies M. C.; Shaw, P. N. Anal. Chem. 1996, 68, 2170-2178.
57. (d) Ascah, T. L.; Kallury, K. M. R.; Szafranski, C. A.; Corman, S. D.; Liu, F. J. Liq. Chromatogr. Relat. Technol. 1996, 19, 3049-3073.
58. (e) Pizzolatto, R. L.; Yang, Y. J.; Wolf, L. K.; Messmer, M. C. Anal. Chim. Acta 1999, 397, 81-92.
59. (f) Willetts, M.; Brown, V. A.; Clench, M. R. J. Chromatogr. A 2000, 903, 33-40.
60. (g) Yu, X.; Zhao, R.; Liu, G. Q. Chromatographia 2000, 52, 517-519.
61. (h) Harnisch, J. A.; Gazda, D. B.; Anderegg, J. W.; Porter, M. D. Anal. Chem. 2001, 73, 3954-3959.
62. (i) Vansant, E. F.; van der Voort, P.; Vrancken, K. C. Characterization and Chemical Modification of the Silica Surface; Elsevier: Amsterdam, 1995; pp 485-510.
63. Woodruff, D. P.; Delchar, T. A. Modern techniques of surface science; Cambridge University Press: Cambridge, U.K., 1996.
64. Practical Surface Analysis: Volume 1 - Auger and X-ray Photoelectron Spectroscopy, 2nd ed.; Briggs, D., Seah, M. P., Eds.; John Wiley and Sons: Chichester, U.K. 1990.
65. (a) Wei, X.-L.; Fahlman, M.; Epstein, K. J. Macromolecules 1999, 32, 3114-3117.
66. (b) Fernández-Ramos, C.; Sayagués, M. J.; Rojas, T. J.; Alcalá, M. D.; Real, C.; Fernández, A. Diamond Relat. Mater. 2000, 9, 212-218.
67. (c) Glidle, A.; Swann, M. J.; Hadyoon, C. S.; Cui, L.; Davis, J.; Ryder, K. S.; Cooper, J. M. J. Electron Spectrosc. Relat. Phenom. 2001, 21, 131-148.
68. (a) Beamson, G.; Briggs, D. High-Resolution XPS of organic polymers. The Scienta ESCA300 Database; John Wiley: New York, 1992.
69. (b) Wagner, C. D.; Naumkin, A. V.; Kraut-Vass, A.; Allison, J. W.; Powell, C. J.; Rumble, J. R., Jr. NIST X-ray Photoelectron Spectroscopy Database, version 3.2, 2000. Web version at http://srdata.nist.gov/xps