The lectin-binding properties of six generations of mannose-functionalized dendrimers

Organic Letters

Volumn 4, Issue 1, 2002, Pages 7-10

  Woller, Eric K ^a   Cloninger, Mary J ^a  

^a MONTANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONCANAVALIN A; MANNOSE; PAMAM STARBURST; POLYAMINE; POLYMER;

ANIMAL; ARTICLE; CHEMISTRY; HEMAGGLUTINATION TEST; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RABBIT;

ANIMALS; CONCANAVALIN A; HEMAGGLUTINATION TESTS; MAGNETIC RESONANCE SPECTROSCOPY; MANNOSE; POLYAMINES; POLYMERS; RABBITS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 0037050414     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016568+     Document Type: Article

References (40)

1. Griffith, L. G. Acta Mater. 2000, 48, 263-277.
2. (a) Singh, R. S.; Tiwary, A. K.; Kennedy, J. F. Crit. Rev. Biotechnol. 1999, 19, 145-178.
3. (b) Lis, H.; Sharon, N. Chem. Rev. 1998, 98, 637-674.
4. (a) Mammen, M.; Choi, S.-K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2754-2794.
5. (b) Page, M. I.; Jencks, W. P. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 1678-1683.
6. (a) Bovin, N. V.; Gabius, H.-J. Chem. Soc. Rev. 1995, 24, 413-421.
7. (b) Sharon, N.; Lis, H. Sci. Am. 1993, 82-89.
8. (c) Kiessling, L. L. In Recent Trends in Molecular Recognition; Diederich, F., Kunzer, H., Ed.; 1998; pp 183-212.
9. For leading references, see: (a) Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Nepogodiev, S. A.; Meijer, E. W.; Peerlings, H. W. I.; Stoddart, J. F. Chem. Eur. J. 1997, 3, 974-984.
10. (b) Page, D.; Roy, R. Bioconjugate Chem. 1997, 8, 714-723.
11. (c) Kieburg, C.; Lindhorst, T. K. Tetrahedron Lett. 1997, 38. 3885-3888.
12. For recent reviews of dendrimer chemistry, see: (a) Matthews, O. A.; Shipway, A. N.; Stoddart, J. F. Prog. Polym. Sci. 1998, 23, 1-56.
13. (b) Zeng, F.; Zimmerman, S. C. Chem. Rev. 1997, 97, 1681-1712.
14. (c) Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1665-1688.
15. (d) Inoue, K. Prog. Polym. Sci. 2000, 25, 453-571.
16. Andre, S.; Ortega, P. J. C.; Perez, M. A.; Gabius, H.-J. Glycobiology 1999, 9, 1253-1261.
17. (a) Bittiger, H.; Schnebli, H. P. Concanavalin A as a Tool; John Wiley & Sons: 1976.
18. (b) Derewenda, Z.; Yariv, J.; Helliwell, J. R.; Kalb. A. J.; Dodson, E. J.; Papiz, M. Z.; Wan, T.; Campbell, J. EMBO J. 1989, 8, 2189-2193.
19. (c) Lis, H.; Sharon, N. FASEB J. 1990, 4, 3198-3208.
20. Quesenberry, M. S.; Lee, R. T.; Lee, Y. C. Biochemistry 1997, 36, 2724-2732.
21. For a broader definition of the glycoside cluster effect, see: Lee, Y. C.; Lee, R. T. Acc. Chem. Res. 1995, 28, 322-327.
22. (a) Ren, T.; Liu, D. Tetrahedron Lett. 1999, 40, 7621-7625.
23. (b) Schmidt, R. R.; Michel, J. Angew. Chem., Int. Ed. Engl. 1980, 19, 731-732.
24. (c) Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235.
25. Synthesized as described in the Supporting Information from 2-(2-aminoethoxy)ethanol with thiophosgene, 70% yield.
26. Our synthesis procedure is similar to our previously reported route using p-isothiocyanatophenyl-α-D-mannopyranoside, except that the aromatic ring in the linkage to the dendrimer was eliminated to improve solubility in aqueous media: Woller, E. K.; Cloninger, M. J. Biomacromolecules 2001, 2, 1052-1054.
27. Tomalia et al. have reported that the average molecular weights of the PAMAMs are actually smaller than the theoretical molecular weights; our MALDI results are consistent with Tomalia's electrospray MS results: Tolic, L. P.; Anderson, G. A.; Smith, R. D.; Brothers, H. M.; Spindler, R.; Tomalia, D. A. Int. J. Mass Spec. Ion Processes 1997, 165/166, 405-418.
28. Dimick, S. M.; Powell, S. C.; McMahon, S. A.; Moothoo, D. N.; Naismith, J. H.; Toone, E. J.; J. Am. Chem. Soc. 1999, 121, 10286-10296.
29. For examples, see: (a) Sigal, G. B.; Mammen, M.; Dahmann, G.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 9-3800.
30. (b) Mortell, K. H.; Weatherman, R. V.; Kiessling, L. L. J. Am. Chem. Soc. 1996, 118, 8, 2297-2298.
31. (c) Roy, R.; Zanini, D.; Meunier, S. J.; Romanowska, A. J. Chem. Soc., Chem. Commun. 1993, 1869-1872.
32. (d) Mandal, D. K.; Brewer, C. F. Biochemistry 1993, 32, 5116-5120.
33. (e) Lehmann, J.; Weitzel, U. P. Carbohydr. Res. 1996, 294, 65-94.
34. (f) Hansen, H. C.; Haataja, S.; Finne, J.; Magnusson, G. J. Am. Chem. Soc. 1997, 119, 6974-6979.
35. A detailed experimental protocol is provided in the Supporting Information. Although precipitation has been observed in previous studies of Con A binding to mannose-functionalized dendrimers (ref 5b), our assays were performed at 30-fold lower concentrations, and no precipitation is observed.
36. The relative activity results for 12 are same order of magnitude as those obtained with ELLA assays in ref 5b. Differences in binding activities for 10-12 (compared to similar compounds in ref 5b) may be caused by changes in the linker between mannose and the PAMAM.
37. It is also possible that the change in shape from circular (G(1)-to G(3)-PAMAM) to spherical (G(4)-to G(6)-PAMAM) causes the observed binding enhancement. Studies with heterogeneously functionalized dendrimers are underway to address this issue.
38. (a) Uppuluri, S.; Keinath, S. E.; Tomalia, D. A.; Dvornic, P. R. Macromolecules 1998, 31, 4498-4510.
39. (b) Li, J.; Piehler, D.; Qin, J. R. B., Jr.; Tomalia, D. A. Langmuir 2000, 16, 5613-5616.
40. Our dendrimer results (and our analysis) are in good agreement with a previous study of polymer length on binding affinity: Kanai, M.; Mortell, K. H.; Kiessling, L. L J. Am. Chem. Soc. 1997, 119, 9931-9932.