Dense-shell glycodendrimers: UV/Vis and electron paramagnetic resonance study of metal ion complexation

Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences

Volumn 466, Issue 2117, 2010, Pages 1489-1513

  Appelhans, Dietmar ^a   Oertel, Ulrich ^a   Mazzeo, Roberto ^b   Komber, Hartmut ^a   Hoffmann, Jan ^c   Weidner, Steffen ^d   Brutschy, Bernhard ^c   Voit, Brigitte ^a   Ottaviani, Maria Francesca ^b  

^a LEIBNIZ INSTITUTE OF POLYMER RESEARCH DRESDEN   (Germany)

^b UNIVERSITY OF URBINO   (Italy)

^c GOETHE UNIVERSITY   (Germany)

^d BAM FEDERAL INSTITUTE FOR MATERIALS RESEARCH AND TESTING   (Germany)

Author keywords

Electron paramagnetic resonance study; Glycodendrimers; Metal ion complexation; Metal ion intradendrimer complexes

Indexed keywords

COORDINATION REACTIONS; COPPER COMPOUNDS; DENDRIMERS; ELECTRON RESONANCE; ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTRONS; EUROPIUM; MALTOSE; METAL IONS; METALS; OLIGOSACCHARIDES; PARAMAGNETIC MATERIALS; SHELLS (STRUCTURES); SILVER COMPOUNDS; SUGAR (SUCROSE);

BIOLOGICAL APPLICATIONS; BIOLOGICAL ENVIRONMENTS; CARRIER SYSTEMS; COMPLEXATION CAPACITY; COORDINATION SPHERE; DECOMPLEXATIONS; DENDRIMER COMPLEXES; DENDRIMER GENERATION; ELECTRON PARAMAGNETIC RESONANCE; EPR SPECTRA; GENERATION NUMBERS; GLYCODENDRIMERS; IN-PROCESS; MALTOTRIOSE; METAL ION COMPLEXATION; METAL PROTEINS; MULTIPLE FEATURES; POLY(PROPYLENE IMINE); PROTECTIVE SHELL; RELATIVE CONCENTRATION; RHOMBIC SYMMETRIES; THIRD GENERATION; UV/ VIS SPECTROSCOPY; WATER MOLECULE;

PARAMAGNETIC RESONANCE;

EID: 77952017797     PISSN: 13645021     EISSN: 14712946     Source Type: Journal    
DOI: 10.1098/rspa.2009.0107     Document Type: Article

References (47)

1. Addison, A. W. 1983 Spectroscopic and redox trends from model copper complexes. In Copper coordination chemistry: bio-chemical and inorganic perspectives (eds K. D. Karlin & J. Zubieta), pp. 109-125. Guilderland, NY: Adenine Press.
2. Agarwal, A., Asthana, A., Gupta, U. & Jain, N. K. 2008 Tumour and dendrimers: a review on drug delivery aspects. J. Pharm. Pharmacol. 60, 671-688. (doi:10.1211/jpp.60.6.0001) (Pubitemid 351702440)
3. Appelhans, D. et al. 2007 Oligosaccharide-modified poly(propylene imine) dendrimers: synthesis, structure determination, and CuII complexation. Macromol. Biosci. 7, 373-383. (doi:10.1002/ mabi.200600260)
4. Astruc, D., Ornelas, C. & Ruiz, J. 2008 Metallocenyl dendrimers and their applications in molecular electronics, sensing, and catalysis. Acc. Chem. Res. 41, 841-856. (doi:10.1021/ar8000074)
5. Banyai, I., Orszagh, I., Berka, M. & Balogh, L. P. 2005 NMR studies of PAMAM dendrimers as intelligent delivery systems of drugs, cosmetics and personal care products. Polym. Prepr. 46, 519-520.
6. Bennett, B., Antholine, W. E., D'souza, V. M., Chen, G. J., Ustinyuk, L. & Holz, R. C. 2002 Structurally distinct active sites in the copper(II)-substituted aminopeptidases from Aeromonas proteolytica and Escherichia coli. J. Am. Chem. Soc. 124, 13 025-13 034. (doi:10.1021/ja026341p) (Pubitemid 35247114)
7. Boas, U. & Heegaard, P. M. H. 2004 Dendrimers in drug research. Chem. Soc. Rev. 33, 43-63. (doi:10.1039/b309043b)
8. Bosman, A. W., Schenning, A. P. H. J., Janssen, R. A. J. & Meijer, E. W. 1997 Welldefined metallodendrimers by site-specific complexation. Chem. Ber. 130, 725-728. (doi:10.1002/ cber.19971300608)
9. Bosman, A. W., Janssen, H. M. & Meijer, E. W. 1999 About dendrimers: structure, physical properties, and applications. Chem. Rev. 99, 1665-1688. (doi:10.1021/cr970069y)
10. Brader, M. L., Borchardt, D. & Dunn M. F. 1992 Ligand effects on the blue copper site. Spectroscopic studies of an insulin-stabilized copper(II) chromophore incorporating an exogenous thiolate ligand. J. Am. Chem. Soc. 114, 4480-4486. (doi:10.1021/ja00038a006)
11. Cheruzel, L. E., Cecil, M. R., Edison, S. E., Mashuta, M. S., Baldwin, M. J. & Buchanan, R. M. 2006 Structural and spectroscopic characterization of copper(II) complexes of a new bisamide functionalized imidazole tripod and evidence for the formation of a mononuclear end-on Cu- OOH species. Inorg. Chem. 45, 3191-3202. (doi:10.1021/ic051280s)
12. Crooks, R. M., Lemon III, B. I., Sun, L., Yeung, L. K. & Zhao, M. 2001a Dendrimers III. Topics in current chemistry, vol.212 (ed. F. Vögtle), p. 82. Berlin, Germany: Springer.
13. Crooks, R. M., Zhao, M., Sun, L., Chechik, V. & Yeung, L. K. 2001b Dendrimer-encapsulated metal nanoparticles: synthesis, characterization and applications to catalysis. Acc. Chem. Res. 34, 181-190. (doi:10.1021/ar000110a) (Pubitemid 32816381)
14. de Jesus, E. & Flores, J. C. 2008 Dendrimers: solutions for catalyst separation and recycling. Indus. Eng. Chem. Res. 47, 7968-7981. (doi:10.1021/ie800381d)
15. Diallo, M. S., Christie, S., Swaminathan, P., Balogh, L., Shi, X., Um, W., Papelis, C., Goddard III, W. A. & Johnson Jr, J. H. 2004 Dendritic chelating agents. 1. Cu(II) binding to ethylene diamine core poly(amidoamine) dendrimers in aqueous solutions. Langmuir 20, 2640-2651. (doi:10.1021/la036108k)
16. Diallo, M. S., Arasho, W., Johnson, J. H. & Goddard III, W. A. 2008 Dendritic chelating agents. 2. U(VI) binding to poly(amidoamine) and poly(propyleneimine) dendrimers in aqueous solutions. Environ. Sci. Technol. 42, 1572-1579. (doi:10.1021/es0715905) (Pubitemid 351419164)
17. Domracheva, N., Mirea, A., Schwörer, M., Torre-Lorente, L. & Lattermann, G. 2004 EPR characterization of Cu-II complexes of poly(propylene imine) dendromesogenes: using the orienting effect of a magnetic field. Chem. Phys. Chem. 6, 110-119. (doi:10.1002/ cphc.200400328)
18. Esumi, K., Hosoya, T., Suzuki, A. & Torigoe, K. 2000 Formation of gold and silver nanoparticles in aqueous solution of sugar-persubstituted poly(amidoamine) dendrimers. J. Colloid. Interf. Sci. 226, 346-352. (doi:10.1006/jcis.2000.6849) (Pubitemid 30395346)
19. Esumi, K., Matsumoto, T., Seto, Y. & Yoshimura, T. 2005 Preparation of gold-, gold/silverdendrimer nanocomposites in the presence of benzoin in ethanol by UV irradiation. J. Colloid. Interf. Sci. 284, 199-203. (doi:10.1016/j.jcis.2004.09.020) (Pubitemid 40332465)
20. Hathaway, B. J. & Tomlinson, A. A. G. 1970 Copper(II) ammonia complexes. Coord. Chem. Rev. 5, 1-43. (doi:10.1016/S0010-8545(00)80073-9)
21. Hwang, S.-H., Moorefield, C. N. & Newkome, G. R. 2008 Dendritic macromolecules for organic light emitting diodes. Chem. Soc. Rev. 37, 2543-2557. (doi:10.1039/b803932c)
22. Imaoka, T., Tanaka, R., Arimoto, S., Sakai, M., Fujii, M. & Yamamoto, K. 2005 Probing stepwise complexation in phenylazomethine dendrimers by a metallo-porphyrin core. J. Am. Chem. Soc. 127, 13 896-13 905. (doi:10.1021/ja0524797) (Pubitemid 41437040)
23. Klajnert, B. et al. 2008 The influence of densely organized maltose shells on the biological properties of poly(propylene imine) dendrimers: new effects dependent on hydrogen bonding. Chem. Eur. J. 14, 7030-7041. (doi:10.1002/chem.200800342)
24. Kodama, H. & Fujisawa, C. 2008 Copper metabolism and inherited copper transport disorders: molecular mechanism, screening, and treatment. Metallomics 1, 42-52. (doi:10.1039/b816011m)
25. Koyama, N., Ishida, T., Nogami, T. & Kogane, T. 2008 A pyrazine-bridged linear penta-nuclear copper(II) complex and related tri- and dinuclear complexes showing various coordination structures and magnetic couplings. Polyhedron 27, 2341-2348. (doi:10.1016/j.poly.2008.04.040)
26. Kurzac, B., Kamecka, A., Bogusz, K. & Jezierska, J. 2008 Stabilities and coordination modes of histidine in copper(II) mixed-ligand complexes with ethylenediamine, diethylenetriamine or N, N, N-, N-, N- pentamethyldiethylenetriamine in aqueous solution. Polyhedron 27, 2952-2958. (doi:10.1016/j.poly.2008.05.029)
27. Lee, C. C., MacKay, J. A., Fréchet, J. M. & Szoka, F. C. 2005 Designing dendrimers for biological applications. Nat. Biotechnol. 23, 1517-1526. (doi:10.1038/nbt1171) (Pubitemid 41752929)
28. Lesniak, W., Bielinska, A. U., Sun, K., Janczak, K. W., Shi, X., Baker Jr, J. R. & Balogh, L. P. 2005 Silver/dendrimer nanocomposites as biomarkers: fabrication, characterization, in vitro toxicity, and intracellular detection. Nano Lett. 5, 2123-2130. (doi:10.1021/nl051077u) (Pubitemid 41698923)
29. Minchin, R. 2008 Sizing up targets with nanoparticles. Nat. Nanotechnol. 3, 12-13. (doi:10.1038/ nnano.2007.433)
30. Morgner, N., Barth, H.-D. & Brutschy, B. 2006 A new way to detect noncovalently bonded complexes of biomolecules from liquid micro-droplets by laser mass spectrometry. Aust. J. Chem. 59, 109-114. (doi:10.1071/CH05285) (Pubitemid 43348561)
31. Ohtsu, H., Itoh, S., Nagatomo, S., Kitagawa, T., Ogo, S., Watanabe, Y. & Fukuzumi, S. 2001 Characterization of imidazolate-bridged dinuclear and mononuclear hydroperoxo complexes. Inorg. Chem. 40, 3200-3207. (doi:10.1021/ic001036v) (Pubitemid 32884131)
32. Ottaviani, M. F., Bossmann, S., Turro, N. J. & Tomalia, D. A. 1994 Characterization of starbust dendrimers by the EPR technique. 1. Copper complexes in water solution. J. Am. Chem. Soc. 116, 661-671. (doi:10.1021/ja00081a029)
33. Ottaviani, M. F., Montalti, F., Turro, N. J. & Tomalia, D. A. 1997 Characterization of starbust dendrimers by EPR technique. Copper(II) ions binding full-generation dendrimers. J. Phys. Chem. B 101, 158-166. (doi:10.1021/jp962857h)
34. Ottaviani, M. F., Favuzza, P., Bigazzi, M., Turro, N. J., Jockusch, S. & Tomalia, D. A. 2000 A TEM and EPR investigation of the competitive binding of uranyl ions to starburst dendrimers and liposomes. Potential use of dendrimers as uranyl ion sponges. Langmuir 16, 7368-7372. (doi:10.1021/ la000355w)
35. Ottaviani, M. F., Valluzzi, R. & Balogh, L. 2002 Internal structure of silver-poly(amidoamine) dendrimer complexes and nanocomposites. Macromolecules 35, 5105-5115. (doi:10.1021/ ma010492f)
36. Peisach, J. & Blumberg, W. E. 1974 Structural implications derived from the analysis of electron paramagnetic resonance spectra of natural and artificial copper proteins. Arch. Biochem. Biophys. 165, 691-708. (doi:10.1016/0003-9861(74)90298-7)
37. Reek, J. N. H., Arevalo, S., Van Heerbeek, R., Kamer, P. C. J. & Van Leeuwen, P. W. N. M. 2006 Dendrimers in catalysis. Adv. Catal. 49, 71-151. (doi:10.1016/S0360-0564(05)49002-1) (Pubitemid 44275040)
38. Saha, M. K., Dey, D. K., Samanta, B., Edwards, A. J., Clegg, W. & Mitra, S. 2003 Synthesis, structure and magnetic properties of a mononuclear Cu(II) complex with a NNO donor Schiff base ligand and its oxalate- and oxamidato-bridged dinuclear complexes. Dalton Trans. 488-492. (doi:10.1039/b206076k)
39. 2+ complexation by dendrimers with 1,4,8,11-tetraazacyclotetradecane (cyclam) cores. Chem. Eur. J. 10, 899-905. (doi:10.1002/chem.200305255)
40. Shi, X., Wang, S., Meshinchi, S., Van Antwerp, M. E., Bi, X., Lee, H. & Baker Jr, J. R. 2007 Dendrimer-entrapped gold nanoparticles as a platform for cancer-cell targeting and imaging. Small 3, 1245-1252. (doi:10.1002/smll. 200700054) (Pubitemid 47114383)
41. Solomon, E. I. & Hanson, M. A. 2006 Bioinorganic spectroscopy in inorganic electronic structure and spectroscopy. In Applications and case studies (eds E. I. Solomon & A. B. P. Lever), vol.II, pp. 1-130. New York, NY: John Wiley & Sons.
42. Takanashi, K., Fujii, A., Nakajima, R., Chiba, H., Higuchi, M., Einaga, Y. & Yamamoto, K. 2007 Heterometal assembly in dendritic polyphenylazomethines. Bull. Chem. Soc. Jap. 80, 1563-1572. (doi:10.1246/bcsj. 80.1563)
43. Tran, M. L., Gahan, L. R. & Gentle, I. R. 2004 Structural studies of copper(II)-amine terminated dendrimer complexes by EXAFS. J. Phys. Chem. B 108, 20 130-20 136. (doi:10.1021/jp037569h) (Pubitemid 40073529)
44. Venditto, V. J., Regino, C. A. S. & Brechbiel, M. W. 2005 PAMAM dendrimer based macromolecules as improved contrast agents. Mol. Pharm. 2, 302-311. (doi:10.1021/mp050019e) (Pubitemid 41186406)
45. Wiener, E. C., Auteri, F. P., Chen, J. W., Brechbiel, M. W., Gansow, O. A., Schneider, D. S., Belford, R. L., Clarkson, R. B. & Lauterbur, P. C. 1996 Molecular dynamics of ion-chelate complexes attached to starburst dendrimers. J. Am. Chem. Soc. 118, 7774-7782. (doi:10.1021/ ja9536126)
46. Zhao, M. & Crooks, R. M. 1999 Intradendrimer exchange of metal nanoparticles. Chem. Mater. 11, 3379-3385. (doi:10.1021/cm990435p)
47. Zhao, M., Sun, L. & Crooks, R. M. 1998 Preparation of Cu nanoclusters within dendrimer templates. J. Am. Chem. Soc. 120, 4877-4878. (doi:10.1021/ja980438n)