Journal of the American Chemical Society
ARTICLE
contrast agent using a Gradient Echo sequence with the following
McKenna, B.; Remmes, N.; Baxter, D.; Kao, C. C.; Dragnea, B. Nano
Lett. 2007, 7, 2407–2416. (c) Dixit, S. K.; Goicochea, N. L.; Daniel,
M. C.; Murali, A.; Bronstein, L.; De, M.; Stein, B.; Rotello, V. M.; Kao,
C. C.; Dragnea, B. Nano Lett. 2006, 6, 1993–1999.
parameters: TR/TE = 130/6 ms, flip angle = 30ꢀ, MTX = 256 ꢀ 256,
2
2
FOV = 25 ꢀ 25 mm (corresponding to 0.098 ꢀ 0.098 mm in-plane
resolution), slice thickness = 1 mm, NEX = 4. The acquisition time for a
single image was 133 s. A phantom containing 1 mM Gd-DTPA in saline
was inserted in the field of view and used to normalize possible
spectrometer drifts during the acquisition.
(6) (a) Webb, B.; Frame, J.; Zhao, Z.; Lee, M. L.; Watt, G. D. Arch.
Biochem. Biophys. 1994, 309, 178–183. (b) Aime, S.; Frullano, L.;
Geninatti Crich, S. Angew. Chem., Int. Ed. 2002, 41, 1017–1019. (c)
Simsek, E.; Kilic, M. A. J. Magn. Magn. Mater. 2005, 293, 509–513. (d)
Colacio, E.; Domínguez-Vera, J. M. Inorg. Chem. 2003, 42, 6983–6985.
’
ASSOCIATED CONTENT
(7) Swift, J.; Butts, C. A.; Cheung-Lau, J.; Yerubandi, V.; Dmo-
chowski, I. J. Langmuir 2009, 25, 5219–5225.
S
Supporting Information. A detailed description of pur-
b
(8) (a) Zhang, H.; Ma, Y.; Sun, X. L. Med. Res. Rev. 2010,
30, 270–289. (b) Seeberger, P. H.; Werz, D. B. Nature 2007,
446, 1046–1051. (c) Park, S.; Lee, M. R.; Shin, I. Chem. Soc. Rev.
2008, 37, 1579–1591.
ification (SI1) and structural characterization (SI2, SI3, and SI4)
of Apomaghemites samples, as well as detailed synthesis and
characterization of the vinyl sulfone derivatized carbohydrates.
This material is available free of charge via the Internet at http://
pubs.acs.org.
(9) Lis, H.; Sharon, N. Chem. Rev. 1998, 98, 637–674.
(10) (a) de la Fuente, J. M.; Penad ꢀe s, S. Biochem. Biophys. Acta 2006,
1760, 636–651. (b) Lartigue, L.; Oumzil, K.; Guari, Y.; Larionova, J.;
Gu ꢀe rin, C.; Montero, J. L.; Barragan-Montero, V.; Sangregorio, C.;
Caneschi, A.; Innocenti, C.; Kalaivani, T.; Arosio, P.; Lascialfari, A. Org.
Lett. 2009, 11, 2992–2995. (c) Earhart, C.; Jana, N. R.; Erathodiyil, N.;
Ying, J. Y. Langmuir 2008, 24, 6215–6219. (d) El-Boubbou, K.; Gruden,
C.; Huang, X. J. Am. Chem. Soc. 2008, 129, 13392–13393. (d) Liu, L. H.;
Dietsch, H.; Schurtenberger, P.; Yan, M. Bioconjugate Chem. 2009,
’
AUTHOR INFORMATION
Corresponding Author
josema@ugr.es; ngalvez@ugr.es
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0, 1349–1355. (e) Liang, C. H.; Wang, C. C.; Lin, Y. C.; Chen,
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ACKNOWLEDGMENT
C. H.; Wong, C. H.; Wu, C. Y. Anal. Chem. 2009, 81, 7750–7756.
(11) Lu, A. H.; Salabas, E. L.; Sch €u th, F. Angew. Chem., Int. Ed. 2007,
46, 1222–1244.
We are grateful to the MEC (project CTQ2009-09344), Junta
de Andalucía project (FQM-02525), and EU I3 Project ESTEEM
contract no. 026019 RII3) for financial support.
(12) Vayssi ꢁe res, L.; Chan ꢀe ac, C.; Tronc, E.; Jolivet, J. P. J. Colloid
(
Interface Sci. 1998, 205, 205–212.
(
(
13) Massart, R. IEEE Trans. Magn. 1981, 1247–1248.
14) (a) Mann, S.; Archibald, D. D.; Didymus, J. M.; Douglas, T.;
’
REFERENCES
(
1) (a) Cheon, J.; Lee, J. H. Acc. Chem. Res. 2008, 41, 1630–1640. (b)
Heywood, B. R.; Meldrum, F. C.; Reeves, N. J. Science 1993,
261, 1286–1292. (b) Wong, K. K. W.; Douglas, T.; Gider, S.; Awschalom,
D. D.; Mann, S. Chem. Mater. 1998, 10, 279–285. (c) Meldrum, F. C.;
Heywood, B. R.; Mann, S. Science 1992, 257, 522–523.
(15) http://www2.uca.es/dept/cmat_qinor/catalisis/tem-uca-ser-
ver.htm.
(16) Tronc, E.; Fiorani, D.; Nogu ꢀe s, M.; Testa, A. M.; Lucari, F.;
D’Orazio, F.; Gren ꢁe che, J. M.; Wernsdorfer, W.; Galvez, N.; Chan ꢀe ac,
C.; Mailly, D.; Jolivet, J. P. J. Magn. Magn. Mater. 2003, 262, 6–14.
(17) (a) Hyeon, T.; Lee, S. S.; Park, J.; Chung, Y.; Na, H. B. J. Am.
Chem. Soc. 2001, 123, 12798–12801. (b) Jun, Y.; Huh, Y. M.; Choi, J. S.;
Lee, J. H.; Song, H. T.; Kim, S. J.; Yoon, S.; Kim, K. S.; Shin, J. S.; Suh,
J. S.; Cheon, J. J. Am. Chem. Soc. 2005, 127, 5732–5733.
Dobson, J. Nat. Nanotechnol. 2008, 3, 139–143. (c) Jun, Y. W.; Seo, J. W.;
Cheon, J. Acc. Chem. Res. 2008, 41, 179–189. (d) Campbell, R. B.
Nanomedicine 2007, 2, 649–652.
(
2) (a) Kettering, M.; Winter, J.; Zeisberger, M.; Streck, S. B.;
Oehring, H.; Bergemann, C.; Alexxiou, C.; Hergt, R.; Halbhuber, K. J.;
Kaiser, W. A.; Hilger, I. Nanotechnology 2007, 18, 175101–175110. (b)
Hergt, R.; Hiergeist, R.; Zeisberger, M.; Glockl, G.; Weitschies, W.;
Ramirez, L. P.; Hilger, I.; Kaiser, W. A. J. Magn. Magn. Mater. 2004,
2
80, 358–368. (c) Weissleder, R.; Moore, A.; Mahmood, U.; Bhorade,
E.; Benveniste, H.; Chiocca, E. A.; Basilion, J. P. Nat. Med. 2000,
, 351–354.
3) (a) Mornet, S.; Vasseur, S.; Grasset, F.; Duguet, E. J. Mater.
6
(
Chem. 2004, 14, 2161–2175. (b) Di Marco, M.; Sadun, C.; Port, M.;
Guilbert, I.; Couvreur, P.; Dubernet, C. Int. J. Nanomed. 2007,
(18) (a) Masotti, A.; Pitta, A.; Ortaggi, G.; Corti, M.; Innocenti, C.;
Lascialfari, A.; Marinone, M.; Marzola, P.; Daducci, A.; Sbarbati, A.;
Micotti, E.; Orsini, F.; Poletti, G.; Sangregorio, C. Magn. Reson. Mater.
Phys. 2009, 22, 77–87. (b) Schwarz, A. J.; Reese, T.; Gozzi, A.; Bifone, A.
Magn. Reson. Imaging 2003, 21, 191–200.
2, 609–622. (c) Corot, C.; Robert, P.; Idee, J. M.; Port, M. Adv. Drug
Delivery Rev. 2006, 58, 1471–1504. (d) Laurent, S.; Forge, D.; Port, M.;
Roch, A.; Robic, C.; Elst, L. V.; Muller, R. N. Chem. Rev. 2008,
1
08, 2064–2110.
4) (a) G ꢀa lvez, N.; S ꢀa nchez, P.; Domínguez-Vera, J. M. Dalton Trans.
005, 2492–2495. (b) Clemente-Le oꢀ n, M.; Coronado, E.; Soriano-
(19) (a) Fernandez, B.; Galvez, N.; Sanchez, P.; Morales, J.; Santoyo,
F.; Cuesta, R.; Dominguez-Vera, J. M. Inorg. Chim. Acta 2007,
360, 3951–3954. (b) Fern ꢀa ndez, B.; G ꢀa lvez, N.; Cuesta, R.; Hungría,
A. B.; Calvino, J. J.; Domínguez-Vera, J. M. Adv. Funct. Mater. 2008,
18, 3931–3935.
(20) (a) Davis, B. G. Chem. Rev. 2002, 102, 579–601. (b) Gamblin,
D. P.; Scanlan, E. M.; Davis, B. G. Chem. Rev. 2009, 109, 131–163.
(21) (a) Lopez-Jaramillo, F. J.; Perez-Banderas, F.; Hernandez-
Mateo, F.; Santoyo-Gonzalez, F. Acta Crystallogr., Sect. F 2005,
61, 435–438. (b) Morales-Sanfrutos, J.; Lopez-Jaramillo, J.; Ortega-
Mu ~n oz, M.; Megia-Fernandez, A.; Perez-Balderas, F.; Hernandez-Ma-
teo, F.; Santoyo-Gonzalez, F. Org. Biomol. Chem. 2010, 8, 667–678.
(22) Taylor, M. E.; Benzou ꢂs ka, K.; Drickamer, K. J. Biol. Chem. 1992,
267, 1719–172.
(
2
Portillo, A.; G ꢀa lvez, N.; Domínguez-Vera, J. M. J. Mater. Chem. 2007,
7, 49–51. (c) Domínguez-Vera, J. M.; G ꢀa lvez, N.; S ꢀa nchez, P.; Mota,
A. J.; Trasobares, S.; Hern ꢀa ndez, J. C.; Calvino, J. J. Eur. J. Inorg. Chem.
007, 4823–4826. (d) Ueno, T.; Suzuki, M.; Goto, T.; Matsumoto, T.;
Nagayama, K.; Watanabe, Y. Angew. Chem., Int. Ed. 2004,
3, 2527–2530. (e) Uchida, M.; Klem, M. T.; Allen, M.; Flenniken,
1
2
4
M. L.; Gillitzer, E.; Varpness, Z.; Suci, P.; Young, M. J.; Douglas, T. Adv.
Mater. 2007, 19, 1025–1042. (f) G ꢀa lvez, N.; Fern ꢀa ndez, B.; S ꢀa nchez, P.;
Cuesta, R.; Ceolín, M.; Clemente-Le ꢀo n, M.; Trasobares, S.; L ꢀo pez-Haro,
M.; Calvino, J. J.; St ꢀe phan, O.; Domínguez-Vera, J. M. J. Am. Chem. Soc.
2
008, 130, 8062–8068.
(
5) (a) Chen, C.; Daniel, M. C.; Quinkert, Z. T.; De, M.; Stein, B.;
Bowman, V. D.; Chipman, P. R.; Rotello, V. M.; Kao, C. C.; Dragnea, B.
Nano Lett. 2006, 6, 611–615. (b) Huang, X.; Bronstein, L. M.; Retrum,
J.; DuFort, C.; Tsvetkova, I.; Aniagyei, S.; Stein, B.; Stucky, G.;
4
895
dx.doi.org/10.1021/ja110014p |J. Am. Chem. Soc. 2011, 133, 4889–4895