Method for enhancing cell penetration of Gd3+-based MRI contrast agents by conjugation with hydrophobic fluorescent dyes

Bioconjugate Chemistry

Volumn 22, Issue 11, 2011, Pages 2227-2236

  Yamane, Takehiro ^a,b   Hanaoka, Kenjiro ^a,b   Muramatsu, Yasuaki ^a,b   Tamura, Keita ^c   Adachi, Yusuke ^c   Miyashita, Yasushi ^c   Hirata, Yasunobu ^d   Nagano, Tetsuo ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

^d UNIVERSITY OF TOKYO HOSPITAL   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CELLS; DIES; FLUORESCENCE; GADOLINIUM COMPOUNDS; HYDROPHOBICITY; IMAGE ENHANCEMENT; MAGNETIC RESONANCE IMAGING; SYNTHESIS (CHEMICAL);

CELL PENETRATION; CELL PERMEABILITY; CELL PERMEATION; FLUORESCENT DYES; GADOLINIUM IONS; HYDROPHOBICS; MAGNETIC RESONANCE IMAGING CONTRAST AGENTS; MR-IMAGES; NOVEL METHODS; SYNTHESISED;

CYTOLOGY;

BORON; FLUORESCENT DYE; GADOLINIUM ION; METAL ION; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CELL MEMBRANE PERMEABILITY; CONTROLLED STUDY; FLOW CYTOMETRY; FLUOROMETRY; HUMAN; HUMAN CELL; MALE; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING;

MUS;

EID: 81255138078     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc200127t     Document Type: Article

References (28)

1. Weissleder, R. and Pittet, M. J. (2008) Imaging in the era of molecular oncology Nature 452, 580-589 (Pubitemid 351483372)
2. Nakahara, K., Adachi, Y., Osada, T., and Miyashita, Y. (2007) Exploring the neural basis of cognition: multi-modal links between human fMRI and macaque neurophysiology Trends Cogn. Sci. 11, 84-92 (Pubitemid 46176699)
3. Aime, S., Botta, M., Fasano, M., and Terreno, E. (1999) Prototropic and water-exchange processes in aqueous solutions of Gd(III) chelates Acc. Chem. Res. 32, 941-949
4. Louie, A. Y., Huber, M. M., Ahrens, E. T., Rothbacher, U., Moats, R., Jacobs, R. E., Fraser, S. E., and Meade, T. J. (2000) In vivo visualization of gene expression using magnetic resonance imaging Nat. Biotechnol. 18, 321-325 (Pubitemid 30159486)
5. Hanaoka, K., Kikuchi, K., Urano, Y., and Nagano, T. (2001) Selective sensing of zinc ions with a novel magnetic resonance imaging contrast agent J. Chem. Soc., Perkins Trans. 2, 1840-1843
6. Allen, M. J., MacRenaris, K. W., Venkatasubramanian, P. N., and Meade, T. J. (2004) Cellular delivery of MRI contrast agents Chem. Biol. 11, 301-307 (Pubitemid 39403869)
7. Lewin, M., Carlesso, N., Tung, C. H., Tang, X. W., Cory, D., Scadden, D. T., and Weissleder, R. (2000) Tat peptide-derivatized magnetic nanoparticles allow in vivo tracking and recovery of progenitor cells Nat. Biotechnol. 18, 410-414 (Pubitemid 30217528)
8. Mishra, R., Su, W., Pohmann, R., Pfeuffer, J., Sauer, M. G., Ugurbil, K., and Engelmann, J. (2009) Cell-penetrating peptides and peptide nucleic acid-coupled MRI contrast agents: evaluation of cellular delivery and target binding Bioconjugate Chem. 20, 1860-1868
9. Olson, E. S., Jiang, T., Aguilera, T. A., Nguyen, Q. T., Ellies, L. G., Scadeng, M., and Tsien, R. Y. (2010) Activatable cell penetrating peptides linked to nanoparticles as dual probes for in vivo fluorescence and MR imaging of proteases Proc. Natl. Acad. Sci. U. S. A. 107, 4311-4316
10. Frankel, A. D. and Pabo, C. O. (1988) Cellular uptake of the tat protein from human immunodeficiency virus Cell 55, 1189-1193 (Pubitemid 19020071)
11. Herce, H. D. and Garcia, A. E. (2007) Molecular dynamics simulations suggest a mechanism for translocation of the HIV-1 TAT peptide across lipid membranes Proc. Natl. Acad. Sci. U. S. A. 104, 20805-20810
12. Juliano, R. L., Alam, R., Dixit, V., and Kang, H. M. (2009) Cell-targeting and cell-penetrating peptides for delivery of therapeutic and imaging agents Wiley Interdiscip. Rev. Nanomed. Nanobiotechnol. 1, 324-335
13. Verdurmen, W. P. and Brock, R. (2011) Biological responses towards cationic peptides and drug carriers Trends Pharmacol. Sci. 32, 116-124
14. Futaki, S., Nakase, I., Tadokoro, A., Takeuchi, T., and Jones, A. T. (2007) Arginine-rich peptides and their internalization mechanisms Biochem. Soc. Trans. 35, 784-787 (Pubitemid 47310368)
15. Endres, P. J., MacRenaris, K. W., Vogt, S., and Meade, T. J. (2008) Cell-permeable MR contrast agents with increased intracellular retention Bioconjugate Chem. 19, 2049-2059
16. Digilio, G., Menchise, V., Gianolio, E., Catanzaro, V., Carrera, C., Napolitano, R., Fedeli, F., and Aime, S. (2010) Exofacial protein thiols as a route for the internalization of Gd(III)-based complexes for magnetic resonance imaging cell labeling J. Med. Chem. 53, 4877-4890
17. Li, H., Gray, B. D., Corbin, I., Lebherz, C., Choi, H., Lund-Katz, S., Wilson, J. M., Glickson, J. D., and Zhou, R. (2004) MR and fluorescent imaging of low-density lipoprotein receptors Acad. Radiol. 11, 1251-1259
18. Huber, M. M., Staubli, A. B., Kustedjo, K., Gray, M. H., Shih, J., Fraser, S. E., Jacobs, R. E., and Meade, T. J. (1998) Fluorescently detectable magnetic resonance imaging agents Bioconjugate Chem. 9, 242-249 (Pubitemid 28147142)
19. Montgomery, C. P., Murray, B. S., New, E. J., Pal, R., and Parker, D. (2009) Cell-penetrating metal complex optical probes: targeted and responsive systems based on lanthanide luminescence Acc. Chem. Res. 42, 925-937
20. New, E. J., Congreve, A., and Parker, D. (2010) Definition of the uptake mechanism and sub-cellular localisation profile of emissive lanthanide complexes as cellular optical probes Chem. Sci. 1, 111-118
21. Mishra, A., Pfeuffer, J., Mishra, R., Engelmann, J., Mishra, A. K., Ugurbil, K., and Logothetis, N. K. (2006) A new class of Gd-based DO3A-ethylamine-derived targeted contrast agents for MR and optical imaging Bioconjugate Chem. 17, 773-780 (Pubitemid 43841388)
22. Caravan, P., Ellison, J. J., McMurry, T. J., and Lauffer, R. B. (1999) Gadolinium(III) chelates as MRI contrast agents: Structure, dynamics, and applications Chem. Rev. 99, 2293-2352 (Pubitemid 30498114)
23. Lauffer, R. B., Parmelee, D. J., Dunham, S. U., Ouellet, H. S., Dolan, R. P., Witte, S., McMurry, T. J., and Walovitch, R. C. (1998) MS-325: Albumin-targeted contrast agent for MR angiography Radiology 207, 529-538 (Pubitemid 28259074)
24. Kawabata, E., Kikuchi, K., Urano, Y., Kojima, H., Odani, A., and Nagano, T. (2005) Design and synthesis of zinc-selective chelators for extracellular applications J. Am. Chem. Soc. 127, 818-819 (Pubitemid 40144267)
25. Sibrian-Vazquez, M., Ortiz, J., Nesterova, I. V., Fernandez-Lazaro, F., Sastre-Santos, A., Soper, S. A., and Vicente, M. G. (2007) Synthesis and properties of cell-targeted Zn(II)-phthalocyanine-peptide conjugates Bioconjugate Chem. 18, 410-420 (Pubitemid 46493512)
26. Olmedilla, L., Perez-Pena, J. M., Ripoll, C., Garutti, I., de Diego, R., Salcedo, M., Jimenez, C., and Banares, R. (2009) Early noninvasive measurement of the indocyanine green plasma disappearance rate accurately predicts early graft dysfunction and mortality after deceased donor liver transplantation Liver Transpl. 15, 1247-1253
27. Abe, T., Kakyo, M., Tokui, T., Nakagomi, R., Nishio, T., Nakai, D., Nomura, H., Unno, M., Suzuki, M., Naitoh, T., Matsuno, S., and Yawo, H. (1999) Identification of a novel gene family encoding human liver-specific organic anion transporter LST-1 J. Biol. Chem. 274, 17159-17163
28. Yamada, T., Yoshikawa, M., Kanda, S., Kato, Y., Nakajima, Y., Ishizaka, S., and Tsunoda, Y. (2002) In vitro differentiation of embryonic stem cells into hepatocyte-like cells identified by cellular uptake of indocyanine green Stem Cells 20, 146-154 (Pubitemid 34297262)