Guanidine-containing molecular transporters: Sorbitol-based transporters show high intracellular selectivity toward mitochondria

Angewandte Chemie - International Edition

Volumn 46, Issue 31, 2007, Pages 5880-5884

  Maiti, Kaustabh K ^a   Lee, Woo Sirl ^a   Takeuchi, Toshihide ^b,c   Watkins, Catherine ^d   Fretz, Marjan ^d   Kim, Dong Chan ^a   Futaki, Shiroh ^b,c   Jones, Arwyn ^d   Kim, Kyong Tai ^a   Chung, Sung Kee ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

^b KYOTO UNIVERSITY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^d CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

Bioorganic chemistry; Carbohydrates; Drug delivery; Membranes; Mitochondria

Indexed keywords

BLOOD; CARBOHYDRATES; CELLS; DRUG DELIVERY;

BIOORGANIC CHEMISTRY; MITOCHONDRIA;

MOLECULAR DYNAMICS;

GUANIDINE; SORBITOL;

ANIMAL; ARTICLE; CELL STRAIN COS1; CERCOPITHECUS; CHEMISTRY; DRUG DELIVERY SYSTEM; HELA CELL; HUMAN; METABOLISM; MITOCHONDRION; MOUSE;

ANIMALS; CERCOPITHECUS AETHIOPS; COS CELLS; DRUG DELIVERY SYSTEMS; GUANIDINE; HELA CELLS; HUMANS; MICE; MITOCHONDRIA; SORBITOL;

EID: 34547728730     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701346     Document Type: Article

References (39)

1. Handbook of Cell-Penetrating Peptides, 2nd ed. (Ed.: Ü. Langel), CRC, Boca Raton, 2006.
2. S. Futaki, Adv. Drug Delivery Rev. 2005, 57, 547.
3. S. Futaki, T. Suzuki, W. Ohashi, T. Yagami, S. Tanaka, K. Ueda, Y. Sugiura, J. Biol. Chem. 2001, 276, 5836.
4. A. Joliot, A. Prochiantz, Nat. Cell Biol. 2004, 6, 189.
5. J. B. Rothbard, S. Garlington, O. Lin, T. Kirschberg, E. Kreider, P. L. McGrane, P. A. Wender, P. A. Khavari, Nat. Med. 2000, 6, 1253.
6. J. S. Wadia, R. V. Stan, S. F. Dowdy, Nat. Med. 2004, 10, 310.
7. I. Nakase, M. Niwa, T. Takeuchi, K. Sonomura, N. Kawabata, Y. Koike, M. Takehashi, S. Tanaka, K. Ueda, J. C. Simpson, A. T. Jones, Y. Sugiura, S. Futaki, Mol. Ther. 2004, 10, 1011.
8. V. P. Torchilin, R. Rammohan, V. Weissig, T. S. Levchenko, Proc. Natl. Acad. Sci. USA 2001, 98, 8786.
9. K. Kogure, R. Moriguchi, K. Sasaki, M. Ueno, S. Futaki, H. Harashima, J. Controlled Release 2004, 98, 317.
10. P. A. Wender, D. J. Mitchell, K. Pattabiraman, E. T. Pelkey, L. Steinman, J. B. Rothbard, Proc. Natl. Acad. Sci. USA 2000, 97, 13 003.
11. P. A. Wender, J. B. Rothbard, T. C. Jessop, E. L. Kreider, B. L. Wylie, J. Am. Chem. Soc. 2002, 124, 13 382.
12. N. Umezawa, M. A. Gelman, M. C. Haigis, R. T. Raines, S. H. Gellman, J. Am. Chem. Soc. 2002, 124, 368.
13. N. Rueping, Y. Mahajan, M. Sauer, D. Seebach, ChemBioChem 2002, 3, 257.
14. P. Zhou, M. Wang, L. Du, G. W. Fisher, A. Waggoner, D. H. Ly, J. Am. Chem. Soc. 2003, 125, 6878.
15. N. W. Luedtke, P. Carmichael, Y. Tor, J. Am. Chem. Soc. 2003, 125, 12 374.
16. J. Fernandez-Carneado, M. Van Gool, V. Martos, S. Castel, P. Prados, J. de Mendoza, E. Giralt, J. Am. Chem. Soc. 2005, 127, 869.
17. H. H. Chung, G. Harms, C. M. Seong, B. H. Choi, C. Min, J. P. Taulane, M. Goodman, Biopolymers 2004, 76, 83.
18. K. K. Maiti, O. Y. Jeon, W. S. Lee, D. C. Kim, K. T. Kim, T. Takeuchi, S. Futaki, S. K. Chung, Angew. Chem. 2006, 118, 2973;
19. Angew. Chem. Int. Ed. 2006, 45, 2907.
20. K. K. Maiti, O. Y. Jeon, W. S. Lee, S. K. Chung, Chem. Eur. J. 2007, 13, 762.
21. J. S. Brimacombe, J. M. Webber in Carbohydrates: Chemistry and Biochemistry, Vol. 1, 2nd ed. (Ed.: W. Pigman, D. Horton), Academic Press, New York, 1972, p. 479.
22. S. K. Chaudhary, O. Hernandez, Tetrahedron Lett. 1979, 20, 95.
23. A. Klemer, K. Homberg, Chem. Ber. 1961, 94, 491.
24. F. M. Braña, G. Dominguez, B. Saez, C. Romerdahl, S. Robinson, T. Barlozzari, Eur. J. Med. Chem. 2002, 37, 541.
25. M. Dubber, K. T. Lindhorst, Org. Lett. 2001, 3, 4019.
26. a) M. F. Ross, A. Filipovska, R. A. J. Smith, M. J. Gate, M. P. Murphy, Biochem. J. 2004, 383, 457;
27. b) M. P. Murphy, R. A. Smith, Annu. Rev. Pharmacol. Toxicol. 2007, 47, 629.
28. V. Weissig, S. M. Cheng, G. G. M. D'Souza, Mitochondrion 2004, 3, 229.
29. The parent structures of the present carriers showed 3-(4,5- dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) toxicity profiles similar to that of R8, that is, virtually no toxicity at 10 μM.
30. D. C. Wallace, Science 1999, 283, 1482.
31. D. R. Green, J. C. Reed, Science 1998, 281, 1309.
32. V. L. Dawson, Nat. Med. 2004, 10, 905.
33. B. I. Bae, S. Igarashi, M. Fujimoro, N. Agrawal, Y. Taya, S. D. Hayward, T. H. Moran, C. A. Ross, S. H. Snyder, A. Sawa, Neuron 2005, 47, 29.
34. M. Manczak, T. S. Anekonda, E. Henson, B. S. Park, J. Quinn, P. M. Reddy, Hum. Mol. Genet. 2006, 15, 1437.
35. S. Al-Taei, N. A. Penning, J. C. Simpson, S. Futaki, T. Takeuchi, I. Nakase, A. T. Jones, Bioconjugate Chem. 2006, 17, 90.
36. M. M. Fretz, N. A. Penning, S. Al-Taei, S. Futaki, T. Takeuchi, I. Nakase, I. G. Storm, A. T. Jones, Biochem. J. 2007, 403, 335.
37. This kind of heterogeneity has been occasionally observed, and may be related to cell cycles of individual cells.
38. S. R. Schwarze, A. Ho, A. Vocero-Akbani, S. F. Dowdy, Science 1999, 285, 1569.
39. S. R. Cai, G. Xu, M. Backer-Hapak, M. Ma, S. F. Dowdy, H. L. McLeod, Eur. J. Pharm. Sci. 2006, 27, 311.