On guanidinium and cellular uptake

Journal of Organic Chemistry

Volumn 79, Issue 15, 2014, Pages 6766-6774

  Wexselblatt, Ezequiel ^a   Esko, Jeffrey D ^b   Tor, Yitzhak ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANIMAL CELL CULTURE; CELL MEMBRANES; CELL PROLIFERATION; HYDROGEN BONDS;

ANIMAL MODEL; BIOLOGICAL BARRIER; CELL SURFACES; CELLULAR UPTAKE; CHARGE PAIRINGS; GUANIDINIUM; SPATIAL RELATIONSHIPS;

SCAFFOLDS (BIOLOGY);

AMINOGLYCOSIDE ANTIBIOTIC AGENT; ARGININE; ARGININE DERIVATIVE; CARBOHYDRATE; GUANIDINE; GUANIDINOGLYCOSIDE; HYDROGEN; INOSITOL; MOLECULAR SCAFFOLD; PEPTIDE DERIVATIVE; SYNTHETIC PEPTIDE; TAT PEPTIDE; UNCLASSIFIED DRUG; CATION;

ARTICLE; CELL FUNCTION; CELL MEMBRANE; CELL SURFACE; CELL TRANSPORT; CELLULAR DISTRIBUTION; CELLULAR UPTAKE; CRYSTAL STRUCTURE; ENDOCYTOSIS; GENETIC TRANSFECTION; HYDROGEN BOND; MAMMAL CELL; PINOCYTOSIS; SYNTHETIC BIOLOGY; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; CULTURE TECHNIQUE; DIMERIZATION; HELA CELL LINE; HUMAN; METABOLISM; TRANSPORT AT THE CELLULAR LEVEL; X RAY CRYSTALLOGRAPHY;

ANIMALS; BIOLOGICAL TRANSPORT; CATIONS; CELL CULTURE TECHNIQUES; CELL MEMBRANE; CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; GUANIDINE; HELA CELLS; HUMANS; HYDROGEN BONDING; MOLECULAR STRUCTURE;

EID: 84905376641     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501101s     Document Type: Article

References (80)

1. Ryser, H. J. P. Science 1968, 159, 390
2. Dietz, G. P. H.; Bahr, M. Mol. Cell. Neurosci. 2004, 27, 85
3. Perez, F.; Joliot, A.; Blochgallego, E.; Zahraoui, A.; Triller, A.; Prochiantz, A. J. Cell Sci. 1992, 102, 717
4. Leroux, I.; Joliot, A. H.; Blochgallego, E.; Prochiantz, A.; Volovitch, M. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 9120
5. Derossi, D.; Joliot, A. H.; Chassaing, G.; Prochiantz, A. J. Biol. Chem. 1994, 269, 10444
6. Derossi, D.; Chassaing, G.; Prochiantz, A. Trends Cell Biol. 1998, 8, 84
7. Frankel, A. D.; Pabo, C. O. Cell 1988, 55, 1189-93
8. Green, M.; Loewenstein, P. M. Cell 1988, 55, 1179
9. Fawell, S.; Seery, J.; Daikh, Y.; Moore, C.; Chen, L. L.; Pepinsky, B.; Barsoum, J. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 664
10. Wadia, J. S.; Dowdy, S. F. Adv. Drug Deliver. Rev. 2005, 57, 579
11. Futaki, S.; Suzuki, T.; Ohashi, W.; Yagami, T.; Tanaka, S.; Ueda, K.; Sugiura, Y. J. Biol. Chem. 2001, 276, 5836
12. Other approaches have recently been reviewed; see: Matile, S.; Fyles, T. Acc. Chem. Res. 2013, 46, 2741
13. Futaki, S.; Nakase, I.; Suzuki, T.; Zhang, Y. J.; Sugiura, Y. Biochemistry 2002, 41, 7925
14. Strecker, A. Liebigs Ann. Chem. 1861, 118, 151
15. Berlinck, R. G. S.; Trindade-Silva, A. E.; Santos, M. F. C. Nat. Prod. Rep. 2012, 29, 1382
16. Gobel, M.; Klapotke, T. M. Chem. Commun. 2007, 3180
17. Yamada, T.; Liu, X. H.; Englert, U.; Yamane, H.; Dronskowski, R. Chem.-Eur. J. 2009, 15, 5651
18. Sawinski, P. K.; Meven, M.; Englert, U.; Dronskowski, R. Cryst. Growth Des. 2013, 13, 1730
19. Yokomori, Y.; Hodgson, D. J. Int. J. Pept. Prot. Res. 1988, 31, 289
20. Houk, R. J. T.; Tobey, S. L.; Anslyn, E. V. Top. Curr. Chem. 2005, 255, 199
21. Fromm, J. R.; Hileman, R. E.; Caldwell, E. E. O.; Weiler, J. M.; Linhardt, R. J. Arch. Biochem. Biophys. 1995, 323, 279
22. Han, J.; Yau, C. W.; Chan, C. W.; Mak, T. C. W. Cryst. Growth Des. 2012, 12, 4457
23. Furberg, S. Acta Chem. Scand. 1972, 26, 3699
24. Grossel, M. C.; Merckel, D. A. S.; Hutchings, M. G. CrystEngComm 2003, 5, 77
25. Tobey, S. L.; Anslyn, E. V. J. Am. Chem. Soc. 2003, 125, 14807
26. Haj-Zaroubi, M.; Mitzel, N. W.; Schmidtchen, F. P. Angew. Chem., Int. Ed. 2002, 41, 104
27. Friend, D. S.; Papahadjopoulos, D.; Debs, R. J. Biochim. Biophys. Acta 1996, 1278, 41
28. Doherty, G. J.; McMahon, H. T. Annu. Rev. Biochem. 2009, 78, 857
29. Takei, K.; Haucke, V. Trends Cell Biol. 2001, 11, 385
30. Matveev, S.; Li, X.; Everson, W.; Smart, E. J. Adv. Drug Deliver. Rev. 2001, 49, 237
31. Conner, S. D.; Schmid, S. L. Nature 2003, 422, 37
32. Swanson, J. A.; Watts, C. Trends Cell Biol. 1995, 5, 424
33. Khalil, I. A.; Kogure, K.; Akita, H.; Harashima, H. Pharmacol. Rev. 2006, 58, 32
34. Subtil, A.; Hemar, A.; Dautryvarsat, A. J. Cell Sci. 1994, 107, 3461
35. Varkouhi, A. K.; Scholte, M.; Storm, G.; Haisma, H. J. J. Controlled Release 2011, 151, 220
36. Vives, E.; Brodin, P.; Lebleu, B. J. Biol. Chem. 1997, 272, 16010
37. Trehin, R.; Merkle, H. P. Eur. J. Pharm. Biopharm. 2004, 58, 209
38. Wender, P. A.; Mitchell, D. J.; Pattabiraman, K.; Pelkey, E. T.; Steinman, L.; Rothbard, J. B. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 13003
39. Sakai, N.; Matile, S. J. Am. Chem. Soc. 2003, 125, 14348
40. Rothbard, J. B.; Jessop, T. C.; Lewis, R. S.; Murray, B. A.; Wender, P. A. J. Am. Chem. Soc. 2004, 126, 9506
41. Stanzl, E. G.; Trantow, B. M.; Vargas, J. R.; Wender, P. A. Acc. Chem. Res. 2013, 46, 2944
42. Colin, V.; Bonduelle, C. V.; Gillies, E. R. Pharmaceuticals 2010, 3, 636
43. Zhi, D.; Zhang, S.; Cui, S.; Zhao, Y.; Wang, Y.; Zhao, D. Bioconjugate Chem. 2013, 24, 487
44. Luedtke, N. W.; Baker, T. J.; Goodman, M.; Tor, Y. J. Am. Chem. Soc. 2000, 122, 12035
45. Luedtke, N. W.; Carmichael, P.; Tor, Y. J. Am. Chem. Soc. 2003, 125, 12374
46. Elson-Schwab, L.; Garner, O. B.; Schuksz, M.; Crawford, B. E.; Esko, J. D.; Tor, Y. J. Biol. Chem. 2007, 282, 13585
47. Dix, A. V.; Fischer, L.; Sarrazin, S.; Redgate, C. P.; Esko, J. D.; Tor, Y. ChemBioChem 2010, 11, 2302
48. Sarrazin, S.; Wilson, B.; Sly, W. S.; Tor, Y.; Esko, J. D. Mol. Ther. 2010, 18, 1268
49. Inoue, M.; Tong, W.; Esko, J. D.; Tor, Y. ACS Chem. Biol. 2013, 8, 1383
50. Inoue, M.; Wexselblatt, E.; Esko, J. D.; Tor, Y. ChemBioChem. 2014, 15, 676
51. Tyagi, M.; Rusnati, M.; Presta, M.; Giacca, M. J. Biol. Chem. 2001, 276, 3254
52. Verdurmen, W. P.; Bovee-Geurts, P. H.; Wadhwani, P.; Ulrich, A. S.; Hallbrink, M.; van Kuppevelt, T. H.; Brock, R. Chem. Biol. 2011, 18, 1000
53. Ziegler, A.; Seelig, J. Biophys. J. 2008, 94, 2142
54. Poon, G. M. K.; Gariepy, J. Biochem. Soc. T. 2007, 35, 788
55. Wallbrecher, R.; Verdurmen, W. P.; Schmidt, S.; Bovee-Geurts, P. H.; Broecker, F.; Reinhardt, A.; van Kuppevelt, T. H.; Seeberger, P. H.; Brock, R. Cell. Mol. Life Sci. 2013.
56. Maiti, K. K.; Jeon, O.-Y.; Lee, W. S.; Kim, D.-C.; Kim, K.-T.; Takeuchi, T.; Futaki, S.; Chung, S.-K. Angew. Chem., Int. Ed. 2006, 45, 2907
57. Maiti, K. K.; Lee, W. S.; Takeuchi, T.; Watkins, C.; Fretz, M.; Kim, D.-C.; Futaki, S.; Jones, A.; Kim, K.-T.; Chung, S.-K. Angew. Chem., Int. Ed. 2007, 46, 5880
58. Jin, J.; Lee, W. S.; Joo, K. M.; Maiti, K. K.; Biswas, G.; Kim, W.; Kim, K.-T.; Lee, S. J.; Kim, K.-H.; Nam, D.-H.; Chung, S.-K. MedChemComm 2011, 2, 270
59. Im, J.; Kim, W.; Kim, K.-T.; Chung, S.-K. Chem. Commun. 2009, 4669
60. Im, J.; Biswas, G.; Kim, W.; Kim, K.-T.; Chung, S.-K. Bull. Korean Chem. Soc. 2011, 32, 873
61. Im, J.; Maiti, K. K.; Kim, W.; Kim, K.-T.; Chung, S.-K. Bull. Korean Chem. Soc. 2011, 32, 1282
62. Higashi, T.; Khalil, I. A.; Maiti, K. K.; Lee, W. S.; Akita, H.; Harashima, H.; Chung, S.-K. J. Controlled Release 2009, 136, 140
63. Biswas, G.; Jeon, O.-Y.; Lee, W. S.; Kim, D.-C.; Kim, K.-T.; Lee, S.; Chang, S.; Chung, S.-K. Chem.-Eur. J. 2008, 14, 9161
64. Lee, W. S.; Im, C.-N.; Teng, Q. Y.; Chang, Y.-T.; Kim, D.-C.; Kim, K.-T.; Chung, S.-K. Mol. BioSyst. 2009, 5, 822
65. Im, J.; Kim, S.; Jeong, Y.-H.; Kim, W.; Lee, D.; Lee, W. S.; Chang, Y.-T.; Kim, K.-T.; Chung, S.-K. MedChemComm 2013, 4, 310
66. Lee, W. S.; Kim, W.; Kim, K.-T.; Chung, S.-K. Bull. Korean Chem. Soc. 2011, 32, 2286
67. Ghosh, S. C.; Kim, B.; Im, J.; Lee, W. S.; Im, C.-N.; Chang, Y.-T.; Kim, W.; Kim, K.-T.; Chung, S.-K. Bull. Korean Chem. Soc. 2010, 31, 3623
68. Tanaka, M.; Machida, Y.; Niu, S.; Ikeda, T.; Jana, N. R.; Doi, H.; Kurosawa, M.; Nekooki, M.; Nukina, N. Nat. Med. 2004, 10, 148
69. Chi, B.; Park, S. J.; Park, M. H.; Lee, S. Y.; Jeong, B. Bioconjugate Chem. 2010, 21, 1473
70. Li, Y.-F.; Morcos, P. A. Bioconjugate Chem. 2008, 19, 1464
71. Battigelli, A.; Wang, J. T.-W.; Russier, J.; Da Ros, T.; Kostarelos, K.; Al-Jamal, K. T.; Prato, M.; Bianco, A. Small 2013, 9, 3610
72. Dudic, M.; Colombo, A.; Sansone, F.; Casnati, A.; Donofrio, G.; Ungaro, R. Tetrahedron 2004, 60, 11613
73. Sansone, F.; Dudic, M.; Donofrio, G.; Rivetti, C.; Baldini, L.; Casnati, A.; Cellai, S.; Ungaro, R. J. Am. Chem. Soc. 2006, 128, 14528
74. Bagnacani, V.; Franceschi, V.; Fantuzzi, L.; Casnati, A.; Donofrio, G.; Sansone, F.; Ungaro, R. Bioconjugate Chem. 2012, 23, 993
75. Bagnacani, V.; Franceschi, V.; Bassi, M.; Lomazzi, M.; Donofrio, G.; Sansone, F.; Casnati, A.; Ungaro, R. Nat. Commun. 2013, 4
76. Fernandez-Carneado, J.; Van Gool, M.; Martos, V.; Castel, S.; Prados, P.; De Mendoza, J.; Giralt, E. J. Am. Chem. Soc. 2005, 127, 869
77. Katritzky, A. R.; Rogovoy, B. V. ARKIVOC 2005, iv, 49
78. Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804
79. Kim, K. S.; Qian, L. G. Tetrahedron Lett. 1993, 34, 7677
80. Drake, B.; Patek, M.; Lebl, M. Synthesis-Stuttgart 1994, 579