Fliposomes: New amphiphiles based on trans-3,4-bis(acyloxy)-piperidine able to perform a pH-triggered conformational flip and cause an instant cargo release from liposomes

Tetrahedron Letters

Volumn 54, Issue 41, 2013, Pages 5600-5604

  Samoshin, Andrey V ^a   Veselov, Ivan S ^b   Chertkov, Vyacheslav A ^b   Yaroslavov, Alexander A ^b   Grishina, Galina V ^b   Samoshina, Nataliya M ^a   Samoshin, Vyacheslav V ^a  

^a UNIVERSITY OF THE PACIFIC   (United States)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

Acid triggered leakage; Controlled drug release; Piperidine conformation pH sensitive liposomes

Indexed keywords

AMPHOPHILE; CERAMIDE; HYDROCARBON; LIPOSOME; METHANOL; PALLADIUM; PIPERIDINE DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; HYDROGEN BOND; PH; PROTON NUCLEAR MAGNETIC RESONANCE; STATIC ELECTRICITY;

EID: 84883487688     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.07.156     Document Type: Article

References (54)

1. H.-J. Schneider Applications of Supramolecular Chemistry 2012 CRC Press Boca Raton
2. M. Shahinpoor, and H.-J. Schneider Intelligent Materials 2008 RSC Publishing Cambridge
3. E.R. Kay, D.A. Leigh, and F. Zerbetto Angew. Chem., Int. Ed. 46 2007 72 191
4. B.L. Feringa Molecular Switches 2001 Wiley-VCH Weinheim
5. H.-J. Schneider, and A. Yatsimirsky Principles and Methods in Supramolecular Chemistry 2000 Wiley Chichester, New York
6. M. Takeuchi, M. Ikeda, A. Sugasaki, and S. Shinkai Acc. Chem. Res. 34 2001 865 873
7. J. Kristl Farm. Vestn. 63 2012 67 73
8. K.C.-F. Leung, C.-P. Chak, C.-M. Lo, W.-Y. Wong, S. Xuan, and C.H.K. Cheng Chem. -Asian J. 4 2009 364 381
9. Y.-L. Zhao, Z. Li, S. Kabehie, Y.Y. Botros, J.F. Stoddart, and J.I. Zink J. Am. Chem. Soc. 132 2010 13016 13025
10. I.M. Jones, H. Lingard, and A.D. Hamilton Angew. Chem., Int. Ed. 50 2011 12569 12571
11. W.-W. Gao, J.M. Chan, and O.C. Farokhzad Mol. Pharm. 7 2010 1913 1920
12. L. Shi, and W. Qiao Chem. Bull. (Huaxue Tongbao) 73 2010 986 994
13. V.V. Samoshin Rev. J. Chem. 1 2011 250 274
14. V.V. Samoshin Mini-Rev. Org. Chem. 2 2005 225 235
15. V.V. Samoshin, B. Brazdova, V.A. Chertkov, D.E. Gremyachinskiy, A.K. Shestakova, E.K. Dobretsova, L.P. Vatlina, J. Yuan, and H.-J. Schneider ARKIVOC 2005 129 141
16. V.V. Samoshin, V.A. Chertkov, D.E. Gremyachinskiy, E.K. Dobretsova, A.K. Shestakova, and L.P. Vatlina Tetrahedron Lett. 45 2004 7823 7826
17. Y.S. Wong, B. Brazdova, S. Koo, A.V. Samoshin, A.H. Franz, and V.V. Samoshin J. Undergrad. Chem. Res. 6 2007 81 85
18. B. Brazdova, N. Zhang, V.V. Samoshin, and X. Guo Chem. Commun. 2008 4774 4776
19. N.M. Samoshina, X. Liu, B. Brazdova, A.H. Franz, V.V. Samoshin, and X. Guo Pharmaceutics 3 2011 379 405 10.3390/pharmaceutics3030379
20. Y. Zheng, X. Liu, N.M. Samoshina, V.A. Chertkov, A.H. Franz, X. Guo, and V.V. Samoshin Nat. Prod. Commun. 7 2012 353 358
21. X. Liu, Y. Zheng, N.M. Samoshina, A.H. Franz, X. Guo, and V.V. Samoshin J. Liposome Res. 22 2012 319 328
22. V.V. Samoshin, O.V. Bychkova, V.A. Chertkov, A.K. Shestakova, L.P. Vatlina, N.A. Simonov, and L.P. Kastorskii Zh. Org. Khim. 32 1996 1104 1105 (Russ. J. Org. Chem. 1996, 1066-1067)
23. V.V. Samoshin, V.A. Chertkov, L.P. Vatlina, E.K. Dobretsova, N.A. Simonov, L.P. Kastorsky, D.E. Gremyachinsky, and H.-J. Schneider Tetrahedron Lett. 37 1996 3981 3984
24. A.J. Garza, M. Nag, W.R. Carroll, W.A. Goddard Iii, and J.D. Roberts J. Am. Chem. Soc. 134 2012 14772 14780
25. X. Guo, and F.C. Szoka Jr. Acc. Chem. Res. 36 2003 335 341
26. W. Li, F. Nicol, and F.C. Szoka Adv. Drug Delivery Rev. 56 2004 967 985
27. S. Simoes, J.N. Moreira, C. Fonseca, N. Duzgunes, and M.C. Pedroso de Lima Adv. Drug Delivery Rev. 56 2004 947 965
28. A.A. Kale, and V.P. Torchilin J. Liposome Res. 17 2007 197 203
29. H. Karanth, and R.S.R. Murthy J. Pharm. Pharmacol. 59 2007 469 483
30. R.R. Sawant, and V.P. Torchilin Soft Matter 6 2010 4026 4044
31. Y.S. Tarahovsky Biochemistry (Moscow) 75 2010 811 824
32. V. Torchilin Pan Stanford Ser. Biomed. Nanotechnol. 1 2011 315 382
33. M.J. Morilla, and E.L. Romero Liposomal pH-Sensitive Nanomedicines in Preclinical Development D.E. Reisner, Bionanotechnology II 2012 CRC Press Boca Raton 383 413
34. H. Hatakeyama, H. Akita, and H. Harashima Biol. Pharm. Bull. 36 2013 892 899
35. A.V. Samoshin, L. Huynh, C. Tran, and V.V. Samoshin J. Undergrad. Chem. Res. 10 2011 50 55
36. A.V. Samoshin, I.S. Veselov, L. Huynh, A.K. Shestakova, V.A. Chertkov, G.V. Grishina, and V.V. Samoshin Tetrahedron Lett. 52 2011 5375 5378
37. A.V. Samoshin, H. Joo, A.Y. Korneichuk, I.S. Veselov, G.V. Grishina, and V.V. Samoshin Tetrahedron Lett. 54 2013 1020 1024
38. P.N. Veremeeva, V.L. Lapteva, V.A. Palyulin, D.A. Davydov, A.A. Yaroslavov, and N.S. Zefirov Dokl. Chem. 447 2012 275 277 (Dokl. Akad. Nauk, 2012, 447, 407-409)
39. G.V. Grishina, A.A. Borisenko, Z.G. Nosan, I.S. Veselov, L.D. Ashkinadze, E.V. Karamov, G.V. Kornilaeva, and N.S. Zefirov Dokl. Chem. 391 2003 195 199 (Dokl. Akad. Nauk, 2003, 391, 487-491)
40. P.B. Terentiev, T.M. Zilberstein, A.A. Borisenko, V.A. Shmorgunov, N.F. Piskunkova, and G.V. Grishina Chem. Heterocycl. Compd. 39 2003 885 890
41. G.V. Grishina, A.A. Borisenko, I.S. Veselov, and A.M. Petrenko Russ. J. Org. Chem. 41 2005 272 278 (Zh. Org. Khim., 2005, 41, 281-287)
42. H. Booth Prog. Nucl. Magn. Reson. Spectrosc. 5 1969 149 381
43. Y. Terui, and K. Tori J. Chem. Soc., Perkin Trans. 2 1975 127 133
44. E.L. Eliel, D. Kandasamy, C.-Y. Yen, and K.D. Hargrave J. Am. Chem. Soc. 102 1980 3698 3707
45. J.M. Bailey, H. Booth, H.A.R.Y. Al-Shirayda, and M.L. Trimble J. Chem. Soc., Perkin Trans. 2 1984 737 743
46. B. Bernet, U. Piantini, and A. Vasella Carbohydr. Res. 204 1990 11 25
47. E.L. Eliel Chem. Ind. 1959 568
48. R.J. Abraham, J.J. Byrne, L. Griffiths, and R. Koniotou Magn. Reson. Chem. 43 2005 611 624
49. H.S. Hansen, and P.H. Huenenberger J. Comput. Chem. 32 2011 998 1032
50. H.J. Schneider, W. Freitag, and E. Weigand Chem. Ber. 111 1978 2656 2664
51. N.S. Zefirov, V.V. Samoshin, O.A. Subbotin, I.V. Baranenkov, and S. Wolfe Tetrahedron 34 1978 2953 2959
52. J.B. Foresman, and A. Frisch Exploring Chemistry with Electronic Structure Methods: A Guide to Using Gaussian 1996 Gaussian, Inc. Pittsburgh
53. H. Ellens, J. Bentz, and F.C. Szoka Biochemistry 23 1984 1532 1538
54. P.-A. Monnard, T. Oberholzer, and P. Luisi Biochim. Biophys. Acta, Biomembr. 1329 1997 39 50