Synthesis of carboxyl-tethered symmetric conjugated polyenes as fluorescent transmembrane probes of lipid bilayers

European Journal of Organic Chemistry

Volumn , Issue 7, 2003, Pages 1308-1318

  Quesada, Ernesto ^a,b   Acuña, A Ulises ^b   Amat Guerri, Francisco ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

Author keywords

Amphiphiles; Cross coupling; Lipids; Membranes; Polyenes

Indexed keywords

AMPHOPHILE; CARBOXYL GROUP; ESTER DERIVATIVE; ETHYLENE DERIVATIVE; FLUORESCENT DYE; IODINE; PALLADIUM; POLYENE; ZINC;

ARTICLE; CATALYST; CHEMICAL BOND; CHROMATOGRAPHY; ISOMERISM; LIPID BILAYER; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SYNTHESIS;

EID: 0037394592     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390187     Document Type: Article

References (134)

1. [1a] P. B. Comita, R. B. Gagosian, H. Pang, C. E. Costello, J. Biol. Chem. 1984, 259, 15234-15241.
2. [1b] A. Gulik, V. Luzzati, M. De Rosa, A. Gambacorta, J. Mol. Biol. 1985, 182, 131-149.
3. [1c] T. A. Langeworthy, J. L. Pond, Syst. Appl. Microbiol. 1986, 2, 253-257.
4. [1d] V. Luzzati, A. Gambacorta, M. De Rosa, Ann. Rev. Biophys. Biophys. Chem. 1987, 16, 25-47.
5. [1e] M. Kates in Membrane Lipids of Archaea, Elsevier, Oxford, 1993, p. 261-295.
6. J. H. Furhop, D. Fritsch, Acc. Chem. Res. 1986, 19, 130-137.
7. [3a] J. M. Delfino, C. J. Stankovic, S. L. Schreiber, Tetrahedron Lett. 1987, 28, 2323-2326.
8. [3b] Y. L. Diyizou, A. Genevois, T. Lazrak, G. Wolff, Y. Nakatani, G. Ourisson, Tetrahedron Lett. 1987, 28, 5743-5746.
9. [3c] J. H. Furhop, H. Hungerbuhler, U. Siggel, Langmuir 1990, 6, 1295-1300.
10. [3d] M. Yamamoto, W. Warnock, A. Milon, Y. Nakatani, G. Ourisson, Angew. Chem. 1993, 105, 302-304; Angew. Chem. Int. Ed. Engl. 1993, 32, 259-261.
11. [3d] M. Yamamoto, W. Warnock, A. Milon, Y. Nakatani, G. Ourisson, Angew. Chem. 1993, 105, 302-304; Angew. Chem. Int. Ed. Engl. 1993, 32, 259-261.
12. [3e] J. M. Delfino, S. L. Schreiber, F. M. Richards, J. Am. Chem. Soc. 1993, 115, 3458-3479.
13. [3f] G. H. Escamilla, G. R. Newkome, Angew. Chem. 1994, 106, 2013-2016; Angew. Chem. Int. Ed. Engl. 1994, 33, 1937-1940.
14. [3f] G. H. Escamilla, G. R. Newkome, Angew. Chem. 1994, 106, 2013-2016; Angew. Chem. Int. Ed. Engl. 1994, 33, 1937-1940.
15. [3g] M. Yamamoto, V. Dollé, W. Warnock, Y. Diyizou, M. Yamada, Y. Nakatani, G. Ourisson, Bull. Soc. Chim. Fr. 1994, 131, 317-329.
16. [3h] Y. Nakatani, M. Yamamoto, Y. Diyizou, W. Warnock, V. Dollé, W. Hahn, A. Milon, G. Ourisson, Chem. Eur. J. 1996, 2, 129-138.
17. [3i] Y. Ogawa, W. Hahn, P. Garnier, N. Higashi, D. Massotte, M-H. Metz-Boutigue, B. Rousseau, J. Sunamoto, G. Ourisson, Y. Nakatani, Angew. Chem. 2001, 113, 1843-1849; Angew. Chem. Int. Ed. 2001, 40, 944-946.
18. [3i] Y. Ogawa, W. Hahn, P. Garnier, N. Higashi, D. Massotte, M-H. Metz-Boutigue, B. Rousseau, J. Sunamoto, G. Ourisson, Y. Nakatani, Angew. Chem. 2001, 113, 1843-1849; Angew. Chem. Int. Ed. 2001, 40, 944-946.
19. [3j] Y. Ogawa, W. Hahn, P. Garnier, N. Higashi, D. Massotte, M-H. Metz-Boutigue, B. Rousseau, M. Kodaka, J. Sunamoto, G. Ourisson, Y. Nakatani, Chem. Eur. J. 2002, 8, 1843-1849.
20. [4a] J. P. Starck, Y. Nakatani, G. Ourisson, Tetrahedron 1995, 51, 2629-2638.
21. [4b] J. P. Starck, Y. Nakatani, G. Ourisson, D. J. Cowley, G. Duportail, New J. Chem. 1996, 20, 1293-1299.
22. [4c] E. Quesada, M. Ardhammar, B. Nordén, M. Miesch, G. Duportail, Y. Bounzi-Coulibaly, Y. Nakatani, G. Ourisson, Helv. Chim. Acta 2000, 83, 2464-2476.
23. [4d] L. Ventelon, S. Charier, L. Moreaux, J. Mertz, M. Blanchard-Desce, Angew. Chem. 2001, 113, 2156-2159; Angew. Chem. Int. Ed. 2001, 40, 2098-2101.
24. [4d] L. Ventelon, S. Charier, L. Moreaux, J. Mertz, M. Blanchard-Desce, Angew. Chem. 2001, 113, 2156-2159; Angew. Chem. Int. Ed. 2001, 40, 2098-2101.
25. [5a] A. A. Souto, A. U. Acuña, F. Amat-Guerri, Tetrahedron Lett. 1994, 35, 5907-5910.
26. [5b] C. Reyes Mateo, A. A. Souto, F. Amat-Guerri, A. U. Acuña, Biophys. J. 1996, 71, 2177-2191.
27. [6a] L. A. Sklar, B. S. Hudson, M. Petersen, J. Diamond, Biochemistry 1977, 16, 813-818.
28. [6b] L. A. Sklar, B. S. Hudson, R. D. Simoni, Biochemistry 1977, 16, 819-828.
29. E. Quesada, A. U. Acuña, F. Amat-Guerri, Angew. Chem. 2661, 113, 2153-2155; Angew. Chem. Int. Ed. 2001, 40, 2095-2097.
30. E. Quesada, A. U. Acuña, F. Amat-Guerri, Angew. Chem. 2661, 113, 2153-2155; Angew. Chem. Int. Ed. 2001, 40, 2095-2097.
31. [8a] K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467-4470.
32. [8b] S. Takahashi, Y. Kuroyama, K. Sonogashira, N. Hagihara, Synthesis 1980, 627-630.
33. Reviews: [8c] K. Sonogashira in Comprehensive Organic Synthesis (Eds.: I. Fleming, B. Trost), Pergamon Press, Oxford, 1991, vol. 3, p. 521-549.
34. [8d] I. B. Campbell in Organocopper Reagents (Ed.: R. J. K. Taylor), I. R. L. Press, Oxford, 1994, p. 217-235.
35. [8e] V. Farina in Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel, F. Gordon, A. Stone, G. Wilkinson), Pergamon Press, Oxford, 1995, vol. 12, p. 222-225.
36. [8f] J. Tsuji, Palladium Reagents and Catalysis, Wiley, Chichester, 1995, p. 168-178.
37. [8g] K. Sonogashira in Met.-Catal. Cross-Coupling React. (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, p. 203-229.
38. For example: [9a] G. P. Rose, D. R. Marshall, J. F. Kadow, S. W. Rose, C. William, W. Solomon, N. Zein, Bioorg. Med. Chem. Lett. 1994, 4, 711-714.
39. [9b] J. W. Grissom, T. L. Calkins, D. Huang, H. McMillen, Tetrahedron 1994, 50, 4635-4650.
40. [9c] J. A. John, J. M. Tour, J. Am. Chem. Soc. 1994, 116, 5011-5012.
41. [9d] D. Chemin, G. Linstrumelle, Tetrahedron 1994, 50, 5335-5344.
42. [9e] G. McGaffin, A. de Meijere, Synthesis 1994, 583-591.
43. [9f] D. Philp, V. Gramlich, P. Seiler, F. Diederich, J. Chem. Soc, Perkin Trans. 2 1995, 5, 875-886.
44. [9g] B. Koenig, W. Pitsch, I. Dix, P. G. Jones, Synthesis 1996, 446-448.
45. [9h] M. Mladenova, M. Alami, G. Linstrumelle, Synth. Commun. 1996, 26, 2831-2842.
46. [9i] G. B. Jones, M. W. Kilgore, R. S. Pollenz, A. Li, J. E. Mathews, J. M. Wright, R. S. Huber, P. L. Tate, T. L. Price, R. P. Sticca, Bioorg Med. Chem. Lett. 1996, 6, 1971-1976.
47. [9j] J. A. John, J. M. Tour, Tetrahedron 1997, 53, 15515-15534.
48. [9k] C. Kosinski, A. Hirsch, F. W. Heinnemann, F. Hampel, Eur. J. Org. Chem. 2001, 3879-3890.
49. [9l] B. Koenig, W. Pitsch, M. Klein, R. Vasold, M. Prall, P. R. Schreiner, J. Org. Chem. 2001, 66, 1742-1746.
50. [9m] V. Fiandanese, D. Bottalico, G. Marchese, Tetrahedron 2001, 57, 10213-10218.
51. [10a] E. Negishi, A. Alimardanov, C. Xu, Org. Lett. 2000, 2, 65-67.
52. [10b] F. Zeng, E. Negishi, Org. Lett. 2001, 719-722, and references-cited therein.
53. P. Villiers, N. Vicart, Y. Ramondenc, G. Plé, Eur. J. Org. Chem. 2001, 561-574, and references cited therein.
54. K. Sonogashira, T. Yatake, Y. Tohda, S. Takahashi, N. Hagihara, J. Chem. Soc., Chem. Commun. 1977, 291-292.
55. M. Hudlilicky in Reductions in Organic Chemistry, Ellis Hordwood, Chichester, 1984, p. 43-45.
56. [14a] K. Stratman, W. Boland, D. G. Müller, Tetrahedron 1993, 49, 3755-3766.
57. [14b] L. L. Vasiljeva, T. A. Manukina, P. M. Demin, M. A. Lapitskaja, K. K. Pivnitsky, Tetrahedron 1993, 49, 4099-4106.
58. [15a] E. N. Marvell, J. Tashiro, J. Org. Chem. 1965, 30, 3991-3993.
59. [15b] B. Lythgoe, I. Waterhouse, J. Chem. Soc., Perkin Trans. 1 1979, 2429-2436.
60. [15c] A. Zumbrum, P. Uebelhart, C. H. Eugster, Helv. Chim. Acta 1985, 68, 1519-1539.
61. [15d] K. C. Nicolaou, S. E. Webber, J. Chem. Soc., Chem. Commun. 1986, 1816-1817.
62. [15e] J. E. Baldwin, V. P. Reddy, J. Org. Chem. 1988, 53, 1129-1132.
63. [15f] U. Hengartner, K. Bernhard, K. Meyer, G. Englert, E. Glinz, Helv. Chim. Acta 1992, 75, 1848-1865.
64. [15g] P. N. Rylander, Catalytic Hydrogenation in Organic Synthesis, Academic Press, New York, 1979, 13-30.
65. [16a] Y. Kataoka, J. Miyai, K. Oshima, K. Takai, K. Utimoto, J. Org. Chem. 1992, 57, 1973-1981.
66. [16b] K. Harada, H. Urabe, F. Sato, Tetrahedron Lett. 1995, 36, 3203-3206.
67. [16c] N. L. Hungerford, W. Kitching, Chem. Commun. 1996, 1697-1698.
68. [17a] W. Boland, N. Schroer, C. Sieler, M. Eigel, Helv. Chim. Acta 1987, 70, 1025-1040.
69. [17b] W. Boland, S. Pantke, J. Prakt. Chem. 1994, 336, 714-715.
70. Some representative examples: [18a] M. Treilhou, A. Fauve, J. R. Pougny, J. C. Promé, H. Veschambre, J. Org. Chem. 1992, 57, 3203-3208.
71. [18b] D. Chemin, G. Linstrumelle, Tetrahedron 1992, 48, 1943-1952.
72. [18c] D. Chemin, S. Ueugnot, G. Linstrumelle, Tetrahedron 1992, 48, 4369-4378.
73. [18d] D. Chemin, G. Linstrumelle, Tetrahedron Lett. 1992, 33, 2681-2684.
74. [18e] D. Chemin, G. Linstrumelle, Synthesis 1993, 377-379.
75. [18f] G. Solladie, G. B. Stone, A. Rubio, Tetrahedron Lett. 1993, 34, 1803-1806.
76. [19a] M. Avignon-Tropis, J. R. Pougny, Tetrahedron Lett. 1989, 30, 4951-4952.
77. [19b] M. Avignon-Tropis, M. Treilhou, J. R. Pougny, Tetrahedron 1991, 47, 7279-7286.
78. [19c] M. Alami, B. Crousse, G. Linstrumelle, Tetrahedron Lett. 1994, 35, 3543-3544.
79. [19d] S. B. Crousse, M. Alami, G. Linstrumelle, Tetrahedron Lett. 1995, 36, 4245-4248.
80. [19e] Gueugnot, M. Alami, G. Linstrumelle, L. Mambu, Y. Ettit, M. Larchevéque, Tetrahedron 1996, 52, 6635-6646.
81. [19f] M. Alami, B. Crousse, G. Linstrumelle, L. Mambu, M. Larchevêque, Tetrahedron: Asymmetry 1997, 53, 2949-2958.
82. [19g] B. Crousse, M. Mladenova, P. Ducept, M. Alami, G. Linstrumelle, Tetrahedron 1999, 55, 4353-4368.
83. B. Borhan, M. L. Souto, J. M. Um, B. Zhou, K, Nakanishi, Chem. Eur. J. 1999, 5, 1172-1175.
84. [21a] L. Jaenicke, W. Boland, Angew. Chem. 1982, 94, 659; Angew. Chem. Int. Ed. Engl. 1982, 21, 643-653.
85. [21a] L. Jaenicke, W. Boland, Angew. Chem. 1982, 94, 659; Angew. Chem. Int. Ed. Engl. 1982, 21, 643-653.
86. [21b] J. Keitel, I. Fischer-Lui, W. Boland, D. G. Mueller, Helv. Chim. Acta 1990, 73, 2101-2112.
87. J. F. Nagle, S. Tristram-Nagle, Curr. Opin. Struc. Biol. 2000, 10, 474-480.
88. For comprehensive reviews, see: [23a] J. K. Stille, Angew. Chem. 1986, 98, 504; Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524.
89. For comprehensive reviews, see: [23a] J. K. Stille, Angew. Chem. 1986, 98, 504; Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524.
90. [23b] T. N. Mitchell, Synthesis 1992, 803-815.
91. [23c] V. Farina, V. Krishnamurthy, W. J. Scott, Org. React. 1997, 50, 1-652.
92. See also: [23d] J. K. Stille, B. L. Groh, J. Am. Chem. Soc. 1987, 109, 813-817.
93. [23e] T. N. Mitchell in Met.-Catal. Cross-Coupling React. (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, p. 167-202.
94. [23f] K. Fugami, M. Kosigi in Cross-Coupling Reactions. A Practical Guide (Ed.: N. Miyaura), Springer, Berlin, 2002, p. 87-130.
95. For selected examples see: [24a] A. G. M. Barret, J. J. Edmunds, J. A. Hendrix, K. Horita, C. J. Parkinson, J. Chem. Soc., Chem. Commun. 1992, 1238-1240.
96. [24b] K. C. Nicolaou, A. D. Piscopio, P. Bertinato, T. K. Chakraborty, N. Minowa, K. Koide, Chem. Eur. J. 1995, 1, 318-333.
97. E. Negishi, A. O. King, N. Okukado, J. Org. Chem. 1977, 42, 1821-1823.
98. For example: [26a] G. Macdonald, L. Alcaraz, X. Wei, N. J. Lewis, R. J. K. Taylor, Tetrahedron 1998, 54, 9823-9836.
99. [26b] R. J. K, Taylor, L. Alcaraz, I. Kapfer-Eyer, G. Macdonald, X. Wei, N. Lewis, Synthesis 1998, 775-790, and references cited therein.
100. [27a] V. Farina, S. R. Baker, D. A. Benigni, S. I. Hanck, C. Sapiro, Jr., J. Org. Chem. 1990, 55, 5833-5847.
101. [27b] V. Farina, B. Krishan, J. Am. Chem. Soc. 1991, 113, 9585.
102. [27c] V. Farina, G. P. Roth, Tetrahedron Lett. 1991, 32, 4243-4246.
103. [27d] V. Farina, B. Krishan, D. R. Marshall, G. P. Roth, J. Org. Chem. 1993, 58, 5434-5444.
104. [28a] Y. Pazos, B. Iglesias, A. R. De Lera, J. Org. Chem. 2001, 66, 8483-8489.
105. [28b] C. J. Sinz, S. D. Rychnovsky, Angew. Chem. 2001, 131, 3324-3327; Angew. Chem. Int. Ed. 2001, 40, 3224-3227.
106. [28b] C. J. Sinz, S. D. Rychnovsky, Angew. Chem. 2001, 131, 3324-3327; Angew. Chem. Int. Ed. 2001, 40, 3224-3227.
107. [29a] A. L. Casado, P. Espinet, J. Am. Chem. Soc. 1998, 120, 8978-8985.
108. [29b] A. L. Casado, P. Espinet, A. M. Gallego, J. Am, Chem. Soc. 2000, 122, 11771-11782.
109. B. Domínguez, B. Iglesias, A. R. de Lera, J. Org. Chem. 1998, 63, 4135-4139.
110. L. Alcaraz, R. J. K. Taylor, Synlett 1999, 791-792, and references cited therein.
111. [32a] I. P. Beletskaya, J. Organomet. Chem. 1983, 250, 551-564.
112. [32b] W. C. Scott, J. K. Stille, J. Am. Chem. Soc. 1986, 108, 3033-3040.
113. [32c] J. K. Stille, J. H. Simpson, J. Am. Chem. Soc. 1987, 109, 2138-2152.
114. [33a] A. Kiehl, A. Eberhardt, M. Adam, V. Enkelmann, K. Müllen, Angew. Chem. 1992, 104, 1623-1126; Angew. Chem. Int. Ed. Engl. 1992, 31, 1588-1591.
115. [33a] A. Kiehl, A. Eberhardt, M. Adam, V. Enkelmann, K. Müllen, Angew. Chem. 1992, 104, 1623-1126; Angew. Chem. Int. Ed. Engl. 1992, 31, 1588-1591.
116. [33b] A. Kiehl, A. Eberhardt, K. Müllen, Liebigs Ann. 1995, 223-230.
117. [34a] D. A. Siesel, S. W. Staley, Tetrahedron 1993, 34, 3679-3682.
118. [34b] D. A. Siesel, S. W. Staley, J. Org. Chem. 1993, 58, 7870-7875.
119. [35a] B. Domínguez, B. Iglesias, A. R. de Lera, Tetrahedron 1999, 55, 15071-15098.
120. [35b] B. Domínguez, Y. Pazos, A. R. de Lera, J. Org. Chem. 2000, 65, 5917-5925.
121. [35c] B. Vaz, R. Alvarez, A. R. de Lera, J. Org. Chem. 2002, 67, 5040-5043.
122. F. Menger, S. Brocchini, X. Chen, Angew. Chem. 1992, 104, 1542-1543; Angew. Chem. Int. Ed. Engl. 1992, 31, 1492-1493.
123. F. Menger, S. Brocchini, X. Chen, Angew. Chem. 1992, 104, 1542-1543; Angew. Chem. Int. Ed. Engl. 1992, 31, 1492-1493.
124. [37a] S. Shak, N. O. Reich, I. M. Goldstein, P. R. Ortiz de Montellano, J. Biol. Chem. 1985, 260, 13023-13028.
125. [37b] N. Hébert, A. Beck, R. B. Lennox, G. Just, J. Org. Chem. 1992, 57, 1777-1783.
126. S. A. Mitchenko, V. P. Ananikov, I. P. Veletskaya, Y. A. Ustynyuk, Mendeleev Commun. 1997, 130-131.
127. [39a] D. Soullez, G. Plé, L. Duhamel, P. Duhamel, J. Chem. Soc., Chem. Commun. 1995, 563-564.
128. [39b] D. Soullez, G. Plé, L. Duhamel, J. Chem. Soc., Perkins Trans. 1 1997, 1639-1645.
129. [39c] N. Vicart, D. Castellet-Caillabet, Y. Ramondec, G. Plé, L. Duhamel, Synlett 1998, 411-412.
130. J. Villeras, M. Rambaud, Synthesis 1983, 300-303.
131. M. I. Dawson, M. Vasser, J. Org. Chem. 1977, 42, 2783.
132. [42a] D. Berger, M. Neuenschwander, Chimia 1995, 49, 72-74.
133. [42b] D. Berger, A. Bartlome, M. Neuenschwander, Helv. Chim. Acta 1996, 79, 179-191.
134. A. F. Renaldo, J. W. Abadie, J. K. Stille, Org. React. 1988, 86-97.