Fluorogenic squaraine dimers with polarity-sensitive folding as bright far-red probes for background-free bioimaging

Journal of the American Chemical Society

Volumn 137, Issue 1, 2015, Pages 405-412

  Karpenko, Iuliia A ^a   Collot, Mayeul ^b   Richert, Ludovic ^b   Valencia, Christel ^c   Villa, Pascal ^c   Mély, Yves ^b   Hibert, Marcel ^a   Bonnet, Dominique ^a   Klymchenko, Andrey S ^b  

^a Faculté de Pharmacie   (France)

^b Faculté de Pharmacie   (France)

^c ULP Strasbourg Faculté de Pharmacie   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AGGREGATES; FLUORESCENCE; PROBES;

CHANGING ENVIRONMENT; EXTINCTION COEFFICIENTS; G PROTEIN COUPLED RECEPTORS; MEMBRANE RECEPTORS; NANOMOLAR CONCENTRATION; NON-SPECIFIC BINDING; SHORT WAVELENGTH BANDS; TIME RESOLVED STUDIES;

DIMERS;

CARBETOCIN; CARBOXYL GROUP; DIMER; FLUORESCENT DYE; OXYTOCIN RECEPTOR; POLARITY SENSITIVE FLUOROGENIC DYE; SQUARAINE DIMER; UNCLASSIFIED DRUG; WATER; CYCLOBUTANE DERIVATIVE; PHENOL DERIVATIVE; SOLVENT; SQUARAINE;

ARTICLE; BRIGHTNESS; CELL SURFACE; CHEMICAL STRUCTURE; CONJUGATE; CONJUGATION; FLUORESCENCE; FLUORESCENCE IMAGING; HEK293 CELL LINE; HUMAN; HUMAN CELL; HYDROPHOBICITY; LIPID MEMBRANE; QUANTUM YIELD; SENSITIVITY ANALYSIS; SOLUBILITY; SYNTHESIS; VISCOSITY; WATER CONTENT; CHEMISTRY; DIMERIZATION;

CYCLOBUTANES; DIMERIZATION; FLUORESCENCE; FLUORESCENT DYES; HEK293 CELLS; HUMANS; MOLECULAR STRUCTURE; PHENOLS; SOLVENTS;

EID: 84921056908     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5111267     Document Type: Article

References (72)

1. Li, X.; Gao, X.; Shi, W.; Ma, H. Chem. Rev. 2014, 114, 590
2. Grimm, J. B.; Heckman, L. M.; Lavis, L. D. Prog. Mol. Biol. Transl. Sci. 2013, 113, 1
3. Nadler, A.; Schultz, C. Angew. Chem., Int. Ed. 2013, 52, 2408
4. Santos-Figueroa, L. E.; Moragues, M. E.; Climent, E.; Agostini, A.; Martínez-Máñez, R.; Sancenón, F. Chem. Soc. Rev. 2013, 42, 3489
5. Devaraj, N. K.; Hilderbrand, S.; Upadhyay, R.; Mazitschek, R.; Weissleder, R. Angew. Chem., Int. Ed. 2010, 49, 2869
6. Reichardt, C. Chem. Rev. 1994, 94, 2319
7. Grabowski, Z. R.; Rotkiewicz, K.; Rettig, W. Chem. Rev. 2003, 103, 3899
8. Haidekker, M. A.; Theodorakis, E. A. Org. Biomol. Chem. 2007, 5, 1669
9. Kuimova, M. K.; Yahioglu, G.; Levitt, J. A.; Suhling, K. J. Am. Chem. Soc. 2008, 130, 6672
10. Demchenko, A. P.; Tang, K. C.; Chou, P. T. Chem. Soc. Rev. 2013, 42, 1379
11. Klymchenko, A. S.; Demchenko, A. P. Phys. Chem. Chem. Phys. 2003, 5, 461
12. Loving, G. S.; Sainlos, M.; Imperiali, B. Trends Biotechnol. 2010, 28, 73
13. Klymchenko, A. S.; Mely, Y. Prog. Mol. Biol. Transl. Sci. 2013, 113, 35
14. Demchenko, A. P.; Mély, Y.; Duportail, G.; Klymchenko, A. S. Biophys. J. 2009, 96, 3461
15. Yang, Z.; Cao, J.; He, Y.; Yang, J. H.; Kim, T.; Peng, X.; Kim, J. S. Chem. Soc. Rev. 2014, 43, 4563
16. Loving, G.; Imperiali, B. J. Am. Chem. Soc. 2008, 130, 13630
17. Vázquez, M. E.; Blanco, J. B.; Imperiali, B. J. Am. Chem. Soc. 2005, 127, 1300
18. Shvadchak, V. V.; Klymchenko, A. S.; De Rocquigny, H.; Mély, Y. Nucleic Acids Res. 2009, 37, e25
19. Strizhak, A. V.; Postupalenko, V. Y.; Shvadchak, V. V.; Morellet, N.; Guittet, E.; Pivovarenko, V. G.; Klymchenko, A. S.; Mély, Y. Bioconjugate Chem. 2012, 23, 2434
20. Postupalenko, V. Y.; Shvadchak, V. V.; Duportail, G.; Pivovarenko, V. G.; Klymchenko, A. S.; Mély, Y. Biochim. Biophys. Acta 2011, 1808, 424
21. Zamotaiev, O. M.; Postupalenko, V. Y.; Shvadchak, V. V.; Pivovarenko, V. G.; Klymchenko, A. S.; Mély, Y. Org. Biomol. Chem. 2014, 12, 7036
22. Karpenko, I. A.; Kreder, R.; Valencia, C.; Villa, P.; Mendre, C.; Mouillac, B.; Mély, Y.; Hibert, M.; Bonnet, D.; Klymchenko, A. S. ChemBioChem 2014, 15, 359
23. Prifti, E.; Reymond, L.; Umebayashi, M.; Hovius, R.; Riezman, H.; Johnsson, K. ACS Chem. Biol. 2014, 9, 606
24. Toutchkine, A.; Kraynov, V.; Hahn, K. J. Am. Chem. Soc. 2003, 125, 4132
25. Greenspan, P.; Fowler, S. D. J. Lipid Res. 1985, 26, 781
26. Kucherak, O. A.; Oncul, S.; Darwich, Z.; Yushchenko, D. A.; Arntz, Y.; Didier, P.; Mely, Y.; Klymchenko, A. S. J. Am. Chem. Soc. 2010, 132, 4907
27. Weber, G.; Farris, F. J. Biochemistry 1979, 18, 3075
28. Slavík, J. Biochim. Biophys. Acta 1982, 694, 1
29. Kucherak, O. A.; Didier, P.; Mèly, Y.; Klymchenko, A. S. J. Phys. Chem. Lett. 2010, 1, 616
30. Giordano, L.; Shvadchak, V. V.; Fauerbach, J. A.; Jares-Erijman, E. A.; Jovin, T. M. J. Phys. Chem. Lett. 2012, 3, 1011
31. Kucherak, O. A.; Richert, L.; Mély, Y.; Klymchenko, A. S. Phys. Chem. Chem. Phys. 2012, 14, 2292
32. Niko, Y.; Kawauchi, S.; Konishi, G. I. Chem.-Eur. J. 2013, 19, 9760
33. Lu, Z.; Lord, S. J.; Wang, H.; Moerner, W. E.; Twieg, R. J. J. Org. Chem. 2006, 71, 9651
34. Niko, Y.; Cho, Y.; Kawauchi, S.; Konishi, G. I. RSC Adv. 2014, 4, 36480
35. Lord, S. J.; Lu, Z.; Wang, H.; Willets, K. A.; Schuck, P. J.; Lee, H. L. D.; Nishimura, S. Y.; Twieg, R. J.; Moerner, W. E. J. Phys. Chem. A 2007, 111, 8934
36. Kasha, M.; Rawls, H. R.; El-Bayoumi, M. A. Pure Appl. Chem. 1965, 11, 371
37. Hecht, S.; Huc, I. Foldamers: Structure, Properties, and Applications; Wiley-VCH: Weinheim, 2007.
38. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893
39. Aoki, I.; Kawabata, H.; Nakashima, K.; Shinkai, S. Chem. Commun. 1991, 1771
40. Nishizawa, S.; Kato, Y.; Teramae, N. J. Am. Chem. Soc. 1999, 121, 9463
41. Rye, H. S.; Yue, S.; Wemmer, D. E.; Quesada, M. A.; Haugland, R. P.; Mathies, R. A.; Glazer, A. N. Nucleic Acids Res. 1992, 20, 2803
42. Ikeda, S.; Kubota, T.; Yuki, M.; Okamoto, A. Angew. Chem., Int. Ed. 2009, 48, 6480
43. Okamoto, A. Chem. Soc. Rev. 2011, 40, 5815
44. Ajayaghosh, A. Acc. Chem. Res. 2005, 38, 449
45. Sreejith, S.; Carol, P.; Chithra, P.; Ajayaghosh, A. J. Mater. Chem. 2008, 18, 264
46. Markova, L. I.; Terpetschnig, E. A.; Patsenker, L. D. Dyes Pigm. 2013, 99, 561
47. Oswald, B.; Patsenker, L.; Duschl, J.; Szmacinski, H.; Wolfbeis, O. S.; Terpetschmg, E. Bioconjugate Chem. 1999, 10, 925
48. Sreejith, S.; Divya, K. P.; Ajayaghosh, A. Angew. Chem., Int. Ed. 2008, 47, 7883
49. Anees, P.; Sreejith, S.; Ajayaghosh, A. J. Am. Chem. Soc. 2014, 136, 13233
50. Ros-Lis, J. V.; García, B.; Jiménez, D.; Martínez-Máñez, R.; Sancenón, F.; Soto, J.; Gonzalvo, F.; Valldecabres, M. C. J. Am. Chem. Soc. 2004, 126, 4064
51. Chen, H.; Farahat, M. S.; Law, K. Y.; Whitten, D. G. J. Am. Chem. Soc. 1996, 118, 2584
52. Chen, H.; Herkstroeter, W. G.; Perlstein, J.; Law, K. Y.; Whitten, D. G. J. Phys. Chem. 1994, 98, 5138
53. Das, S.; Thomas, K. G.; Thomas, K. J.; Madhavan, V.; Liu, D.; Kamat, P. V.; George, M. V. J. Phys. Chem. 1996, 100, 17310
54. Liang, K.; Farahat, M. S.; Perlstein, J.; Law, K. Y.; Whitten, D. G. J. Am. Chem. Soc. 1997, 119, 830
55. Arunkumar, E.; Chithra, P.; Ajayaghosh, A. J. Am. Chem. Soc. 2004, 126, 6590
56. Block, M. A. B.; Hecht, S. Macromolecules 2004, 37, 4761
57. Arunkumar, E.; Ajayaghosh, A.; Daub, J. J. Am. Chem. Soc. 2005, 127, 3156
58. Markova, L. I.; Malinovskii, V. L.; Patsenker, L. D.; Häner, R. Org. Biomol. Chem. 2012, 10, 8944
59. Pisoni, D. D. S.; De Abreu, M. P.; Petzhold, C. L.; Rodembusch, F. S.; Campo, L. F. J. Photochem. Photobiol., A 2013, 252, 77
60. Daly, C. J.; McGrath, J. C. Pharmacol. Ther. 2003, 100, 101
61. Sridharan, R.; Zuber, J.; Connelly, S. M.; Mathew, E.; Dumont, M. E. Biochim. Biophys. Acta 2014, 1838, 15
62. Albizu, L.; Teppaz, G.; Seyer, R.; Bazin, H.; Ansanay, H.; Manning, M.; Mouillac, B.; Durroux, T. J. Mater. Chem. 2007, 50, 4976
63. Rosenbaum, D. M.; Rasmussen, S. G. F.; Kobilka, B. K. Nature 2009, 459, 356
64. Gimpl, G.; Fahrenholz, F. Physiol. Rev. 2001, 81, 629
65. MacDonald, K.; MacDonald, T. M. Harv. Rev. Psychiatry 2010, 18, 1
66. Romieu, A.; Brossard, D.; Hamon, M.; Outaabout, H.; Portal, C.; Renard, P. Y. Bioconjugate Chem. 2008, 19, 279
67. Fuhrhop, J. H.; Wang, T. Chem. Rev. 2004, 104, 2901
68. Soriano, A.; Ventura, R.; Molero, A.; Hoen, R.; Casado, V.; Corte, A.; Fanelli, F.; Albericio, F.; Lluís, C.; Franco, R.; Royo, M. J. Med. Chem. 2009, 52, 5590
69. Deda, M. L.; Ghedini, M.; Aiello, I.; Pugliese, T.; Barigelletti, F.; Accorsi, G. J. Organomet. Chem. 2005, 690, 857
70. Shcherbo, D.; Merzlyak, E. M.; Chepurnykh, T. V.; Fradkov, A. F.; Ermakova, G. V.; Solovieva, E. A.; Lukyanov, K. A.; Bogdanova, E. A.; Zaraisky, A. G.; Lukyanov, S.; Chudakov, D. M. Nat. Methods 2007, 4, 741
71. Lin, M. Z.; McKeown, M. R.; Ng, H. L.; Aguilera, T. A.; Shaner, N. C.; Campbell, R. E.; Adams, S. R.; Gross, L. A.; Ma, W.; Alber, T.; Tsien, R. Y. Chem. Biol. 2009, 16, 1169
72. Egawa, T.; Hanaoka, K.; Koide, Y.; Ujita, S.; Takahashi, N.; Ikegaya, Y.; Matsuki, N.; Terai, T.; Ueno, T.; Komatsu, T.; Nagano, T. J. Am. Chem. Soc. 2011, 133, 14157