Microwave-assisted synthesis of thiophene fluorophores, labeling and multilabeling of monoclonal antibodies, and long lasting staining of fixed cells

Journal of the American Chemical Society

Volumn 131, Issue 31, 2009, Pages 10892-10900

  Zambianchi, Massimo ^a   Di Maria, Francesca ^a   Cazzato, Antonella ^b   Gigli, Giuseppe ^c   Piacenza, Manuel ^c   Della Sala, Fabio ^c   Barbarella, Giovanna ^a  

^a CNR   (Italy)

^b Mediteknology Srl   (Italy)

^c NATIONAL NANOTECHNOLOGY LABORATORY   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

FIRST-PRINCIPLES; FLUORESCENCE EMISSION; FLUORESCENT ANTIBODIES; IMMUNOSTAINING; LONG LASTING; MICROWAVE ASSISTED SYNTHESIS; MULTILABELING; SUCCINIMIDYL ESTER; THEORETICAL CALCULATIONS;

ESTERIFICATION; ESTERS; LABELS; MICROWAVES; MONOCLONAL ANTIBODIES; SURFACE PLASMON RESONANCE; SYNTHESIS (CHEMICAL); THIOPHENE;

FLUOROPHORES;

4 SULFO 2,3,5,6 TETRAFLUOROPHENYL ESTER; MONOCLONAL ANTIBODY; SUCCINIMIDE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBODY LABELING; ANTIGEN ANTIBODY REACTION; ARTICLE; CHEMICAL ENGINEERING; CHEMICAL STRUCTURE; COMPARATIVE STUDY; DENSITY FUNCTIONAL THEORY; FIELD EMISSION; FLUORESCENCE; IMMUNOHISTOCHEMISTRY; MICROWAVE RADIATION; SYNTHESIS;

ANTIBODIES, MONOCLONAL; CELL LINE; FLUORESCENT DYES; HUMANS; LYMPHOCYTES; MICROWAVES; STAINING AND LABELING; THIOPHENES; TISSUE FIXATION;

EID: 68249150547     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja902416s     Document Type: Article

References (71)

1. (a) Sameiro, M.; Gonçalves, T. Chem. Rev. 2009, 109, 190-212.
2. (b) Lavis, L. D.; Raines, R. T. ACS Chem. Biol. 2008, 3, 142-155.
3. (c) Mann, S. Angew. Chem., Int. Ed. 2008, 47, 2-17.
4. (d) Resch-Ganger, U.; Grabolle, M.; Cavaliere-Jaricot, S.; Nitschke, R.; Nann, T. Nat. Methods 2008, 5, 763-775.
5. (e) Chen, A. K.; Cheng, Z.; Behlke, M. A.; Tsourkas, A. Anal. Chem. 2008, 80, 7437-7444.
6. (f) Simeonov, A.; Jadhav, A.; Thomas, C. J.; Wang, Y.; Huang, R.; Southall, N. T.; Shinn, P.; Smith, J.; Austin, C. P.; Auld, D. S.; Inglese, J. J. Med. Chem. 2008, 51, 2363-2371.
7. (g) Longmire, M. R.; Ogawa, M.; Hama, Y.; Kosaka, N.; Regino, C. A. S.; Choyke, P. L.; Kobayashi, H. Bioconjugate Chem. 2008, 19, 1735-1742.
8. (h) Johnsson, N.; Johnsson, K. ACS Chem. Biol. 2007, 2, 31-38.
9. (i) Martí, A. A.; Jockusch, S.; Stevens, N.; Ju, J.; Turro, N. J. Acc. Chem. Res. 2007, 40, 402-409.
10. (l) Willis, R. C. Anal. Chem. 2007, 1785-1788.
11. (m) Hama, Y.; Urano, Y.; Koyama, Y.; Bernardo, M.; Choyke, P. L.; Kobayashi, H. Bioconjugate Chem. 2006, 17, 426-1431.
12. (o) Yuste, R. Nat. Methods 2005, 2, 902-904.
13. (p) Lichtman, J. W.; Fraser, S. E. Nat. Neuroscience 2001, 4, 1215-1220.
14. (q) Selvin, P. R. Nat. Struct. Biol. 2000, 7, 730-734.
15. Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 3rd ed.; Springer: New York, 2006.
16. http://nobelprize.org/nobel-prizes/chemistry/laureates/2008/tsienlecture. html.
17. Sullivan, K. F., Ed. Fluorescent Proteins, 2nd ed.;Book Series: Methods in Cell Biology; Academic Press, Amsterdam 2008; Vol. 85.
18. (a) Remington, S. J. Curr. Opin. Struct. Biol. 2006, 16, 714-721.
19. (b) Ai, H.; Hazelwood, K. L.; Davidson, M. W.; Campbell, R. E. Nat. Methods 2008, 5, 401-403.
20. (c) Shaner, N. C.; Lin, M. Z.; McKeown, M. R.; Steinbach, P. A.; Hazelwood, K. L.; Davidson, M. W.; Tsien, R. Y. Nat. Methods 2008, 5, 545-551.
21. (d) Shaner, N. C.; Campbell, R. E.; Steinbach, P. A.; Giepmans, B. N. G.; Palmer, A. E.; Tsien, R. Y. Nat. Biotechnol. 2004, 22, 1567-1572.
22. (a) Michalet, X.; Pinaud, F. F.; Bentolila, L. A.; Tsay, J. M.; Doose, S.; Li, J. J.; Sundaresan, G.; Wu, A. M.; Gambhir, S. S.; Weiss, S. Science 2005, 307, 538-544.
23. (b) Gill, R.; Zayats, M.; Willner, I. Angew. Chem., Int. Ed. 2008, 47, 7602-7625.
24. (c) Medints, I. L.; Tetsuo, H.; Goldman, U. E. R.; Mattoussi, H. Nat. Mater. 2005, 4, 436-4462.
25. (d) Mahler, B.; Spinicelli, P.; Buil, S.; Quelin, X. Nat. Mater. 2008, 7, 659-664.
26. (e) Wu, X.; Liu, H.; Liu, J.; Haley, K. N.; Treadway, J. A.; Larson, J. P.; Ge, N.; Peale, F.; Bruchez, M. P. Nat. Biotechnol. 2002, 21, 41-46.
27. Temirov, J. P.; Bradbury, A. R. M.; Werner, J. H. Anal. Chem. 2008, 80, 8642-8648.
28. (a) Kim, B. Y. S.; Jiang, W.; Oreopoulos, J.; Yip, C. M.; Rutka, J. T.; Chan, W. C. W. Nano Lett. 2008, 8, 3887-3892.
29. (b) Chang, E.; Thekkek, N.; Yu, W. W.; Colvin, V. L.; Drezek, R. Small 2006, 2, 1412-1417.
30. (c) Jamieson, T.; Bakhshi, R.; Petrova, D.; Pocock, R.; Imani, M.; Seifalian, A. M. Biomaterials 2007, 28, 4717-4732.
31. (a) Ho, H. A.; Najari, A.; Leclerc, M. Acc. Chem. Res. 2008, 41, 168-178.
32. (b) Herland, A.; Thomsson, D.; Mirzov, O.; Scheblykin, I. G.; Inganäs, O. J. Mater. Chem. 2008, 18, 126-132.
33. (c) Liu, B.; Bazan, G. C. Chem. Mater. 2004, 16, 4467-4476.
34. (d) Thomas, S. W., III; Joly, J. D.; Swager, T. M. Chem. Rev. 2007, 107, 1339-1386.
35. Nilsson, K. P. R.; Hammarström, P.; Ahlgren, F.; Herland, A.; Schnell, E. A.; Lindgren, M.; Westermark, G. T.; Inganäs, O. ChemBioChem 2006, 7, 1096-1104.
36. Chi, C.; Chworos, A.; Zhang, J.; Mikhailovsky, A.; Bazan, G. C. Adv. Funct. Mater. 2008, 18, 3606-3612.
37. Haugland, R. P. A Guide to Fluorescent Probes and Labeling Technologies; Molecular Probes Inc.: Eugene, OR, 2005.
38. (a) Ö zhalici-Ü nal, H.; Pow, C. L.; Marks, S. A.; Jesper, L. D.; Silva, G. L.; Shank, N. I.; Jones, E. W.; Burnette, J. M.; Berget, P. B.; Armitage, B. A. J. Am. Chem. Soc. 2008, 130, 12620-12621.
39. (b) Richard, J. A.; Massonneau, M.; Renard, P. Y.; Romieu, A. Org. Lett. 2008, 10, 4175-4178.
40. (c) Mottram, L. F.; Boonyarattanakalin, S.; Kovel, R. E.; Peterson, B. R. Org. Lett. 2006, 8, 581-584.
41. (d) Peneva, K.; Mihov, G.; Herrmann, A.; Zarrabi, N.; Börsch, M.; Duncan, T. M.; Müllen, K. J. Am. Chem. Soc. 2008, 130, 5398-5399.
42. (e) Kim, D. S.; Ahn, K. H. J. Org. Chem. 2008, 73, 6831-6834.
43. (f) Umezawa, K.; Nakamura, Y.; Makino, H.; Citterio, D.; Suzuki, K. J. Am. Chem. Soc. 2008, 130, 1550-1551.
44. (g) Li, L.; Han, J.; Nguyen, B.; Burgess, K. J. Org. Chem. 2008, 73, 1963-1970.
45. Garnier, F. Acc. Chem. Res. 1999, 32, 209-215.
46. (a) Barbarella, G.; Melucci, M.; Sotgiu, G. Adv. Mater. 2005, 17, 1581-1593.
47. (b) Barbarella, G.; Zambianchi, M.; Pudova, O.; Paladini, V.; Ventola, A.; Cipriani, F.; Gigli, G.; Cingolani, R.; Citro, G. J. Am. Chem. Soc. 2001, 123, 11600-11607.
48. (c) Barbarella, G.; Zambianchi, M.; Ventola, A.; Fabiano, E.; Della Sala, F.; Gigli, G.; Anni, M.; Bolognesi, A.; Polito, L.; Naldi, M.; Capobianco, M. Bioconjugate Chem. 2006, 17, 58-67.
49. (d) Zambianchi, M.; Barbieri, A.; Ventola, A.; Favaretto, L.; Bettini, C.; Galeotti, M.; Barbarella, G. Bioconjugate Chem. 2007, 18, 1004-1009.
50. (e) Capobianco, M. L.; Cazzato, A.; Alesi, S.; Barbarella, G. Bioconjugate Chem. 2008, 19, 171-177.
51. (f) Quarta, A.; Di Corato, R.; Manna, L.; Argentiere, S.; Cingolani, R.; Barbarella, G.; Pellegrino, T. J. Am. Chem. Soc. 2008, 130, 10545-10555.
52. (g) Piacenza, M.; Zambianchi, M.; Barbarella, G.; Gigli, G.; Della Sala, F. Phys. Chem. Chem. Phys. 2008, 10, 5363-5373.
53. Ahlrichs, R, et al. Universität Karlsruhe2007. See also: http://www.turbomole.com.
54. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
55. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
56. Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829-5835.
57. Furche, F.; Ahlrichs, R. J. Chem. Phys. 2002, 117, 7433-7447.
58. Brinkley, M. Bioconjugate Chem. 1992, 3, 2-13.
59. (a) Polshettiwar, V.; Varma, R. S. Chem. Soc. Rev. 2008, 37, 1546-1557.
60. (b) Alesi, A.; Di Maria, F.; Melucci, M.; Macquarrie, D. J.; Luqueb, R.; Barbarella, G. Green Chem. 2008, 10, 517-523.
61. (c) Melucci, M.; Barbarella, G.; Zambianchi, M.; Di Pietro, P.; Bongini, A. J. Org. Chem. 2004, 69, 4821-4828.
62. Becker, R. S.; Seixas de Melo, J.; Macüanita, A. L.; Elisei, F. J. Phys. Chem. 1996, 100, 18683-18695.
63. Barbarella, G.; Zambianchi, M.; Antolini, L.; Folli, U.; Goldoni, F.; Iarossi, D.; Schenetti, L.; Bongini, A. J. Chem. Soc. Perkin Trans. 2 1995, 1869-1873.
64. (a) Deaglio, S.; Mallone, R.; Baj, G.; Donati, D.; Giraudo, G.; Corno, F.; Bruzzone, S.; Geuna, M.; Ausiello, C.; Malavasi, F. FASEB J. 2001, 15, 580-582.
65. (b) Alessio, M.; Roggero, S.; Funaro, A.; De Monte, L.B.,; Peruzzi, L.; Geuna, M.; Malavasi, F. J. Immunol. 1990, 145, 878-3884.
66. Patten, P. E. M.; Buggins, A. G. S.; Richards, J.; Wotherspoon, A.; Salisbury, J.; Mufti, G. J.; Hamblin, T. J.; Devereux, S. Blood 2008, 111, 5173-5181.
67. (a) Zhu, S.; Zhang, Q.; Guo, L. H. Anal. Chim. Acta 2008, 624, 141-146.
68. (b) Zhang, Q.; Guo, L. H. Bioconj. Chem 2007, 18, 1668-1672.
69. (c) Luchowski, R.; Matveeva, E. G.; Gryczynski, I.; Terpetschnig, E. A.; Patsenker, L.; Laczko, G.; Borejdo, J.; Gryczynski, Z. Curr. Pharm. Biotechnol. 2008, 9, 411-420.
70. Anni, M.; Gigli, G.; Paladini, V.; Cingolani, R.; Barbarella, G.; Favaretto, L.; Sotgiu, G.; Zambianchi, M. Appl. Phys. Lett. 2000, 77, 2458-2460.
71. Kozlov, V. G.; Bulovic, V.; Burrows, P. E.; Baldo, M.; Khalfin, V. B.; Parthasarathy, G.,; Forrest, S. R. J. Appl. Phys. 1998, 84, 4096-4108.