Biotin as acylating agent in the Friedel-Crafts reaction. Avidin affinity of biotinyl derivatives of ferrocene, ruthenocene and pyrene and fluorescence properties of 1-biotinylpyrene

Organic and Biomolecular Chemistry

Volumn 9, Issue 2, 2011, Pages 408-417

  Plazuk, Damian ^a   Zakrzewski, Janusz ^a   Salmain, Michèle ^b  

^a UNIVERSITY OF LODZ   (Poland)

^b PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATING AGENTS; AMIDE BOND; AQUEOUS SOLUTIONS; BENZOIC ACID; ELECTRON-RICH AROMATICS; EMISSION BANDS; ENZYMATIC ASSAY; FERROCENES; FLUORESCENCE EMISSION; FLUORESCENCE MAXIMA; FLUORESCENCE PROPERTIES; FRIEDEL-CRAFTS ACYLATION; HIGH AFFINITY; QUENCHING OF THE FLUORESCENCE; RESONANCE ENERGY TRANSFER; RUTHENOCENES; SOLID-PHASE; TRIFLUOROACETIC ANHYDRIDES; TRIFLUOROMETHANE SULFONIC ACID; TRYPTOPHAN RESIDUES;

AMIDES; AMINO ACIDS; COENZYMES; ENERGY TRANSFER; FRIEDEL-CRAFTS REACTION; IRON COMPOUNDS;

FLUORESCENCE;

1 BIOTINYLPYRENE; 1-BIOTINYLPYRENE; AVIDIN; BIOTIN; FERROCENE; FERROUS ION; FLUORESCENT DYE; ORGANOMETALLIC COMPOUND; PYRENE; PYRENE DERIVATIVE; RUTHENOCENE;

ACYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE RESONANCE ENERGY TRANSFER;

ACYLATION; AVIDIN; BIOTIN; FERROUS COMPOUNDS; FLUORESCENCE RESONANCE ENERGY TRANSFER; FLUORESCENT DYES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PYRENES;

EID: 78650754121     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00319k     Document Type: Article

References (70)

1. M. Wilchek E. A. Bayer O. Livnah Immunol. Lett. 2006 103 27 32
2. P. S. Stayton S. Freitag L. A. Klumb A. Chilkoti V. Chu J. E. Penzotti R. To D. Hyre I. L. Trong T. P. Lybard R. E. Stenkamp Biomol. Eng. 1999 16 39 44
3. G. T. Hermanson, Bioconjugate Techniques, Academic Press, London, 2nd Edition 2008, Chapter 23, pp. 900-923
4. M. Aslam and A. Dent, Bioconjugation: Protein Coupling Techniques for Biomedical Sciences, Macmillan Reference Ltd, London, 1998, pp. 316-329
5. A. Pordea T. R. Ward Synlett 2009 3225 3236
6. J. Steinreiber T. R. Ward Top. Organomet. Chem. 2009 25 93 112
7. C. R. Thomas T. R. Ward Appl. Organomet. Chem. 2005 19 33 39
8. T. Kasuya J. Jung R. Kinoshita Y. Goh T. Matsuzaki M. Iijma N. Yoshimoto K. Tanizawa S. Kuroda Methods Enzymol. 2009 464 147 166
9. G. Dancey R. G. Begent T. Meyer Targeted Oncology 2009 4 201 207
10. S.-L. Huang Adv. Drug Delivery Rev. 2008 60 1167 1176
11. C. M. Niemeyer Angew. Chem., Int. Ed. 2001 40 4128 4158
12. G. T. Hermanson, Bioconjugate Techniques, Academic Press, London, 2nd Edition 2008, Chapter 11, pp. 507-543, pp. 900-923
13. G. Elia Proteomics 2008 8 4012 4024
14. K. Kodama S. Fukuzawa H. Nakayama K. Sakamoto T. Kigawa T. Yabuki M. Shirozou K. Takio S. Yokoyama K. Tachibana ChemBioChem 2007 8 232 238
15. C. Corona B. K. Bryant J. B. Arterburn Org. Lett. 2006 8 1883 1886
16. T. M. Hansen M. M. Engler C. J. Forsyth Bioorg. Med. Chem. Lett. 2003 13 2127 2130
17. For a recent review, see: G. Satori and R. Maggi, Advances in Friedel-Crafts Acylation Reactions: Catalytic and Green Processes, CRC Press, Boca Raton, 2010
18. D. Plażuk J. Zakrzewski Synth. Commun. 2004 34 99 108
19. D. Plażuk J. Zakrzewski J. Organomet. Chem. 2009 694 1802 1806
20. A. J. Pearson, Metallo-organic Chemistry, Wiley, Chichester, 1985, p. 313
21. P. H. Gore Chem. Rev. 1955 55 229 281
22. A. Bogusiewicz N. I. Mock D. M. Mock Anal. Biochem. 2004 327 156 161
23. R. Singh E. K. Maloney Anal. Biochem. 2002 304 147 156
24. N. Metzler-Nolte and M. Salmain in Ferrocenes: Ligands, Materials and Biomolecules,, P. Stepnika, (Ed.), Wiley, Chichester, 2008, Chapter 13, pp. 499-639
25. D. R. van Staveren N. Metzler-Nolte Chem. Rev. 2004 104 5931 5986
26. H. B. Kraatz J. Inorg. Organomet. Polym. Mater. 2005 15 83 106
27. M. F. R. Fouda M. M. Abd-Elzaher R. A. Abdelsmaia A. R. Labib Appl. Organomet. Chem. 2007 21 613 625
28. A. Vessières S. Top W. Beck E. Hillard G. Jaouen Dalton Trans. 2006 529 541
29. D. Dive C. Biot ChemMedChem 2008 3 383 391
30. A. Gross N. Metzler-Nolte J. Organomet. Chem. 2009 694 1185 1188
31. K. Schlotter F. Boeckler H. Hübner P. Gmeiner J. Med. Chem. 2005 48 3696 3699
32. K. K.-W. Lo T. K.-M. Lee Inorg. Chem. 2004 43 5275 5282
33. K. K.-W. Lo K. H.-K. Tsang K.-S. Sze C.-K. Chung T. K.-M. Lee K. Y. Zhang W.-K. Hui C.-K. Li J. S.-Y. Lau D. C.-M. Ng N. Zhu Coord. Chem. Rev. 2007 251 2292 2310
34. H. J. Gruber M. Marek H. Schindler K. Kaiser Bioconjugate Chem. 1997 8 552 559
35. M. Marek K. Kaiser H. J. Gruber Bioconjugate Chem. 1997 8 560 566
36. H. J. Gruber G. Kada M. Marek K. Kaiser Biochim. Biophys. Acta, Gen. Subj. 1998 1381 203 212
37. G. Kada K. Kaiser H. Falk H. J. Gruber Biochim. Biophys. Acta, Gen. Subj. 1999 1427 33 43
38. G. Kada K. Kaiser H. Falk H. J. Gruber Biochim. Biophys. Acta, Gen. Subj. 1999 1427 44 48
39. A. Ebner, M. Marek, K. Kaiser, G. Kada, C. D. Hahn, B. Lackner and H. J. Gruber in Methods in Molecular Biology. Vol. 418: Avidin-Biotin Interactions, Methods and Applications, Ed., R. J. McMahon,, Humana Press, Totova N J. pp 73-88
40. L. Chaisemartin P. Chinestra G. Favre C. Blonski J. C. Faye Bioconjugate Chem. 2009 20 847 855
41. D. S. Wilbur P. P. Pathare D. K. Hamlin M. B. Frownfelter B. B. Kegley W.-Y. Leung K. R. Gee Bioconjugate Chem. 2000 11 584 598
42. K. Agiamarnioti T. Triantis D. Dimotikali K. Papadopoulos J. Photochem. Photobiol., A 2005 172 215 221
43. A. Scorilas K. Agiamarniotiand K. Papadopoulos Clin. Chim. Acta 2005 357 159 167
44. K. Agiamarnioti T. Triantis K. Papadopoulos J. Photochem. Photobiol., A 2006 181 126 131
45. K. K.-W. Hui C.-K. Chung K. H.-K. Tsang T. K.-M. Lee J. S.-Y. Lau D. C.-M. Ng Coord. Chem. Rev. 2006 250 1724 1736
46. K. K.-W. Lo M.-W. Louie K. Y. Zhang Coord. Chem. Rev. 2010 10.1016/j.ccr.2010.01.014
47. V. Fernandéz-Moreira F. L. Thorp-Greenwood M. P. Coogan Chem. Commun. 2010 46 186 202
48. F. Liao Y. Xie X. Yang P. Deng Y. Chen G. Xie S. Zhu B. Liu H. Yuan J. Liao Y. Zhao M. Yu Biosens. Bioelectron. 2009 25 112 117
49. X. Song B. I. Swanson Anal. Chim. Acta 2001 442 79 87
50. K. Kalyanasundaram J. K. Thomas J. Phys. Chem. 1977 81 2176 2180
51. K. P. Ananthapadmanabhan E. D. Goodard N. J. Turro P. L. Kuo Langmuir 1985 1 352 355
52. E. H. Ellison D. Moodley J. Hime J. Phys. Chem. B 2006 110 4772 4781
53. X. Sheng A. Peng H. Fu J. Yao Colloids Surf., A 2007 308 136 140
54. C. Ambruster M. Knapp K. Rechthaler R. Schamschule A. B. J. Parusel G. Köhler W. Wehrman J. Photochem. Photobiol., A 1999 125 29 28
55. L. Búcsiová P. Hrdlovi. Chmela J. Photochem. Photobiol., A 2001 143 59 68
56. E. Pazos O. Vázquez J. L. Mascareñas M. E. Vázquez Chem. Soc. Rev. 2009 38 3348 3359
57. P. Kroning Z. Naturforsch. A 1973 28 109 116
58. S. Ke J. C. Wright G. S. Kwon Bioconjugate Chem. 2007 18 2109 2114
59. J.-P. Bingham S. Bian Z.-Y. Tan Z. Takacs E. Moczydlowski Bioconjugate Chem. 2006 17 689 699
60. K. Kaiser M. Marek T. Haselgrübler H. Schindler H. J. Gruber Bioconjugate Chem. 1997 8 545 551
61. C. Rosano P. Arosio M. Bolognesi Biomol. Eng. 1999 16 5 12
62. T. W. Kim H. Y. Yoon J.-H. Park O.-H. Kwon D. J. Jang J.-H. Hong Org. Lett. 2005 7 111 114
63. F. Luschtinetz C. Doschem M. U. Kuhmke Bioconjugate Chem. 2009 20 576 582
64. H. J. Gruber C. D. Hahn G. Kada C. K. Riener G. S. Harms W. Ahrer T. G. Dax H.-G. Knaus Bioconjugate Chem. 2000 11 696 704
65. A. Fürstenberg O. Kel J. Gradinaru T. R. Ward D. Emery G. Bollot J. Mareda E. Vauthey ChemPhysChem 2009 10 1517 1532
66. J. N. Miller Analyst 2005 130 265 270
67. G. Kurzban G. Gitlin A. E. Bayer M. Wilchek P. M. Horowitz Biochemistry 1989 28 8537 8542
68. D. C. D. Butler C. J. Richards Organometallics 2002 21 5433 5436
69. N. M. Green Biochem. J. 1965 94 23c 24c
70. R. Thomsen M. H. Christensen J. Med. Chem. 2006 49 3315 3321