Synthesis of steroid-oligonucleotide conjugates for a DNA site-encoded SPR immunosensor

Bioconjugate Chemistry

Volumn 23, Issue 11, 2012, Pages 2183-2191

  Tort, Nuria ^a,d   Salvador, J Pablo ^a,d   Aviñó, Anna ^a,d,e   Eritja, Ramón ^a,d,e   Comelles, Jordi ^b,d   Martínez, Elena ^b,d   Samitier, Josep ^b,c,d   Marco, M Pilar ^a,d  

^a INSTITUTE OF ADVANCED CHEMISTRY OF CATALONIA IQAC CSIC   (Spain)

^b INSTITUTE FOR BIOENGINEERING OF CATALONIA IBEC   (Spain)

^c UNIVERSITY OF BARCELONA   (Spain)

^d BIOMATERIALES Y NANOMEDICINA CIBER BBN   (Spain)

^e INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODIES; BINDING ENERGY; DNA; GOLD; REFRACTIVE INDEX; SURFACE PLASMON RESONANCE;

ANALYTES; CONDITION; HYBRIDISATION; OLIGONUCLEOTIDE CONJUGATES; PHASE COUPLING; SELF-ASSEMBLING PROPERTIES; STANOZOLOL; SURFACE PLASMON RESONANCE IMMUNOSENSORS; SURFACE-PLASMON RESONANCE; TETRAHYDROGESTRINONE;

OLIGONUCLEOTIDES;

BOLDENONE; DNA; HAPTEN; OLIGONUCLEOTIDE; STANOZOLOL; STEROID; TETRAHYDROGESTRINONE;

ARTICLE; BINDING SITE; COVALENT BOND; DNA HYBRIDIZATION; IMMUNOSENSOR; MOLECULAR WEIGHT; NUCLEIC ACID IMMOBILIZATION; NUCLEOTIDE SEQUENCE; REFRACTION INDEX; SOLID PHASE SYNTHESIS; STEROID BINDING; SURFACE PLASMON RESONANCE;

EID: 84869765422     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc300138p     Document Type: Article

References (47)

1. WADA (2010) The 2010 prohibited list. http://www.wada-ama.org/documents/ world-anti-doping-program/wadp-prohibited-list/wada-prohibited-list-2010-en.pdf.
2. EECC (1996) Directive 96/23/EC Off. J. Eur. Commun. L 125, 3
3. Mullett, W. M., Lai, E. P. C., and Yeung, J. M. (2000) Surface plasmon resonance-based immunoassays Methods 22, 77-91
4. Shankaran, D. R., Gobi, K. V., and Miura, N. (2007) Recent advancements in surface plasmon resonance immunosensors for detection of small molecules of biomedical, food and environmental interest Sens. Actuators, B 121, 158-177
5. Hoa, X. D., Kirk, A. G., and Tabrizian, M. (2007) Towards integrated and sensitive surface plasmon resonance biosensors: A review of recent progress Biosens. Bioelectron. 23, 151-160
6. Ricci, F., Volpe, G., Micheli, L., and Palleschi, G. (2007) A review on novel developments and applications of immunosensors in food analysis Anal. Chim. Acta 605, 111-129
7. Campbell, C. T. and Kim, G. (2007) SPR microscopy and its applications to high-throughput analyses of biomolecular binding events and their kinetics Biomaterials 28, 2380-2392
8. Cooper, M. (2003) Label-free screening of bio-molecular interactions Anal. Bioanal. Chem. 377, 834-842
9. Boozer, C., Kim, G., Cong, S., Guan, H., and Londergan, T. (2006) Looking towards label-free biomolecular interaction analysis in a high-throughput format: a review of new surface plasmon resonance technologies Curr. Opin. Biotechnol. 17, 400-405
10. Yuan, J., Oliver, R., Aguilar, M.-I., and Wu, Y. (2008) Surface plasmon resonance assay for chloramphenicol Anal. Chem. 80, 8329-8333
11. Yuan, J., Oliver, R., Li, J., Lee, J., Aguilar, M., and Wu, Y. (2007) Sensitivity enhancement of SPR assay of progesterone based on mixed self-assembled monolayers using nanogold particles Biosens. Bioelectron. 23, 144-148
12. Fernández, F., Hegnerová, K., Piliarik, M., Sanchez-Baeza, F., Homola, J., and Marco, M. P. (2010) A label-free and portable multichannel surface plasmon resonance immunosensor for on site analysis of antibiotics in milk samples Biosens. Bioelectron. 26, 1231-1238
13. Mizuta, Y., Onodera, T., Singh, P., Matsumoto, K., Miura, N., and Toko, K. (2008) Development of an oligo(ethylene glycol)-based SPR immunosensor for TNT detection Biosens. Bioelectron. 24, 191-197
14. Mitchell, J. S. and Lowe, T. E. (2009) Ultrasensitive detection of testosterone using conjugate linker technology in a nanoparticle-enhanced surface plasmon resonance biosensor Biosens. Bioelectron. 24, 2177-2183
15. Lee, W., Oh, B. K., Min Bae, Y., Paek, S. H., Hong Lee, W., and Choi, J. W. (2003) Fabrication of self-assembled protein A monolayer and its application as an immunosensor Biosens. Bioelectron. 19, 185-192
16. Niemeyer, C. M. (2002) The developments of semisynthetic DNA-protein conjugates Trends Biotechnol. 20, 395-401
17. Jung, Y., Lee, J. M., Jung, H., and Chung, B. H. (2007) Self-directed and self-oriented immobilization of antibody by protein G-DNA Conjugate Anal. Chem. 79, 6534-6541
18. Boozer, C., Ladd, J., Chen, S., and Jiang, S. (2006) DNA-Directed protein immobilization for simultaneous detection of multiple analytes by surface plasmon resonance biosensor Anal. Chem. 78, 1515-1519
19. Boozer, C., Ladd, J., Chen, S., Yu, Q., Homola, J., and Jiang, S. (2004) DNA directed protein immobilization on mixed ssDNA/oligo(ethyleneglycol) self-assembled monolayers for sensitive biosensors Anal. Chem. 76, 6967-6972
20. Tort, N., Salvador, J. P., Eritja, R., Poch, M., Martínez, E., Samitier, J., and Marco, M. P. (2009) Fluorescence site-encoded DNA addressable hapten microarray for anabolic androgenic steroids TrAC Trends Anal. Chem. 28, 718-728
21. Bier, F. F., Kleinjung, F., Ehrentreich-Förster, E., and Scheller, F. W. (1999) Changing functionality of surfaces by directed self-assembly using oligonucleotides-The oligo-tag BioTechniques 27, 752-760
22. Homola, J., Vaisocherová, H., Dostálek, J., and Piliarik, M. (2005) Multi-analyte surface plasmon resonance biosensing Methods 37, 26-36
23. Kanda, V., Kariuki, J. K., Harrison, D. J., and McDermott, M. T. (2004) Label-free reading of microarray-based immunoassays with surface plasmon resonance imaging Anal. Chem. 76, 7257-7262
24. Ladd, J., Taylor, A. D., Piliarik, M., Homola, J., and Jiang, S. (2008) Hybrid surface platform for the simultaneous detection of proteins and DNAs using a surface plasmon resonance imaging sensor Anal. Chem. 80, 4231-4236
25. Rebe Raz, S., Bremer, M. G. E. G., Haasnoot, W., and Norde, W. (2009) Label-free and multiplex detection of antibiotic residues in milk using imaging surface plasmon resonance-based immunosensor Anal. Chem. 81, 7743-7749
26. Kanoh, N., Kyo, M., Inamori, K., Ando, A., Asami, A., Nakao, A., and Osada, H. (2006) SPR Imaging of photo-cross-linked small-molecule arrays on gold Anal. Chem. 78, 2226-2230
27. Lee, H. J., Nedelkov, D., and Corn, R. M. (2006) Surface plasmon resonance imaging measurements of antibody arrays for the multiplexed detection of low molecular weight protein biomarkers Anal. Chem. 78, 6504-6510
28. Salvador, J.-P., Sanchez-Baeza, F., and Marco, M.-P. (2007) Preparation of antibodies for the designer steroid tetrahydrogestrinone and development of an enzyme-linked immunosorbent assay for human urine analysis Anal. Chem. 79, 3734-3740
29. Salvador, J. P., Sánchez-Baeza, F., and Marco, M. P. (2008) Simultaneous immunochemical detection of stanozolol and the main human metabolite, 3′-hydroxy-stanozolol, in urine and serum samples Anal. Biochem. 376, 221-228
30. Kramer, K., Hubauer, A., Lausterer, R., Salvador, J. P., and Marco, M. P. (2007) Production of antibodies for the quantitative detection of the anabolically active Androgens 17β-boldenone and methylboldenone Anal. Lett. 40, 1461-1472
31. Connolly, B. A. (1987) The synthesis of oligonucleotides containing a primary amino group at the 5′-terminus Nucleic Acids Res. 15, 3131-3139
32. LeDoan, T., Etore, F., Tenu, J. P., Letourneux, Y., and Agrawal, S. (1999) Cell binding, uptake and cytosolic partition of HIV anti-gag phosphodiester oligonucleotides 3′-linked to cholesterol derivatives in macrophages Bioorg. Med. Chem. 7, 2263-2269
33. Letsinger, R. L. and Chaturvedi, S. (1998) Tailored hydrophobic cavities in oligonucleotide-steroid conjugates Bioconjugate Chem. 9, 826-830
34. Ketola, J., Hurskainen, P., and Hovinen, J. (2009) Derivatization of 11-hydroxyprogesterone using phosphoramidite chemistry Bioconjugate Chem. 20, 625-628
35. Acedo, M., Tarrason, G., Piulats, J., Mann, M., Wilm, M., and Eritja, R. (1995) Preparation of oligonucleotide-dexamethasone conjugates Bioorg. Med. Chem. Lett. 5, 1577-1580
36. Escarceller, M., Rodriguez-Frias, F., Jardi, R., San Segundo, B., and Eritja, R. (1992) Detection of hepatitis B virus DNA in human serum samples: Use of digoxigenin-labeled oligonucleotides as modified primers for the polymerase chain reaction Anal. Biochem. 206, 36-42
37. Bhatia, D., Yue-Ming, L., and Ganesh, K. N. (1999) Steroid-DNA conjugates: improved triplex formation with 5-amido-(7-deoxycholic acid)-dU incorporated oligonucleotides Bioorg. Med. Chem. Lett. 9, 1789-94
38. Rump, E. T., de Vrueh, R. L. A., Sliedregt, L. A. J. M., Biessen, E. A. L., van Berkel, T. J. C., and Bijsterbosch, M. K. (1998) Preparation of conjugates of oligodeoxynucleotides and lipid structures and their interaction with low-density lipoprotein Bioconjugate Chem. 9, 341-349
39. Starke, D., Lischka, K., Pagels, P., Uhlmann, E., Kramer, W., Wess, G., and Petzinger, E. (2001) Bile acid-oligodeoxynucleotide conjugates: synthesis and liver excretion in rats Bioorg. Med. Chem. Lett. 11, 945-949
40. de Fougerolles, A., Vornlocher, H. P., Maraganore, J., and Lieberman, J. (2007) Interfering with disease: a progress report on siRNA-based therapeutics Nat. Rev. Drug Discovery 6, 443-453
41. Thompson, S. (2003) Small-molecule-protein conjugation procedures. In Molecular Diagnosis of Infectious Diseases, Decker, J. and Reische, U., Eds.; pp 255-265, Chapter 17, Springer Protocols Vol 94, Humana Press, Springer Science, Heidelberg.
42. Merrifield, B. (1986) Solid phase synthesis Science 232, 341-347
43. Odom, D. T., Dill, E. A., and Barton, J. K. (2000) Robust charge transport in DNA double crossover assemblies Chem. Biol. 7, 475-481
44. Yoo, K. H., Ha, D. H., Lee, J. O., Park, J. W., Kim, J., Kim, J. J., Lee, H. Y., Kawai, T., and Choi, H. Y. (2001) Electrical conduction through poly(dA)-poly(dT) and poly(dG)-poly(dC) DNA molecules Phys. Rev. Lett. 87, 198102
45. Taniguchi, M. and Kawai, T. (2005) Electron-molecular-vibration coupling for small polarons in DNAs Phys. Rev. E 72, 061909
46. Georgiadis, R., Peterlinz, K. A., Rahn, J. R., Peterson, A. W., and Grassi, J. H. (2000) Surface plasmon resonance spectroscopy as a probe of in-plane polymerization in monolayer organic conducting films Langmuir 16, 6759-6762
47. Kang, X., Cheng, G., and Dong, S. (2001) A novel electrochemical SPR biosensor Electrochem. Commun. 3, 489-493