Abstract
A new type of coating for manufacturing DNA chips was constructed on the basis of an organicinorganic nanocomposite based on the polyvinylbutyral-tetraethoxysilane copolymer. The organosilicon composite was functionalized by introduction of ethanolamine vinyl ether copolymers, which contain amino groups and anchor vinyloxide units capable of reacting with silanol groups of the nanocomposite. The resulting coatings form a film on glass slides with a high surface density of amino groups (up to 700 groups/nm2) suitable for three-dimensional immobilization of oligonucleotides. The use of bifunctional reagents (e.g., phenylene diisothiocyanate) for the attachment of oligonucleotides bearing amino linkers to the amino-containing surface provides an immobilization density of 0.5–1.6 pmol/mm2. Immobilization with a higher density (10–12 pmol/mm2) was achieved for attachment to amino-containing glass slides upon the use of oligonucleotides containing a selectively activated terminal phosphate group. The activation of oligonucleotides was carried out with the triphenylphosphine-dithiodipyridine pair in the presence of dimethylaminopyridine N-oxide. The resulting DNA chips were shown to be useful in principle for DNA detection.
Similar content being viewed by others
Abbreviations
- AIBN:
-
azoisobutyronitrile
- BCIP:
-
5-bromo-4-chloro-3-indolyl phosphate
- BSA:
-
bovine serum albumin
- DGDV:
-
diethyleneglycol divinyl ether
- DMAPO:
-
4,4-dimethylaminopyridine N-oxide
- EGVG:
-
ethyleneglycol vinylglycidyl ether
- EVE:
-
ethanolamine vinyl ether
- PVB:
-
polyvinylbutyral
- Py2S2 :
-
2,2’-dithiodipyridine
- NBT:
-
Nitro Blue Tetrazolium Chloride
- TEOS:
-
tetraethoxysilane. Prefix d in designation of oligodeoxyribonucleotides is omitted
References
Shishkina, I.G., Levina, A.S., and Zarytova, V.F., Usp. Khim., 2001, vol. 70, pp. 581–607.
Podyminogin, M.A., Lukhtanov, E.A., and Reed, M.W., Nucleic Acids Res., 2001, vol. 29, pp. 5090–5098.
Taylor, S., Smith, S., Windle, B., and Guiseppi-Eliel, A., Nucleic Acids Res., 2003, vol. 31, p. e81.
Kumar, P. and Gupta, K.C., Bioconjugate Chem., 2003, vol. 14, pp. 507–512.
Hackler, L., Dorman, G., Kele, Z., Urge, L., Darvas, F., and Puskas, L.G., Mol. Divers, 2003, vol. 7, no. 1, pp. 25–36.
Zammatteo, N., Jeanmart, L., Hamels, S., and Courtois, S., Anal. Biochem., 2000, vol. 280, pp. 143–150.
Shchepinov, M.S., Case-Green, S.C., and Southern, E.M., Nucleic Acids Res., 1997, vol. 25, pp. 1155–1161.
Zhao, X., Nampalli, S., Serino, A.J., and Kumar, S., Nucleic Acid Res., 2001, vol. 29, pp. 955–959.
Beier, M. and Hoheisel, J.D., Nucleic Acids Res., 1999, vol. 27, pp. 1970–1977.
Benets, R., Niemeyer, C.M., Drutschmann, D., Blohm, D., and Wöhrle, D., Nucleic Acids Res., 2002, vol. 30.
Afanassiev, V., Hanemann, V., and Wolfl, S., Nucleic Acid Res., 2000, vol. 28, p. e66.
Timofeev, E.N., Kochetkova, S.V., Mirzabekov, A.D., and Florentiev, V.L., Nucleic Acids Res., 1996, vol. 24, pp. 3142–3148.
Timofeev, E. and Mirzabekov, A., Nucleic Acids Res., 2001, vol. 29, pp. 2626–2634.
Consolandi, C., Castiglioni, B., Bordoni, R., Busti, E., Battaglia, C., Bernardi, L.R., and De Bellis, G., Nucleos. Nucleot. Nucl. Acids, 2002, vol. 21, pp. 561–580.
Lee, P.H., Sawan, S.P., Modrusan, Z., Arnold, L.J., and Reynolds, M.A., Bioconjugate Chem., 2000, vol. 13, pp. 97–103.
Kimura, N., Oda, R., Inaki, Y., and Suzuki, O., Nucleic Acids Res., 2004, vol. 32.
Gupta, R., Mozumdar, S., and Chaudhury, N.K., Biosensors Bioelectronics, 2005, vol. 20, pp. 1358–1365.
Annenkov, V.V., Danilovtseva, E.N., Filina, E.A., Mikhaleva, A.I., Skotheim, T.A., and Trofimov, B.A., Polym. Int., 2004, vol. 53, pp. 772–776.
Shostakovskii, M.F., Prostye vinilovye efiry (Vinyl Ethers), Moscow: Nauka, 1952.
Filina, E.A., Danilovtseva, E.N., Vanina, A.S., and Annenkov, V.V., Struktura i Dinamika Molekulyamykh Sistem, (Structure and Dynamics of Molecular Systems), Abstracts of Papers, XI All-Russia Conf., Yal’chik, 2004, p. 263.
Godovikova, T.S., Zarytova, V.F., and Khalimskaya, L.M., Bioorg. Khim., 1986, vol. 12, pp. 475–481.
Zarytova, V.F. and Shishkina, I.G., Anal. Biochem., 1990, vol. 188, pp. 214–218.
Kabilov, M.R., Pyshnyi, D.V., Dymshits, G.M., Gashnikova, N.M., Pokrovskii, A.G., Zarytova, V.F., and Ivanova, E.M., Mol. Biol. (Moscow), 2002, vol. 36, pp. 424–431.
Trofimov, B.A., Kudyakova, R.N., Oparina, L.A., Parshina, L.N., and Vins, V.V., Zh. Prikl. Khim., 1991, vol. 64, pp. 873–877.
Trofimov, B.A., Vyalykh, E.P., Kruglov, V.V., Istomina, S.N., Maksimov, S.M., Yakubov, R.D., Grigorenko, V.I., Nedolya, N.A., Rappoport, L.Ya., Petrov, G.N., and Voronkov, M.G., USSR Inventor’s Certificate no. 602501, Byul. Izobr., 1978, no. 14, p. 485.
Lavrov, V.I., Oparina, L.A., Parshina, L.N., Vins, V.V., and Trofimov, B.A., Zh. Prikl. Khim., 1990, vol. 63, pp. 835–839.
Cantor, C.R. and Tinoko, I., J. Mol. Biol., 1965, vol. 13, pp. 65–77.
Berkner, K.L. and Folk, W.R., J. Biol. Chem., 1977, vol. 252, pp. 3176–3184.
Lokhov, S.G., Podyminogin, M.A., Sergeev, D.S., Silnikov, V.N., Shishkin, G.V., Kutyavin, I.V., and Zarytova, V.F., Bioconjugate Chem., 1992, vol. 3, pp. 414–419.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © V.V. Annenkov, A.S. Levina, E.N. Danilovtseva, E.A. Filina, E.A. Mikhaleva, V.F. Zarytova, 2006, published in Bioorganiche skaya Khimiya, 2006, Vol. 32, No. 5, pp. 511–519.
Rights and permissions
About this article
Cite this article
Annenkov, V.V., Levina, A.S., Danilovtseva, E.N. et al. Functionalized nanocomposite coating of a glass surface for oligonucleotide immobilization. Russ J Bioorg Chem 32, 460–467 (2006). https://doi.org/10.1134/S1068162006050086
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1134/S1068162006050086