Abstract
Binding affinity between calix[4]crown-5-ether and amino acids have been compared by studying the complexation association constant, and the best value has been obtained from complex of calix[4]crown-5 ether, and HrSOD tagged with Arg and Lys were tested to investigate the effects of specific residues in protein immobilization on calix[4]crown-5-ether. The protein tagged with 9Args has been shown to have much better immobilization potential. Taking advantage of the similar structure of a moiety of guanine base to that of Arg side chain, different homo-oligonucleotides have been immobilized, and it was found that calix[4]crown-5-ether is an appropriate agent in the immobilization of dGTP homo-oligonucleotides. The results demonstrate that calix[4]crown-5-ether on glass slide chip could be applied as an excellently oriented immobilization agent for protein or for DNA microarray designing. It has the ability of single base differentiation in SNP sequence detection.
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Abbreviations
- Arg:
-
Arginine
- Lys:
-
Lysine
- G:
-
Guanine nucleotide
- hrSOD:
-
Human recombinant superoxide dismutase
- PBST:
-
PBS-Tween 20
- SNP:
-
Single nucleotide polymorphism
- SSC:
-
Sodium citrate
References
Jain, K.K.: Biochips for gene spotting. Science 294, 621–623 (2002)
Templin, M., Stoll, D., Schrenk, M., Traub, P.C., Vöhringer, C.F., Joos, T.O.: Protein microarray technology. Trends Biotechnol. 20, 160–166 (2002)
Abbort, A.: A post-genomic challenge: learning to read patterns of protein synthesis. Nature 402, 715–720 (1999)
Anderson, K.S., Ramachandran, N., Wong, J., Raphael, J.V., Hainsworth, E., Demirkan, G., Cramer, D., Aronzon, D., Hodi, F.S., Harris, L., Logvinenko, T., LaBaer, J.: Application of protein microarrays for multiplexed detection of antibodies to tumor antigens in breast cancer. J. Proteome. Res. 7, 1490–1499 (2008)
Lueking, A., Horn, M., Eickhoff, H., Bussow, K., Lehrach, H., Walter, G.: Protein microarrays for gene expression and antibody screening. Anal. Biochem. 270, 103–111 (1999)
Jain, K.K.: Applications of nanobiotechnology in clinical diagnostics. Clin. Chem. 53, 2002–2009 (2007)
Blohm, D.H., Guiseppi-Elie, A.: New developments in microarray technology. Curr. Opin. Biotechnol. 12, 41–47 (2001)
Turkova, J.: Oriented immobilization of biologically active proteins as a tool for revealing protein interactions and function. J. Chromatography B 722, 11–31 (1999)
Høyer-Hansen, G., Hamers, M.J., Pedersen, A.N., Nielsen, H.J., Brünner, N., Danø, K., Stephens, R.W.: Loss of ELISA specificity due to biotinylation of monoclonal antibodies. J. Immunol. Methods 235, 91–99 (2000)
Nakagawa, T., Tanaka, T., Niwa, D., Osaka, T., Takeyama, H., Matsunaga, T.: Fabrication of amino silane-coated microchip for DNA extraction from whole blood. J. Biotechnol. 116, 105–111 (2005)
Taylor, S., Smith, S., Windle, B., Guiseppi-Elie, A.: Impact of surface chemistry and blocking strategies on DNA microarrays. Nucleic Acids Res. 31, e87 (2003)
MacBeath, G., Schreiber, S.L.: Printing proteins as microarrays for high-throughput function determination. Science 289, 1760–1763 (2000)
Coleman, A.W., Perret, F., Moussa, A., Dupin, M., Guo, Y., Perron, H.: Calix[n]arenes as protein sensors. Top. Curr. Chem. 277, 31–88 (2007)
Mutihac, L., Mutihac, R.: Liquid–liquid extraction and transport through membrane of amino acid methylesters by calix[n]arene derivatives. J. Incl. Phenom. Macrocycl. Chem. 59(1–2), 177–181 (2007)
Mutihac, L., Hong Lee, J., Seung Kim, J., Vicens, J.: Recognition of amino acids by functionalized calixarenes. Chem. Soc. Rev. 40, 2777–2796 (2011)
Bew, S.P., Barter, A.W.J., Sharma, S.V.: Mass spectroscopic investigation of bis-1,3-urea calix[4]arenes and their ability to complex N-protected α-amino acids. J. Incl. Phenom. Macrocycl. Chem. 66(1–2), 195–208 (2010)
Oshima, T., Saisho, R., Ohe, K., Baba, Y., Ohto, K.: Adsorption of amino acid derivatives on calixarene carboxylic acid impregnated resins. React. Funct. Polym. 69, 105–110 (2009)
Perret, F., Coleman, W.: Biochemistry of anionic calix[n]arenes, Chem. Commun. (Camb.), 47(26), 7303–7319 (2011)
Oh, S.W., Moon, J.D., Lim, H.J., Park, S.Y., Kim, T.S., Park, J., Han, M.H., Snyder, M., Choi, E.Y.: Calixarene derivative as a tool for highly sensitive detection and oriented immobilization of proteins in a microarray format through noncovalent molecular interaction. FASEB J. 19, 1335–1337 (2005)
Lee, Y., Lee, E.K., Cho, Y.W., Matsui, T., Kang, I.C., Kim, T.S., Han, M.H.: ProteoChip: a highly sensitive protein microarray prepared by a novel method of protein immobilization for application of protein–protein interaction studies. Proteomics 3, 2289–2304 (2003)
Amiri, A., Yul Choi, E., Jeong Kim, H.: Development and molecular recognition of Calixcrownchip as an electrochemical ALT immunosensor. J. Incl. Phenom. Macrocycl. Chem. 66, 185–195 (2010)
de Namor, A.F.D., Gil, E., Llosa Tanco, M.A., Tanaka, D.A.P., Salazar, L.E.P., Sculz, R.A., Wang, J.: J. Phys. Chem. 99, 16776–16781 (1995)
Philip, T., Fraisse, J., Sinet, P.M., Lauras, B., Robert, J.M., Freycon, F.: Confirmation of the assignment of the human SOD gene to chromosome 21q22 Cytogenetics. Cell Genet. 22, 521–523 (1978)
Martoglio, B., Graf, R., Dobberstein, B.: Signal peptide fragments of preprolactin and HIV-1 p-gp160 interact with calmodulin. EMBO J. 16, 6636–6645 (1997)
Romkes, M., Faletto, M.B., Blaisdell, J.A., Raucy, J.L., Goldstein, J.A.: Cloning and expression of complementary DNAs for multiple members of the human cytochrome P450IIC subfamily. Biochemistry 30, 3247–3255 (1991)
Gutsche, C.D.: Calixarene Revisited: Monographs in Supramolecular Chemistry. Royal Society of Chemistry, Cambridge (1998)
Mandolini, L., Ungaro, R.: Calixarenes in Action. Imperial College press, London (2000)
Miyamoto, S., Kollman, P.A.: Molecular dynamics studies of calixspherand complexes with alkali metal cations: calculation of the absolute and relative free energies of binding of cations to a calixspherand. J. Am. Chem. Soc. 114, 3668–3674 (1992)
Ramirez, J., Ahn, S., Grogorean, G., Lebrilla, C.B.: Evidence for the formation of gas-phase inclusion complexes with cyclodextrins and amino acids. J. Am. Chem. Soc. 122, 6884–6890 (2000)
Cheng, Y., Hercules, D.M.: Measurement of chiral complexes of cyclodextrins and amino acids by electrospray ionization time-of-flight mass spectrometry. J. Mass Spectrom. 36, 834–836 (2001)
Stone, M.M., Franz, H.F., Lebrilla, C.B.: Non-covalent calixarene–amino acid complexes formed by MALDI-MS. J. Am. Soc. Mass Spectrom. 13, 964–974 (2002)
Oshima, T., Goto, M., Furusaki, S.: Complex formation of cytochrome c with a calixarene carboxylic acid derivatives: a novel solubilization method for biomolecules in organic media. Biomacromolecules 3, 438–444 (2002)
Lin, Q., Park, H.S., Hamuro, Y., Lee, C.S., Hamilton, A.D.: Protein surface recognition by synthetic agents: design and structural requirements of a family of artificial receptors that bind to cytochrome c. Biopolymers 47, 285–297 (1998)
Sato, H., Feix, J.B., Frank, D.W.: Identification of superoxide dismutase as a cofactor for the pseudomonas type III toxin, ExoU. Biochemstry 45, 10368–10375 (2006)
Kudo, Y., Maeda, S., Tikida, S., Kudo, M.: Colorimetric chiral recognition by a molecular sensor. Nature 382, 522–524 (1996)
Marston, F.A., Hartley, D.L.: Solubilization of protein aggregates. Methods Enzymol. 182, 264–276 (1990)
Hiller, R., Laffer, S., Harwanegg, C., Huber, M., et al.: Microarrayed allergen molecules: diagnostic gatekeepers for allergy treatment. FASEB J. 16, 414–416 (2002)
Busse, P.J., Järvinen, K.M., Vila, L., Beyer, K., Sampson, H.A.: Identification of sequential IgE-binding epitopes on bovine alpha (s2)-casein in cow’s milk allergic patients. Int. Arch. Allergy Immunol. 129, 93–96 (2002)
Sasakura, Y., Kanda, K., Yoshimura-Suzuki, T., Matsui, T., Fukuzono, S., Han, M.H., Shimizu, T.: Protein microarray system for detecting protein–protein interactions using an anti-His-tag antibody and fluorescence scanning: effects of the heme redox state on protein–protein interactions of heme-regulated phosphodiesterase from Escherichia coli. Anal. Chem. 76, 6521–6527 (2004)
Büssow, K., Nordhoff, E., Lubbert, C., Leharch, H., Walter, G.: A human cDNA library for high-throughput protein expression screening. Genomics 65, 1–8 (2000)
Sansone, F., Dudic, M., Donofrio, G., Rivetti, C., Baldini, L., Casnati, A., Cellai, S., Ungaro, R.: DNA condensation and cell transfection properties of guanidinium calixarenes: dependence on macrocycle lipophilicity, size, and conformation. J. Am. Chem. Soc. 128, 14528–14536 (2006)
Schug, K.A., Lindner, W.: Noncovalent binding between guanidinium and anionic groups: focus on biological- and synthetic-based arginine/guanidinium interactions with phosph[on]ate and sulf[on]ate residues. Chem. Rev. 105, 67–114 (2005)
Perreault, D.M., Cabell, L.A., Anslyn, E.V.: Using guanidinium groups for the recognition of RNA and as catalysts for the hydrolysis of RNA. Bioorg. Med. Chem. 5, 1209–1220 (1997)
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Amiri, A., Choi, E.Y. Calix[4]crown-5-ether as a biolinker for immobilization of protein and DNA in fluorescence glass slide chip. J Incl Phenom Macrocycl Chem 76, 317–326 (2013). https://doi.org/10.1007/s10847-012-0201-1
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DOI: https://doi.org/10.1007/s10847-012-0201-1