Bishydrazide glycoconjugates for lectin recognition and capture of bacterial pathogens

Bioconjugate Chemistry

Volumn 21, Issue 11, 2010, Pages 2065-2075

  Adak, Avijit Kumar ^a   Leonov, Alexei P ^a   Ding, Ning ^a,b   Thundimadathil, Jyothi ^a,c   Kularatne, Sumith ^a   Low, Philip S ^a   Wei, Alexander ^a  

^a PURDUE UNIVERSITY   (United States)

^b FUDAN UNIVERSITY   (China)

^c Peptisyntha Inc ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADHESIN; BISHYDRAZIDE DERIVATIVE; CARBON DISULFIDE; DITHIOCARBAMIC ACID DERIVATIVE; GLYCOCONJUGATE; GOLD; HYDRAZIDE DERIVATIVE; LECTIN; UNCLASSIFIED DRUG;

ADSORPTION; ARTICLE; BACTERIAL VIRULENCE; BACTERIUM DETECTION; CARBOXY TERMINAL SEQUENCE; CELL SURFACE; CONTROLLED STUDY; HOSPITAL INFECTION; NONHUMAN; PSEUDOMONAS AERUGINOSA; SYNTHESIS;

BACTERIA (MICROORGANISMS); PSEUDOMONAS AERUGINOSA;

EID: 78649233183     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc100288c     Document Type: Article

References (90)

1. Stevens, J., Blixt, O., Paulson, J. C., and Wilson, I. A. (2006) Glycan microarray technologies: tools to survey host specificity of influenza viruses Nat. Rev. Microbiol. 4, 857-864
2. Wang, H. F., Gu, L. R., Lin, Y., Lu, F. S., Meziani, M. J., Luo, P. G. J., Wang, W., Cao, L., and Sun, Y. P. (2006) Unique aggregation of anthrax (Bacillus anthracis) spores by sugarcoated single-walled carbon nanotubes J. Am. Chem. Soc. 128, 13364-13365
3. El-Boubbou, K., Gruden, C., and Huang, X. (2007) Magnetic glyco-nanoparticles: A unique tool for rapid pathogen detection, decontamination, and strain differentiation J. Am. Chem. Soc. 129, 13392-13393
4. Kale, R. R., Mukundan, H, Price, D. N., Harris, J. F., Lewallen, D. M., Swanson, B. I., Schmidt, G. J., and Iyer, S. S. (2008) Detection of intact influenza viruses using biotinylated biantennary S -sialosides J. Am. Chem. Soc. 130, 8169-8171
5. Liu, L.-H., Dietsch, H., Schurtenberger, P., and Yan, M. (2009) Photoinitiated coupling of unmodified monosaccharides to iron oxide nanoparticles for sensing proteins and bacteria Bioconjugate Chem. 20, 1349-1355
6. Disney, M. D. and Seeberger, P. H. (2004) The use of carbohydrate microarrays to study carbohydrate-cell interactions and to detect pathogens Chem. Biol. 11, 1701-1707
7. Ngundi, M. M., Kulagina, N. V., Anderson, G. P., and Taitt, C. R. (2006) Nonantibody-based recognition: alternative molecules for detection of pathogens Exp. Rev. Proteom. 3, 511-524
8. Kulkarni, A. A., Weiss, A. A., and Iyer, S. S. (2010) Glycan-based high-affinity ligands for toxins and pathogen receptors Med. Res. Rev. 30, 327-393
9. Wu, C.-Y., Liang, P.-H., and Wong, C.-H. (2009) New development of glycan arrays Org. Biomol. Chem. 7, 2247-2254
10. Laurent, N., Voglmeir, J., and Flitsch, S. L. (2008) Glycoarrays-tools for determining protein-carbohydrate interactions and glycoenzyme specificity Chem. Commun. 4400-4412
11. Park, S., Lee, M.-R., and Shin, I. (2008) Carbohydrate microarrays as powerful tools in studies of carbohydrate-mediated biological processes Chem. Commun. 37, 4389-4399
12. Horlacher, T. and Seeberger, P. H. (2008) Carbohydrate arrays as tools for research and diagnostics Chem. Soc. Rev. 37, 1414-1422
13. Park, S., Lee, M.-R., Pyo, S. J., and Shin, I. (2004) Carbohydrate chips for studying high-throughput carbohydrate-protein interactions J. Am. Chem. Soc. 126, 4812-4819
14. Park, S. and Shin, I. (2002) Fabrication of carbohydrate chips for studying protein-carbohydrate interactions Angew. Chem., Int. Ed. 41, 3180-3182
15. Ratner, D. M., Adams, E. W., Disney, M. D., and Seeberger, P. H. (2004) Tools for glycomics: mapping interactions of carbohydrates in biological systems ChemBioChem 5, 1375-1383
16. Houseman, B. T., Gawalt, E. S., and Mrksich, M. (2003) Maleimide-functionalized self-assembled monolayers for the preparation of peptide and carbohydrate biochips Langmuir 19, 1522-1531
17. Houseman, B. T. and Mrksich, M. (2002) Carbohydrate arrays for the evaluation of protein binding and enzymatic modification Chem. Biol. 9, 443-454
18. Bryan, M. C., Fazio, F., Lee, H. K., Huang, C. Y., Chang, A., Best, M. D., Calarese, D. A., Blixt, C., Paulson, J. C., Burton, D., Wilson, I. A., and Wong, C. H. (2004) Covalent display of oligosaccharide arrays in microtiter plates J. Am. Chem. Soc. 126, 8640-8641
19. Michel, O. and Ravoo, B. J. (2008) Carbohydrate microarrays by microcontact "click" chemistry Langmuir 24, 12116-12118
20. Lee, M.-R. and Shin, I. (2005) Fabrication of chemical microarrays by efficient immobilization of hydrazide-linked substances on epoxide-coated glass surfaces Angew. Chem., Int. Ed. 44, 2881-2884
21. Park, S. and Shin, I. (2007) Carbohydrate microarrays for assaying galactosyltransferase activity Org. Lett. 9, 1675-1678
22. Blixt, O., Head, S., Mondala, T., Scanlan, C., Huflejt, M. E., Alvarez, R., Bryan, M. C., Fazio, F., Calarese, D., Stevens, J., Razi, N., Stevens, D. J., Skehel, J. J., van Die, I., Burton, D. R., Wilson, I. A., Cummings, R., Bovin, N., Wong, C. H., and Paulson, J. C. (2004) Printed covalent glycan array for ligand profiling of diverse glycan binding proteins Proc. Natl. Acad. Sci. U.S.A. 101, 17033-17038
23. De Paz, J. L., Noti, C., and Seeberger, P. H. (2006) Microarrays of synthetic heparin oligosaccharides J. Am. Chem. Soc. 128, 2766-2767
24. Köhn, M., Wacker, R., Peters, C., Schröder, H., Soulère, L., Breinbauer, R., Niemeyer, C. M., and Waldmann, H. (2003) Staudinger ligation: a new immobilization strategy for the preparation of small-molecule arrays Angew. Chem., Int. Ed. 42, 5830-5834
25. Hermanson, G. T. (2008) Bioconjugate Techniques, 2nd ed., Academic Press, San Diego.
26. Xia, B. Y., Kawar, Z. S., Ju, T. Z., Alvarez, R. A., Sachdev, G. P., and Cummings, R. D. (2005) Versatile fluorescent derivatization of glycans for glycomic analysis Nat. Methods 2, 845-850
27. Lee, M.-R. and Shin, I. (2005) Facile preparation of carbohydrate microarrays by site-specific, covalent immobilization of unmodified carbohydrates on hydrazide-coated glass slides Org. Lett. 7, 4269-4272
28. Park, S., Lee, M.-R., and Shin, I. (2009) Construction of carbohydrate microarrays by using one-step direct immobilizations of diverse unmodified glycans on solid surfaces Bioconjugate Chem. 20, 155-162
29. Zhi, Z. L., Powell, A. K., and Turnbull, J. E. (2006) Fabrication of carbohydrate microarrays on gold surfaces: Direct attachment of nonderivatized oligosaccharides to hydrazide modified self-assembled monolayers Anal. Chem. 78, 4786-4793
30. Bohorov, O., Andersson-Sand, H., Hoffmann, J., and Blixt, O. (2006) Arraying glycomics: a novel bi-functional spacer for one-step microscale derivatization of free reducing glycans Glycobiology 16, 21C-27C
31. Liu, Y., Feizi, T., Campanerorhodes, M., Childs, R., Zhang, Y., Mulloy, B., Evans, P., Osborn, H., Otto, D., and Crocker, P. (2007) Neoglycolipid probes prepared via oxime ligation for microarray analysis of oligosaccharide-protein interactions Chem. Biol. 14, 847-859
32. Chen, G. and Pohl, N. (2008) Synthesis of fluorous tags for incorporation of reducing sugars into a quantitative microarray platform Org. Lett. 10, 785-788
33. Cló, E., Blixt, O., and Jensen, K. J. (2010) Chemoselective reagents for covalent capture and display of glycans in microarrays Eur. J. Org. Chem. 540-554
34. Thygesen, M. B., Sauer, J., and Jensen, K. J. (2009) Chemoselective capture of glycans for analysis on gold nanoparticles: carbohydrate oxime tautomers provide functional recognition by proteins. Chem.-Eur. J. 15, 1649-1660
35. Cervigni, S. E., Dumy, P., and Mutter, M. (1996) Synthesis of glycopeptides and lipopeptides by chemoselective ligation Angew. Chem., Int. Ed. 35, 1230-1232
36. Zhao, Y. M., Kent, S. B. H., and Chait, B. T. (1997) Rapid, sensitive structure analysis of oligosaccharides Proc. Natl. Acad. Sci. U.S.A. 94, 1629-1633
37. Zhi, Z. L., Laurent, N., Powell, A. K., Karamanska, R., Fais, M., Voglmeir, J., Wright, A., Blackburn, J. M., Crocker, P. R., Russell, D. A., Flitsch, S., Field, R. A., and Turnbull, J. E. (2008) A versatile gold surface approach for fabrication and interrogation of glycoarrays ChemBioChem 9, 1568-1575
38. Guillaumie, F., Thomas, O. R. T., and Jensen, K. J. (2002) Immobilization of pectin fragments on solid supports: novel coupling by thiazolidine formation Bioconjugate Chem. 13, 285-294
39. Lohse, A., Martins, R., Jørgensen, M. R., and Hindsgaul, O. (2006) Solid-Phase oligosaccharide tagging (SPOT): validation on glycolipid-derived structures Angew. Chem., Int. Ed. 45, 4167-4172
40. Bacchi, A., Carcelli, M., Pelizzi, G., Solinas, C., and Sorace, L. (2006) Trinuclear copper(II) complexes of bis(acylhydrazone) ligands. Structural analysis and magnetic properties of a sulfato-bridged hexanuclear dimer Inorg. Chim. Acta 359, 2275-2280
41. Dydio, P., Zieliński, T., and Jurczak, J. (2009) Bishydrazide derivatives of isoindoline as simple anion receptors J. Org. Chem. 74, 1525-1530
42. Bystrický, S., Machová, E., Malovíková, A., and Kogan, G. (1999) Determination of the cross-linking effect of adipic acid dihydrazide on glycoconjugate preparation Glycoconjugate J. 16, 691-695
43. Urmenyi, A. M., Poot, A. A., Wessling, M., and Mulder, M. H. V. (2005) Affinity membranes for hormone removal from aqueous solutions J. Membr. Sci. 259, 91-102
44. Ono, T., Fujii, S., Nobori, T., and Lehn, J.-M. (2007) Soft-to-hard transformation of the mechanical properties of dynamic covalent polymers through component incorporation Chem. Commun. 46-48
45. Price, D. and Ahearn, D. G. (1988) Incidence and persistence of Pseudomonas aeruginosa in whirlpools J. Clin. Microbiol. 26, 1650-1654
46. Guidelines for safe recreational water environments. Vol 2: Swimming pools and similar environments (2006) pp 43 - 45, World Health Organization, Geneva.
47. Zhao, Y., Pérez-Segarra, W., Shi, Q., and Wei, A. (2005) Dithiocarbamate assembly on gold J. Am. Chem. Soc. 127, 7328-7329
48. Zhu, H., Coleman, D. M., Dehen, C. J., Geisler, I. M., Zemlyanov, D., Chmielewski, J., Simpson, G. J., and Wei, A. (2008) Assembly of dithiocarbamate-anchored monolayers on gold surfaces in aqueous solutions Langmuir 24, 8660-8666
49. Gilboa-Garber, N. (1982). Pseudomonas aeruginosa lectins. Methods in Enzymology. Vol. 83: Complex Carbohydrates, Part D (Kaplan, N. P., Colowick, N. P., and Ginsburg, V., Eds.) pp 378 - 385, Chapter 32, Academic Press, San Diego.
50. Doorneweerd, D. D., Henne, W. A., Reifenberger, R. G., and Low, P. S. (2010) Selective capture and identification of pathogenic bacteria using an immobilized siderophore. Langmuir 26, 15424-15429.
51. Bélot, F. and Jacquinet, J.-C. (2000) Unexpected stereochemical outcome of activated 4,6-O-benzylidene derivatives of the 2-deoxy-2- trichloroacetamido-D- galacto series in glycosylation reactions during the synthesis of a chondroitin 6-sulfate trisaccharide methyl glycoside Carbohydr. Res. 325, 95-106
52. Matsuoka, K., Goshu, Y., Takezawa, Y., Mori, T., Sakamoto, J.-I., Yamada, A., Onaga, T., Koyama, T., Hatano, K., Snyder, P. W., Toone, E. J., and Daiyo Terunuma, D. (2007) Practical synthesis of fully protected globotriaose and its glycopolymers Carbohydr. Polym. 69, 326-335
53. Vercruysse, K. P., Marecak, D. M., Marecek, J. F., and Prestwich, G. D. (1997) Synthesis and in vitro degradation of new polyvalent hydrazide cross-linked hydrogels of hyaluronic acid Bioconjugate Chem. 8, 686-694
54. Leteux, C., Childs, R. A., Chai, W., Stoll, M. S., Kogelberg, H., and Feizi, T. (1998) Biotinyl-l-3-(2-naphthyl)alanine hydrazide derivatives of N -glycans: versatile solid-phase probes for carbohydrate-recognition studies Glycobiology 8, 227-236
55. Shinohara, Y., Sota, H., Gotoh, M., Hasebe, M., Tosu, M., Nakao, J., and Hasegawa, Y. (1996) Bifunctional labeling reagent for oligosaccharides to incorporate both chromophore and biotin groups Anal. Chem. 68, 2573-2579
56. Ojala, C. R., Ostman, J. M., and Ojala, W. H. (2002) The saccharide-hydrazide linkage: molecular and crystal structures of the semicarbazide derivatives of D-glucose, D-galactose, and D-xylose, including a 'forbidden' conformation of the galactose derivative Carbohydr. Res. 337, 21-29
57. Flinn, N. S., Quibell, M., Monk, T. P., Ramjee, M. K., and Urch, C. J. (2005) A single-step method for the production of sugar hydrazides: intermediates for the chemoselective preparation of glycoconjugates Bioconjugate Chem. 16, 722-728
58. Krivan, H. C., Roberts, D. D., and Ginsburg, V. (1988) Many pulmonary pathogenic bacteria bind specifically to the carbohydrate sequence GalNAcβ1-4Gal found in some glycolipids Proc. Natl. Acad. Sci. U.S.A. 85, 6157-6161
59. Yu, L., Lee, K. K., Hodges, R. S., Paranchych, W., and Irvin, R. T. (1994) Adherence of Pseudomonas aeruginosa and Candida albicans to glycosphingolipid (Asialo-GM1) receptors is achieved by a conserved receptor-binding domain present on their adhesions Infect. Immunol. 62, 5213-5219
60. Mitchell, E., Houles, C., Sudakevitz, D., Wimmerova, M., Gautier, C., Perez, S., Wu, A. M., Gilboa-Garber, M., and Imberty, A. (2002) Structural basis for oligosaccharide-mediated adhesion of Pseudomonas aeruginosa in the lungs of cystic fibrosis patients Nat. Struct. Biol. 9, 918-921
61. Imberty, A., Wimmerova, M., Mitchell, E. P., and Gilboa-Garber, N. (2004) Structures of the lectins from Pseudomonas aeruginosa: Insights into the molecular basis for host glycan recognition Microb. Infect. 6, 221-228
62. Huff, T. B., Hansen, M. H., Zhao, Y., Cheng, J.-X., and Wei, A. (2007) Controlling the cellular uptake of gold nanorods Langmuir 23, 1596-99
63. Huff, T. B., Tong, L., Zhao, Y., Hansen, M. N., Cheng, J.-X., and Wei, A. (2007) Hyperthermic effects of gold nanorods on tumor cells Nanomedicine 2, 125-132
64. Zhao, Y., Newton, J. N., Liu, J., and Wei, A. (2009) Dithiocarbamate- coated SERS substrates: sensitivity gain by partial surface passivation Langmuir 25, 13833-13839
65. Guerrini, L., Garcia-Ramos, J. V., Domingo, C., and Sanchez-Cortes, S. (2009) Sensing polycyclic aromatic hydrocarbons with dithiocarbamate- functionalized Ag nanoparticles by surface-enhanced Raman scattering Anal. Chem. 81, 953-960
66. Cao, R., Jr., Diaz, A., Cao, R., Otero, A., Cea, R., C. R.-A., Maria, and Serra, C. (2007) Building layer-by-layer a bis(dithiocarbamato)copper(II) complex on Au{111} surfaces J. Am. Chem. Soc. 129, 6927-6930
67. Park, M. H., Ofir, Y., Samanta, B., and Rotello, V. M. (2009) Robust and responsive dendrimer-gold nanoparticle nanocomposites via dithiocarbamate crosslinking Adv. Mater. 21, 2323-2325
68. Patel, G., Kumar, A., Pal, U., and Menon, S. (2009) Potassium ion recognition by facile dithiocarbamate assembly of benzo-15-crown-5-gold nanoparticles Chem. Commun. 1849-1851
69. Morf, P., Raimondi, F., Nothofer, H.-G., Schnyder, B., Yasuda, A., Wessels, J. M., and Jung, T. A. (2006) Dithiocarbamates: functional and versatile linkers for the formation of self-assembled monolayers Langmuir 22, 658-663
70. Lee, A. W. M., Chan, W. H., Chiu, C. M. L., and Tang, K. T. (1989) Ultraviolet spectrophotometric determination of primary and secondary aliphatic amines by formation of dithiocarbamates Anal. Chim. Acta 218, 157-160
71. Ito, Y. (2006) Photoimmobilization for microarrays Biotechnol. Prog. 924-932
72. Carroll, G. T., Wang, D. N., Turro, N. J., and Koberstein, J. T. (2008) Photons to illuminate the universe of sugar diversity through bioarrays Glycoconjugate J. 25, 5-10
73. Carroll, G. T., Wang, D. N., Turro, N. J., and Koberstein, J. T. (2006) Photochemical micropatterning of carbohydrates on a surface Langmuir 22, 2899-2905
74. Liu, L.-H., Dietsch, H., Schurtenberger, P., and Yan, M. (2009) Photoinitiated coupling of unmodified monosaccharides to iron oxide nanoparticles for sensing proteins and bacteria Bioconjugate Chem. 20, 1349-1355
75. Norberg, O., Deng, L., Yan, M., and Ramström., O. (2009) Photo-Click immobilization of carbohydrates on polymeric surfacess: a quick method to functionalize surfaces for biomolecular recognition studies Bioconjugate Chem. 20, 2364-2370
76. 2 Biochemistry 16, 5650-5654
77. Kumar, A. and Whitesides, G. M. (1993) Features of gold having micrometer to centimeter dimensions can be formed through a combination of stamping with an elastomeric stamp and an alkanethiol "ink" followed by chemical etching Appl. Phys. Lett. 63, 2002-2004
78. Bernard, A., Renault, J. P., Michel, B., Bosshard, H. R., and Delamarche, E. (2000) Microcontact printing of proteins Adv. Mater. 12, 1067-1070
79. Inerowicz, H. D., Howell, S., Regnier, F. E., and Reifenberger, R. (2002) Multiprotein immunoassay arrays fabricated by microcontact printing Langmuir 18, 5263-5268
80. Godula, K., Rabuka, D., Nam, K. T., and Bertozzi, C. R. (2009) Synthesis and microcontact printing of dual end-functionalized mucin-like glycopolymers for microarray applications Angew. Chem., Int. Ed. 48, 4973-4976
81. Wendeln, C., Heile, A., Arlinghaus, H. F., and Ravoo, B. J. (2010) Carbohydrate microarrays by microcontact printing Langmuir 26, 4933-4940
82. Keizer, D. W., Slupsky, C. M., Kalisiak, M., Campbell, A. P., Crumpi, M. P., Sastry, P. A., Hazes, B., Irvin, R. T., and Sykes, B. D. (2001) Structure of a pilin monomer from pseudomonas aeruginosa J. Biol. Chem. 276, 24186-24193
83. Winzer, K., Falconer, C., Garber, N.-C., Diggle, S. P., Camara, M., and Williams, P. (2000) The Pseudomonas aeruginosa lectins PA-IL and PA-IIL are controlled by quorum sensing and by RpoS J. Bacteriol. 182, 6401-6411
84. Duan, K. and Surette, M. G. (2007) Environmental regulation of Pseudomonas aeruginosa PAO1 Las and Rhl quorum-sensing systems J. Bacteriol. 189, 4827-4836
85. Homola, J. (2008) Surface plasmon resonance sensors for detection of chemical and biological species Chem. Rev. 108, 462-493 (Pubitemid 351350388)
86. Marx, K. A. (2003) Quartz crystal microbalance: a useful tool for studying thin polymer films and complex biomecolecular systems at the solution-surface interface Biomacromolecules 4, 1099-1120
87. Love, C. J., Estroff, L. A., Kriebel, J. K., Nuzzo, R. G., and Whitesides, G. M. (2005) Self-assembled monolayers of thiolates on metals as a form of nanotechnology Chem. Rev. 105, 1103-1170
88. Flynn, N. T., Tran, T. N., Cima, M. J., and Langer, R. (2003) Long-term stability of self-assembled monolayers in biological media Langmuir 19, 10909-10915
89. Lakowicz, J. R. (2001) Radiative decay engineering: biophysical and biomedical applications Anal. Biochem. 298, 1-24
90. Castelino, K., Kannan, B., and Majumdar, A. (2005) Characterization of grafting density and binding efficiency of DNA and proteins on gold surfaces Langmuir 21, 1956-1961