General chemoselective and redox-responsive ligation and release strategy

Bioconjugate Chemistry

Volumn 25, Issue 3, 2014, Pages 543-551

  Park, Sungjin ^a   Westcott, Nathan P ^a   Luo, Wei ^a,b   Dutta, Debjit ^a   Yousaf, Muhammad N ^a,b  

^a University of North Carolina at Chapel Hill   (United States)

^b YORK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

TISSUE ENGINEERING;

CHEMOSELECTIVE; ELECTROCHEMICAL REDOX; ON DEMANDS; PHYSIOLOGICAL CONDITION; REACTION STRATEGIES; REDOX SIGNALS; REDOX-RESPONSIVE; RELEASE STRATEGIES; SWITCHABLE; ]+ CATALYST;

PEPTIDES;

ARGINYLGLYCYLASPARTIC ACID; BENZOQUINONE; CYCLOPEPTIDE; HYDROQUINONE; OXIME;

ANALYTIC METHOD; ANIMAL CELL; ARTICLE; CATALYST; CELL ADHESION; CELL ASSAY; CHEMICAL REACTION; CHEMOSELECTIVE REDOX RESPONSIVE LIGATION; CLICK CHEMISTRY; CONTROLLED STUDY; DRUG CONJUGATION; DRUG RELEASE; ELECTROCHEMISTRY; FLUORESCENCE RESONANCE ENERGY TRANSFER; MOLECULAR BIOLOGY; MOLECULE; NANOTECHNOLOGY; NONHUMAN; OXIDATION REDUCTION STATE; PEPTIDE SYNTHESIS; QUANTITATIVE ANALYSIS; SIGNAL TRANSDUCTION; STEREOCHEMISTRY; TISSUE ENGINEERING; 3T3 CELL LINE; ANIMAL; CHEMISTRY; DRUG EFFECTS; METABOLISM; MOUSE; OXIDATION REDUCTION REACTION; SYNTHESIS;

ANIMALS; CELL ADHESION; FLUORESCENCE RESONANCE ENERGY TRANSFER; MICE; OXIDATION-REDUCTION; PEPTIDES, CYCLIC; SWISS 3T3 CELLS;

EID: 84896515378     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc400565y     Document Type: Article

References (44)

1. Tiefenbrunn, T. K. and Dawson, P. E. (2010) Chemoselective ligation techniques: modern applications of time-honored chemistry Pept. Sci. 94, 95-106
2. Iha, R. K., Wooley, K. L., Nystrom, A. M., Burke, D. J., Kade, M. J., and Hawker, C. J. (2009) Applications of orthogonal 'Click' chemistries in the synthesis of functional soft materials Chem. Rev. 109, 5620-5686
3. Sletten, E. M. and Bertozzi, C. R. (2009) Bioorthogonal chemistry: fishing for selectivity in the sea of functionality Angew. Chem., Int. Ed. 48, 6974-6998
4. Tully, S. E., Rawat, M., and Hsieh-Wilson, L. C. (2006) Discovery of a TNF-α antagonist using chondroitin sulfate microarrays J. Am. Chem. Soc. 128, 7740-7741
5. Kiessling, L. L. and Splain, R. A. (2010) Chemical approaches to glycobiology Annu. Rev. Biochem. 79, 619-63
6. Luo, W. and Yousaf, M. N. (2011) Developing a self-assembled monolayer microarray to study stem cell differentiation J. Colloid Interface Sci. 360, 325-330
7. Foillard, S., Jin, Z. H., Garanger, E., Boturyn, D., Favrot, M. C., Coll, J. L., and Dumy, P. (2008) Synthetic and biological characterization of targeted pro-apoptotic peptide ChemBioChem 9, 2326-2332
8. Furuta, T., Mochizuki, M., Ito, M., Takahashi, T., Suzuki, T., and Kan, T. (2008) Versatile synthesis of head group functionalized phospholipids via oxime bond formation Org. Lett. 10, 4847-4850
9. Nazarpack-Kandlousy, N., Nelen, M. I., Goral, V., and Eliseev, A. V. (2002) Synthesis and mass spectroscopy studies of branched oxime ether libraries. Mapping the substitution motif via linker stability and fragmentation pattern J. Org. Chem. 67, 59-65
10. Rose, K. (1994) Facile synthesis of homogeneous artificial proteins J. Am. Chem. Soc. 116, 30-33
11. Marcaurelle, L. A., Rodriguez, E. C., and Bertozzi, C. R. (1998) Synthesis of an oxime-linked neoglycopeptide with glycosylation-dependent activity similar to its native counterpart Tetrahedron Lett. 39, 8417-8420
12. Barrett, D. G. and Yousaf, M. N. (2008) Preparation of a class of versatile, chemoselective, and amorphous polyketoesters Biomacromolecules 9, 2029-2035
13. Lempens, E. H. M., Helms, B. A., Merkx, M., and Meijer, E. W. (2009) Efficient and chemoselective surface immobilization of proteins by using aniline-catalyzed oxime chemistry ChemBioChem 10, 658-662
14. Jencks, W. P. (1959) Studies on the mechanism of oxime and semicarbazone formation J. Am. Chem. Soc. 81, 475-481
15. Lee, E.-J., Chan, E. W. L., and Yousaf, M. N. (2009) Spatio-temporal control of cell coculture interactions on surfaces ChemBioChem 10, 1648-1653
16. Park, S. and Yousaf, M. N. (2009) An interfacial oxime reaction to immobilize ligands and cells in patterns and gradients to photo-active surfaces Langmuir 24, 6201-6207
17. Rappoport, Z. and Liebman, E. D., Eds. (2009) The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids, John Wiley & Sons, Chichester, U.K.
18. Baldwin, J. E. and Norris, R. K. (1981) Stereoelectronic control in organic chemistry: addition reactions of some 1,4-benzoquinone 4-(O-methyloximes) J. Org. Chem. 46, 697-703
19. Shanab, K., Pongprom, N., Wulz, E., Holzer, W., Spreitzer, H., Schmidt, P., Aicher, B., Muller, G., and Gunther, E. (2007) Synthesis and biological evaluation of novel cytotoxic azanaphthoquinone pyrrolo-annelated oximes Bioorg. Med. Chem. Lett. 17, 6091-6095
20. Reindl, W., Yuan, J., Krämer, A., Strebhardt, K., and Berg, T. (2008) Inhibition of Polo-like kinase 1 by blocking Polo-Box domain-dependent protein-protein interactions Chem. Biol. 15, 459-466
21. Hwu, J. R., Tsay, S. C., Hong, S. C., Leu, Y. J., Liu, C. F., and Chou, S. S. P. (2003) Oxime esters of anthraquinone as photo-induced DNA-cleaving agents for single- and double- strand scissions Tetrahedron Lett. 44, 2957-2960
22. Chan, E. W. L. and Yousaf, M. N. (2006) Immobilization of ligands with precise control of density to electroactive surfaces J. Am. Chem. Soc. 128, 15542-15546
23. Chan, E. W. L., Park, S., and Yousaf, M. N. (2008) An electroactive catalytic dynamic substrate that immobilizes and releases patterned ligands, proteins, and cells Angew. Chem., Int. Ed. 47, 6267-6271
24. Lamb, B. M. and Yousaf, M. N. (2011) A redox switchable surface for controlling peptide structure J. Am. Chem. Soc. 133, 8870-8873
25. Luo, W., Chan, E. W. L., and Yousaf, M. N. (2010) Tailored electroactive and quantitative ligand density microarrays applied to stem cell differentiation J. Am. Chem. Soc. 132, 2614-2621
26. Luo, W. and Yousaf, M. N. (2011) Tissue morphing control on dynamic gradient surfaces J. Am. Chem. Soc. 133, 10780-10783
27. Luo, W., Westcott, N. P., Pulsipher, A., and Yousaf, M. N. (2008) Renewable and optically transparent electroactive indium tin oxide surfaces for chemoselective ligand immobilization and biospecific cell adhesion Langmuir 24, 13096-13101
28. Pulsipher, A., Westcott, N. P., Luo, W., and Yousaf, M. N. (2009) Rapid microfluidic generation of patterned aldehydes from hydroxy-terminated self-assembled monolayers for ligand and cell immobilization on optically transparent indium tin oxide surfaces Adv. Mater. 21, 3082-3086
29. Pulsipher, A., Westcott, N. P., Luo, W., and Yousaf, M. N. (2009) Rapid in situ generation of two patterned chemoselective surface chemistries from a single hydroxy-terminated surface using controlled microfluidic oxidation J. Am. Chem. Soc. 131, 7626-7632
30. Miller, E. W. and Chang, C. J. (2007) Fluorescent probes for nitric oxide and hydrogen peroxide in cell signaling Curr. Opin. Chem. Biol. 11, 620-625
31. Scott, P., Ed. (2009) Linker Strategies in Solid-Phase Organic Synthesis, John Wiley & Sons, West Sussex, U.K.
32. Trakselis, M. A., Alley, S. C., and Ishmael, F. T. (2005) Identification and mapping of protein-protein interactions by a combination of cross-linking, cleavage, and proteomics Bioconjugate Chem. 16, 741-750
33. Hermanson, G. T., Ed. (1996) Bioconjugate Techniques, Academic Press, London, U.K.
34. Lambert, J. M., Senter, P. D., Yau-Young, A., Blattler, W. A., and Goldmacher, V. S. (1985) Purified immunotoxins that are reactive with human lymphoid cells. Monoclonal antibodies conjugated to the ribosome-inactivating proteins gelonin and the pokeweed antiviral proteins J. Biol. Chem. 260, 12035-12041
35. Snead, W. K. and Remick, A. E. (1957) Studies on oxidation-reduction mechanism. II. The anodic oxidation of p-aminophenol J. Am. Chem. Soc. 79, 6121-6127
36. Pierschbacher, M. D. and Ruoslahti, E. (1984) Cell attachment activity of fibronectin can be duplicated by small synthetic fragments of the molecule Nature 309, 30-33
37. Aota, S., Nomizu, M., and Yamada, K. M. (1994) The short amino acid sequence Pro-His-Ser-Arg-Asn in human fibronectin enhances cell adhesive functions J. Biol. Chem. 269, 24756-24761
38. Feng, Y. and Mrksich, M. (2004) The synergy peptide PHSRN and the adhesion peptide RGD mediate cell adhesion through a common mechanism Biochemistry 43, 15811-15821
39. Pfaff, M., Tangemann, K., Muller, B., Gurrath, M., Muller, G., Kessler, H., Timple, R., and Engel, J. (1994) Selective recognition of cyclic RGD peptides of NMR defined conformation of alpha IIb beta 3, alpha V beta 3, and alpha 5 beta 1 integrins J. Biol. Chem. 269, 20233-20238
40. Kalia, J. and Raines, R. T. (2008) Hydrolytic stability of hydrazones and oximes Angew. Chem., Int. Ed. 47, 7523-7526
41. Wischerhoff, E., Badi, N., Lutz, J., and Laschewsky, A. (2010) Smart bioactive surfaces Soft Matter 6, 705-713
42. Schnolzer, M. and Kent, S. B. (1992) Constructing proteins by dovetailing unprotected synthetic peptides: backboned engineered HIV protease Science 256, 221-225
43. Dutta, D., Pulsipher, P., Luo, W., and Yousaf, M. N. (2011) Engineering cell surfaces via liposome fusion Bioconjugate Chem. 22, 2423-2433
44. Dutta, D., Pulsipher, A., Luo, W., and Yousaf, M. N. (2011) Synthetic chemoselective rewiring of cell surfaces: generation of three-dimensional tissue structures J. Am. Chem. Soc. 133, 8704-8710