Single-molecule force-clamp experiments reveal kinetics of mechanically activated silyl ester hydrolysis

ACS Nano

Volumn 6, Issue 2, 2012, Pages 1314-1321

  Schmidt, Sebastian W ^a,b,c   Filippov, Pavel ^a   Kersch, Alfred ^a   Beyer, Martin K ^b   Clausen Schaumann, Hauke ^a,c  

^a MUNICH UNIVERSITY OF APPLIED SCIENCES   (Germany)

^b UNIVERSITY OF KIEL   (Germany)

^c UNIVERSITY OF MUNICH   (Germany)

Author keywords

acyloxysilane; force clamp spectroscopy; hydrolysis; mechanochemistry; silyl ester; single molecule force spectroscopy

Indexed keywords

ACTIVATION ENERGY; ESTERS; HYDROLYSIS; KINETICS; MOLECULES; MORSE POTENTIAL; RATE CONSTANTS; SILICON COMPOUNDS; SILICON OXIDES;

ACYLOXYSILANE; FORCE CLAMP; MECHANO-CHEMISTRY; SILYL ESTERS; SINGLE MOLECULE FORCE SPECTROSCOPY;

MAXIMUM LIKELIHOOD ESTIMATION;

EID: 84857720312     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn204111w     Document Type: Article

References (61)

1. Rief, M.; Gautel, M.; Oesterhelt, F.; Fernandez, J. M.; Gaub, H. E. Reversible Unfolding of Individual Titin Immunoglobulin Domains by AFM Science 1997, 276, 1109-1112 (Pubitemid 27218118)
2. Smith, S. B.; Finzi, L.; Bustamante, C. Direct Mechanical Measurements of the Elasticity of Single DNA Molecules by Using Magnetic Beads Science 1992, 258, 1122-1126
3. Rief, M.; Clausen-Schaumann, H.; Gaub, H. E. Sequence-Dependent Mechanics of Single DNA Molecules Nat. Struct. Biol. 1999, 6, 346-349 (Pubitemid 29166483)
4. Florin, E. L.; Moy, V. T.; Gaub, H. E. Adhesion Forces between Individual Ligand-Receptor Pairs Science 1994, 264, 415-417 (Pubitemid 24179839)
5. Hinterdorfer, P.; Baumgartner, W.; Gruber, H. J.; Schilcher, K.; Schindler, H. Detection and Localization of Individual Antibody-Antigen Recognition Events by Atomic Force Microscopy Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 3477-3481 (Pubitemid 26125645)
6. Merkel, R.; Nassoy, P.; Leung, A.; Ritchie, K.; Evans, E. Energy Landscapes of Receptor-Ligand Bonds Explored with Dynamic Force Spectroscopy Nature 1999, 397, 50-53 (Pubitemid 29038244)
7. Schwesinger, F.; Ros, R.; Strunz, T.; Anselmetti, D.; Guntherodt, H. J.; Honegger, A.; Jermutus, L.; Tiefenauer, L.; Pluckthun, A. Unbinding Forces of Single Antibody-Antigen Complexes Correlate with Their Thermal Dissociation Rates Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 9972-9977
8. Grandbois, M.; Beyer, M.; Rief, M.; Clausen-Schaumann, H.; Gaub, H. E. How Strong is a Covalent Bond? Science 1999, 283, 1727-1730 (Pubitemid 129502058)
9. Lantz, M. A.; Hug, H. J.; Hoffmann, R.; van Schendel, P. J. A.; Kappenberger, P.; Martin, S.; Baratoff, A.; Guntherodt, H. J. Quantitative Measurement of Short-Range Chemical Bonding Forces Science 2001, 291, 2580-2583 (Pubitemid 32249678)
10. Wiita, A. P.; Ainavarapu, S. R. K.; Huang, H. H.; Fernandez, J. M. Force-Dependent Chemical Kinetics of Disulfide Bond Reduction Observed with Single-Molecule Techniques Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 7222-7227 (Pubitemid 43727814)
11. Schwaderer, P.; Funk, E.; Achenbach, F.; Weis, J.; Bräuchle, C.; Michaelis, J. Single-Molecule Measurement of the Strength of a Siloxane Bond Langmuir 2007, 24, 1343-1349
12. Schmidt, S. W.; Beyer, M. K.; Clausen-Schaumann, H. Dynamic Strength of the Silicon-Carbon Bond Observed over Three Decades of Force-Loading Rates J. Am. Chem. Soc. 2008, 130, 3664-3668 (Pubitemid 351456071)
13. Schmidt, S. W.; Kersch, A.; Beyer, M. K.; Clausen-Schaumann, H. Mechanically Activated Rupture of Single Covalent Bonds: Evidence of Force Induced Bond Hydrolysis Phys. Chem. Chem. Phys. 2011, 13, 5994-5999
14. Zheng, P.; Li, H. Highly Covalent Ferric-Thiolate Bonds Exhibit Surprisingly Low Mechanical Stability J. Am. Chem. Soc. 2011, 133, 6791-6798
15. Oberhauser, A. F.; Hansma, P. K.; Carrion-Vazquez, M.; Fernandez, J. M. Stepwise Unfolding of Titin under Force-Clamp Atomic Force Microscopy Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 468-472 (Pubitemid 32105065)
16. Fernandez, J. M.; Li, H. Force-Clamp Spectroscopy Monitors the Folding Trajectory of a Single Protein Science 2004, 303, 1674-1678 (Pubitemid 38338326)
17. Bullard, B.; Garcia, T.; Benes, V.; Leake, M. C.; Linke, W. A.; Oberhauser, A. F. The Molecular Elasticity of the Insect Flight Muscle Proteins Projectin and Kettin Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 4451-4456
18. Ainavarapu, S. R. K.; Wiita, A. P.; Dougan, L.; Uggerud, E.; Fernandez, J. M. Single-Molecule Force Spectroscopy Measurements of Bond Elongation during a Bimolecular Reaction J. Am. Chem. Soc. 2008, 130, 6479-6487 (Pubitemid 351706111)
19. Szoszkiewicz, R.; Ainavarapu, S. R. K.; Wiita, A. P.; Perez-Jimenez, R.; Sanchez-Ruiz, J. M.; Fernandez, J. M. Dwell Time Analysis of a Single-Molecule Mechanochemical Reaction Langmuir 2008, 24, 1356-1364 (Pubitemid 351345857)
20. Liang, J.; Fernandez, J. M. Kinetic Measurements on Single-Molecule Disulfide Bond Cleavage J. Am. Chem. Soc. 2011, 133, 3528-3534
21. Schmidt, S. W.; Christ, T.; Glockner, C.; Beyer, M. K.; Clausen-Schaumann, H. Simple Coupling Chemistry Linking Carboxyl-Containing Organic Molecules to Silicon Oxide Surfaces under Acidic Conditions Langmuir 2010, 26, 15333-15338
22. Hudrlik, P. F.; Feasley, R. The Reactions of Nucleophiles with Acyloxysilanes Tetrahedron Lett. 1972, 13, 1781-1784
23. Cunico, R. F.; Bedell, L. The Triisopropylsilyl Group as a Hydroxyl-Protecting Function J. Org. Chem. 1980, 45, 4797-4798
24. Gitto, S. P.; Wooley, K. L. Poly(silyl ester)s: A New Family of Hydrolytically-Degradable Polymers with Attunable Stabilities Macromolecules 1995, 28, 8887-8889
25. Weinberg, J. M.; Gitto, S. P.; Wooley, K. L. Synthesis and Characterization of Degradable Poly(silyl ester)s Macromolecules 1998, 31, 15-21 (Pubitemid 128569491)
26. Wang, M.; Weinberg, J. M.; Wooley, K. L. Synthesis, Characterization and Degradation of Poly(silyl ester)s Macromolecules 1998, 31, 7606-7612 (Pubitemid 128557091)
27. Wang, M.; Weinberg, J. M.; Wooley, K. L. Geminal Poly(silyl ester)s: Highly Labile Degradable Polymers J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 3606-3613
28. Liu, Z.; Han, N.; Dong, J. Poly(silyl ester)s: A New Route of Synthesis via the Condensation of Di- tert -butyl Ester of Dicarboxylic Acid with Dichlorosilane J. Appl. Polym. Sci. 2006, 100, 1378-1384
29. Downing, C. M.; Missaghi, M. N.; Kung, M. C.; Kung, H. H. Design and Synthesis of Readily Degradable Acyloxysilane Dendrimers Tetrahedron 2011, 67, 7502-7509
30. Bressy, C.; Nguyen, M. N.; Tanguy, B.; Ngo, V. G.; Margaillan, A. Poly(trialkylsilyl methacrylate)s: A Family of Hydrolysable Polymers with Tuneable Erosion Profiles Polym. Degrad. Stab. 2011, 95, 1260-1268
31. Vert, M.; Li, S. M.; Spenlehauer, G.; Guerin, P. Bioresorbability and Biocompatibility of Aliphatic Polyesters J. Mater. Sci.: Mater. Med. 1992, 3, 432-446
32. Ikada, Y.; Tsuji, H. Biodegradable Polyesters for Medical and Ecological Applications Macromol. Rapid Commun. 2000, 21, 117-132
33. Mohanty, A. K.; Misra, M.; Hinrichsen, G. Biofibres, Biodegradable Polymers and Biocomposites: An Overview Macromol. Mater. Eng. 2000, 276-277, 1-24
34. Nair, L. S.; Laurencin, C. T. Biodegradable Polymers as Biomaterials Prog. Polym. Sci. 2007, 32, 762-798 (Pubitemid 47198287)
35. Brandt, S. In Data Analysis: Statistical and Computational Methods for Scientists and Engineers, 3 rd ed.; Springer Verlag: Berlin, 1998; pp 187-211.
36. Rief, M.; Oesterhelt, F.; Heymann, B.; Gaub, H. E. Single Molecule Force Spectroscopy on Polysaccharides by Atomic Force Microscopy Science 1997, 275, 1295-1297 (Pubitemid 27114155)
37. Marszalek, P. E.; Oberhauser, A. F.; Pang, Y. P.; Fernandez, J. M. Polysaccharide Elasticity Governed by Chair-Boat Transitions of the Glucopyranose Ring Nature 1998, 396, 661-664 (Pubitemid 29003941)
38. Li, H. B.; Rief, M.; Oesterhelt, F.; Gaub, H. E.; Zhang, X.; Shen, J. C. Single-Molecule Force Spectroscopy on Polysaccharides by AFMî - ̧Nanomechanical Fingerprint of α-(1,4)-Linked Polysaccharides Chem. Phys. Lett. 1999, 305, 197-201 (Pubitemid 129607058)
39. Heymann, B.; Grubmüller, H. 'Chair-Boat' Transitions and Side Groups Affect the Stiffness of Polysaccharides Chem. Phys. Lett. 1999, 305, 202-208 (Pubitemid 129607059)
40. Fraile, R.; Garcia-Ortega, E. Fitting an Exponential Distribution J. Appl. Meteorol. 2005, 44, 1620-1625 (Pubitemid 41694299)
41. Zhurkov, S. N.; Korsukov, V. E. Atomic Mechanism of Fracture of Solid Polymers J. Polym. Sci., Part B: Polym. Phys. 1974, 12, 385-398
42. Bell, G. I. Models for Specific Adhesion of Cells to Cells Science 1978, 200, 618-627
43. Kauzmann, W.; Eyring, H. The Viscous Flow of Large Molecules J. Am. Chem. Soc. 1940, 62, 3113-3125
44. Beyer, M. K. The Mechanical Strength of a Covalent Bond Calculated by Density Functional Theory J. Chem. Phys. 2000, 112, 7307-7312
45. Hanke, F.; Kreuzer, H. J. Breaking Bonds in the Atomic Force Microscope: Theory and Analysis Phys. Rev. E 2006, 74, 0319091-0319095
46. Iozzi, M. F.; Helgaker, T.; Uggerud, E. Assessment of Theoretical Methods for the Determination of the Mechanochemical Strength of Covalent Bonds Mol. Phys. 2009, 107, 2537-2546
47. Konieczny, S.; Wojnowski, W. Beiträge zur Chemie der Silicium-Schwefel-Verbindungen. 52 [1]. Reaktion von Trialkoxysilanthiolen mit Carbonsäuren. Darstellung und Hydrolyse der Trialkoxyacyloxysilane Z. Anorg. Allg. Chem. 1988, 562, 153-159
48. Sharp, K. G. A Two-Component, Non-aqueous Route to Silica Gel J. Sol-Gel Sci. Technol. 1994, 2, 35-41
49. Lourderaj, U.; McAfee, J. L.; Hase, W. L. Potential Energy Surface and Unimolecular Dynamics of Stretched n -Butane J. Chem. Phys. 2008, 129, 0947011-09470110
50. Liu, G. B.; Zhao, H. Y.; Thiemann, T. Triphenylphosphine-Catalyzed Dehydrogenative Coupling Reaction of Carboxylic Acids with Silanes - A Convenient Method for the Preparation of Silyl Esters Adv. Synth. Catal. 2007, 349, 807-811
51. García, S. J.; Fischer, H. R.; White, P. A.; Mardel, J.; González-García, Y.; Mol, J. M. C.; Hughes, A. E. Self-Healing Anticorrosive Organic Coating Based on an Encapsulated Water Reactive Silyl Ester: Synthesis and Proof of Concept Prog. Org. Coat. 2011, 70, 142-149
52. Schlierf, M.; Rief, M. Single-Molecule Unfolding Force Distributions Reveal a Funnel-Shaped Energy Landscape Biophys. J. 2006, 90, L33-L35
53. Ribas-Arino, J.; Shiga, M.; Marx, D. Unravelling the Mechanism of Force-Induced Ring-Opening of Benzocyclobutenes Chem. - Eur. J. 2009, 15, 13331-13335
54. Li, W. J.; Gräter, F. Atomistic Evidence of How Force Dynamically Regulates Thiol/Disulfide Exchange J. Am. Chem. Soc. 2010, 132, 16790-16795
55. Bershtein, V. A.; Egorova, L. M.; Solov'ev, V. V. Disintegration of Polymers by a Hydrolytic Mechanism Mech. Compos. Mater. 1977, 13, 715-721
56. Mabey, W.; Mill, T. Critical Review of Hydrolysis of Organic Compounds in Water under Environmental Conditions J. Phys. Chem. Ref. Data 1978, 7, 383-415 (Pubitemid 8612537)
57. Wang, H.; Harris, J. M. Surface Diffusion of Organosiloxane Ligands Covalently Bound to Silica J. Am. Chem. Soc. 1994, 116, 5754-5761 (Pubitemid 24981182)
58. Arkles, B. Tailoring Surfaces with Silanes CHEMTECH 1977, 7, 766-778
59. Ribas-Arino, J.; Shiga, M.; Marx, D. Understanding Covalent Mechanochemistry Angew. Chem., Int. Ed. 2009, 48, 4190-4193
60. Ribas-Arino, J.; Shiga, M.; Marx, D. Mechanochemical Transduction of Externally Applied Forces to Mechanophores J. Am. Chem. Soc. 2010, 132, 10609-10614
61. Butt, H.-J.; Jaschke, M. Calculation of Thermal Noise in Atomic Force Microscopy Nanotechnology 1995, 6, 1-7