Interactions of oligomers of organic polyethers with histidine amino acid

Rapid Communications in Mass Spectrometry

Volumn 26, Issue 5, 2012, Pages 532-540

  Zobnina, Valentina G ^a   Kosevich, Marina V ^a   Chagovets, Vitaliy V ^a   Boryak, Oleg A ^a   Vékey, Károly ^b   Gömöry, Ágnes ^b   Kulyk, Anna N ^c  

^a B VERKIN INSTITUTE FOR LOW TEMPERATURE PHYSICS AND ENGINEERING   (Ukraine)

^b CHEMICAL RESEARCH CENTER   (Hungary)

^c ALT Ukraine Ltd   (Ukraine)

Author keywords

[No Author keywords available]

Indexed keywords

CHAINS; COORDINATION REACTIONS; DRUG DELIVERY; ETHERS; HYDROGEN BONDS; MASS SPECTROMETRY; MOLECULAR DYNAMICS; NANOPARTICLES; OLIGOMERS; PROTONATION;

AMINO-ACIDS; CRYO PROTECTIONS; DYNAMICS SIMULATION; ELECTROSPRAY MASS SPECTROMETRY; INTERMOLECULAR INTERACTIONS; MODELLING SYSTEMS; NONCOVALENT; ORGANIC NANOPARTICLES; ORGANICS; POLYETHER OLIGOMERS;

AMINO ACIDS;

EID: 84856731496     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.5342     Document Type: Article

References (47)

1. J. Chen, S. K. Spear, J. G. Huddleston, R. D. Rogers,. Polyethylene glycol and solutions of polyethylene glycol as green reaction media. Green Chem. 2005, 7, 64.
2. J. M. Harris, S. Zalipsky,. Poly(Ethylene Glycol): Chemistry and Biological Applications. American Chemical Society, Washington, 1997.
3. A. McPherson Jr,. Crystallization of proteins from polyethylene glycol. J. Biol. Chem. 1976, 251, 6300.
4. Y. Mi, G. Wood, L. Thoma,. Cryoprotection mechanisms of polyethylene glycols on lactate dehydrogenase during freeze-thawing. AAPS J. 2004, 6, 45.
5. F. M. Veronese, G. Pasut,. PEGylation, successful approach to drug delivery. Drug Discovery Today 2005, 10, 1451.
6. P. B. Crowley, K. Brett, J. Muldoon,. NMR spectroscopy reveals cytochrome c-poly(ethylene glycol) interactions. ChemBioChem 2008, 9, 685.
7. R. Michel, S. Pasche, M. Textor, D. G. Castner,. The influence of PEG architecture on protein adsorption and conformation. Langmuir 2005, 21, 12327.
8. G. Hart-Smith, C. Barner-Kowollik,. Contemporary mass spectrometry and the analysis of synthetic polymers: trends, techniques and untapped potential. Macromol. Chem. Phys. 2010, 211, 1507.
9. S. M. Weidner, S. Trimpin,. Mass spectrometry of synthetic polymers. Anal. Chem. 2010, 82, 4811.
10. T. Wyttenbach, G. Helden, M. T. Bowers,. Conformations of alkali ion cationized polyethers in the gas phase: polyethylene glycol and bis[(benzo-15-crown-5)-15-ylmethyl] pimelate. Int. J. Mass Spectrom. Ion Processes 1997, 165/166, 377.
11. J. Gidden, T. Wyttenbach, A. T. Jackson, J. H. Scrivens, M. T. Bowers,. Gas-phase conformations of synthetic polymers: poly(ethylene glycol), poly(propylene glycol), and poly(tetramethylene glycol). J. Am. Chem. Soc. 2000, 122, 4692.
12. A. T. Jackson, J. H. Scrivens, J. P. Williams, E. S. Baker, J. Gidden, M. T. Bowers,. Microstructural and conformational studies of polyether copolymers. Int. J. Mass Spectrom. 2004, 238, 287.
13. Y. Wang, H. Rashidzadeh, B. Guo,. Structural effects on polyether cationization by alkali metal ions in matrix-assisted laser desorption/ ionization. J. Am. Soc. Mass. Spectrom. 2000, 11, 639.
14. K. Shimada, S. Matsuyama, T. Saito, S. Kinugasa, R. Nagahata, S. Kawabata,. Conformational effects on cationization of poly(ethylene glycol) by alkali metal ions in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Int. J. Mass Spectrom. 2005, 247, 85.
15. Y. Yokoyama, R. Hirajima, K. Morigaki, Y. Yamaguchi, K. Ueda,. Alkali-cation affinities of polyoxyethylene dodecylethers and helical conformations of their cationized molecules studied by electrospray mass spectrometry. J. Am. Soc. Mass Spectrom. 2007, 18, 1914.
16. S. Ude, J. F. de la Mora, B. A. Thomson,. Charge-induced unfolding of multiply charged polyethylene glycol ions. J. Am. Chem. Soc. 2004, 126, 12184.
17. S. Trimpin, M. Plasencia, D. Isailovic, D. E. Clemmer,. Resolving oligomers from fully grown polymers with IMS-MS. Anal. Chem. 2007, 79, 7965.
18. P. Hurtado, A. R. Hortal, F. Gámez, S. Hamad, B. Martínez-Haya,. Gas-phase complexes of cyclic and linear polyethers with alkali cations. Phys. Chem. Chem. Phys. 2010, 12, 13752.
19. +: a first-principles study. Eur. J. Mass Spectrom. 2011, 17, 33.
20. M. V. Kosevich, V. G. Zobnina, V. V. Chagovets, O. A. Boryak,. Observation of poly(ethylene glycol) clusters with the chlorine anion in the gas phase under electrospray conditions. Rapid Commun. Mass Spectrom. 2011, 25, 713.
21. D. Q. Xu, S. P. Luo, Y. F. Wang, A. B. Xia, H. D. Yue, L. P. Wang, Z. Y. Xu,. Organocatalysts wrapped around by poly(ethylene glycol)s (PEGs): a unique host-guest system for asymmetric Michael addition reactions. Chem. Commun. 2007, 42, 4393.
22. M. L. Colgrave, C. J. Bramwell, C. S. Creaser,. Nanoelectrospray ion mobility spectrometry and ion trap mass spectrometry studies of the noncovalent complexes of amino acids and peptides with polyethers. Int. J. Mass Spectrom. 2003, 229, 209.
23. M. D. Howdle, C. Eckers, A. M.-F. Laures, C. S. Creaser,. The use of shift reagents in ion mobility-mass spectrometry: Studies on the complexation of an active pharmaceutical ingredient with polyethylene glycol excipients. J. Am. Soc. Mass Spectrom. 2009, 20, 1.
24. I. V. Terekhova, O. V. Kulikov, R. S. Kumeev, M. Yu. Nikiforov, G. A. Al'per. Complexation of amino acids with 18-crown-6. Russ. J. Gen. Chem. 2005, 75, 409.
25. R. R. Julian, J. L. Beauchamp,. Site specific sequestering and stabilization of charge in peptides by supramolecular adduct formation with 18-crown-6 ether by way of electrospray ionization. Int. J. Mass Spectrom. 2001, 210/211, 613.
26. P. Gerbaux, J. De Winter, D. Cornil, K. Ravicini, G. Pesesse, J. Cornil, R. Flammang,. Noncovalent interactions between ([18]crown-6)-tetracarboxylic acid and amino acids: electrospray-ionization mass spectrometry investigation of the chiral-recognition processes. Chem. Eur. J. 2008, 14, 11039.
27. A. I. Zhmakin,. Fundamentals of Cryobiology: Physical Phenomena and Mathematical Models (Biological and Medical Physics, Biomedical Engineering). Springer-Verlag, Berlin Heidelberg, 2009.
28. B. W. W. Grout, G. J. Morris,. The Effects of Low Temperatures on Biological Systems. Edward Arnold, London, 1987.
29. M. V. Kosevich,. Low temperature secondary emission mass spectrometry. Cryobiological applications. Eur. Mass Spectrom. 1998, 4, 251.
30. F. M. Veronese,. Peptide and protein PEGylation: a review of problems and solutions. Biomaterials 2001, 22, 405.
31. L. E. van Vlerken, T. K. Vyas, M. M. Amiji,. Poly(ethylene glycol)-modified nanocarriers for tumor-targeted and intracellular delivery. Pharm. Res. 2007, 24, 1405.
32. O. A. Boryak, M. V. Kosevich, V. S. Shelkovsky,. Mass spectrometric study of liquid solution of amino acid proline in ethanol at temperatures below 0°C. Proc. Kharkov State Univ.: Biophys. Bull. 2000, 488, 44.
33. M. V. Kosevich, V. G. Zobnina, O. A. Boryak, V. S. Shelkovsky, A. Gomory, K. Vekey,. Study of amino acid valine solution in ethylene glycol cryoprotector at low temperatures by means of secondary ion mass spectrometry. Mass-Spectrometria 2006, 3, 33 (in Russian).
34. V. G. Zobnina, V. V. Chagovets, M. V. Kosevich, O. A. Boryak, A. Gomory,. Mass spectrometric and molecular dynamics study of polyethers noncovalent binding to charged groups of amino acids. Abstracts, 28th Informal Meeting on Mass Spectrometry, Koszeg, Hungary, May 2-6, 2010, 100.
35. A. B. Hughes,. Amino Acids, Peptides and Proteins in Organic Chemistry, vol. 1. Origins and Synthesis of Amino Acids. Wiley-VCH, Weinheim, 2009.
36. Z. Fisher, J. A. Hernandez Prada, C. Tu, D. Duda, C. Yoshioka, H. An, L. Govindasamy, D. N. Silverman, R. McKenna,. Structural and kinetic characterization of active-site histidine as a proton shuttle in catalysis by human carbonic anhydrase II. Biochemistry 2005, 44, 1097.
37. B. R. Brooks, C. L. Brooks III, A. D. Mackerell, L. Nilsson Jr, R. J. Petrella, B. Roux, Y. Won, G. Archontis, C. Bartels, S. Boresch, A. Caflisch, L. Caves, Q. Cui, A. R. Dinner, M. Feig, S. Fischer, J. Gao, M. Hodoscek, W. Im, K. Kuczera, T. Lazaridis, J. Ma, V. Ovchinnikov, E. Paci, R. W. Pastor, C. B. Post, J. Z. Pu, M. Schaefer, B. Tidor, R. M. Venable, H. L. Woodcock, X. Wu, W. Yang, D. M. York, M. Karplus,. CHARMM: The biomolecular simulation program. J. Comput. Chem. 2009, 30, 1545.
38. H. Lee, R. M. Venable, A. D. MacKerell Jr, R. W. Pastor,. Molecular dynamics studies of polyethylene oxide and polyethylene glycol: hydrodynamic radius and shape anisotropy. Biophys. J. 2008, 95, 1590.
39. J. C. Phillips, R. Braun, W. Wang, J. Gumbart, E. Tajkhorshid, E. Villa, C. Chipot, R. D. Skeel, L. Kale, K. Schulten,. Scalable molecular dynamics with NAMD. J. Comput. Chem. 2005, 26, 1781.
40. ChemCraft. Available:.
41. R. B. Cole,. Electrospray Ionization Mass Spectrometry: Fundamentals, Instrumentation and Applications. Wiley-Interscience, New York, 1997.
42. J. F. de la Mora, G. J. Van Berkel, C. G. Enke, R. B. Cole, M. Martinez-Sanchez, J. B. Fenn,. Electrochemical processes in electrospray ionization mass spectrometry. J. Mass Spectrom. 2000, 35, 939.
43. P. Kebarle, U. H. Verkerk,. Electrospray: from ions in solution to ions in the gas phase, what we know now. Mass Spectrom. Rev. 2009, 28, 898.
44. T. Wyttenbach, M. Witt, M. T. Bowers,. On the stability of amino acid zwitterions in the gas phase: The influence of derivatization, proton affinity, and alkali ion addition. J. Am. Chem. Soc. 2000, 122, 3458.
45. B. Gao, T. Wyttenbach, M. T. Bowers,. Protonated arginine and protonated lysine: Hydration and its effect on the stability of salt-bridge structures. J. Phys. Chem. B 2009, 113, 9995.
46. R. A. Jockusch, A. S. Lemoff, E. R. Williams,. Effect of metal ion and water coordination on the structure of a gas-phase amino acid. J. Am. Chem. Soc. 2001, 123, 12255.
47. Y. Xue, M. L. O'Mara, P. P. T. Surawski, M. Trau, A. E. Mark,. Effect of poly(ethylene glycol) (PEG) spacers on the conformational properties of small peptides: A molecular dynamics study. Langmuir 2011, 27, 296.