Biomimetic N-terminal alkylation of peptoid analogues of surfactant protein C

Biophysical Journal

Volumn 101, Issue 5, 2011, Pages 1076-1085

  Brown, Nathan J ^a   Dohm, Michelle T ^b   Bernardino De La Serna, Jorge ^c   Barron, Annelise E ^a,b  

^a Northwestern University   (United States)

^b Stanford University   (United States)

^c UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMIMETIC MATERIAL; PEPTOID; SURFACTANT PROTEIN C;

ALKYLATION; AMINO ACID SEQUENCE; ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL PHENOMENA; CHEMISTRY; DRUG DESIGN; FLUORESCENCE MICROSCOPY; HUMAN; PROTEIN SECONDARY STRUCTURE; SURFACE PROPERTY;

ALKYLATION; AMINO ACID SEQUENCE; BIOMIMETIC MATERIALS; DRUG DESIGN; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MICROSCOPY, ATOMIC FORCE; MICROSCOPY, FLUORESCENCE; PEPTOIDS; PROTEIN STRUCTURE, SECONDARY; PULMONARY SURFACTANT-ASSOCIATED PROTEIN C; SURFACE PROPERTIES;

EID: 80052469095     PISSN: 00063495     EISSN: 15420086     Source Type: Journal    
DOI: 10.1016/j.bpj.2011.04.055     Document Type: Article

References (43)

1. R. Veldhuizen, and K. Nag F. Possmayer The role of lipids in pulmonary surfactant Biochim. Biophys. Acta 1408 1998 90 108 (Pubitemid 28517860)
2. A. Almlén, and G. Stichtenoth T. Curstedt Surfactant proteins B and C are both necessary for alveolar stability at end expiration in premature rabbits with respiratory distress syndrome J. Appl. Physiol. 104 2008 1101 1108 (Pubitemid 351507950)
3. L. Gómez-Gil, and D. Schürch J. Pérez-Gil Pulmonary surfactant protein SP-C counteracts the deleterious effects of cholesterol on the activity of surfactant films under physiologically relevant compression-expansion dynamics Biophys. J. 97 2009 2736 2745
4. J. Johansson, and T. Szyperski K. Wüthrich The NMR structure of the pulmonary surfactant-associated polypeptide SP-C in an apolar solvent contains a valyl-rich α-helix Biochemistry 33 1994 6015 6023 (Pubitemid 24184607)
5. G. Vandenbussche, and A. Clercx J.M. Ruysschaert Structure and orientation of the surfactant-associated protein C in a lipid bilayer Eur. J. Biochem. 203 1992 201 209
6. A. Gonzalez-Horta, and D. Andreu J. Perez-Gil Effects of palmitoylation on dynamics and phospholipid-bilayer-perturbing properties of the N-terminal segment of pulmonary surfactant protein SP-C as shown by 2H-NMR Biophys. J. 95 2008 2308 2317
7. T.E. Weaver, and J.J. Conkright Function of surfactant proteins B and C Annu. Rev. Physiol. 63 2001 555 578
8. M.A. Oosterlaken-Dijksterhuis, and H.P. Haagsman R.A. Demel Characterization of lipid insertion into monomolecular layers mediated by lung surfactant proteins SP-B and SP-C Biochemistry 30 1991 10965 10971
9. S.G. Taneva, and K.M.W. Keough Dynamic surface properties of pulmonary surfactant proteins SP-B and SP-C and their mixtures with dipalmitoylphosphatidylcholine Biochemistry 33 1994 14660 14670
10. D.Y. Takamoto, and M.M. Lipp J.A. Zasadzinski Interaction of lung surfactant proteins with anionic phospholipids Biophys. J. 81 2001 153 169 (Pubitemid 32605959)
11. A. von Nahmen, and M. Schenk M. Amrein The structure of a model pulmonary surfactant as revealed by scanning force microscopy Biophys. J. 72 1997 463 469 (Pubitemid 27043458)
12. N.J. Brown, J. Johansson, and A.E. Barron Biomimicry of surfactant protein C Acc. Chem. Res. 41 2008 1409 1417
13. M. Gustafsson, and J. Thyberg J. Johansson Amyloid fibril formation by pulmonary surfactant protein C FEBS Lett. 464 1999 138 142 (Pubitemid 30017930)
14. C.W. Wu, and S.L. Seurynck A.E. Barron Helical peptoid mimics of lung surfactant protein C Chem. Biol. 10 2003 1057 1063 (Pubitemid 37496436)
15. N.J. Brown, and C.W. Wu A.E. Barron Effects of hydrophobic helix length and side chain chemistry on biomimicry in peptoid analogues of SP-C Biochemistry 47 2008 1808 1818 (Pubitemid 351231230)
16. R.N. Zuckermann, and J.M. Kerr W.H. Moos Efficient method for the preparation of peptoids oligo(n-substituted glycines) by submonomer solid-phase synthesis J. Am. Chem. Soc. 114 1992 10646 10647
17. C.W. Wu, and K. Kirshenbaum A.E. Barron Structural and spectroscopic studies of peptoid oligomers with α-chiral aliphatic side chains J. Am. Chem. Soc. 125 2003 13525 13530 (Pubitemid 37352134)
18. P. Armand, and K. Kirshenbaum E.K. Bradley NMR determination of the major solution conformation of a peptoid pentamer with chiral side chains Proc. Natl. Acad. Sci. USA 95 1998 4309 4314 (Pubitemid 28207908)
19. T.J. Sanborn, and C.W. Wu A.E. Barron Extreme stability of helices formed by water-soluble poly-N-substituted glycines (polypeptoids) with α-chiral side chains Biopolymers 63 2002 12 20 (Pubitemid 34076032)
20. I. Plasencia, K.M.W. Keough, and J. Perez-Gil Interaction of the N-terminal segment of pulmonary surfactant protein SP-C with interfacial phospholipid films Biochim. Biophys. Acta 1713 2005 118 128 (Pubitemid 40965532)
21. J. Pérez-Gil, A. Cruz, and C. Casals Solubility of hydrophobic surfactant proteins in organic solvent/water mixtures. Structural studies on SP-B and SP-C in aqueous organic solvents and lipids Biochim. Biophys. Acta 1168 1993 261 270 (Pubitemid 23197695)
22. S.L. Seurynck, and N.J. Brown M. Johnson Optical monitoring of bubble size and shape in a pulsating bubble surfactometer J. Appl. Physiol. 99 2005 624 633 (Pubitemid 41061158)
23. F. Bringezu, and J.Q. Ding J.A. Zasadzinski Changes in model lung surfactant monolayers induced by palmitic acid Langmuir 17 2001 4641 4648 (Pubitemid 35330270)
24. M.D. Abramoff, P.J. Magelhaes, and S.J. Ram Image processing with ImageJ Biophoton. Int. 11 2004 36 42
25. M.T. Dohm, and N.J. Brown A.E. Barron Mimicking SP-C palmitoylation on a peptoid-based SP-B analogue markedly improves surface activity Biochim. Biophys. Acta 1798 2010 1663 1678
26. P. Na Nakorn, and M.C. Meyer H.J. Galla Surfactant protein C and lung function: new insights into the role of α-helical length and palmitoylation Eur. Biophys. J. 36 2007 477 489 (Pubitemid 46626196)
27. Z.D. Wang, S.B. Hall, and R.H. Notter Roles of different hydrophobic constituents in the adsorption of pulmonary surfactant J. Lipid Res. 37 1996 790 798 (Pubitemid 26140815)
28. J. Johansson, T. Curstedt, and B. Robertson Artificial surfactants based on analogues of SP-B and SP-C Pediatr. Pathol. Mol. Med. 20 2001 501 518 (Pubitemid 32983394)
29. E.C. Smith, and J.M. Crane S.B. Hall Metastability of a supercompressed fluid monolayer Biophys. J. 85 2003 3048 3057 (Pubitemid 37345792)
30. A. Gopal, and K.Y.C. Lee Morphology and collapse transitions in binary phospholipid monolayers J. Phys. Chem. B 105 2001 10348 10354 (Pubitemid 35338587)
31. K. Nag, and J. Perez-Gil K.M. Keough Fluorescently labeled pulmonary surfactant protein C in spread phospholipid monolayers Biophys. J. 71 1996 246 256 (Pubitemid 26227311)
32. J. Pérez-Gil, and K. Nag K.M. Keough Pulmonary surfactant protein SP-C causes packing rearrangements of dipalmitoylphosphatidylcholine in spread monolayers Biophys. J. 63 1992 197 204
33. M. Amrein, A. von Nahmen, and M. Sieber A scanning force- and fluorescence light microscopy study of the structure and function of a model pulmonary surfactant Eur. Biophys. J. 26 1997 349 357 (Pubitemid 27431867)
34. J.Q. Ding, and D.Y. Takamoto J.A. Zasadzinski Effects of lung surfactant proteins, SP-B and SP-C, and palmitic acid on monolayer stability Biophys. J. 80 2001 2262 2272 (Pubitemid 32401991)
35. J.M. Crane, and S.B. Hall Rapid compression transforms interfacial monolayers of pulmonary surfactant Biophys. J. 80 2001 1863 1872
36. R.W. Walters, R.R. Jenq, and S.B. Hall Distinct steps in the adsorption of pulmonary surfactant to an air-liquid interface Biophys. J. 78 2000 257 266 (Pubitemid 30207135)
37. P. Krüger, and J.E. Baatz M. Lösche Effect of hydrophobic surfactant protein SP-C on binary phospholipid monolayers. Molecular machinery at the air/water interface Biophys. Chem. 99 2002 209 228 (Pubitemid 36158920)
38. A. Kramer, and A. Wintergalen R. Guckenberger Distribution of the surfactant-associated protein C within a lung surfactant model film investigated by near-field optical microscopy Biophys. J. 78 2000 458 465 (Pubitemid 30207154)
39. J. Perez-Gil Structure of pulmonary surfactant membranes and films: the role of proteins and lipid-protein interactions Biochim. Biophys. Acta 1778 2008 1676 1695
40. X.H. Bi, and C.R. Flach R. Mendelsohn Secondary structure and lipid interactions of the N-terminal segment of pulmonary surfactant SP-C in Langmuir films: IR reflection-absorption spectroscopy and surface pressure studies Biochemistry 41 2002 8385 8395 (Pubitemid 34705492)
41. M. Gustafsson, and M. Palmblad S. Schurch Palmitoylation of a pulmonary surfactant protein C analogue affects the surface associated lipid reservoir and film stability Biochim. Biophys. Acta 1466 2000 169 178 (Pubitemid 30312974)
42. I. Plasencia, and F. Baumgart J. Perez-Gil Effect of acylation on the interaction of the N-Terminal segment of pulmonary surfactant protein SP-C with phospholipid membranes Biochim. Biophys. Acta 1778 2008 1274 1282
43. A. ten Brinke, L.M.G. van Golde, and J.J. Batenburg Palmitoylation and processing of the lipopeptide surfactant protein C Biochim. Biophys. Acta 1583 2002 253 265