Conformation of the Poly(ethylene Glycol) Chains in DiPEGylated Hemoglobin Specifically Probed by SANS: Correlation with PEG Length and in Vivo Efficiency

Langmuir

Volumn 31, Issue 30, 2015, Pages 8402-8410

  Le Cœur, Clémence ^a,c   Combet, Sophie ^a   Carrot, Géraldine ^a   Busch, Peter ^b   Teixeira, José ^a   Longeville, Stéphane ^a  

^a LABORATOIRE LÉON BRILLOUIN   (France)

^b FORSCHUNGSZENTRUM JÜLICH   (Germany)

^c CNRS Université Paris Est Créteil Val de Marne   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCOMPATIBILITY; CHAINS; ETHYLENE GLYCOL; GRAFTING (CHEMICAL); HEMOGLOBIN; NEUTRON SCATTERING; PHYSIOLOGICAL MODELS; PHYSIOLOGY; POLYETHYLENE OXIDES; POLYMERS; POLYOLS; PROTEINS;

BIOCOMPATIBLE POLYMER; CELL FREE HEMOGLOBIN; CHAIN CONFORMATIONS; CONTRAST VARIATION; PHYSIOLOGICAL DATA; POLY(ETHYLENE GLYCOL) CHAINS; POLYMER MOLECULAR WEIGHT; RADIUS OF GYRATION;

POLYETHYLENE GLYCOLS;

HEMOGLOBIN; MACROGOL DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HUMAN; NEUTRON DIFFRACTION; SMALL ANGLE SCATTERING;

HEMOGLOBINS; HUMANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NEUTRON DIFFRACTION; POLYETHYLENE GLYCOLS; SCATTERING, SMALL ANGLE;

EID: 84938629639     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/acs.langmuir.5b01121     Document Type: Article

References (38)

1. Alayash, A. I. Oxygen therapeutics: Can we tame haemoglobin? Nat. Rev. Drug Discovery 2004, 3, 152-159 10.1038/nrd1307
2. Winslow, R. M. Cell-free oxygen carriers: Scientific foundations, clinical development, and new directions Biochim. Biophys. Acta, Proteins Proteomics 2008, 1784, 1382-1386 10.1016/j.bbapap.2008.04.032
3. Kluger, R. Red cell substitutes from hemoglobin-Do we start all over again? Curr. Opin. Chem. Biol. 2010, 14, 538-543 10.1016/j.cbpa.2010.03.021
4. Rohlfs, R. J.; Bruner, E.; Chiu, A.; Gonzales, A.; Gonzales, M. L.; Magde, D.; Magde, M. D.; Vandegriff, K. D.; Winslow, R. M. Arterial blood pressure responses to cell-free hemoglobin solutions and the reaction with nitric oxide J. Biol. Chem. 1998, 273, 12128-12134 10.1074/jbc.273.20.12128
5. Zhang, J.; Cao, S. Y.; Kwansa, H.; Crafa, D.; Kibler, K. K.; Koehler, R. C. Transfusion of hemoglobin-based oxygen carriers in the carboxy state is beneficial during transient focal cerebral ischemia J. Appl. Physiol. 2012, 113, 1709-1717 10.1152/japplphysiol.01079.2012
6. Vandegriff, K. D.; Winslow, R. M. Hemospan: Design Principles for a New Class of Oxygen Therapeutic Artif. Organs 2009, 33, 133-138 10.1111/j.1525-1594.2008.00697.x
7. Veronese, F. M. Peptide and protein PEGylation: a review of problems and solutions Biomaterials 2001, 22, 405-417 10.1016/S0142-9612(00)00193-9
8. Roberts, M. J.; Bentley, M. D.; Harris, J. M. Chemistry for peptide and protein PEGylation Adv. Drug Delivery Rev. 2002, 54, 459-476 10.1016/S0169-409X(02)00022-4
9. Rogers, M. S.; Ryan, B. B.; Cashon, R. E.; Alayash, A. I. Effects of polymerization on the oxygen-carrying and redox properties of diaspirin cross-linked hemoglobin Biochim. Biophys. Acta, Protein Struct. Mol. Enzymol. 1995, 1248, 135-142 10.1016/0167-4838(95)00017-O
10. Manjula, B. N.; Tsai, S.; Upadhya, R.; Perumalsamy, K.; Smith, P. K.; Malavalli, A.; Vandegriff, K.; Winslow, R. M.; Intaglietta, M.; Prabhakaran, M.; Friedman, J. M.; Acharya, A. S. Site-specific PEGylation of hemoglobin at cys-93(beta): Correlation between the colligative properties of the PEGylated protein and the length of the conjugated PEG chain Bioconjugate Chem. 2003, 14, 464-472 10.1021/bc0200733
11. Portörö, I.; Kocsis, L.; Herman, P.; Caccia, D.; Perrella, M.; Ronda, L.; Bruno, S.; Bettati, S.; Micalella, C.; Mozzarelli, A.; Varga, A.; Vas, M.; Lowe, K. C.; Eke, A. Towards a novel haemoglobin-based oxygen carrier: Euro-PEG-Hb, physico-chemical properties, vasoactivity and renal filtration Biochim. Biophys. Acta, Proteins Proteomics 2008, 1784, 1402-1409 10.1016/j.bbapap.2008.03.005
12. Manjula, B. N.; Tsai, A. G.; Intaglietta, M.; Tsai, C. H.; Ho, C.; Smith, P. K.; Perumalsamy, K.; Kanika, N. D.; Friedman, J. M.; Acharya, S. A. Conjugation of multiple copies of polyethylene glycol to hemoglobin facilitated through thiolation: Influence on hemoglobin structure and function Protein J. 2005, 24, 133 10.1007/s10930-005-7837-2
13. Caccia, D.; Ronda, L.; Frassi, R.; Perrella, M.; Del Favero, E.; Bruno, S.; Pioselli, B.; Abbruzzetti, S.; Viappiani, C.; Mozzarelli, A. PEGylation Promotes Hemoglobin Tetramer Dissociation Bioconjugate Chem. 2009, 20, 1356-1366 10.1021/bc900130f
14. Ronda, L.; Pioselli, B.; Bruno, S.; Faggiano, S.; Mozzarelli, A. Electrophoretic analysis of PEGylated hemoglobin-based blood substitutes Anal. Biochem. 2011, 408, 118-123 10.1016/j.ab.2010.08.043
15. Svergun, D. I.; Ekstrom, F.; Vandegriff, K. D.; Malavalli, A.; Baker, D. A.; Nilsson, C.; Winslow, R. M. Solution structure of poly(ethylene) glycol-conjugated hemoglobin revealed by small-angle x-ray scattering: Implications for a new oxygen therapeutic Biophys. J. 2008, 94, 173-181 10.1529/biophysj.107.114314
16. Pai, S. S.; Hammouda, B.; Hong, K.; Pozzo, D. C.; Przybycien, T. M.; Tilton, R. D. The Conformation of the Poly(ethylene glycol) Chain in Mono-PEGylated Lysozyme and Mono-PEGylated Human Growth Hormone Bioconjugate Chem. 2011, 22, 2317-2323 10.1021/bc2003583
17. He, L.; Wang, H.; Garamus, V. M.; Hanley, T.; Lensch, M.; Gabius, H.-J.; Fee, C. J.; Middelberg, A. Analysis of MonoPEGylated Human Galectin-2 by Small-Angle X-ray and Neutron Scattering: Concentration Dependence of PEG Conformation in the Conjugate Biomacromolecules 2010, 11, 3504-3510 10.1021/bm100999a
18. Perutz, M. F. Preparation of Haemoglobin crystals J. Cryst. Growth 1968, 2, 54-56 10.1016/0022-0248(68)90071-7
19. Jelkmann, W.; Bauer, C. What is best method to remove 2,3-diphosphoglycerate from hemoglobin Anal. Biochem. 1976, 75, 382-388 10.1016/0003-2697(76)90092-0
20. Antonini, E.; Brunori, M. Hemoglobin and myoglobin in their reactions with ligands. In Frontiers of Biology; Neuberger, A.; Tatum, E. L., Eds.; North-Holland Publishing Company: Amsterdam, 1971.
21. Jacrot, B. Study of biological structures by neutron scattering from solution Rep. Prog. Phys. 1976, 39, 911-953 10.1088/0034-4885/39/10/001
22. Brulet, A.; Lairez, D.; Lapp, A.; Cotton, J.-P. Improvement of data treatment in small-angle neutron scattering J. Appl. Crystallogr. 2007, 40, 165-177 10.1107/S0021889806051442
23. Lairez, D. Pasinet 2, http://didier.lairez.fr/pasinet2/doku.php.
24. Zemb, T.; Lindner, P. Neutron, X-Ray, and Light Scattering; North-Holland: Amsterdam, 1991; p 376.
25. Debye, P. Molecular-weight determination by light scattering J. Phys. Colloid Chem. 1947, 51, 18-32 10.1021/j150451a002
26. Debye, P. The intrinsic viscosity of polymer solutions J. Chem. Phys. 1946, 14, 636-639 10.1063/1.1724075
27. Cotton, J. P. Variations on contrast in SANS: Determination of self and distinct correlation functions Adv. Colloid Interface Sci. 1996, 69, 1-29 10.1016/S0001-8686(96)00306-5
28. Hammouda, B. SANS from Polymers-Review of the Recent Literature Polym. Rev. 2010, 50, 14-39 10.1080/15583720903503460
29. Zimm, B. H. The scattering of light and the radial distribution function of high polymer solutions J. Chem. Phys. 1948, 16, 1093-1099 10.1063/1.1746738
30. Pedersen, J. S. Form factors of block copolymer micelles with spherical, ellipsoidal and cylindrical cores J. Appl. Crystallogr. 2000, 33, 637-640 10.1107/S0021889899012248
31. Hammouda, B. Structure factor for starburst dendrimers J. Polym. Sci., Part B: Polym. Phys. 1992, 30, 1387-1390 10.1002/polb.1992.090301209
32. Park, S.-Y.; Yokoyama, T.; Shibayama, N.; Shiro, Y.; Tame, J. R. H. 1.25 angstrom resolution crystal structures of human haemoglobin in the oxy, deoxy and carbonmonoxy forms J. Mol. Biol. 2006, 360, 690-701 10.1016/j.jmb.2006.05.036
33. Elder, A. N.; Hannes, S. K.; Atoyebi, S. F.; Washburn, N. R. Effects on peptide binding affinity for TNF alpha, by PEGylation and conjugation to hyaluronic acid Eur. Polym. J. 2013, 49, 2968-2975 10.1016/j.eurpolymj.2013.06.037
34. Garcia-Arellano, H.; Valderrama, B.; Saab-Rincon, G.; Vazquez-Duhalt, R. High temperature biocatalysis by chemically modified cytochrome c Bioconjugate Chem. 2002, 13, 1336-1344 10.1021/bc025561p
35. Bhat, R.; Timasheff, S. N. Steric exclusion is the principal source of the preferential hydration of proteins in the presence of polyethylene glycols Protein Sci. 1992, 1, 1133-1143 10.1002/pro.5560010907
36. Le Coeur, C.; Demé, B.; Longeville, S. Compression of random coils due to macromolecular crowding Phys. Rev. E 2009, 79, 031910 10.1103/PhysRevE.79.031910
37. Le Coeur, C.; Teixeira, J.; Busch, P.; Longeville, S. Compression of random coils due to macromolecular crowding: Scaling effects Phys. Rev. E 2010, 81, 061914 10.1103/PhysRevE.81.061914
38. Harris, J. M.; Chess, R. B. Effect of pegylation on pharmaceuticals Nat. Rev. Drug Discovery 2003, 2, 214-221 10.1038/nrd1033