Artificial oxygen carriers, hemoglobin vesicles and albumin-hemes, based on bioconjugate chemistry

Bioconjugate Chemistry

Volumn 20, Issue 8, 2009, Pages 1419-1440

  Tsuchida, Eishun ^a   Sou, Keitaro ^a   Nakagawa, Akito ^a   Sakai, Hiromi ^a   Komatsu, Teruyuki ^a,b   Kobayashi, Koichi ^c  

^a WASEDA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c KEIO UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; BIOCOMPATIBILITY; BIOMOLECULES; BIOSYNTHESIS; BLOOD; DEGRADATION; HEMOGLOBIN; IRON COMPOUNDS; LIPOSOMES; MEDICAL APPLICATIONS; OXYGEN; PHOSPHOLIPIDS;

ARTIFICIAL OXYGEN CARRIER; BINDING AFFINITIES; BIOCONJUGATES; BLOOD COMPATIBILITY; HAEMOGLOBINS; HEMOGLOBIN VESICLES; HUMAN SERUM ALBUMINS; IN-VIVO; PROTEIN COMPONENTS; RED BLOOD CELL;

PORPHYRINS;

1,2 DIPALMITOYL SN GLYCERO 3 PHOSPHATIDYLGLYCEROL; ALBUMIN; AMINO ACID; ARGININE; BLOOD SUBSTITUTE; DEXTRAN; FERROUS PORPHYRIN; GELATIN; GLYCEROL DERIVATIVE; HEME; HEMOGLOBIN; HETASTARCH; LEUCINE; LIPOSOME; MACROGOL; PHENYLALANINE; PHOSPHOLIPID; PORPHYRIN; PROTOPORPHYRIN; TECHNETIUM 99M; TYROSINE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ANTIINFLAMMATORY ACTIVITY; ARTIFICIAL OXYGEN CARRIER; BINDING AFFINITY; BIOCHEMISTRY; BIOCONJUGATE CHEMISTRY; BLOOD COMPATIBILITY; BLOOD RHEOLOGY; BLOOD TRANSFUSION; CELL FUNCTION; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CIRCULATION TIME; CLINICAL RESEARCH; CONJUGATION; CROSS LINKING; DISPERSION; DRUG DISTRIBUTION; DRUG EFFICACY; DRUG HALF LIFE; DRUG METABOLISM; DRUG SAFETY; ENCAPSULATION; ERYTHROCYTE; ERYTHROCYTE STRUCTURE; HUMAN; IMMUNOCYTOCHEMISTRY; IN VIVO STUDY; MOLECULAR MIMICRY; MOLECULAR STABILITY; NONHUMAN; OXYGEN AFFINITY; OXYGEN THERAPY; PHYSICAL CHEMISTRY; POLYMERIZATION; PROTEIN MODIFICATION; PULMONARY HYPERTENSION; PURIFICATION; REVIEW; SITE DIRECTED MUTAGENESIS; SURFACE PROPERTY; SUSPENSION; THROMBOCYTOPENIA; TISSUE OXYGENATION; TRANSPORT VESICLE; VASOCONSTRICTION;

BLOOD SUBSTITUTES; HEMOGLOBINS; HUMANS; METALLOPORPHYRINS; OXYGEN; PHOSPHOLIPIDS; POLYETHYLENE GLYCOLS; SERUM ALBUMIN;

EID: 70349091472     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc800431d     Document Type: Review

References (188)

1. Perutz, M. F. (1970) Stereochemistry of cooperative effects in haemoglobin. Nature 228, 726-739.
2. Jones, R. D., Summerville, A., and Basolo, F. (1979) Synthetic oxygen carriers related to biological systems. Chem. Rev. 79, 139-179.
3. Collman, J. P. (1977) Synthetic model for the oxygen-binding hemoproteins. Acc. Chem. Res. 10, 265-272.
4. Momenteau, M., and Reed, C. (1994) Synthetic heme dioxygen complexes. Chem. Rev. 94, 659-698.
5. Collman, J. P., Gagne, R. R., Halbert, T. R., Marchon, J.-C., and Reed, C. A. (1973) Reversible oxygen adduct formation in ferrous complexes derived from "picket fence" porphyrins. A model for oxymyoglobin. J. Am. Chem. Soc. 73, 7868-7870.
6. Collman, J. P., Gagne, R. R., Reed, C. A., Halbert, T. R., Lang, G., and Robinson, W. T. (1975) "Picket fence porphyrins." Synthetic models for oxygen binding hemoproteins. J. Am. Chem. Soc. 97, 1427-1439.
7. Matsushita, Y., Hasegawa, E., Eshima, K., and Tsuchida, E. (1983) Synthesis of amphiphilic porphinatoiron complexes having phosphocholine groups. Chem. Lett. 1983, 1387-1389.
8. Tsuchida, E. (1985) Liposome-embedded iron-porphyrins as an artificial oxygen carrier. Ann. N.Y. Acad. Sci. 446, 429-442.
9. Tsuchida, E., and Nishide, H. (1986) Hemoglobin model - artificial oxygen carrier composed of porphinatoiron complexes. Top. Curr. Chem. 1132, 63-99.
10. Komatsu, T., Moritake, M., Nakagawa, A., and Tsuchida, E. (2002) Self-organized lipid-porphyrin bilayer membranes in vesicular form: nanostructure, photophysical properties and dioxygen coordination. Chem. Eur. J. 8, 5469-5480. (Pubitemid 35453349)
11. 2-transport albumin - a new hybrid hemoprotein incorporating tetraphenylporphinatoiron(II). Chem. Lett. 813-814.
12. Savitsky, J. P., Doczi, J., Black, J., and Arnold, J. D. (1978) A clinical safety trial of stroma-free hemoglobin. Clin. Pharm. Ther. 23, 73-80. (Pubitemid 8290413)
13. Greenwald, R. B., Pendri, A., Martinez, A., Gilbert, C., and Bradley, P. (1996) PEG thiazolidine-2-thione, a novel reagent for facile protein modification: conjugation of bovine hemoglobin. Bioconjugate Chem. 7, 638-641. (Pubitemid 27012705)
14. Kluger, R., and Li, X. (1997) Efficient chemical introduction of a disulfide cross-link and conjugation site into human hemoglobin at β-lysine-82 utilizing a bifunctional aminoacyl phosphate. Bioconjugate Chem. 8, 921-926. (Pubitemid 27526422)
15. Sakai, H., Yuasa, M., Onuma, H., Takeoka, S., and Tsuchida, E. (2000) Synthesis and physicochemical characterization of a series of hemoglobin-based oxygen carriers: objective comparison between cellular and acellular types. Bioconjugate Chem. 11, 56-64. (Pubitemid 30063344)
16. Hai, T. T., Pereira, D. E., Nelson, D. J., Catarello, J., and Srnak, A. (2000) Surface modification of diaspirin cross-linked hemoglobin (DCLHb) with chondroitin-4-sulfate derivatives. Part 1. Bioconjugate Chem. 11, 705-713. (Pubitemid 30738221)
17. Manjula, B. N., Tsai, A., Upadhya, R., Perumalsamy, K., Smith, P. K., Malavalli, A., Vandegriff, K., Winslow, R. M., Intaglietta, M., Prabhakaran, M., Friedman, J. M., and Acharya, A. S. (2003) Site-specific PEGylation of hemoglobin at Cys-93(β): correlation between the colligative properties of the PEGylated protein and the length of the conjugated PEG chain. Bioconjugate Chem. 14, 464-472. (Pubitemid 36348671)
18. Murray, J. A., Ledlow, A., Launspach, J., Evans, D., Loveday, M., and Conklin, J. L. (1995) The effects of recombinant human hemoglobin on esophageal motor function in humans. Gastroenterology 1091241-1248.
19. 2). J. Biol. Chem. 261, 9929-9937.
20. 2 carrier. Artif. Organs Today 1, 89-114.
21. Riess, J. G. (2001) Oxygen carriers ("blood substitutes") - raison d'etre, chemistry, and some physiology. Chem. Rev. 101, 2797-2920.
22. de Figueiredo, L. F., Mathru, M., Solanki, D., Macdonald, V. W., Hess, J., and Kramer, G. C. (1997) Pulmonary hypertension and systemic vasoconstriction might offset the benefits of acellular hemoglobin blood substitutes. J. Trauma 42, 847-854. (Pubitemid 27258315)
23. Tsai, A. G., Kerger, H., and Intaglietta, M. (1995) Microcirculatory consequences of blood substitution with αα-hemoglobin. In Blood Substitutes: Physiological Basis of Efficacy (Winslow, R. M., Vandegriff, K., Intaglietta, M., Eds.) pp155-174, Birkhauser, Boston.
24. Goda, N., Suzuki, K., Naito, M., Takeoka, S., Tsuchida, E., Ishimura, Y., Tamatani, T., and Suematsu, M. (1998) Distribution of heme oxygenase isoforms in rat liver. Topographic basis for carbon monoxide-mediated microvascular relaxation. J. Clin. Invest. 101, 604-612. (Pubitemid 28084244)
25. 2 carriers determine constriction of resistance arteries and hypertension. Am. J. Physiol. Heart Circ. Physiol. 279, H908-H915.
26. Burhop, K., Gordon, D., and Estep, T. (2004) Review of hemoglobin-induced myocardial lesions. Artif. Cells Blood Substit. Immobil. Biotechnol. 32, 353-374.
27. Neragi-Miandoab, S., and Vlahakes, G. J. (2006) Elevated troponin I level with hemoglobin based oxygen carrying solutions (HBOCs) as a priming solution despite improved left ventricular function. Interact. Cardiovasc. Thorac. Surg. 5, 135-138.
28. Natanson, C., Kern, S. J., Lurie, P., Banks, S. M., and Wolfe, S. M. (2008) Cell-free hemoglobin-based blood substitutes and risk of myocardial infarction and death: a meta-analysis. JAMA 299, 2304-2312. (Pubitemid 351724397)
29. Balla, J., Jacob, H. S., Balla, G., Nath, K., Eaton, J. W., and Vercellotti, G. M. (1993) Endothelial-cell heme uptake from heme proteins: induction of sensitization and desensitization to oxidant damage. Proc. Natl. Acad. Sci. U.S.A. 90, 9285-9289. (Pubitemid 23315768)
30. Sakai, H., Sato, A., Masuda, K., Takeoka, S., and Tsuchida, E. (2008) Encapsulation of concentrated hemoglobin solution in phospholipid vesicles retards the reaction with NO, but not CO, by intracellular diffusion barrier. J. Biol. Chem. 283, 1508-1517.
31. Sakai, H., Sato, A., Sobolewski, P., Takeoka, S., Frangos, J. A., Kobayashi, K., Intaglietta, M., and Tsuchida, E. (2008) NO and CO binding profiles of hemoglobin vesicles as artificial oxygen carriers. Biochim. Biophys. Acta 1784, 1441-1447.
32. Martini, J., Cabrales, P., Tsai, A. G., and Intaglietta, M. (2006) Mechanotransduction and the homeostatic significance of maintaining blood viscosity in hypotension, hypertension and haemorrhage. J. Intern. Med. 259, 364-372. (Pubitemid 43384227)
33. 2-permeable tube: comparison with RBCs and acellular Hbs. Am. J. Physiol. Heart Circ. Physiol. 285, H2543-H2555.
34. 2 release by human red blood cells in the presence of external sodium dithionite. J. Biol. Chem. 259, 12609-12618.
35. Chang, T. M. S. (2005) Therapeutic applications of polymeric artificial cells. Nat. Rev. Drug Discov. 4, 221-235.
36. Toyoda, T. (1965) Artificial blood. Kagaku 35, 7-13 (in Japanese).
37. Kimoto, S., Hori, M., Toyoda, T., and Sekiguchi, W. (1968) Artificial red cells. Gekachiryou (Surgical Therapy) 19, 324-332 (in Japanese).
38. Bangham, A. D., and Horne, R. W. (1964) Negative staining of phospholipids and their structure modification by surface-active agents as observed in the electron microscope. J. Mol. Biol. 8, 660-668.
39. Bangham, A. D., Standish, M. M., and Watkins, J. C. (1965) Diffusion of univalent ions across the lamellae of swollen phospholipids. J. Mol. Biol. 13, 238-252.
40. Djordjevich, L., and Miller, I. F. (1977) Lipid encapsulated hemoglobin as a synthetic erythrocyte. Fed. Proc. 36, 567-571. (Pubitemid 10096899)
41. Farmer, M. C., Rudolph, A. S., Vandegriff, K. D., Hayre, M. D., Bayne, S. A., and Johnson, S. A. (1988) Liposome-encapsulated hemoglobin: oxygen binding properties and respiratory function. Biomater. Artif. Cells Artif. Organs 16, 289-299.
42. 99mTc- labeled liposome-encapsulated hemoglobin in an anesthetized rabbit. Proc. Natl. Acad. Sci. U.S.A. 88, 10976-10980.
43. Phillips, W. T., Klipper, R. W., Awasthi, V. D., Rudolph, A. S., Cliff, R., Kwasiborski, V., and Goins, B. A. (1999) Polyethylene glycol-modified liposome-encapsulated hemoglobin: a long circulating red cell substitute. J. Pharmacol. Exp. Ther. 288, 665-670. (Pubitemid 29119679)
44. Usuba, A., Osuka, F., Kimura, T., Sato, R., Ogata, Y., Gotoh, H., Kimura, T., and Fukui, H. (1998) Effect of liposome-encapsulated hemoglobin, neo red cells, on hemorrhagic shock. Surg. Today 28, 1027-1035. (Pubitemid 28482058)
45. Yoshioka, H. (1991) Surface modification of haemoglobin-containing liposomes with polyethylene glycol prevents liposome aggregation in blood plasma. Biomaterials 12, 861-864.
46. Sakai, H., Hamada, K., Takeoka, S., Nishide, H., and Tsuchida, E. (1996) Physical properties of hemoglobin vesicles as red cell substitutes. Biotechnol. Prog. 12, 119-125. (Pubitemid 126596030)
47. Takeoka, S., Ohgushi, T., Terase, K., Ohmori, T., and Tsuchida, E. (1996) Layer-controlled hemoglobin vesicles by interaction of hemoglobin with a phospholipid assembly. Langmuir 12, 1755-1759. (Pubitemid 126568169)
48. Sou, K., Naito, Y., Endo, T., Takeoka, S., and Tsuchida, E. (2003) Effective encapsulation of proteins into size-controlled phospholipid vesicles using freeze-thawing and extrusion. Biotechnol. Prog. 19, 1547-1552. (Pubitemid 37250047)
49. Sakai, H., Takeoka, S., Yokohama, H., Seino, Y., Nishide, H., and Tsuchida, E. (1993) Purification of concentrated Hb using organic solvent and heat treatment. Protein Expression Purif. 4, 563-569. (Pubitemid 2007179)
50. Abe, H., Ikebuchi, K., Hirayama, J., Fujihara, M., Takeoka, S., Sakai, H., Tsuchida, E., and Ikeda, H. (2001) Virus inactivation in hemoglobin solution by heat treatment. Artif. Cells Blood Substit. Immobil. Biotechnol. 29, 381-388. (Pubitemid 33029531)
51. Chung, J., Hamada, K., Sakai, H., Takeoka, S., and Tsuchida, E. (1995) Ligand-exchange reaction of carbonylhemoglobin to oxyhemoglobin in a hemoglobin liquid membrane. Nippon Kagaku Kaishi 2, 123-127 (in Japanese).
52. Takeoka, S., Sakai, H., Kose, T., Mano, Y., Seino, Y., Nishide, H., and Tsuchida, E. (1997) Methemoglobin formation in hemoglobin vesicles and reduction by encapsulated thiols. Bioconjugate Chem. 8, 539-544. (Pubitemid 27347562)
53. Teramura, Y., Kanazawa, H., Sakai, H., Takeoka, S., and Tsuchida, E. (2003) Prolonged oxygen-carrying ability of hemoglobin vesicles by coencapsulation of catalase in vivo. Bioconjugate Chem. 14, 1171-1176. (Pubitemid 37449045)
54. 2-binding of concentrated hemoglobin solution coencapsulated in phospholipid vesicles. Bioconjugate Chem. 15, 1037-1045.
55. Atoji, T., Aihara, M., Sakai, H., Tsuchida, E., and Takeoka, S. (2006) Hemoglobin vesicles containing methemoglobin and L-tyrosine to suppress methemoglobin formation in vitro and in vivo. Bioconjugate Chem. 17, 1241-1245. (Pubitemid 44455333)
56. Sakai, H., Takeoka, S., Seino, Y., and Tsuchida, E. (1994) Suppression of methemoglobin formation by glutathione in a concentrated hemoglobin solution and in a Hb-vesicle. Bull. Chem. Soc. Jpn. 67, 1120-1125. (Pubitemid 24193112)
57. Rameez, S., Alosta, H., and Palmer, A. F. (2008) Biocompatible and biodegradable polymersome encapsulated hemoglobin: a potential oxygen carrier. Bioconjugate Chem. 19, 1025-1032. (Pubitemid 351748310)
58. Zhao, J., Liu, C. S., Yuan, Y., Tao, X. Y., Shan, X. Q., Sheng, Y., and Wu, F. (2007) Preparation of hemoglobin-loaded nanosized particles with porous structure as oxygen carriers. Biomaterials 28, 1414-1422. (Pubitemid 44959037)
59. Rudolph, A. S. (1988) The freeze-dried preservation of liposome encapsulated hemoglobin: a potential blood substitute. Cryobiology 25, 277-284.
60. Rabinovici, R., Rudolph, A. S., Vernick, J., and Feuerstein, G. (1994) Lyophilized liposome encapsulated hemoglobin: evaluation of hemodynamic, biochemical, and hematologic responses. Crit. Care Med. 22, 480-485. (Pubitemid 24085301)
61. Ringsdorf, H., Schlarb, B., and Venzmer, J. (1988) Molecular architecture and function of polymeric oriented systems - models for the study of organization, surface recognition, and dynamics of biomembranes. Angew. Chem., Int. Ed. 27, 113-158. (Pubitemid 18043271)
62. Kato, A., Arakawa, M., and Kondo, T. (1984) Preparation and stability of liposome-type artificial red blood cells stabilized with carboxymethylchitin. J. Microencapsul. 1, 105-112.
63. Mobed, M., Nishiya, T., and Chang, T. M. (1992) Preparation of carboxymethylchitin-incorporated submicron bilayer-lipid membrane artificial cells (liposomes) encapsulating hemoglobin. Biomater. Artif. Cells Immobil. Biotechnol. 20, 365-368.
64. Li, S., Nickels, J., and Palmer, A. F. (2005) Liposome-encapsulated actin-hemoglobin (LEAcHb) artificial blood substitutes. Biomaterials 26, 3759-3769. (Pubitemid 40038171)
65. Tsuchida, E., Hasegawa, E., Kimura, N., Hatashita, M., and Makino, C. (1992) Polymerization of unsaturated phospholipids as large unilamellar liposomes at low temperature. Macromolecules 25, 2007-2212
66. Sakai, H., Takeoka, S., Yokohama, H., Nishide, H., and Tsuchida, E. (1992) Encapsulation of Hb into unsaturated lipid vesicles and gamma-ray polymerization. Polym. Adv. Technol. 3, 389-394.
67. Akama, K., Awai, K., Yano, Y., Tokuyama, S., and Nakano, Y. (2000) In vitro and in vivo stability of polymerized mixed liposomes composed of 2,4-octadecadienoyl groups of phospholipids. Polym. Adv. Technol 11, 280-287. (Pubitemid 30893946)
68. Sakai, H., Takeoka, S., Park, S. I., Kose, T., Nishide, H., Izumi, Y., Yoshizu, A., Kobayashi, K., and Tsuchida, E. (1997) Surface-modification of hemoglobin vesicles with poly(ethylene glycol) and effects on aggregation, viscosity, and blood flow during 90%-exchange transfusion in anesthetized rats. Bioconjugate Chem. 8, 23-30. (Pubitemid 27064218)
69. Sakai, H., Tsai, A. G., Kerger, H., Park, S. I., Takeoka, S., Nishide, H., Tsuchida, E., and Intaglietta, M. (1998) Subcutaneous microvascular responses to hemodilution with red cell substitutes consisting of polyethylene glycol-modified vesicles encapsulating hemoglobin. J. Biomed. Mater. Res. 40, 66-78. (Pubitemid 28110152)
70. Sakai, H., Okamoto, M.,; Ikeda E., Horinouchi H., Kobayashi K., and Tsuchida, E. (2008) Histopathological changes of rat brain after direct injection of hemoglobin vesicles (oxygen carriers) and neurological impact in an intracerebral hemorrhage model. J. Biomed. Mater. Res., Part A (in press).
71. Sakai, H., Tomiyama, K., Sou, K., Takeoka, S., and Tsuchida, E. (2000) Poly(ethylene glycol)-conjugation and deoxygenation enable long-term preservation of hemoglobin vesicles as oxygen carriers in a liquid state. Bioconjugate Chem. 11, 425-432. (Pubitemid 30324910)
72. Sou, K., Endo, T., Takeoka, S., and Tsuchida, E. (2000) Poly(ethylene glycol)-modification of the phospholipid vesicles by using the spontaneous incorporation of poly(ethylene glycol)-lipid into the vesicles. Bioconjugate Chem. 11, 372-379. (Pubitemid 30324903)
73. Sato, T., Sakai, H., Sou, K., Buchner, R., and Tsuchida, E. (2007) Poly(ethylene glycol)-conjugated phospholipids in aqueous micellar solutions: hydration, static structure, and interparticle interactions. J. Phys. Chem. B 111, 1393-1401. (Pubitemid 46339067)
74. Szebeni, J. (2005) Complement activation-related pseudoallergy: a new class of drug-induced acute immune toxicity. Toxicology 216, 106-121.
75. Van de Velde, M., Wouters, P. F., Rolf, N., Van Aken, H., and Vandermeersch, E. (1998) Comparative hemodynamic effects of three different parenterally administered lipid emulsions in conscious dogs. Crit. Care Med. 26, 132-137. (Pubitemid 28028452)
76. Vercellotti, G. M., Hammerschmidt, D. E., Craddock, P. R., and Jacob, H. S. (1982) Activation of plasma complement by perfluorocarbon artificial blood: probable mechanism of adverse pulmonary reactions in treated patients and rationale for corticosteroids prophylaxis. Blood 59, 1299-1304.
77. Phillips, W. T., Klipper, R., Fresne, D., Rudolph, A. S., Javors, M., and Goins, B. (1997) Platelet reactivity with liposome-encapsulated hemoglobin in the rat. Exp. Hematol. 25, 1347-1356. (Pubitemid 28015612)
78. Szebeni, J., Fontana, J. L., Wassef, N. M., Mongan, P. D., Morse, D. S., Dobbins, D. E., Stahl, G. L., Bunger, R., and Alving, C. R. (1999) Hemodynamic changes induced by liposomes and liposome-encapsulated hemoglobin in pigs: a model for pseudoallergic cardiopulmonary reactions to liposomes. Role of complement and inhibition by soluble CR1 and anti-C5a antibody. Circulation 99, 2302-2309. (Pubitemid 29201138)
79. Izumi, Y., Sakai, H., Kose, T., Hamada, K., Takeoka, S., Yoshizu, A., Horinouchi, H., Kato, R., Nishide, H., Tsuchida, E., and Kobayashi, K. (1997) Evaluation of the capabilities of a hemoglobin vesicle as an artificial oxygen carrier in a rat exchange transfusion model. ASAIO J. 43, 289-297. (Pubitemid 27315122)
80. Loughrey, H. C., Bally, M. B., Reinish, L. W., and Cullis, P. R. (1990) The binding of phosphatidylglycerol liposomes to rat platelets is mediated by complement. Thromb. Haemost. 64, 172-176.
81. Chonn, A., Cullis, P. R., and Devine, D. V. (1991) The role of surface charge in the activation of the classical and alternative pathways of complement by liposomes. J. Immunol. 146, 4234-4241.
82. Sou, K., and Tsuchida, E. (2008) Electrostatic interactions and complement activation on the surface of phospholipid vesicle containing acidic lipids: effect of the structure of acidic groups. Biochim. Biophys. Acta - Biomembr. 1778, 1035-1041.
83. Abe, H., Azuma, H., Yamaguchi, M., Fujihara, M., Ikeda, H., Sakai, H., Takeoka, S., and Tsuchida, E. (2007) Effects of hemoglobin vesicles, a liposomal artificial oxygen carrier, on hematological responses, complement and anaphylactic reactions in rats. Artif. Cells Blood Substit. Biotechnol. 35, 157-172. (Pubitemid 46514900)
84. Abe, H., Fujihara, M., Azuma, H., Ikeda, H., Ikebuchi, K., Takeoka, S., Tsuchida, E., and Harashima, H. (2006) Interaction of hemoglobin vesicles, a cellular-type artificial oxygen carrier, with human plasma: effects on coagulation, kallikrein-kinin, and complement systems. Artif. Cells Blood Substit. Immobil. Biotechnol. 34, 1-10. (Pubitemid 43127930)
85. Wakamoto, S., Fujihara, M., Abe, H., Yamaguchi, M., Azuma, H., Ikeda, H., Takeoka, S., and Tsuchida, E. (2005) Effects of hemoglobin vesicles on resting and agonist-stimulated human platelets in vitro. Artif. Cells Blood Substit. Immobil. Biotechnol. 33, 101-111. (Pubitemid 40770185)
86. Wakamoto, S., Fujihara, M., Abe, H., Sakai, H., Takeoka, S., Tsuchida, E., Ikeda, H., and Ikebuchi, K. (2001) Effects of poly(ethyleneglycol)-modified hemoglobin vesicles on agonist-induced platelet aggregation and RANTES release in vitro. Artif. Cells Blood Substit. Immobil. Biotechnol. 29, 191-201. (Pubitemid 32429354)
87. Takeoka, S., Mori, K., Ohkawa, H., Sou, K., and Tsuchida, E. (2000) Synthesis and assembly of poly(ethylene glycol)-lipids with mono-, di-, and tetraacyl chains and a poly(ethylene glycol) chain of various molecular weights. J. Am. Chem. Soc. 122, 7927-7935. (Pubitemid 30659414)
88. Okamura, Y., Maekawa, I., Teramura, Y., Maruyama, H., Handa, M., Ikeda, Y., and Takeoka, S. (2005) Hemostatic effects of phospholipid vesicles carrying fibrinogen gamma chain dodecapeptide in vitro and in vivo. Bioconjugate Chem. 16, 1589-1596. (Pubitemid 41681527)
89. Ohkawa, H., Teramura, Y., Takeoka, S., and Tsuchida, E. (2000) Synthesis of multiacyl poly(ethylene glycol) for the conjugation of cytochrome c to phospholipid vesicle. Bioconjugate Chem. 11, 815-821.
90. Sou, K., Goins, B., Takeoka, S., Tsuchida, E., and Phillips, W. T. (2007) Selective uptake of surface-modified phospholipid vesicles by bone marrow macrophages in vivo. Biomaterials 28, 2655-2666. (Pubitemid 46367213)
91. Teramura, Y., and Iwata, H. (2008) Islets surface modification prevents blood-mediated inflammatory responses. Bioconjugate Chem. 19, 1389-1395. (Pubitemid 352032338)
92. Obata, Y., Suzuki, D., and Takeoka, S. (2008) Evaluation of cationic assemblies constructed with amino acid based lipids for plasmid DNA delivery. Bioconjugate Chem. 19, 1055-1063. (Pubitemid 351748314)
93. Sou, K., Inenaga, S., Takeoka, S., and Tsuchida, E. (2008) Loading of curcumin into macrophages using lipid-based nanoparticles. Int. J. Pharm. 352, 287-293.
94. Sou, K., Klipper, R., Goins, B., Tsuchida, E., and Phillips, W. T. (2005) Circulation kinetics and organ distribution of Hb vesicles developed as a red blood cell substitute. J. Pharmacol. Exp. Ther. 312, 702-709. (Pubitemid 40189569)
95. Bradley, A. J., Devine, D. V., Ansell, S. M., Janzen, J., and Brooks, D. E. (1998) Inhibition of liposome-induced complement activation by incorporated poly(ethylene glycol)-lipids. Arch. Biochem. Biophys. 357, 185-194. (Pubitemid 28419200)
96. Hu, Q., and Liu, D. (1996) Co-existence of serum-dependent and serum-independent mechanisms for liposome clearance and involvement of non-Kupffer cells in liposome uptake by mouse liver. Biochim. Biophys. Acta 1284, 153-161. (Pubitemid 26356149)
97. Shibuya-Fujiwara, N., Hirayama, F., Ogata, Y., Ikeda, H., and Ikebuchi, K. (2001) Phagocytosis in vitro of polyethylene glycol-modified liposome-encapsulated hemoglobin by human peripheral blood monocytes plus macrophages through scavenger receptors. Life Sci. 70, 291-300. (Pubitemid 34014904)
98. Sakai, H., Horinouchi, H., Tomiyama, K., Ikeda, E., Takeoka, S., Kobayashi, K., and Tsuchida, E. (2001) Hemoglobin-vesicles as oxygen carriers: influence on phagocytic activity and histopathological changes in reticuloendothelial system. Am. J. Pathol. 159, 1079-1088. (Pubitemid 32847198)
99. Sakai, H., Horinouchi, H., Masada, Y., Takeoka, S., Kobayashi, K., and Tsuchida, E. (2004) Metabolism of hemoglobin-vesicles (artificial oxygen carriers) and their influence on organ functions in a rat model. Biomaterials 25, 4317-4325. (Pubitemid 38388593)
100. Sakai, H., Masada, Y., Horinouchi, H., Ikeda, E., Sou, K., Takeoka, S., Suematsu, M., Takaori, M., Kobayashi, K., and Tsuchida, E. (2004) Physiologic capacity of reticuloendothelial system for degradation of hemoglobin-vesicles (artificial oxygen carriers) after massive intravenous doses by daily repeated infusions for 14 days. J. Pharmacol. Exp. Ther. 311, 874-884. (Pubitemid 39612691)
101. Sakai, H., Horinouchi, H., Yamamoto, M., Ikeda, E., Takeoka, S., Takaori, M., Tsuchida, E., and Kobayashi, K. (2006) Acute 40% exchange-transfusion with hemoglobin-vesicles (HbV) suspended in recombinant human serum albumin solution: degradation of HbV and erythropoiesis in a rat spleen for 2 weeks. Transfusion 46, 339-347. (Pubitemid 43334085)
102. Sakai, H., Seishi, Y., Obata, Y., Takeoka, S., Horinouichi, H., Tsuchida, E., and Kobayashi, K. (2009) Fluid resuscitation with artificial oxygen carriers in hemorrhaged rats: Profiles of hemoglobin-vesicle degradation and hematopoiesis for 14 days, Shock 31, 192-200.
103. Yamaoka, T., Tabata, Y., and Ikada, Y. (1994) Distribution and tissue uptake of poly(ethylene glycol) with different molecular weights after intravenous administration to mice. J. Pharm. Sci. 83, 601-606. (Pubitemid 24222392)
104. Ohki, N., Kimura, T., and Ogata, Y. (1998) The reduction of methemoglobin in Neo Red Cell. Artif. Cells Blood Substit. Immobil. Biotechnol. 26, 477-485. (Pubitemid 28556490)
105. 2 affinity. Am. J. Physiol. Heart Circ. Physiol. 276, H553-H562.
106. Wang, L., Morizawa, K., Tokuyama, S., Satoh, T., and Tsuchida, E. (1992) Modulation of oxygen-carrying capacity of artificial red cells (ARC). Polym. Adv. Technol. 4, 8-11.
107. Cabrales, P., Sakai, H., Tsai, A. G., Takeoka, S., Tsuchida, E., and Intaglietta, M. (2005) Oxygen transport by low and normal oxygen affinity hemoglobin vesicles in extreme hemodilution. Am. J. Physiol. Heart Circ. Physiol. 288, H1885-H1892. (Pubitemid 40418017)
108. Izumi, Y., Sakai, H., Hamada, K., Takeoka, S., Yamahata, T., Kato, R., Nishide, H., Tsuchida, E., and Kobayashi, K. (1996) Physiologic responses to exchange transfusion with hemoglobin vesicles as an artificial oxygen carrier in anesthetized rats: changes in mean arterial pressure and renal cortical oxygen tension. Crit. Care Med. 24, 1869-1873. (Pubitemid 26382931)
109. Sakai, H., Takeoka, S., Wettstein, R., Tsai, A. G., Intaglietta, M., and Tsuchida, E. (2002) Systemic and Microvascular responses to the hemorrhagic shock and resuscitation with Hb vesicles. Am. J. Physiol. Heart Circ. Physiol. 283, H1191-H1199. (Pubitemid 34941057)
110. Sakai, H., Masada, Y., Horinouchi, H., Yamamoto, M., Ikeda, E., Takeoka, S., Kobayashi, K., and Tsuchida, E. (2004) Hemoglobin vesicles suspended in recombinant human serum albumin for resuscitation from hemorrhagic shock in anesthetized rats. Crit. Care Med. 32, 539-545. (Pubitemid 38234138)
111. Yoshizu, A., Izumi, Y., Park, S. I., Sakai, H., Takeoka, S., Horinouchi, H., Ikeda, E., Tsuchida, E., and Kobayashi, K. (2004) Hemorrhagic shock resuscitation with an artificial oxygen carrier hemoglobin vesicle (HbV) maintains intestinal perfusion and suppresses the increase in plasma necrosis factor alpha (TNFα). ASAIO J. 50, 458-463. (Pubitemid 39237955)
112. Terajima, K., Tsueshita, T., Sakamoto, A., and Ogawa, R. (2006) Fluid resuscitation with hemoglobin vesicles in a rabbit model of acute hemorrhagic shock. Shock 25, 184-189. (Pubitemid 43755974)
113. Yamazaki, M., Aeba, R., Yozu, R., and Kobayashi, K. (2006) Use of hemoglobin vesicles during cardiopulmonary bypass priming prevents neurocognitive decline in rats. Circulation 114 (1 Suppl), I220-I225. (Pubitemid 44297154)
114. 2 therapeutics. Am. J. Physiol. Heart Circ. Physiol. 285, H1411-H1419.
115. Plock, J. A., Tromp, A. E., Contaldo, C., Spanholtz, T., Sinovcic, D., Sakai, H., Tsuchida, E., Leunig, M., Banic, A., and Erni, D. (2007) Hemoglobin vesicles reduce hypoxia-related inflammation in critically ischemic hamster flap tissue. Crit. Care Med. 35, 899-905. (Pubitemid 46407808)
116. Nolte, D., Pickelmann, S., Lang, M., Keipert, P., and Messmer, K. (2000) Compatibility of different colloid plasma expanders with perflubron emulsion: an intravital microscopic study in the hamster. Anesthesiology 93, 1261-1270. (Pubitemid 30822841)
117. Jouan-Hureaux, V., Audonnet-Blaise, S., Lacatusu, D., Krafft, M. P., Dewachter, P., Cauchois, G., Stoltz, J. F., Longrois, D., and Menu, P. (2006) Effects of a new perfluorocarbon emulsion on human plasma and whole-blood viscosity in the presence of albumin, hydroxyethyl starch, or modified fluid gelatin: an in vitro rheologic approach. Transfusion 46, 1892-1898. (Pubitemid 44631595)
118. Vandegriff, K. D., McCarthy, M., Rohlfs, R. J., and Winslow, R. M. (1997) Colloid osmotic properties of modified hemoglobins: chemically cross-linked versus polyethylene glycol surface-conjugated. Biophys. Chem. 69, 23-30. (Pubitemid 28010759)
119. Kobayashi, K. (2006) Summary of recombinant human serum albumin development. Biologicals 34, 55-59. (Pubitemid 43295419)
120. Meyuhas, D., Nir, S., and Lichtenberg, D. (1996) Aggregation of phospholipid vesicles by water-soluble polymers. Biophys. J. 71, 2602-2612. (Pubitemid 26367723)
121. Neu, B., and Meiselman, H. J. (2002) Depletion-mediated red blood cell aggregation in polymer solutions. Biophys. J. 83, 2482-2490. (Pubitemid 35265742)
122. Sakai, H., Sato, A., Takeoka, S., and Tsuchida, E. (2007) Rheological property of hemoglobin vesicles (artificial oxygen carriers) suspended in a series of plasma substitute aqueous solutions. Langmuir 23, 8121-8128. (Pubitemid 47155325)
123. Tsai, A. G., Friesenecker, B., McCarthy, M., Sakai, H., and Intaglietta, M. (1998) Plasma viscosity regulates capillary perfusion during extreme hemodilution in hamster skinfold model. Am. J. Physiol. Heart Circ. Physiol. 275, H2170-H2180. (Pubitemid 128731586)
124. Intaglietta, M., Cabrales, P., and Tsai, A. G. (2006) Microvascular perspective of oxygen-carrying and -noncarrying blood substitutes. Annu. Rev. Biomed. Eng. 8, 289-321. (Pubitemid 44314819)
125. Rebel, A., Ulatowski, J. A., Kwansa, H., Bucci, E., and Koehler, R. C. (2003) Cerebrovascular response to decreased hematocrit: effect of cell-free hemoglobin, plasma viscosity, and CO2. Am. J. Physiol. Heart Circ. Physiol. 285, H1600-H1608. (Pubitemid 37169515)
126. 2 affinity hemoglobin-based oxygen carriers synthesized via polymerization of hemoglobin with ring-opened 2-chloroethyl-β-D-fructopyranoside and 1-o-octyl-β-D-glucopyranoside. Biotechnol. Bioeng. 97, 462-472.
127. Plock, J. A., Contaldo, C., Sakai, H., Tsuchida, E., Leunig, M., Banic, A., Menger, M. D., and Erni, D. (2005) Is the Hb in Hb vesicles infused for isovolemic hemodilution necessary to improve oxygenation in critically ischemic hamster skin? Am. J. Physiol. Heart Circ. Physiol. 289, H2624-H2631. (Pubitemid 41698579)
128. Contaldo, C., Plock, J., Sakai, H., Takeoka, S., Tsuchida, E., Leunig, M., Banic, A., and Erni, D. (2005) New generation of hemoglobin-based oxygen carriers evaluated for oxygenation of critically ischemic hamster flap tissue. Crit. Care Med. 33, 806-812. (Pubitemid 40504392)
129. Verdu, E. F., Bercik, P., Huang, X. X., Lu, J., Al-Mutawaly, N., Sakai, H., Tompkins, T. A., Croitoru, K., Tsuchida, E., Perdue, M., and Collins, S. M. (2008) The role of luminal factors in the recovery of gastric function and behavioral changes after chronic Helicobacter pylori infection. Am. J. Physiol. Gastrointest. Liver Physiol. 295, G664-G670.
130. Komatsu, H., Furuya, T., Sato, N., Ohta, K., Matsuura, A., Ohmura, T., Takagi, S., Matsuura, M., Yamashita, M., Itoda, M., Itoh, J., Horinouchi, H., and Kobayashi, K. (2007) Effect of hemoglobin vesicle, a cellular-type artificial oxygen carrier, on middle cerebral artery occlusion- and arachidonic acid-induced stroke models in rats. Neurosci. Lett. 421, 121-125. (Pubitemid 46908939)
131. Yamamoto, M., Izumi, Y., Horinouchi, H., Teramura, Y., Sakai, H., Kohno, M., Watanabe, M., Kawamura, M., Adachi, T., Ikeda, E., Takeoka, S., Tsuchida, E., Kobayashi, K. (2009) Systemic administration of hemoglobin vesicle elevates tumor tissue oxygen tension and modifies tumor response to irradiation. J. Surg. Res. doi:10.1016/j.jss. 2007 12 770.
132. Sakai, H., Horinouchi, H., Tsuchida, E., Kobayashi, K. (2008) Hemoglobin-vesicles and red blood cells as carriers of carbon monoxide prior to oxygen for resuscitation after hemorrhagic shock in a rat model. Shock. doi:10 1097/SHK.0b013e318189017a.
133. Peters, T. (1996) All about Albumin: Biochemistry, Genetics and Medical
134. He, X. M., and Carter, D. C. (1992) Atomic structure and chemistry of human serum albumin. Nature 358, 209-215.
135. Carter, D. C., and Ho, J. X. (1994) Structure of serum albumin. Adv. Protein Chem. 45, 153-203.
136. Curry, S., Madelkow, H., Brick, P., and Franks, N. P. (1998) Crystal structure of human serum albumin complexed with fatty acid reveals an asymmetric distribution of binding sites. Nat. Struct. Biol. 5, 827-835. (Pubitemid 28402087)
137. Bhattacharya, A. A., Grune, T., and Curry, S. (2000) Crystal structures of human serum albumin complexed with monounsaturated and polyunsaturated fatty acids. J. Mol. Biol. 303, 721-732. (Pubitemid 34073060)
138. Ghuman, J., Zunszain, P. A., Petitpas, I., Bhattacharya, A. A., Otagiri, M., and Curry, S. (2007) Structural basis of the drug-binding specificity of humans serum albumin. J. Mol. Biol. 353, 38-52. (Pubitemid 41338838)
139. 2-carrying hemoprotein. Bioconjugate Chem. 10, 797-802.
140. 2-coordination structure of human serum albumin incorporating tetrakis-(o-pivalamido) phenylporphyrinatoiron(II) derivatives. Bioconjugate Chem. 10, 82-86.
141. 2-carrier. Polym. Adv. Technol. 13, 848-850.
142. 2 carrier) with blood cell components. J. Biomed. Mater. Res. 66A, 292-297.
143. 2-carrying plasma hemoprotein "albumin-heme" on complement system and platelet activation in vitro and physiological responses to exchange transfusion. J. Biomed. Mater. Res. 81A, 821-826.
144. Tsuchida, E., Nakagawa, A., and Komatsu, T. (2003) Coordination structure of active site in synthetic hemoprotein (albumin-heme) with dioxygen and carbon monoxide. Macromol. Symp. 195, 275-280.
145. Komatsu, T., Matsukawa, Y., and Tsuchida, E. (2000) Nitrosyl iron(II) complex of meso-tetrakis(α,α,α,α-o-pivalamidophenyl) porphyrin with a covalently linked 2-methylimidazolylalkyl group. Chem. Lett. 1060-1061.
146. Komatsu, T., Matsukawa, Y., and Tsuchida, E. (2001) Reaction of nitric oxide with synthetic hemoprotein, human serum albumin incorporating tetraphenylporphinatoiron(II) derivatives. Bioconjugate Chem. 12, 71-75. (Pubitemid 32111456)
147. 2 and CO binding to iron(II) porphyrins: A comparison of the "picket fence" and "pocket" porphyrins. J. Am. Chem. Soc. 105, 3052-3064.
148. 2 and RNC binding. J. Am. Chem. Soc. 107, 604-614.
149. 2 binding to human serum albumin-heme hybrid. Bioconjugate Chem. 11, 772-776.
150. 2-adduct complex. Bioconjugate Chem 13, 397-402.
151. 2 binding to human serum albumin incorporating iron porphyrin with a covalently linked methyl-L-histidine isomer. Bioconjugate Chem. 19, 581-584.
152. 2 coordination in aqueous media. Chem. Lett. 36, 640-641.
153. 2-binding properties of double-sided porphinatoiron(II)s with polar substituents and their human serum albumin hybrids. Bull. Chem. Soc. Jpn. 74, 1695-1702.
154. Nakagawa, A., Komatsu, T., Iizuka, M., and Tsuchida, E. (2006) Human serum albumin hybrid incorporating tailed porphyrinatoiron( II) in the α,α,α,β-conformer as an O2-binding site. Bioconjugate Chem. 17, 146-151. (Pubitemid 43157596)
155. Nakagawa, A., Komatsu, T., Ohmichi, N., and Tsuchida, E. (2003) Synthetic dioxygen-carrying hemoprotein. human serum albumin including iron(II) complex of protoporphyrin IX with an axially coordinated histidylglycyl-propionate. Chem. Lett. 32, 504-505. (Pubitemid 37094324)
156. Nakagawa, A., Komatsu, T., Ohmichi, N., and Tsuchida, E. (2004) Synthesis of protoheme IX derivatives with a covalently linked proximal base and their human serum albumin hybrids as artificial hemoprotein. Org. Biomol. Chem. 2, 3108-3112.
157. 22-coordination sites. Bioconjugate Chem. 16, 23-26.
158. Harris, J. M. (1992) Poly(ethylene glycol) Chemistry: Biotechnical and Biomedical Applications (Harris, J. M., Ed.) Plenum Press, New York.
159. Veronese, F. M., and Harris, J. M. (2002) Introduction and overview of peptide and protein PEGylation. Adv. Drug Delivery Rev. 54, 453-456.
160. Roberts, M. J., Bentley, M. D., and Harris, J. M. (2002) Chemistry for peptide and protein PEGylation. Adv. Drug Delivery Rev. 54, 459-476. (Pubitemid 34615543)
161. Veronese, F. M. (2001) Peptide and protein PEGylation: a review of problems and solutions. Biomaterials 22, 405-417.
162. Nucci, M. L., Shorr, R., and Abuchowski, A. (1991) The therapeutic value of poly(ethylene glycol) modified proteins. Adv. Drug Delivery Rev. 6, 133-151.
163. Kawahara, N. Y., and Ohno, H. (1997) Induced thermostability of poly(ethylene oxide)-modified hemoglobin in glycols. Bioconjugate Chem. 8, 643-648.
164. 2-transporting ability. Bioconjugate Chem. 17, 393-398.
165. Cabrales P., Tsai, A. G., Intaglietta, M. (2004) Microvascular pressure and functional capillary density in extreme hemodilution with low- and high-viscosity dextran and a low-viscosity Hb-based O2 carrier. Am. J. Physiol. Heart Circ. Physiol. 287, H363-H373. (Pubitemid 38802372)
166. Martini, J., Cabrales, P., K, A., Acharya, S. A., Intaglietta, M., Tsai, A. G. (2008) Survival time in severe hemorrhagic shock after perioperative hemodilution is longer with PEG-conjugated human serum albumin than HES 130/0.4: a microvasucular perspective. Crit. Care 12, R54. (Pubitemid 351722570)
167. Sugawara, Y., and Shikama, K. (1980) Autoxidation of native oxymyoglobin. Eur. J. Biochem. 110, 241-246.
168. 2-delivery, and reduction of the oxidized hemin sites by red blood cells. Bioconjugate Chem. 11, 46-50.
169. Huang, Y., Komatsu, T., Yamamoto, H., Horinouchi, H., Kobayashi, K., and Tsuchida, E. (2006) PEGylated albumin-heme as an oxygen-carrying plasma expander: exchange transfusion into acute anemia rat model. Biomaterials 27, 4477-4483.
170. Tsuchida, E., Komatsu, T., Matsukawa, Y., Nakagawa, A., Sakai, H., Kobayashi, K., and Suematsu, M. (2003) Human serum albumin incorporating synthetic heme: red blood cell substitute without hypertension by nitric oxide scavenging. J. Biomed. Mater. Res. 64A, 257-261. (Pubitemid 37521445)
171. 2-binding albumin thin films: solid membranes of poly(ethylene glycol)-conjugated human serum albumin incorporating iron porphyrin. Bioconjugate Chem. 18, 1673-1677.
172. Goa, K. L., and Benfield, P. (1994) Hyaluronic-acid - a review of its pharmacology and use as a surgical and in ophthalmology, and its therapeutic potential in joint disease and wound-healing. Drugs 47, 536-566. (Pubitemid 24087116)
173. Adams, P. A., and Berman, M. C. (1980) Kinetics and mechanism of the interaction between human serum albumin and monomeric haemin. Biochem. J. 191, 95-102.
174. Zunszain, P. A., Ghuman, J., Komatsu, T., Tsuchida, E., and Curry, S. (2003) Crystal structural analysis of human serum albumin complexed with hemin and fatty acid. BMC Struct. Biol. 3, 6. (Pubitemid 38809175)
175. Wardell, M., Wang, Z., Ho, J. X., Robert, J., Ruker, F., Ruble, J., and Carter, D. C. (2002) The atomic structure of human methemalbumin at 1.9 Å. Biochem. Biophys. Res. Commun. 291, 813-819. (Pubitemid 34694348)
176. Komatsu, T., Ohmichi, N., Zunszain, P. A., Curry, S., and Tsuchida, E. (2004) Dioxygenation of human serum albumin having a prosthetic-heme group in a tailor-made heme pocket. J. Am. Chem. Soc. 126, 14304-14305. (Pubitemid 39463585)
177. 2 and CO binding properties of artificial hemoproteins formed by complexing iron protoporphyrin IX with human serum albumin mutants. J. Am. Chem. Soc. 127, 15933-15942.
178. Vickery, L., Nozawa, T., and Sauer, K. (1976) Magnetic circular dichroism studies of myoglobin complexes. Correlation with-heme spin state and axial ligation. J. Am. Chem. Soc. 98, 343-350.
179. Antonini, E., and Brunori, M. Hemoglobin and Myoglobin in Their Reactions with Ligands, p 18, North-Holland Publishers, Amsterdam.
180. Rohlfs, R., Mathews, A. J., Carver, T. E., Olson, J. S., Springer, B. A., Egeberg, K. D., and Sligar, S. G. (1990) The effects of amino acid substitution at position E7 (residue 64) on the kinetics of ligand binding to sperm whale myoglobin. J. Biol. Chem. 265, 3168-3176. (Pubitemid 20087297)
181. Imai, K., Morimoto, H., Kotani, M., Watari, H., Hirata, W., and Kuroda, M. (1970) Studies of the function of abnormal hemoglobins I. An improved method for automatic measurement of the oxygen equilibrium curve of hemoglobin. Biochim. Biphys. Acta 200, 189-197.
182. Vandegriff, K. D., Young, M. A., Lohman, J., Bellelli, A., Samaja, M., Malavalli, A., and Winslow, R. M. (2008) CO-MP4, a polyethylene glycol-conjugated haemoglobin derivative and carbon monoxide carrier that reduces myocardial infarct size in rats. Br. J. Pharmacol. 154, 1649-11561
183. Creighton, T. E. (1992) Proteins: Structures and Molecular Properties, p 242, W. H. Freeman and Co., New York.
184. Chu, M. M. L., Castro, C. E., and Hathaway, G. M. (1978) Oxidation of low-spin iron(II) porphyrins by molecular oxygen. An outer sphere mechanism. Biochemistry 17, 481-486.
185. Tsuchida, E., Nishide, H., Sato, Y., and Kaneda, M. (1982) The preparation of protoheme mono-N-[5-(2-methyl-1-imidazolyl) pentyl]amide and its oxygenation. Bull. Chem. Soc. Jpn. 55, 1890-1895.
186. Uno, T., Sakamoto, R., and Tomisugi, Y. (2003) Inversion of axial coordination in myoglobin to create a "proximal" ligand binding pocket. Biochemistry 42, 10191-10199.
187. Springer, B. A., Sligar, S. G., Olson, J. S., and Philips, G. N. (1994) Mechanisms of a ligand recognition in myoglobin. Chem. Rev. 94, 699-714.
188. 2 binding of iron protoporphyrin IX by variation of distal amino acids. J. Am. Chem. Soc. 129, 11286-11295.