Modification of a dioxygen carrier, HemoCD, with PEGylated dendrons for extension of circulation time in the bloodstream

Bioconjugate Chemistry

Volumn 23, Issue 12, 2012, Pages 2365-2376

  Karasugi, Keiichi ^a   Kitagishi, Hiroaki ^a   Kano, Koji ^a  

^a DOSHISHA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CONDENSATION; CONDENSATION REACTIONS; DIMERS; ESTERS; MOLECULAR OXYGEN; POLYETHYLENE GLYCOLS; SOLUTIONS; SUPRAMOLECULAR CHEMISTRY;

CIRCULATION TIME; CORE COMPONENTS; DENDRONS; DEPROTECTION; DIATOMICS; DIOXYGENS; HALF LIVES; PEGYLATED; PORPHIN; T-BUTYL ESTER;

DENDRIMERS;

4 AMINO 4 (2 TERT BUTOXYCARBONYLETHYL)HEPTANEDIOIC ACID DI TERT BUTYL ESTER; 4 OXO 4 [[4 [10,15,20 TRIS(4 SULFONATOPHENYL) 21H,23H PORPHIN 5 YL]PHENYL]AMINO]BUTANOIC ACID; DIMER; HEMOCD RECEPTOR; IRON COMPLEX; RECEPTOR; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CIRCULATION TIME; DEPROTECTION REACTION; HYDROLYSIS;

EID: 84871275713     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc300303z     Document Type: Article

References (50)

1. Collman, J. P., Boulatov, R., Sunderland, C. J., and Fu, L. (2004) Functional analogues of cytochrome c oxidase, myoglobin, and hemoglobin Chem. Rev. 104, 561-588
2. Magnus, K. A., Ton-That, H., and Carpenter, J. E. (1994) Recent structural work on the oxygen transport protein hemocyanin Chem. Rev. 94, 727-735
3. Momenteau, M. and Reed, C. A. (1994) Synthetic heme-dioxygen complexes Chem. Rev. 94, 659-698
4. Shikama, K. (1998) The molecular mechanism of autoxidation of myoglobin and haemoglobin: a venerable puzzle Chem. Rev. 98, 1357-1373
5. Tsuchida, E., Sou, K., Nakagawa, A., Sakai, H., Komatsu, T., and Kobayashi, K. (2009) Artificial oxygen carriers, hemoglobin vesicles and albumin-hemes, based on bioconjugate chemistry Bioconjugate Chem. 20, 1419-1440
6. Tsuchida, E. (1985) Liposome-embedded iron-porphyrins as an artificial oxygen carrier Ann. N.Y. Acad. Sci. 446, 429-442
7. Kano, K., Kitagishi, H., Kodera, M., and Hirota, S. (2005) Dioxygen binding to a simple myoglobin model in aqueous solution Angew. Chem., Int. Ed. 44, 435-438
8. Kano, K., Kitagishi, H., Dagallier, C., Kodera, M., Matsuo, T., Hayashi, T., Hisaeda, Y., and Hirota, S. (2006) Iron porphyrin-cyclodextrin supramolecular complex as a functional model of myoglobin in aqueous solution Inorg. Chem. 45, 4448-4460
9. Kano, K., Chimoto, S., Tamaki, M., Itoh, Y., and Kitagishi, H. (2012) Supramolecular dioxygen receptors composed of an anionic water-soluble porphinatoiron(II) and cyclodextrin dimers Dalton Trans. 41, 453-461
10. Kitagishi, H., Negi, S., Kiriyama, A., Honbo, A., Sugiura, Y., Kawaguchi, A. T., and Kano, K. (2010) A diatomic molecule receptor that removes CO in a living organism Angew. Chem., Int. Ed. 49, 1312-1315
11. 2 and CO) in aqueous solution Chem.-Asian J. 6, 2946-2955
12. 2 and CO) in aqueous solution Chem.-Asian J. 6, 825-833
13. Wijagkanalan, W., Kawakami, S., and Hashida, M. (2011) Designing dendrimers for drug delivery and imaging: pharmacokinetic considerations Pharm. Rev. 28, 1500-1519
14. Medina, S. H. and El-Sayed, M. E. H. (2009) Dendrimers as carriers for delivery of chemotherapeutic agents Chem. Rev. 109, 3141-3157
15. Singh, P., Gupta, U., Asthana, A., and Jain, N. K. (2008) Folate and folate-PEG-PAMAM dendrimers: synthesis, characterization, and targeted anticancer drug derivery potential in tumor bearing mice Bioconjugate Chem. 19, 2239-2252
16. Kaminskas, L. M., McLeod, V. M., Kelly, B. D., Sberna, G., Boyd, B. J., Williamson, M., Owen, D. J., and Porter, C. J. H. (2012) A comparison of charges to doxorubicin pharmacokinetics, antitumor activity, and toxicity mediated by PEGylated dendrimer and PEGylated liposome drug delivery systems Nanomedicine 8, 103-111
17. Jiang, D.-L. and Aida, T. (1996) A dendritic iron porphyrin as a novel haemoprotein mimic: effects of the dendrimer cage on dioxygen-binding activity Chem. Commun. 1523-1524
18. Jiang, D.-L. and Aida, T. (1997) Dendrimer-encapsulated iron porphyrin as a novel hemoprotein mimic for dioxygen binding J. Macromol. Sci. A34, 2047-2055
19. Collman, J. P., Fu, L., Zingg, A., and Diederich, F. (1997) Dioxygen and carbon monoxide binding in dendritic iron(II)porphyrins Chem. Commun. 193-194
20. 2 complexes in dendrimers with H-bond-donor centers Helv. Chim. Acta 85, 333-351
21. 2 binding of dendritic cobalt(II) porphyrins ChemPhysChem 3, 659-667
22. Elbert, D, L. and Hubbell, J, A. (2001) Conjugate addition reactions combined with free-radical cross-linking for the design of materials for tissue engineering Biomacromolecules 2, 430-441
23. Kruper, W. J., Jr., Chamberlin, T. A., and Kochanny, M. (1989) Regiospecific aryl nitration of meso-substituted tetraarylporphyrins: a simple route to bifunctional porphyrins J. Org. Chem. 54, 2753-2756
24. Karim, N. and Ali, S. S. (2009) Jugular vein cannulation in rats-a mini review Can. J. Pure Appl. Sci. 3, 929-935
25. Newkome, G. R., Behera, R. K., Moorefield, C. N., and Baker, G. R. (1991) Cascade polymers: syntheses and characterization of one-directional arborols based on adamantane J. Org. Chem. 56, 7162-7167
26. Ornelas, C., Broichhagen, J., and Weck, M. (2010) Strain-promoted alkyne azide cycloaddition for the functionalization of poly(amide)-based dendrons and dendrimers J. Am. Chem. Soc. 132, 3923-3931
27. Huang, K., Voss, B., Kumar, D., Hamm, H. E., and Harth, E. (2007) Dendritic molecular transporters provide control of delivery to intracellular compartments Bioconjugate Chem. 18, 403-409
28. Gandini, S. C. M., Yushmanov, V. E., and Tabak, M. (2001) Interaction of Fe(III)- and Zn(II)-tetra(4-sulfonatophenyl) porphyrins with ionic and nonionic surfactants: aggregation and binding J. Inorg. Biochem. 85, 263-277
29. Kano, K., Kitagishi, H., Tamura, S., and Yamada, A. (2004) Anion binding to a ferric porphyrin complexed with per- O -methylated β-cyclodextrin in aqueous solution J. Am. Chem. Soc. 126, 15202-15210
30. 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 a "picket fence" porphyrin. A model for oxymyoglobin J. Am. Chem. Soc. 95, 7868-7870
31. Laurent, T. C. and Killander, J. (1964) A theory of gel filtration and its experimental verification J. Chromatogr. 14, 317-330
32. Kunji, E. R. S., Harding, M., Butler, P. J. G., and Akamine, P. (2008) Determination of the molecular mass and dimensions of membrane proteins by size exclusion chromatography Methods 46, 62-72
33. Bagchi, B. (2005) Water dynamics in the hydration layer around proteins and micelles Chem. Rev. 105, 3197-3219
34. Fox, M. E., Szoka, F. C., and Fréchet, J. M. J. (2009) Soluble polymer carriers for the treatment of cancer: the importance of molecular architecture Acc. Chem. Res. 42, 1141-1151
35. Collman, J. P., Zhang, X., Wong, K., and Brauman, J. I. (1994) Dioxygen binding in iron and cobalt picnic basket porphyrins J. Am. Chem. Soc. 116, 6245-6251
36. Niederhoffer, E. C., Timmons, J. H., and Martell, A. E. (1984) Thermodynamics of oxygen binding in natural and synthetic dioxygen complexes Chem. Rev. 84, 137-203
37. Pedersen, C. L., Faggiano, S., Helbo, S., Gesser, H., and Fago, A. (2010) Roles of nitric oxide, nitrite and myoglobin on myocardial efficiency in trout (Oncorhynchus mykiss) and goldfish (Carassius auratus): implications for hypoxia tolerance J. Experimental Biol. 213, 2711-2762
38. Schenkman, K. A., Marble, D. R., Burns, D. H., and Feigl, E. O. (1997) Myoglobin oxygen dissociation by multiwavelength spectroscopy J. Appl. Physiol. 82, 86-92
39. 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
40. Tsuruga, M. and Shikama, K. (1997) Biphasic nature in the autoxidation reaction of human oxyhemoglobin Biochim. Biophys. Acta 1337, 96-104
41. 2, NO, and CO by electrostatic interactions with the bound ligand J. Biol. Inorg. Chem. 2, 544-552
42. 2 and CO receptor: synthesis, characterization and pharmacokinetic study Org. Biomol. Chem. 10, 4337-4347
43. Gillies, E. R., Dy, E., Fréchet, J. M. J., and Szoka, F. C. (2005) Biological evaluation of polyester dendrimer: poly(ethylene oxide) "bow-tie" hybrids with tunable molecular weight and architecture Mol. Pharmaceutics 2, 129-138
44. Kaminskas, L. M., Boyd, B. J., Karellas, P., Krippner, G. Y., Lessene, R., Kelly, B., and Porter, C. J. H. (2008) The impact of molecular weight and PEG chain length on the systemic pharmacokinetics of PEGylated poly L-lysine dendrimers Mol. Pharmaceutics 5, 449-463
45. Guillaudeu, S. J., Fox, M. E., Haidar, Y. M., Dy, E. E., Szoka, F. C., and Fréchet, J. M. J. (2008) PEGylated dendrimers with core functionality for biological applications Bioconjugate Chem. 19, 461-469
46. Lim, J., Guo, Y., Rostollan, C. L., Stanfield, J., Hsieh, J.-T., Sun, X., and Simanek, E. E. (2008) The role of the size and number of polyethylene glycol chains in the biodistribution and tumor localization of triazine dendrimers Mol. Pharmaceutics 5, 540-547
47. Kojima, C., Regino, C., Umeda, Y., Kobayashi, H., and Kono, K. (2010) Influence of dendrimer generation and polyethylene glycol length on the biodistribution of PEGylated dendrimers Int. J. Pharm. 383, 293-296
48. 2-transporting ability Bioconjugate Chem. 17, 393-398
49. Chen, H.-T., Neerman, M. F., Parrish, A. R., and Simanek, E. E. (2004) Cytotoxicity, hemolysis, and acute in vivo toxicity of dendrimers based on melamine, candidate vehicles for drug delivery J. Am. Chem. Soc. 126, 10044-10048
50. Kano, K., Kitagishi, H., Mabuchi, T., Kodera, M., and Hirota, S. (2006) A myoglobin functional model composed of a ferrous porphyrin and a cyclodextrin dimer with an imidazole linker Chem.-Asian J. 1, 358-366