SMA-copolymer conjugate of AHPP: A polymeric inhibitor of xanthine oxidase with potential antihypertensive effect

Journal of Controlled Release

Volumn 135, Issue 3, 2009, Pages 211-217

  Fang, Jun ^a   Iyer, Arun K ^a   Seki, Takahiro ^b   Nakamura, Hideaki ^a   Greish, Khaled ^a   Maeda, Hiroshi ^a  

^a SOJO UNIVERSITY   (Japan)

^b KUMAMOTO UNIVERSITY   (Japan)

Author keywords

AHPP; Antihypertension; Nitric oxide; SMA; Superoxide anion

Indexed keywords

AHPP; ANTIHYPERTENSION; ANTIHYPERTENSIVE EFFECTS; GOOD WATER SOLUBILITIES; IN-VIVO; IN-VIVO EXPERIMENTS; INHIBITORY ACTIVITIES; ORAL ADMINISTRATIONS; POLYMERIC CONJUGATES; POLYMERIC INHIBITORS; POTENTIAL VALUES; SMA; SPONTANEOUSLY HYPERTENSIVE RATS; STYRENE MALEIC ACID COPOLYMERS; SUPEROXIDE ANION; VASCULAR SYSTEMS; VASORELAXATION; WATER SOLUBLE; XANTHINE OXIDASE;

AGENTS; AMINES; BLOOD PRESSURE; COPOLYMERIZATION; NEGATIVE IONS; NITRIC OXIDE; OXYGEN; POLYMERS; RATS; STYRENE;

WATER INJECTION;

4 AMINO 6 HYDROXYPYRAZOLO[3,4 D]PYRIMIDINE PLUS STYRENE MALEIC ACID; ANTIHYPERTENSIVE AGENT; UNCLASSIFIED DRUG; XANTHINE OXIDASE; XANTHINE OXIDASE INHIBITOR;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIHYPERTENSIVE ACTIVITY; ARTICLE; BLOOD PRESSURE; CONTROLLED STUDY; DRUG RELEASE; DRUG SOLUBILITY; ENZYME INHIBITION; ESSENTIAL HYPERTENSION; IN VIVO STUDY; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; SPONTANEOUSLY HYPERTENSIVE RAT;

ANIMALS; ANTIHYPERTENSIVE AGENTS; BUFFERS; CARBODIIMIDES; DOSE-RESPONSE RELATIONSHIP, DRUG; HYDROGEN-ION CONCENTRATION; KINETICS; MALE; MALEIC ANHYDRIDES; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; POLYMERS; RATS; RATS, INBRED SHR; SOLUBILITY; STYRENE; WATER; XANTHINE OXIDASE;

EID: 63649153523     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jconrel.2009.01.006     Document Type: Article

References (52)

1. Miyamoto Y., Akaike T., Yoshida M., Goto S., Horie H., and Maeda H. Potentiation of nitric oxide-mediated vasorelaxation by xanthine oxidase inhibitors. Proc. Soc. Exp. Biol. Med. 211 4 (1996) 366-373
2. McCord J.M. Oxygen-derived free radicals in postischemic tissue injury. N. Engl. J. Med. 312 3 (1985) 159-163
3. - generation by xanthine oxidase of pathogenesis of influenza virus infection in mice. J. Clin. Invest. 85 3 (1990) 739-745
4. Blough N.V., and Zafiriou O.C. Reaction of superoxide with nitric oxide to form peroxynitrite in alkaline aqueous solution. Inorg. Chem. 24 (1985) 3502-3504
5. Gryglewski R.J., Palmer R.M., and Moncada S. Superoxide anion is involved in the breakdown of endothelium-derived vascular relaxing factor. Nature 320 6061 (1986) 454-456
6. Huie R.E., and Padmaja S. The reaction of NO with superoxide. Free Radic. Res. Commun. 18 4 (1993) 195-199
7. Jarasch E.D., Grund C., Bruder G., Heid H.W., Keenan T.W., and Franke W.W. Localization of xanthine oxidase in mammary-gland epithelium and capillary endothelium. Cell 25 1 (1981) 67-82
8. Jarasch E.D., Bruder G., and Heid H.W. Significance of xanthine oxidase in capillary endothelial cells. Acta Physiol. Scand. Suppl. 548 (1986) 39-46
9. Adachi T., Fukushima T., Usami Y., and Hirano K. Binding of human xanthine oxidase to sulphated glycosaminoglycans on the endothelial-cell surface. Biochem. J. 289 Pt 2 (1993) 523-527
10. Moncada S., Palmer R.M., and Higgs E.A. Nitric oxide: physiology, pathophysiology, and pharmacology. Pharmacol. Rev. 43 2 (1991) 109-142
11. Yoshida M., Akaike T., Wada Y., Sato K., Ikeda K., Ueda S., and Maeda H. Therapeutic effects of imidazolineoxyl N-oxide against endotoxin shock through its direct nitric oxide-scavenging activity. Biochem. Biophys. Res. Commun. 202 2 (1994) 923-930
12. Cooke J.P., and Dzau V.J. Nitric oxide synthase: role in the genesis of vascular disease. Annu. Rev. Med. 48 (1997) 489-509
13. Harrison D.G. Cellular and molecular mechanisms of endothelial cell dysfunction. J. Clin. Invest. 100 9 (1997) 2153-2157
14. Huang P.L., Huang Z., Mashimo H., Bloch K.D., Moskowitz M.A., Bevan J.A., and Fishman M.C. Hypertension in mice lacking the gene for endothelial nitric oxide synthase. Nature 377 6546 (1995) 239-242
15. Rudic R.D., Shesely E.G., Maeda N., Smithies O., Segal S.S., and Sessa W.C. Direct evidence for the importance of endothelium-derived nitric oxide in vascular remodeling. J. Clin. Invest. 101 4 (1998) 731-736
16. Channon K.M., Qian H., and George S.E. Nitric oxide synthase in atherosclerosis and vascular injury: insights from experimental gene therapy. Arterioscler. Thromb. Vasc. Biol. 20 8 (2000) 1873-1881
17. Kosaka H., Watanabe M., Yoshihara H., Harada N., and Shiga T. Detection of nitric oxide production in lipopolysaccharide-treated rats by ESR using carbon monoxide hemoglobin. Biochem. Biophys. Res. Commun. 184 2 (1992) 1119-1124
18. Akaike T., Yoshida M., Miyamoto Y.K., Sato K., Kohno M., Sasamoto K., Miyazaki K., Ueda S., and Maeda H. Antagonistic action of imidazolineoxyl N-oxides against endothelium-derived relaxing factor/.NO through a radical reaction. Biochemistry 32 3 (1993) 827-832
19. White C.R., Brock T.A., Chang L.Y., Crapo J., Briscoe P., Ku D., Bradley W.A., Gianturco S.H., Gore J., Freeman B.A., et al. Superoxide and peroxynitrite in atherosclerosis. Proc. Natl. Acad. Sci. U. S. A. 91 3 (1994) 1044-1048
20. Harrison D.G., and Ohara Y. Physiologic consequences of increased vascular oxidant stresses in hypercholesterolemia and atherosclerosis: implications for impaired vasomotion. Am. J. Cardiol. 75 6 (1995) 75B-81B
21. Xanthine oxidase (milk). Worthington Enzyme Manual (1972), Worthington Biochemical, Freehold, NJ 30-31
22. Takahashi K., Akaike T., Sato K., Mori K., and Maeda H. Superoxide anion generation by Pacific oyster (Crassostrea gigas) hemocytes: identification by electron spin resonance spin trapping and chemiluminescence analysis. Comp. Biochem. Physiol. 105B (1993) 35-41
23. Cleland W.W. Statistical analysis of enzyme kinetic data. Methods Enzymol, 63 (1979) 103-138
24. Iyer A.K., Greish K., Fang J., Murakami R., and Maeda H. High loading nanosized micelles of copoly(styrene-maleic acid)-zinc protoporphyrin for targeted delivery of a potent heme oxygenase inhibitor. Biomaterials 28 10 (2007) 1871-1881
25. Nishino T., Nishino T., Schopfer L.M., and Massey V. The reactivity of chicken liver xanthine dehydrogenase with molecular oxygen. J. Biol. Chem. 264 5 (1989) 2518-2527
26. Sato K., Akaike T., Suga M., Ando M., and Maeda H. Generation of free radicals from neocarzinostatin mediated by NADPH/cytochrome P-450 reductase via activation of enediyne chromophore. Biochem. Biophys. Res. Commun. 205 3 (1994) 1716-1723
27. Channon K.M., and Guzik T.J. Mechanisms of superoxide production in human blood vessels: relationship to endothelial dysfunction, clinical and genetic risk factors. J. Physiol. Pharmacol. 53 4 Pt 1 (2002) 515-524
28. Akaike T., and Maeda H. Nitric oxide and virus infection. Immunology 101 (2000) 300-308
29. Akaike T., and Maeda H. Pathophysiological effects of high-output production of nitric oxide. In: Ignarro L.J. (Ed). Nitric Oxide: Biology and pathobiology (2000), Academic Press, San Diego 733-745
30. Wolin M.S. Interactions of oxidants with vascular signaling systems. Arterioscler. Thromb. Vasc. Biol. 20 6 (2000) 1430-1442
31. Ballinger S.W., Patterson C., Yan C.N., Doan R., Burow D.L., Young C.G., Yakes F.M., Van Houten B., Ballinger C.A., Freeman B.A., and Runge M.S. Hydrogen peroxide- and peroxynitrite-induced mitochondrial DNA damage and dysfunction in vascular endothelial and smooth muscle cells. Circ. Res. 86 9 (2000) 960-966
32. Houston M., Estevez A., Chumley P., Aslan M., Marklund S., Parks D.A., and Freeman B.A. Binding of xanthine oxidase to vascular endothelium. Kinetic characterization and oxidative impairment of nitric oxide-dependent signaling. J. Biol. Chem. 274 (1999) 4985-4994
33. Takeshita J., Maeda H., and Kanamaru R. In vitro mode of action, pharmacokinetics, and organ specificity of poly (maleic acid-styrene)-conjugated neocarzinostatin, SMANCS. Gann 73 (1982) 278-284
34. Kobayashi A., Oda T., and Maeda H. Protein binding of macromolecular anticancer agent SMANCS: characterization of poly(styrene-co-maleic acid) derivatives as an albumin binding ligand. J. Bioact. Compat. Polym. 3 (1988) 319-333
35. Greish K., Nagamitsu A., Fang J., and Maeda H. Copoly(styrene-maleic acid)-pirarubicin micelles: high tumor-targeting efficiency with little toxicity. Bioconjug. Chem. 16 1 (2005) 230-236
36. Matsumura Y., and Maeda H. A new concept for macromolecular therapeutics in cancer chemotherapy: mechanism of tumoritropic accumulation of proteins and the antitumor agent SMANCS. Cancer Res. 46 (1986) 6387-6392
37. Maeda H. SMANCS and polymer-conjugated macromolecular drugs: advantages in cancer chemotherapy. Adv. Drug. Delivery Rev. 46 (2001) 169-185
38. Fang J., Sawa T., and Maeda H. Factors and mechanism of "EPR" effect and the enhanced antitumor effects of macromolecular drugs including SMANCS. Adv. Exp. Med. Biol. 519 (2003) 29-49
39. Duncan R. The dawning era of polymer therapeutics. Nat. Rev. Drug Discov. 2 (2003) 347-360
40. Iyer A.K., Greish K., Fang J., and Maeda H. Exploiting the enhanced permeability and retention effect for tumor targeting. Drug Discov. Today 11 (2006) 812-818
41. Maeda H., Sawa T., and Konno T. Mechanism of tumor-targeted delivery of macromolecular drugs, including the EPR effect in solid tumor and clinical overview of the prototype polymeric drug SMANCS. J. Control. Release 74 (2001) 47-61
42. T. Seki, J. Fang, H. Maeda, Tumor targeted macromolecular drug delivery based on the enhanced permeability and retention effect in solid tumor, In: Pharmaceutical Perspectives of Cancer Therapeutics, AAPS-Springer publishing (in press).
43. H. Maeda, G.Y. Bharate, J. Daruwalla, Polymeric drugs and nanomedicines for efficient tumor targeted drug delivery based on EPR-effect. Eur. J. Phar. Biophar. (in press), doi:10.1016/j.ejpb.2008.11.010.
44. Maeda H., Greish K., and Fang J. The EPR effect and polymeric drugs: a paradigm shift for cancer chemotherapy in the 21st century. Adv. Polym. Sci. 193 (2006) 103-121
45. Vicent M.J., and Duncan R. Polymer conjugates: nanosized medicines for treating cancer. Trends Biotechnol. 24 (2006) 39-47
46. Oates J.A., and Brown N.J. Antihypertensive agents and the drug therapy of hypertension. In: Hardman J.G., Limbird L.E., and Gilman A.G. (Eds). Goodman & Gilman's the pharmacological basis of therapeutics (Tenth Edition) (2001), The McGraw-Hill Companies, Inc., New York 871-896
47. In: Halliwell B., and Gutteridge J.M.C. (Eds). Free radicals in biology and medicine (1999), Oxford University Press, NJ, USA 617-859
48. Oda T., Akaike T., Hamamoto T., Suzuki F., Hirano T., and Maeda H. Oxygen radicals in influenza-induced pathogenesis and treatment with pyran polymer-conjugated SOD. Science 244 (1989) 974-976
49. - generation by xanthine oxidase of pathogenesis of influenza virus infection in mice. J. Clin. Invest. 85 (1990) 739-745
50. Maeda H., and Akaike T. Oxygen free radicals as pathogenic molecules in viral diseases. Proc. Soc. Exp. Biol. Med. 198 (1991) 721-727
51. Akaike T., and Maeda H. Nitric oxide and virus infection. Immunology 101 (2000) 300-308
52. Crow J.P., and Beckman J.S. The role of peroxynitrite in nitric oxide-mediated toxicity. In: Koprowski H., and Maeda H. (Eds). The Role of Nitric Oxide in Physiology and Pathophysiology. Current Topics in Microbiology and Immunology vol. 196 (1995), Springer-Verlag, Berlin 57-73