S-guanylation of human serum albumin is a unique posttranslational modification and results in a novel class of antibacterial agents

Journal of Pharmaceutical Sciences

Volumn 101, Issue 9, 2012, Pages 3222-3229

  Ishima, Yu ^a   Hoshino, Hitomi ^a   Shinagawa, Takuya ^a   Watanabe, Kaori ^a   Akaike, Takaaki ^b   Sawa, Tomohiro ^b   Kragh hansen, Ulrich ^c   Kai, Toshiya ^a,d   Watanabe, Hiroshi ^a   Maruyama, Toru ^a   Otagiri, Masaki ^a,e  

^a KUMAMOTO UNIVERSITY   (Japan)

^b KUMAMOTO UNIVERSITY   (Japan)

^c AARHUS UNIVERSITY   (Denmark)

^d Nipro Corporation   (Japan)

^e SOJO UNIVERSITY   (Japan)

Author keywords

Albumin; Antibacterial activity; Biomaterials; Cysteine; Drug design; Ligand binding; Nanoparticles; Nitric oxide; Oxidation; Posttranslational modification

Indexed keywords

ANTIBIOTIC AGENT; HUMAN SERUM ALBUMIN; S GUANYLATED HUMAN SERUM ALBUMIN; UNCLASSIFIED DRUG;

ADULT; AGED; ANTIBACTERIAL ACTIVITY; ARTICLE; CLINICAL ARTICLE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ENZYME LINKED IMMUNOSORBENT ASSAY; ESCHERICHIA COLI; FEMALE; HEMODIALYSIS; HUMAN; IN VITRO STUDY; IN VIVO STUDY; KIDNEY FAILURE; MALE; MAXIMUM INHIBITORY CONCENTRATION; NONHUMAN; PHYSICAL CHEMISTRY; PROTEIN PROCESSING; QUANTITATIVE ANALYSIS; SEPTICEMIA;

EID: 84864070597     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23143     Document Type: Article

References (21)

1. Ignarro LJ, Kadowitz PJ, Baricos WH. 1981. Evidence that regulation of hepatic guanylate cyclase activity involves interactions between catalytic site -SH groups and both substrate and activator. Arch Biochem Biophys 208(1):75-86.
2. Ignarro LJ, Lippton H, Edwards JC, Baricos WH, Hyman AL, Kadowitz PJ, Gruetter CA. 1981. Mechanism of vascular smooth muscle relaxation by organic nitrates, nitrites, nitroprusside and nitric oxide: Evidence for the involvement of S-nitrosothiols as active intermediates. J Pharmacol Exp Ther 218(3):739-749.
3. Ignarro LJ, Barry BK, Gruetter DY, Edwards JC, Ohlstein EH, Gruetter CA, Baricos WH. 1980. Guanylate cyclase activation of nitroprusside and nitrosoguanidine is related to formation of S-nitrosothiol intermediates. Biochem Biophys Res Commun 94(1):93-100.
4. Hogg N. 2000. Biological chemistry and clinical potential of S-nitrosothiols. Free Radic Biol Med 28(10):1478-1486.
5. Foster MW, McMahon TJ, Stamler JS. 2003. S-nitrosylation in health and disease. Trends Mol Med 9(4):160-168.
6. Stamler JS, Simon DI, Osborne JA, Mullins ME, Jaraki O, Michel T, Singel DJ, Loscalzo J. 1992. S-nitrosylation of proteins with nitric oxide: Synthesis and characterization of biologically active compounds. Proc Natl Acad Sci USA 89(1):444-448.
7. Sawa T, Zaki MH, Okamoto T, Akuta T, Tokutomi Y, Kim-Mitsuyama S, Ihara H, Kobayashi A, Yamamoto M, Fujii S, Arimoto H, Akaike T. 2007. Protein S-guanylation by the biological signal 8-nitroguanosine 3′, 5′-cyclic monophosphate. Nat Chem Biol 3(11):727-735.
8. Fujii S, Sawa T, Ihara H, Tong KI, Ida T, Okamoto T, Ahtesham AK, Ishima Y, Motohashi H, Yamamoto M, Akaike T. 2010. The critical role of nitric oxide signaling, via protein S-guanylation and nitrated cyclic GMP, in the antioxidant adaptive response. J Biol Chem 285(31):23970-23984.
9. Sawa T, Tatemichi M, Akaike T, Barbin A, Ohshima H. 2006. Analysis of urinary 8-nitroguanine, a marker of nitrative nucleic acid damage, by high-performance liquid chromatography-electrochemical detection coupled with immunoaffinity purification: Association with cigarette smoking. Free Radic Biol Med 40(4):711-720.
10. Peters T Jr. 1996. All about albumin: Biochemistry, genetics, and medical applications. San Diego, California: Academic Press.
11. Chen RF. 1967. Removal of fatty acids from serum albumin by charcoal treatment. J Biol Chem 242(2):173-181.
12. Ishima Y, Akaike T, Kragh-Hansen U, Hiroyama S, Sawa T, Suenaga A, Maruyama T, Kai T, Otagiri M. 2008. S-nitrosylated human serum albumin-mediated cytoprotective activity is enhanced by fatty acid binding. J Biol Chem 283(50):34966-34975.
13. Ishima Y, Sawa T, Kragh-Hansen U, Miyamoto Y, Matsushita S, Akaike T, Otagiri M. 2007. S-Nitrosylation of human variant albumin Liprizzi (R410C) confers potent antibacterial and cytoprotective properties. J Pharmacol Exp Ther 320(3):969-977.
14. Akaike T, Inoue K, Okamoto T, Nishino H, Otagiri M, Fujii S, Maeda H. 1997. Nanomolar quantification and identification of various nitrosothiols by high performance liquid chromatography coupled with flow reactors of metals and Griess reagent. J Biochem (Tokyo) 122(2):459-466.
15. Mera K, Anraku M, Kitamura K, Nakajou K, Maruyama T, Otagiri M. 2005. The structure and function of oxidized albumin in hemodialysis patients: Its role in elevated oxidative stress via neutrophil burst. Biochem Biophys Res Commun 334(4):1322-1328.
16. Ishima Y, Akaike T, Kragh-Hansen U, Hiroyama S, Sawa T, Maruyama T, Kai T, Otagiri M. 2007. Effects of endogenous ligands on the biological role of human serum albumin in S-nitrosylation. Biochem Biophys Res Commun 364(4):790-795.
17. Fang FC. 2004. Antimicrobial reactive oxygen and nitrogen species: Concepts and controversies. Nat Rev Microbiol 2(10):820-832.
18. Miyamoto Y, Akaike T, Alam MS, Inoue K, Hamamoto T, Ikebe N, Yoshitake J, Okamoto T, Maeda H. 2000. Novel functions of human alpha(1)-protease inhibitor after S-nitrosylation: Inhibition of cysteine protease and antibacterial activity. Biochem Biophys Res Commun 267(3):918-923.
19. Stamler JS, Jaraki O, Osborne J, Simon DI, Keaney J, Vita J, Singel D, Valeri CR, Loscalzo J. 1992. Nitric oxide circulates in mammalian plasma primarily as an S-nitroso adduct of serum albumin. Proc Natl Acad Sci USA 89(16):7674-7677.
20. Sarnak MJ, Jaber BL. 2000. Mortality caused by sepsis in patients with end-stage renal disease compared with the general population. Kidney Int 58(4):1758-1764.
21. Okamoto T, Khan S, Oyama K, Fujii S, Sawa T, Akaike T. 2010. A new paradigm for antimicrobial host defense mediated by a nitrated cyclic nucleotide. J Clin Biochem Nutr 46(1):14-19.