Arginine as a synergistic virucidal agent

Molecules

Volumn 15, Issue 3, 2010, Pages 1408-1424

  Ohtake, Satoshi ^a   Arakawa, Tsutomu ^c   Koyama, A Hajime ^b  

^a Aridis Pharmaceuticals   (United States)

^b WAKAYAMA MEDICAL UNIVERSITY   (Japan)

^c NONE

Author keywords

Arginine; Disinfectant; Infectivity; Virus aggregation; Virus inactivation

Indexed keywords

ANTIVIRUS AGENT; ARGININE;

ANIMAL; DRUG POTENTIATION; PH; REVIEW; VIRUS INACTIVATION;

ANIMALS; ANTIVIRAL AGENTS; ARGININE; DRUG SYNERGISM; HYDROGEN-ION CONCENTRATION; VIRUS INACTIVATION;

EID: 77950345668     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15031408     Document Type: Review

References (67)

1. Ellebedy, A. H.; Webby, R. J. Influenza vaccines. Vaccine 2009, 27, D65-D68.
2. Toplak, N.; Avcin, T. Influenza and autoimmunity. Ann. N. Y. Acad. Sci. 2009, 1173, 619-626.
3. Mathews, J. D.; Chesson, J. M.; McCaw, J. M.; McVerson, J. Understanding influenza transmission, immunity and pandemic threats. Influenza Other Respir. Viruses 2009, 3, 143-149.
4. Wanaratana, S.; Tantilertcharoen, R.; Sasipreeyajan, J.; Pakpinyo, S. The inactivation of avian virus subtype H5N1 isolated from chickens in Thailand by chemical and physical treatments. Vet. Microbiol. 2009, 140, 43-48.
5. Patnayak, D. P.; Prasad, A. M.; Malik, Y. S.; Ramakrishnan, M. A.; Goyal, S. M. Efficacy of disinfectants and hand sanitizers against respiratory viruses. Avian Dis. 2008, 52, 199-202.
6. Grayson, M. L.; Melvani, S.; Druce, J.; Barr, I. G.; Ballard, S. A.; Johnson, P. D.; Mastorakos, T.; Birch, C. Efficacy of soap and water and alcohol-based hand-rub preparations against live H1N1 influenza virus on the hands of human volunteers. Clin. Infect. Dis. 2009, 48, 285-291.
7. Lombardi, M. E.; Ladman, B. S.; Alphin, R. L.; Benson, E. R. Inactivation of avian influenza virus using common detergents and chemicals. Avian Dis. 2008, 52, 118-123.
8. Alphin, R. L.; Johnson, K. J.; Ladman, B. S.; Benson, E. R. Inactivation of avian influenza virus using four common chemicals and one detergent. Poult. Sci. 2009, 88, 1181-1185.
9. Rennie, O.; Bowtell, P.; Hull, D.; Charbonneau, D.; Lambkin-Williams, R.; Oxford, J. Low pH gel intranasal sprays inactivate influenza viruses in vitro and protect ferrets against influenza infection. Respir. Res. 2007, 8, 38.
10. Yamasaki, H.; Tsujimoto, K.; Koyama, A. H.; Ejima, D.; Arakawa, T. Arginine facilitates inactivation of enveloped viruses. J. Pharm. Sci. 2008, 97, 3063-3073.
11. Katsuyama, Y.; Yamasaki, H.; Tsujimoto, K.; Koyama, A. H.; Ejima, D.; Arakawa, T. Butyroylarginine as a potent virus inactivation agent. Int. J. Pharm. 2008, 361, 92-98.
12. Utsunimoya, H.; Ichinose, M.; Tsujimoto, K.; Katsuyama, Y.; Yamasaki, H.; Koyama, A. H.; Ejima, D.; Arakawa, T. Co-operative thermal inactivation of herpes simplex virus and influenza virus by arginine ans NaCl. Int. J. Pharm. 2009, 366, 99-102.
13. Arakawa, T.; Kita, Y.; Koyama, A. H. Synergistic virus inactivation effects of arginine. Biotechnol. J. 2009, 4, 174-178.
14. Arakawa, T.; Tsumoto, K. The effects of argnine on refolding of aggregated proteins: not facilitate refolding, but suppress aggregation. Biochem. Biophys. Res. Commun. 2003, 304, 148-152.
15. Tsumoto, K.; Ejima, D.; Kita, Y.; Arakawa, T. Review: why is arginine effective in suppressing aggregation? Protein Pept. Lett. 2005, 12, 613-619.
16. Arakawa, T.; Kita, Y.; Tsumoto, K.; Fukada, H.; Ejima, D. Aggregation suppression of proteins by arginine during thermal unfolding. Protein Pept. Lett. 2006, 13, 921-927.
17. Shiraki, K.; Kudou, M.; Fujiwara, S.; Imanaka, T.; Takagi, M. Biophysical effect of amino acids on the prevention of protein aggregation. J. Biochem. 2002, 132, 591-595.
18. Tsumoto, K.; Umetsu, M.; Kumaga, I.; Ejima, D.; Arakawa, T. Solubilization of active green fluorescent protein from insoluble particles by guanidine and arginine. Biochem. Biophys. Res. Commun. 2003, 312, 1382-1386.
19. Sakai, N.; Takeuchi, T.; Futaki, S.; Matile, S. Direct observation of anion-mediated translocation of fluorescent oligoarginine carriers into and across liquid and anionic bilayer membranes. ChemBioChem 2005, 6, 114-122.
20. Hirai, A.; Kawasaki, H.; Tanaka, S.; Nemoto, N.; Suzuki, M.; Maeda, H. Effects of L-arginine on aggregate of fatty-acid/potassium soap in the aqueous media. Colloid. Polym. Sci. 2006, 284, 520-528.
21. Arakawa, T.; Philo, J. S.; Tsumoto, K.; Yumioka, R.; Ejima, D. Elution of antibodies from a Protein-A column by aqueous arginine solution. Protein Expression Purif. 2004, 36, 244-248.
22. Ejima, D.; Yumioka, R.; Tsumoto, K.; Arakawa, T. Effective elution of antibodies by arginine and arginine derivatives in affinity colum chromatography. Anal. Biochem. 2005, 345, 250-257.
23. Tsumoto, K.; Ejima, D.; Nagase, K.; Arakawa, T. Arginine improves protein elution in hydrophobic interaction chromatography. The cases of human interleukin-6 and activin-A. J. Chromatogr. A 2007, 1154, 81-86. (Pubitemid 46843018)
24. Ejima, D.; Yumioka, R.; Arakawa, T.; Tsumoto, K. Arginine as an effective additive in gel permeation chromatography. J. Chromatogr. A 2005, 1094, 49-55.
25. Arakawa, T.; Tsumoto, K.; Nagase, K.; Ejima, D. The effects of arginine on protein binding and elution in hydrophobic interaction and ion-exchange chromatography. Protein Expr. Purif. 2007, 54, 110-116. (Pubitemid 46636321)
26. Abe, R.; Kudou, M.; Tanaka, Y.; Arakawa, T.; Tsumoto, K. Immobilized metal affinity chromatography in the presence of arginine. Biochem. Biophys. Res. Commun. 2009, 381, 306-310.
27. Futatsumori-Sugai, M.; Abe, R.; Watanabe, M.; Kudou, M.; Yamamoto, T.; Ejima, D.; Arakawa, T.; Tsumoto, K. Utilization of Arg-elution method for FLAG-tag based chromatography. Protein Expr. Purif. 2009, 67, 148-155.
28. Brorson, K.; Norling, L. Current and future approaches to ensure the viral safety of biopharmaceuticals. Dev. Biol. 2004, 118, 17-29.
29. Yap, P. L. The viral safety of intravenous immune globulin. Clin. Exp. Immunol. 1996, 104, 35-42.
30. Tsujimoto, K.; Uozaki, M.; Yamazaki, H.; Utsunomiya, H.; Ichinose, M.; Koyama, A. H.; Arakawa, T. Solvent-induced virus inactivation by acidic arginine solution. Int. J. Mol. Med. 2010, 25, 433-437.
31. Ikeda, K.; Yamasaki, H.; Minami, S.; Naito, T.; Irie, H.; Arakawa, T.; Koyama, A. H. Virucidal ability of arginine and its possible application as an antiherpetic agent. In From the Hallowed Halls of Herpesvirology; Baines, J.; Blaho, J., Eds.; Imperial College Press: London, UK, 2009; in press.
32. Kissmann, J.; Ausar, S. F.; Rudolph, A.; Braun, C.; Cape, S. P.; Sievers, R. E.; Federspiel, M. J.; Joshi, S. B.; Middaugh, C. R. Stabilization of measles virus for vaccine formulation. Human Vaccines 2008, 4, 350-359.
33. Ausar, S. F.; Rexroad, J.; Frolov, V. G.; Look, J. L.; Konar, N.; Middaugh, C. R. Analysis of the thermal and pH stability of human respiratory syncytial virus. Molecular Pharma. 2005, 2, 491-499.
34. Rexroad, J.; Martin, T. T.; McNeilly, D.; Godwin, S.; Middaugh, C. R. Thermal stability of adenovirus 2 as a function of pH. J. Pharm. Sci. 2006, 95, 1469-1479.
35. Rexroad, J.; Evans, R. K.; Middaugh, C. R. Effect of pH and ionic strength on the physical stability of adenovirus type 5. J. Pharm. Sci. 2006, 95, 237-247.
36. Ausar, S. F.; Foubert, T. R.; Hudson, M. H.; Vedvick, T. S.; Middaugh, C. R. Conformational stability and disassembly of Norwalk virus like particles: effect of pH and temperature. J. Biol. Chem. 2006, 281, 19478-19488.
37. Thomas, A. A. M.; Brioen, P.; Boeye, A. A monoclonal antibody that neutralizes poliovirus by cross-linking virions. J. Virol. 1985, 54, 7-13.
38. Daher, K. A.; Selsted, M. E.; Lehrer, R. Direct inactivation of viruses by human granulocyte defensins. J. Virol. 1986, 60, 1068-1074.
39. Wimley, W. C.; Selsted, M. E.; White, S. H. Interactions between human defensins and lipid bilayers: evidence for formation of multimeric pores. Protein Sci. 1994, 3, 1362-1373.
40. Peetermans, J.; Colinet, G.; Stephenne, J.; Bouillet, A. Stability of freeze-dried and reconstituted measles vaccines. Dev. Biol. Stand. 1978, 41, 259-264.
41. Ohtake, S.; Martin, R. A.; Yee, L.; Chen, D.; Kristensen, D. D.; Lechuga-Ballesteros, D.; Truong-Le, V. Heat-stable measles vaccine produced by spray drying. Vaccine In Press.
42. Ver, B. A.; Melnick, J. L.; Wallis, C. Efficient filtration and sizing of viruses with membrane filters. J. Virol. 1968, 2, 21-25.
43. Thomas, A. A. M.; Vrijsen, R.; Boeye, A. Relationship between poliovirus neutralization and aggregation. J. Virol. 1986, 59, 479-485.
44. Wallis, C.; Melnick, J. L. Virus aggregation as the cause of the non-neutralizable persisted fraction. J. Virol. 1967, 1, 478-488.
45. Pinto, F.; Maillard, J. Y.; Denyer, S. P.; McGeechan, P. Polyhexamethylene biguanide exposure leads to viral aggregation. J. Appl. Microbiol. In Press.
46. Kim, Y. C.; Quan, F. S.; Compans, R. W.; Kang, S. M.; Prausnitz, M. R. Formulation and coating of microneedles with inactivated influenza virus to improve vaccine stability and immunogenicity. J. Control. Release 2010, 142, 187-195.
47. Michalsky, R.; Pfromm, P. H.; Czermak, P.; Sorensen, C. M.; Passarelli, A. L. Effects of temperature and shear force on infectivity of the baculovirus Autographa californica M nucleopolyhechovirus. J. Virol. Methods 2008, 153, 90-96.
48. Melnick, J. L. Preservation of viruses by freezing. Federation Proc. 1965, 15, 280-283.
49. Watson, D. H.; Wildy, O. Some serological properties of herpesvirus particles studied by the electron microscope. Virology 1963, 21, 100-110.
50. Merryman, H. T. Mechanics of freezing in living cells and tissues. Science 1956, 124, 515-521.
51. Wallis, C.; Melnick, J. L. Stabilization of enveloped virus by dimethyl sulfoxide. J. Virol. 1968, 2, 953-954.
52. Lebon, P.; Protat, A.; Molinie, P. L-arginine elution of measles virus adsorbed on monkey erythrocytes. Infect. Immunity 1975, 11, 1407-1408.
53. Yumioka, R.; Sato, H.; Tomizawa, H.; Yamasaki, Y.; Ejima, D. Mobile phase containing arginine provides more reliable SEC condition for aggregation analysis. J. Pharm. Sci. 2010, 99, 618-620.
54. Arakawa, T.; Ejima, D.; Li, T.; Philo, J. S. The critical role of mobile phase composition in size exclusion chromatography of protein pharmaceuticals. J. Pharm. Sci. 2010, 99, 1674-1692.
55. Herce, H. D.; Garcia, A. E.; Litt, K.; Kane, R. S.; Martin, P.; Enrique, N.; Rebolledo, A.; Milesi, V. Arginine-rich peptides destabilize the plasma membrane, consistent with a pore formation translocation mechanism of cell penetrating peptides. Biophys. J. 2009, 97, 1917-1925.
56. Bouchet, A.; Lairion, F.; Disalvo, E. A. Role of guanidinium group in the interaction of l-arginine in DMPE and DMPC lipid interphases. Biochim. Biophys. Acta 2009, 1798, 616-623.
57. Schmidt, N.; Mishra, A.; Lai, G. H.; Wong, G. C. Arginine-rich cell-penetrating peptides. FEBS Lett. 2009, doi:10.1016/j.febslet.2009.11.046.
58. Fukuyama, K.; Abdel-Mequid, S. S.; Johnson, J. E.; Rossmann, M. G. Structure of a T = 1 aggregate of alfalfa mosaic virus coat protein seen at 4.5 A resolution. Mol. Biol. 1983, 167, 873-894.
59. Rould, M. A.; Perona, J. J.; Steitz, T. A. Structure of E. coli glutaminyl-tRNA synthetase complexed with tRNA (Gln) and ATP at 2.8 A resolution. Science 1989, 246, 1135-1142.
60. Xu, S.; Zheng, W.; Radisic, D.; Bowen, K. H., Jr. The stabilization of arginine's zwitterions by dipole-binding of an excess electron. J. Chem. Phys. 2005, 122, 091103.
61. Yoo, J.; Cui, Q. Does arginine remain protonated in the lipid membrane? Insight from microscopic pKa calculations. Biophys. J. 2008, 94, L61-L63.
62. Kita, Y.; Arakawa, T.; Lin, T. Y.; Timasheff, S. N. Contribution of the surface free energy perturbation to protein-solvent interactions. Biochemistry 1994, 33, 15178-15189.
63. Schneider, C. P.; Trout, B. L. Investigation of cosolute-protein preferential interaction coefficients: new insight into the mechanism by which arginine inhibits aggregation. J. Phys. Chem. 2009, 113, 2050.
64. Arakawa, T.; Timasheff, S. N. Preferential interactions of proteins with salts in concentrated solutions. Biochemistry 1982, 21, 6545-6552.
65. Arakawa, T.; Timasheff, S. N. The mechanism of action of Na glutamate, lysine HCl, and piperazine-N, N'-bis (2-ethanesulfonic acid) in the stabilization of tubulin and microtuble formation. J. Biol. Chem. 1984, 259, 4979-4986.
66. Arakawa, T.; Timasheff, S. N. The stabilization of proteins by osmolytes. Biophys. J. 1985, 47, 411-414.
67. Ausar, S. F.; Espina, M.; Brock, J.; Thyagarayapuran, N.; Repetto, R.; Khandke, L.; Middaugh, C. R. High-throughput screening of stabilizers for respiratory syncytial virus. Human Vaccines 2007, 3, 68-77.