Linker-extended native cyanovirin-N facilitates PEGylation and potently inhibits HIV-1 by targeting the glycan ligand

PLoS ONE

Volumn 9, Issue 1, 2014, Pages

  Chen, Jia ^a   Huang, Dane ^b,f   Chen, Wei ^a   Guo, Chaowan ^c   Wei, Bo ^a   Wu, Chongchao ^a   Peng, Zhou ^a   Fan, Jun ^d   Hou, Zhibo ^a   Fang, Yongsheng ^a   Wang, Yifei ^a   Kitazato, Kaio ^c   Yu, Guoying ^e   Zou, Chunbin ^e   Qian, Chuiwen ^a   Xiong, Sheng ^a,e  

^a JINAN UNIVERSITY   (China)

^b SUN YAT SEN UNIVERSITY   (China)

^c NAGASAKI UNIVERSITY   (Japan)

^d KYOTO UNIVERSITY   (Japan)

^e UNIVERSITY OF PITTSBURGH SCHOOL OF MEDICINE   (United States)

^f Guangdong Provincial Institute of Traditional Chinese Medicine   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; CYANOVIRIN N; CYANOVIRIN N DERIVATIVE; GLYCAN; MANNOSE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ANTIVIRAL ACTIVITY; ARTICLE; BINDING AFFINITY; CELL FUSION; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG SPECIFICITY; DRUG TARGETING; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROPHILICITY; IN VITRO STUDY; KERATINOCYTE; MOLECULAR DOCKING; NONHUMAN; PEGYLATION; T LYMPHOCYTE; VIRUS INACTIVATION;

BACTERIAL PROTEINS; CARRIER PROTEINS; DIMERIZATION; DRUG DESIGN; HIV INFECTIONS; HIV-1; HUMANS; MODELS, MOLECULAR; MOLECULAR DOCKING SIMULATION; OLIGOSACCHARIDES; POLYETHYLENE GLYCOLS; PROTEIN ENGINEERING;

EID: 84899953551     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0086455     Document Type: Article

References (36)

1. UNAIDS website. Available: http://www.unaids.org/en/resources/documents/ 2012/name,76121,en.asp. Accessed 2013 Dec 18.
2. Shattock RJ, Moore JP (2003) Inhibiting sexual transmission of HIV-1 infection. Nature Reviews Microbiology 1: 25-34.
3. Shattock RJ, Warren M, McCormack S, Hankins CA (2011) AIDS. Turning the tide against HIV. Science 333: 42-43.
4. Balzarini J, Van Damme L (2007) Microbicide drug candidates to prevent HIV infection. Lancet 369: 787-797. (Pubitemid 46335821)
5. Bewley CA, Gustafson KR, Boyd MR, Covell DG, Bax A, et al. (1998) Solution structure of cyanovirin-N, a potent HIV-inactivating protein. Nat Struct Biol 5: 571-578.
6. Xiong S, Fan J, Kitazato K (2010) The antiviral protein cyanovirin-N: the current state of its production and applications. Applied Microbiology and Biotechnology 86: 805-812.
7. Zappe H, Snell ME, Bossard MJ (2008) PEGylation of cyanovirin-N, an entry inhibitor of HIV. Adv Drug Deliv Rev 60: 79-87. (Pubitemid 350181168)
8. Roberts MJ, Bentley MD, Harris JM (2002) Chemistry for peptide and protein PEGylation. Adv Drug Deliv Rev 54: 459-476. (Pubitemid 34615543)
9. Pasut G, Veronese FM (2012) State of the art in PEGylation: the great versatility achieved after forty years of research. J Control Release 161: 461-472.
10. Huston JS, Levinson D, Mudgett-Hunter M, Tai MS, Novotny J, et al. (1988) Protein engineering of antibody binding sites: recovery of specific activity in an anti-digoxin single-chain Fv analogue produced in Escherichia coli. Proc Natl Acad Sci U S A 85: 5879-5883.
11. Gao X, Chen W, Guo C, Qian C, Liu G, et al. (2010) Soluble cytoplasmic expression, rapid purification, and characterization of cyanovirin-N as a His-SUMO fusion. Appl Microbiol Biotechnol 85: 1051-1060.
12. Tochikura TS, Nakashima H, Tanabe A, Yamamoto N (1988) Human immunodeficiency virus (HIV)-induced cell fusion: quantification and its application for the simple and rapid screening of anti-HIV substances in vitro. Virology 164: 542-546.
13. Botos I, Mori T, Cartner LK, Boyd MR, Wlodawer A (2002) Domain-swapped structure of a mutant of cyanovirin-N. Biochem Biophys Res Commun 294: 184-190. (Pubitemid 34687235)
14. Vorontsov, II, Miyashita O (2009) Solution and crystal molecular dynamics simulation study of m4-cyanovirin-N mutants complexed with di-mannose. Biophys J 97: 2532-2540.
15. Bewley CA (2001) Rapid validation of the overall structure of an internal domain-swapped mutant of the anti-HIV protein cyanovirin-N using residual dipolar couplings. J Am Chem Soc 123: 1014-1015.
16. Sandstrom C, Hakkarainen B, Matei E, Glinchert A, Lahmann M, et al. (2008) Atomic mapping of the sugar interactions in one-site and two-site mutants of cyanovirin-N by NMR spectroscopy. Biochemistry 47: 3625-3635. (Pubitemid 351431351)
17. Botos I, O'Keefe BR, Shenoy SR, Cartner LK, Ratner DM, et al. (2002) Structures of the complexes of a potent anti-HIV protein cyanovirin-N and high mannose oligosaccharides. J Biol Chem 277: 34336-34342.
18. Barrientos LG, Matei E, Lasala F, Delgado R, Gronenborn AM (2006) Dissecting carbohydrate-Cyanovirin-N binding by structure-guided mutagenesis: functional implications for viral entry inhibition. Protein Engineering Design and Selection 19: 525-535. (Pubitemid 44950458)
19. Corine Sandström, Berteau O (2005) Atomic Mapping of the Interactions between the Antiviral Agent Cyanovirin-N and Oligomannosides by Saturation-Transfer Difference NMR†. Biochemistry 43: 13926-13931.
20. Geyer H, Holschbach C, Hunsmann G, Schneider J (1988) Carbohydrates of human immunodeficiency virus. Structures of oligosaccharides linked to the envelope glycoprotein 120. J Biol Chem 263: 11760-11767.
21. Montero M, van Houten NE, Wang X, Scott JK (2008) The membrane-proximal external region of the human immunodeficiency virus type 1 envelope: dominant site of antibody neutralization and target for vaccine design. Microbiol Mol Biol Rev 72: 54-84, table of contents. (Pubitemid 351398055)
22. Shattock R, Solomon S (2004) Microbicides-aids to safer sex. Lancet 363: 1002-1003.
23. Moscoso CG, Sun Y, Poon S, Xing L, Kan E, et al. (2011) Quaternary structures of HIV Env immunogen exhibit conformational vicissitudes and interface diminution elicited by ligand binding. Proc Natl Acad Sci U S A 108: 6091-6096.
24. Chen X, Zaro JL, Shen WC (2013) Fusion protein linkers: Property, design and functionality. Adv Drug Deliv Rev 65: 1357-1369.
25. Liu Y, Carroll JR, Holt LA, McMahon J, Giomarelli B, et al. (2009) Multivalent interactions with gp120 are required for the anti-HIV activity of Cyanovirin. Biopolymers 92: 194-200.
26. Kelley BS, Chang LC, Bewley CA (2002) Engineering an obligate domain-swapped dimer of cyanovirin-N with enhanced anti-HIV activity. J Am Chem Soc 124: 3210-3211. (Pubitemid 34270352)
27. Contarino M, Bastian AR, Kalyana Sundaram RV, McFadden K, Duffy C, et al. (2013) Chimeric Cyanovirin-MPER recombinantly engineered proteins cause cell-free virolysis of HIV-1. Antimicrob Agents Chemother 57: 4743-4750.
28. NIH. Available: http://chemdb.niaid.nih.gov/struct-search/misc/invitro. asp?aids=045707. Accessed 2012 May 12.
29. Xiong S, Fan J, Kitazato K (2010) The antiviral protein cyanovirin-N: the current state of its production and applications. Appl Microbiol Biotechnol 86: 805-812.
30. Boyd MR, Gustafson KR, McMahon JB, Shoemaker RH, O'Keefe BR, et al. (1997) Discovery of cyanovirin-N, a novel human immunodeficiency virus-inactivating protein that binds viral surface envelope glycoprotein gp120: potential applications to microbicide development. Antimicrob Agents Chemother 41: 1521-1530. (Pubitemid 27289680)
31. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, et al. (2000) The Protein Data Bank. Nucleic Acids Res 28: 235-242. (Pubitemid 30047768)
32. Nemoto Y, Ikeda J, Katoh K, Koshimoto H, Yoshihara Y, et al. (1993) R2D5 antigen: a calcium-binding phosphoprotein predominantly expressed in olfactory receptor neurons. J Cell Biol 123: 963-976. (Pubitemid 23333583)
33. Katoh M, Shikoshi K, Takada M, Umeda M, Tsukahara T, et al. (1993) [Neutrophil functions during treatment with granulocyte colony-stimulating factor (G-CSF) in the elderly with non-Hodgkin's lymphoma: including two patients accompanied with interstitial pneumonitis during the treatment with G-CSF]. Nihon Ronen Igakkai Zasshi 30: 953-957.
34. Nakashima H, Tanabe A, Tochikura TS, Yamamoto N (1988) Rapid screening method with a cell multisizer for inhibitors of human immunodeficiency virus-induced cell fusion in vitro. J Clin Microbiol 26: 1229-1232.
35. Katoh H, Satomura S, Matsuura S (1993) Analytical method for sugar chain structures involving lectins and membrane ultrafiltration. J Biochem 113: 118-122. (Pubitemid 23068853)
36. Buckheit RW Jr, Roberson JL, Lackman-Smith C, Wyatt JR, Vickers TA, et al. (1994) Potent and specific inhibition of HIV envelope-mediated cell fusion and virus binding by G quartet-forming oligonucleotide (ISIS 5320). AIDS Res Hum Retroviruses 10: 1497-1506. (Pubitemid 24382202)