Phenylboronic-acid-based carbohydrate binders as antiviral therapeutics: Bisphenylboronic acids

Antiviral Chemistry and Chemotherapy

Volumn 21, Issue 3, 2011, Pages 129-142

  Trippier, Paul C ^a   Balzarini, Jan ^b   McGuigan, Christopher ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLBORONIC ACID DERIVATIVE; ANTIVIRUS AGENT; BORONIC ACID DERIVATIVE; BROMIDE; CARBOHYDRATE; FUNCTIONAL GROUP; GLYCOPROTEIN GP 120; MANNOSE; PHENYL GROUP; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOPATHOGENIC EFFECT; DRUG BINDING; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; MOLECULAR LIBRARY; MOLECULAR MODEL; NONHUMAN; PRIORITY JOURNAL; SENSOR; SIMIAN IMMUNODEFICIENCY VIRUS; STRUCTURE ACTIVITY RELATION; VIRUS ENVELOPE;

ANIMALS; ANTIVIRAL AGENTS; BORONIC ACIDS; CERCOPITHECUS AETHIOPS; MODELS, MOLECULAR; POLYSACCHARIDES; STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS INTERNALIZATION;

EID: 78951488387     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: 10.3851/IMP1707     Document Type: Article

References (18)

1. Balzarini J. Carbohydrate-binding agents: a potential future cornerstone for the chemotherapy of enveloped viruses? Antivir Chem Chemother 2007; 18:1-11. (Pubitemid 46426933)
2. Balzarini J. Targeting the glycans of glycoproteins: a novel paradigm for antiviral therapy. Nat Rev Microbiol 2007; 5:583-597. (Pubitemid 47074114)
3. Trippier PC, McGuigan C, Balzarini J. Phenylboronicacid-based carbohydrate binders as antiviral therapeutics: monophenylboronic acids. Antivir Chem Chemother 2010; 20:249-257.
4. Kwong PD, Wyatt R, Robinson J, Sweet RW, Sodroski J, Hendrickson WA. Structure of an HIV gp120 envelope glycoprotein in complex with the CD4 receptor and a neutralizing human antibody. Nature 1998; 393:648-659.
5. Helenius A, Aebi M. Intracellular functions of N-linked glycans. Science 2001; 291:2364-2369.
6. Chen B, Vogan EM, Gong H, Skehel JJ, Wiley DC, Harrison SC. Structure of an unliganded simian immunodeficiency virus gp120 core. Nature 2005; 433:834-841.
7. Tsukagoshi K, Shinkai S. Specific complexation with mono- and disaccharides that can be detected by circular dichroism. J Org Chem 1991; 56:4089-4091.
8. Takeuchi M, Yoda S, Imada T, Shinkai S. Chiral sugar recognition by a diboronic-acid-appended binaphthyl derivative through rigidification effect. Tetrahedron 1997; 53:8335-8348.
9. Klis T, Serwatowski J. Halogen-lithium exchange versus deprotonation: synthesis of diboronic acids derived from aryl-benzyl ethers. Tetrahedron Lett 2007; 48:1169-1173.
10. Hall DG (Editor). Boronic acids: preparation, applications in organic synthesis and medicine. Weinheim: Wiley-VCH 2005; pp. 61.
11. Llewellyn G, Stein BK. Boronic acid analysis by mass spectrometry - I: cis-diol derivatisation for EI and CI analysis. Available from http://www.swan.ac.uk/nmssc/documents/NMSSC-AN6-BOH2-EG.pdf
12. Longstaff C, Rose ME. Derivatization and mass spectrometric investigations of substituted benzeneboronic acids. The use of linked scanning during gas chromatography mass spectrometry. Org Mass Spectrom 1982; 17:508-518.
13. Kasák P, Brath H, Dubovská M, Juríček M, Putala M. Suzuki arylation at positions 2 and 2′ of 1,1′- binaphthyls: stereochemical result depending on the sense of polarity of substrates. Tetrahedron Lett 2004; 45:791-794.
14. Azizi N, Akbari E, Amiri AK, Saidi MR. Highly chemoselective reductive amination-coupling by one-pot reaction of aldehydes, HMDS and NaBH4. Tetrahedron Lett 2008; 49:6682-6684.
15. Leblanc C, Pulz RA, Stiefl NK, inventors; Novartis AG, Switzerland, assignee. Preparation of pyrrolopyrimidines and pyrrolopyridines for treating ALK-5 and ALK-4 receptor-mediated diseases. PCT Int. Appl. WO 2009087225, 2009 January 9.
16. Lee SH, Kohn H. Efficient synthesis of medium-sized cyclic ether diamines. J Org Chem 2002; 67:1692-1695.
17. Tecle T, White MR, Sorensen G, et al. Critical role for cross-linking of trimeric lectin domains of surfactant protein D in antiviral activity against influenza A virus. Biochem J 2008; 412:323-329.
18. Jay JI, Lai BE, Myszka DG, et al. Multivalent benzoboroxole functionalized polymers as gp120 glycan targeted microbicide entry inhibitors. Mol Pharm 2010; 7:116-129.