Synthesis, conformation, and bioactivity of novel analogues of the antiviral lipopeptide halovir(501 views) Dalla Bona A, Formaggio F, Peggion C, Kaptein B, Broxterman Quirinus B, Galdiero S, Galdiero M, Vitiello M, Benedetti E, Toniolo C
Keywords: Antiviral Activity, C α-Methylated α-Amino Acids, Peptide Conformation, Peptide Synthesis, Spectroscopy, Alpha Amino Acid, Antivirus Agent, Halovir A, Leucine, Lipopeptide, Methionine, Valine, Absorption Spectroscopy, Article, Biological Activity, Cell Culture, Concentration Response, Controlled Study, Cytotoxicity, Functional Proteomics, Herpes Simplex Virus 1, Human, Human Cell, Infrared Spectroscopy, Nonhuman, Nuclear Magnetic Resonance, Priority Journal, Protein Analysis, Protein Conformation, Protein Determination, Protein Function, Protein Synthesis, Vero Cell, Virus Infectivity, Virus Inhibition, Animals, Antiviral Agents, Cercopithecus Aethiops, Dose-Response Relationship, Drug, Herpesvirus 1, Magnetic Resonance Spectroscopy, Fourier Transform Infrared, Stereoisomerism, Structure-Activity Relationship, Human Herpesvirus 1, C-Methylated-Amino Acids,
Affiliations: *** IBB - CNR ***
Department of Chemistry, University of Padova, via Marzolo 1, 35131 Padova, Italy
DSM Research, Life Sciences, Advanced Synthesis and Catalysis, 6160 MD Geleen, Netherlands
Department of Biological Sciences, Division of Biostructures, University of Naples 'Federico II', 80134 Napoli, Italy
Centro Interuniversitario di Ricerca sui Peptidi Bioattivi, University of Naples 'Federico II', 80134 Napoli, Italy
Istituto di Biostrutture e Bioimmagini, CNR, 80134 Napoli, Italy
Department of Experimental Medicine, 2nd University of Naples, 80138 Napoli, Italy
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Karle, I. L., Balaram, P., Structural characteristics of -helical peptide molecules containing Aib residues (1990) Biochemistry, 29, pp. 6747-6756
Rowley, D. C., Kelly, S., Kauffman, C. A., Jensen, P. R., Fenical, W., Halovirs A-E, new antiviral agents from a marine-derived fungus of the genus Scytalidium (2003) Bioorg. Med. Chem., 11, pp. 4263-4274
Stanberry, L. R., Jorgensen, D. M., Nahmias, A. J., Herpes simplex viruses 1 and 2 (1997) Viral Infections of Humans: Epidemiology and Control, pp. 419-454. , Evans AS, Kaslow RA (eds), 4th edn. Plenum Medical Book Company: New York
Kruizinga, W. H., Bolster, J., Kellogg, R. M., Kamphuis, J., Boesten, W. H. J., Meijer, E. M., Schoemaker, H. E., Synthesis of optically pure -alkylated -amino acids and a single-step method for enantiomeric excess determination (1988) J. Org. Chem., 58, pp. 1826-1827
Schoemaker, H. E., Boesten, W. H. J., Kaptein, B., Hermes, H. F. M., Sonke, T., Broxterman, Q. B., van den Tweel, W. H. J., Kamphuls, J., Chemoenzymatic synthesis of amino acids and derivatives (1992) Pure Appl. Chem., 64, pp. 1171-1175
K nig, W., Geiger, R., Eine neue Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexylcarbodiimid unter Zusatz von 1-Hydroxy-benzotriazolen (1970) Chem. Ber., 103, pp. 788-798
Carpino, L. A., 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive (1993) J. Am. Chem. Soc., 115, pp. 4397-4398
Jones, D. S., Kenner, G. W., Preston, J., Sheppard, R. C., Peptides. Part XVII. Synthesis of peptides and polymers of some sterically hindered amino acids via oxazolone intermediates (1965) J. Chem. Soc., pp. 6227-6239
Brown, H. C., Narasimhan, S., New powerful catalysts for the reduction of esters by lithium borohydride (1982) J. Org. Chem., 47, pp. 1604-1606
W thrich, K., (1986) NMR of Proteins and Nucleic Acids, pp. 192-196. , Wiley: New York
Synthesis, conformation, and bioactivity of novel analogues of the antiviral lipopeptide halovir
We synthesized by solution-phase methods three analogues, [L-Leu(6)-OMe], [L-(alpha Me)Leu(3), L-Leu(6)-OMe], and [L-(alpha Me)Val(4), L-Leu(6)-OMe] of halovir A. The [L-Leu(6)-OMe] analogue is known to be biologically equipotent to its naturally occurring, antiviral, lipopentapeptide amide parent compound. The preferred conformations of the L-(alpha Me)Leu- and L(alpha Me)Val-containing analogues, with a potentially reinforced helicity, were compared with those Of [L-Leu(6)-OMe] halovir A and the natural peptide itself by use of a combination of FT-IR absorption and NMR techniques. Measurements of the antiviral activities against herpes simplex virus type-1 (HSV-1) of halovir A and its three analogues were also carried out. Interestingly, the [L-(alpha Me)Val(4), L-Leu(6)-OMe] analogue exhibits the most significant activity in reducing HSV-1 infectivity, notably higher than that of halovir A itself. Copyright (c) 2006 European Peptide Society and John Wiley & Sons, Ltd.
Synthesis, conformation, and bioactivity of novel analogues of the antiviral lipopeptide halovir
Kállay C, Dávid A, Timári S, Nagy EM, Sanna D, Garribba E, Micera G, De Bona P, Pappalardo G, Rizzarelli E, Sóvágó I * Copper(II) complexes of rat amylin fragments(360 views) Dalton T (ISSN: 1477-9234, 1477-9226, 1477-9234electronic), 2011 Oct 14; 40(38): 9711-9721. Impact Factor:3.838 ViewExport to BibTeXExport to EndNote