Polycyclic peptide and glycopeptide antibiotics and their derivatives as inhibitors of HIV entry

Antiviral Research

Volumn 71, Issue 2-3 SPEC. ISS., 2006, Pages 227-236

  Preobrazhenskaya, Maria N ^a   Olsufyeva, Eugenia N ^a  

^a GAUSE INSTITUTE OF NEW ANTIBIOTICS   (Russian Federation)

Author keywords

Complestatin; Eremomycin; Hydrophobic derivatives; Kistamicin; Vancomycin; Viral entry

Indexed keywords

AGLYCONE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ANTIBIOTIC AGENT; ANTIVIRUS AGENT; CHLOROEREMOMYCIN; CHLOROPEPTIN 1; CHLOROPEPTIN DERIVATIVE; CHLOROPEPTIN I; COMPLESTATIN; CYTOSTATIC AGENT; EREMOMYCIN; EREMOMYCIN AGLYCON; EREMOSAMINE; GLYCOPEPTIDE; HEPTAPEPTIDE; ISOCOMPLESTATIN; KISTAMYCIN; MICROBICIDE; PENTAPEPTIDE; POLYPEPTIDE ANTIBIOTIC AGENT; RIBAVIRIN; RISTOCETIN; RISTOCETIN A; SCH 204698; TEICOPLANIN; TEICOPLANIN AGLYCON; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANCOMYCIN; VANCOMYCIN AGLYCON; VANCOSAMINE;

ANTIMICROBIAL ACTIVITY; ANTIVIRAL ACTIVITY; CHEMICAL MODIFICATION; COLON CARCINOMA; CORONAVIRUS; CYTOTOXICITY; DRUG EFFICACY; DRUG MECHANISM; DRUG POTENCY; FLAVIVIRUS; HERPES VIRUS; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; HYDROPHOBICITY; INFLUENZA VIRUS; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; RETROVIRUS; SEXUAL TRANSMISSION; SHORT SURVEY; STRUCTURE ACTIVITY RELATION; VIRUS TRANSMISSION;

ANTI-BACTERIAL AGENTS; ANTI-HIV AGENTS; CELLS, CULTURED; GLYCOPEPTIDES; HIV-1; HUMANS; PEPTIDES, CYCLIC; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33747103063     PISSN: 01663542     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.antiviral.2006.04.008     Document Type: Short Survey

References (34)

1. Anon, 2002. Patent WO 2004/019970. Priority date August 30, 2002.
2. Balzarini J., Pannecouque C., DeClercq E., Pavlov A., Printsevskaya S., Miroshnikova O., Reznikova M., and Preobrazhenskaya M.N. Antiretroviral activity of semisynthetic derivatives of glycopeptide antibiotics. J. Med. Chem. 46 13 (2003) 2755-2764
3. Bourinbaiar A.S., and Jirathitikal V. Low-cost anti-HIV compounds: potential application for AIDS therapy in developing countries. Curr. Pharm. Des. 9 (2003) 1419-1431
4. Bugg T.D.H., Wright G.D., Dutka-Malen S., Arthur M., Courvalin P., and Walsh C.T. Molecular basis for vancomycin resistance in Enterococcus faecium BM4147: biosynthesis of a depsipeptide peptidoglycan precursor by vancomycin resistance proteins VanH and VanA. Biochemistry 30 (1991) 10408-10415
5. Cooper R.D.G., Snyder N.J., Zweifel M.J., Staszak M.A., Rodrigues M.J., Huff B.E., and Thomphson R.C. Reductive alkylation of glycopeptide antibiotics: synthesis and antibacterial activity. J. Antibiot. 49 (1996) 575-581
6. DeClercq E. New developments in anti-HIV chemotherapy. Curr. Med. Chem. 8 13 (2001) 1543-1572
7. DeClercq E. Emerging anti-HIV drugs. Expert Opin. Emerg. Drugs 10 (2005) 241-274
8. DeClercq E. New approaches towards anti-HIV chemotherapy. J. Med. Chem. 48 (2005) 1297-1313
9. Deng H., Jung J.-K., Liu T., Kuntz K.W., Snapper M.L., and Hoveyda A.H. Total synthesis of anti-HIV agent chloropeptin I. JACS 125 (2003) 9032-9034
10. Endo A. Enhancement of plasminogen binding and fibrinolysis by chloropeptin I. Thromb. Res. 87 (1997) 571-576
11. Ge M., Chen Z., Onishi H.R., Kohler J., Silver L.L., Kerns R., Fukuzawa S., Thompson C., and Kahne D. Vancomycin derivatives that inhibit peptidoglycan biosynthesis without binding d-Ala-d-Ala. Science 284 (1999) 507-511
12. Hedge V.R., Puar M.S., Dai P., Patel M., Gullo V.P., Chan T.-M., Praamanik B.N., and Jenh Ch.-H. Condensed aromatic peptide family of microbial metabolites. Inhibitors of CD28-CD80 interactions. Bioorg. Med. Chem. Lett. 44 (2003) 573-575
13. Jayasurriya H., Salituro G.M., Smith S.K., Heck J.V., Gould S.J., and Singh S.B. Complestatin to chloropeptin I via a quantitative acid catalyzed rearrangement. Absolute stereochemical determination of complestatin. Tetrahedron Lett. 39 (1998) 2247-2248
14. Kaneko I., Kamoshida K., and Takahashi S. Complestatin, a potent anti-complement substance produced by Streptomyces lavendulae. I. Fermentation, isolation and biological characterization. J. Antibiot. 42 (1989) 236-241
15. Kim E.-Ch., Yun B.-S., Ryoo I.-J., Min J.-K., Won M.H., Lee K.S., Kim Y.-M., Yoo I.-D., and Kwoon Y.-G. Complestatin prevents apoptic cell death: inhibition of a mitochondrial caspase pathway through AKT/PKB activation. Biochem. Biophys. Res. Commun. 313 (2004) 193-204
16. Matsuzaki K., Ikeda H., Ogino T., Matsumoto A., Woodruff H.B., Tanaka H., and Omura S. Chloropeptins I and II novel inhibitors against gp120-CD4 binding from Streptomyces sp. J. Antibiot. 47 (1994) 1173-1174
17. Memota, K., Kaneko, I., Kimura, S. Mitamura, K., Shimada, K, 1999. Inhibition of human immunodeficiency virus type-1-induced syncytium formation and cytopathicity by complestatin. Biochem. Biophys. Res. Commun. 179, 243-250.
18. Naruse N., Tomita K., Yamamoto S., Tenmyo O., and Oki T. New antiviral antibiotics, kistamicins A and B. I. Taxonomy, production, isolation, physico-chemical properties and biological activities. J. Antibiot. 46 (1993) 1804-1811
19. Polianova M.T., Ruscetti F.W., Pert C.B., Tractenberg R.E., Leoung G., Strang S., and Ruff M.R. Antiviral and immunological benefits in HIV patients receiving intranasal peptide T (DAPTA). Peptides 24 (2003) 1093-1098
20. Preobrazhenskaya M.N., and Olsufyeva E.N. Patents on glycopeptides of the vancomycin family and their derivatives as antimicrobials: January 1999-June 2003. Expert Opin. Ther. Patents 14 (2004) 141-173
21. Printsevskaya S.S., Pavlov A.Y., Olsufyeva E.N., Mirchink E.P., Isakova E.B., Reznikova M.I., Goldman R.C., Brandstrom A.A., Baizman E.R., Longley C.B., Sztaricskai F., Batta G., and Preobrazhenskaya M.N. Synthesis and mode of action of hydrophobic derivatives of glycopeptide antibiotic eremomycin and des-(N-methyl-d-leucyl) eremomycin against glycopeptide-sensitive and -resistant bacteria. J. Med. Chem. 45 (2002) 1340-1345
22. Printsevskaya S.S., Solovieva S.E., Olsufyeva E.N., Mirchink E.P., Isakova E.B., De Clercq E., Balzarini J., and Preobrazhenskaya M.N. Structure-activity relationships studies on a series of antiviral and antibacterial aglycon derivatives of the glycopeptide antibiotics vancomycin, eremomycin and dechloroeremomycin. J. Med. Chem. 45 (2005) 3885-3889
23. Reeves J.D., and Piefer A.J. Emerging drugs targets for antiretroviral therapy. Drugs 65 (2005) 1747-1766
24. Rusconi S., Bulgheroni E., and Citterio P. Entry and fusion inhibitors of HIV. Expert Opin. Ther. Patents 14 (2004) 733-748
25. Shinohara T., Deng H., Snapper M.L., and Hoveyda A.H. Isocompklestatin: total synthesis and stereochemical revision. JACS 127 (2005) 7334-7336
26. Seo S.Y., Yun B.S., Ryoo I.-J., Choi J.S., Joo C.K., Chang S.Y., Chung J.M., Oh S., Gwag B.J., and Yoo I.-D. Complestatin is a noncompetitive peptide antagonist of N-methyl-d-aspartate and α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid/kainate receptors: secure blockade of ischemic neuronal death. J. Pharmacol. Exp. Ther. 299 (2001) 377-384
27. Seto H., Fujioka T., Furihata K., Kaneko I., and Takahashi S. Structure of complestatin, a very strong inhibitor of protease activity of complement in the human complement system. Tetrahedron Lett. 30 (1989) 4987-4990
28. Singh S.B., Jayasuriya H., Hazuda D.L., Felock P., Homnick C.F., Sardans M., and Patane M.A. Selective and controlled hydrolysis of chloropeptin I HIV-1 integrase activity of fragments. Tetrahedron Lett. 39 (1998) 8769-8770
29. Singh S.B., Jayasuriya H., Salituro G.M., Zink D.L., Shafiee A., Heimbuch B., Silverman K.C., Lingham R.B., Genilloud O., Teran A., Vilella D., Felock P., and Hazuda D. The complestatins as HIV-1 integrase inhibitors. Efficient isolation, structure elucidation, and inhibitory activities of complestatin, chloropeptin I, new complestatins, A and B, and acid-hydrolyses products of chloropeptin I. J. Nat. Prod. 64 (2001) 874-882
30. Smith III A.B., Chruma J.J., Han Q., and Barbosa J. Complestatin synthetic studies: the effect of amino acid configuration on peptide backbone conformation in the common western BCD macrocycle. Bioorg. Med. Chem. Lett. 14 (2004) 1697-1702
31. Tanaka H., Matsuzaki K., Nakashima H., Ogino T., Matsumoto A., Ikeda H., Woodruff H.B., and Omura S. Chloropeptins, new anti-HIV antibiotics inhibiting gp120-CD4 binding from Streptomyces sp. J. Antibiot. 50 (1997) 58-65
32. Tandon V.K., and Chhor R.B. Current status of anti-HIV agents. Curr. Med. Chem. Anti-Infective Agents 4 (2005) 3-28
33. Walsh C. Antibiotics: Actions, Origins, Resistance (2003), ASM Press, Washington, DC p. 47
34. Zhou N., Luo Z., Luo J., Fan X., Pesavento J., Dong C.-Z., Wang Y., An J., Kaji H., Sodroski J.G., and Huang Z. Exploring the stereochemistry of CXCR4-peptide recognition and inhibiting HIV-1 with d-peptides derived from chemokins. J. Biol. Chem. 277 (2002) 17476-17485